Family friendly vacation rentals in West Harwich, MA

Explore 124 family-friendly vacation rentals, homes, and villas in West Harwich, MA for your next getaway. With space for everyone, enjoy the comfort and privacy of a home filled with premium amenities such as Air Condition Homes, Homes with Free Parking and Best Affordable Homes. Throughout your stay, settle in, spend quality time together, and enjoy a space designed for making memories. With options starting as low as $90 per night and homes offering up to 11 bedrooms and 10 bathrooms, it's easy to book a comfortable, personalized stay for your family. And with 24/7 local support and high-speed Wi-Fi, everyone stays connected and protected even while on vacation. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, making each trip more rewarding than the last. Book your next family escape and enjoy the moments that matter most.

124 Family-Friendly Homes in West Harwich

Sleeps 14 Home w/ Pool Great for Families!

Harwich, MA, US
6 Bedrooms 14 Guests
Sep 1 - 3
$502 night

17743 - Casa del Sol: Sleeps 14 Home w/ Pool Great for Families! Soak up the sun this summer, at Casa del Sol! Enjoy the brand new hot tub, or cool off in the pool!<br><br>Walk across the home’s front porch and push open the door into a beautiful living room, where three sofas giving plenty of space to sit and relax as you watch your favorite flick on the wall mounted TV. At the rear of the home, a dining room with natural light spilling in has easy access to the home’s kitchen, where meal creation is a breeze.<br><br>Out back, a spacious yard gives plenty of space for your four-legged friends to run around. Anchoring the yard, an in-ground swimming pool offers the perfect place to cool off in the summer sun. Once done swimming, there’s plenty of areas to lounge and dine outdoors as well.<br><br>This sleeps 14 home has four bedrooms on the first floor, and two bedrooms on the second floor. The second floor is a great space for the kids to hang out with their own bedrooms separated by a foosball table and TV room. Other amenities include two sets of washers and dryers, a covered porch at the front of the home, and an outdoor shower. Harwich, Cape Cod, is a beloved destination for visitors seeking a quintessential New England experience. With its picturesque harbors, sandy beaches, and quaint village center, Harwich has something to offer for everyone. Come enjoy the idyllic scenery, warm hospitality, and laid-back atmosphere that makes Harwich a treasured gem of Cape Cod, at Casa del Sol!<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 14<br>-2 Floors (1st Floor + 2nd Floor)<br>-Hot Tub (NEW for 2025)<br>-2,442 Sq Ft<br>Bedrooms<br>-Total 6<br>-1st Floor Bedroom: 1 King Bed<br>-1st Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom: 3 Twin Beds<br>-2nd Floor Bedroom: 3 Twin Beds<br>Bathrooms<br>-Total 2.5<br>-1st Floor: Tub/Shower combo<br>-1st Floor: Shower<br>-2nd Floor: Half Bathroom<br>Other Amenities<br>-Fully Equipped Kitchen with Dishwasher<br>-Central A/C<br>-Fireplace is NOT for guest use<br>-Smart Lock/Self Check-In<br>-WiFi<br>-Smart TV with Streaming<br>-2 Sets of Full Washer & Dryers (1st Floor)<br>-Patio with Outdoor Dining and Built-In Seating<br>-In-Ground Unheated Pool (Pool Open from Memorial Day to Labor Day - may be longer but not guaranteed)<br>-Propane Grill<br>-Outdoor Shower<br>-Private Yard<br>-1.3 Miles to Pleasant Road Beach<br>-1.6 Miles to Swan Pond<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C1554918503

Renovated Classic Cape w/ Guest House, Game Room!

Dennis, MA, US
7 Bedrooms 14 Guests
Aug 28 - 30
$750 night

19929 - Sands of Time: Renovated Classic Cape w/ Guest House, Game Room! Located in the heart of beautiful Dennis Port, this incredible property offers a unique opportunity to large groups looking to vacation in one of the most sought after areas of Cape Cod. With professional interior design work completed in early 2022 to lovingly restore this antique home, this home sleeps 14 total guests and features a 2700 square foot main house with a separate 774 square foot guest house, along with a huge half acre of fenced in yard. Conveniently situated directly south of Main St, you will be right around the corner from many of the great restaurants and shops of Dennis Port, like Red Nun, Oyster Company, and Rory’s Kitchen. Best of all - you will be 7/10 mile from a number of gorgeous sandy beaches on Nantucket Sound like Inman Road Beach and West Dennis Beach!<br><br>This home sleeps 10 in the main house across two floors, and features a cozy living room and spacious kitchen. Please note, the stairs up to the second floor are steep. The guest house sleeps 4 guests across two bedrooms and has it’s own kitchen. A game barn located in the backyard is the perfect place to spend a rainy day or unwind after dinner. The huge fenced in backyard is great for yard games, lounging in the sun, and your dogs! Other amenities include window A/C units in all the bedrooms, a propane grill, WiFi, and sheets and bath towels provided at no extra cost with beds made upon arrival. Don’t miss out on the opportunity to stay at this incredible property!<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog<br>-Sleeps 14<br>Bedrooms<br>-Total 7<br>Main House:<br>-Bedroom #1: 1 Queen Bed, 1st Floor<br>-Bedroom #2: 1 Queen Bed, 1st Floor (walk-through bedroom).<br>-Bedroom #3: 2 Twin Beds (bunk beds), 1st Floor<br>-Bedroom #4: 1 King Bed, 2nd Floor<br>-Bedroom #5: 2 Twin Beds, 2nd Floor<br>Bathrooms<br>-Total 3.5<br>-Bathroom #1: Full Bath w/ Shower, 1st Floor<br>-Bathroom #2: Full Bath w/ Shower, 1st Floor<br>-Bathroom #3: Half Bath, 2nd Floor<br>Guest House: <br>-Bedroom #1: 1 Queen Bed<br>-Bedroom #2: 2 Twin Beds (bunk beds)<br>- Bathroom #4: Full Bath w/Shower, 1st Floor<br>-Window AC units in bedroom<br>-Game Room<br>-WiFi<br>-Smart TVs<br>-Washer/Dryer <br>-Propane Grill<br>-Indoor Fireplaces are not for guest use(fines remitted)<br>-Please note outdoor amenities are available seasonally<br>-Please note there is a security camera facing the driveway<br>-Walk to Downtown<br>-Short Drive to Nantucket Sound Beaches<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-Parking for 6 cars maximum<br>-C0463930750<br><br><br><br><br> Please note there is a security camera facing the driveway and the stairs to the second floor are steep

Pet-Friendly Yard! Fun Family Home in Cape Cod

Harwich, MA, US
3 Bedrooms 8 Guests
Aug 29 - 31
$554 night

Ready for a relaxing beach vacation? This 3-bedroom, 2-bathroom vacation rental home is the perfect place to embrace Cape Cod’s laid-back lifestyle. The home features both a living room and a basement family room, so there is plenty of space to lounge with a book in the central A/C. In the fenced-in yard, you’ll find comfortable chairs and a fit pit. Pack up the beach towels and head to Sea Street Beach, less than a mile away. Book today and let the Nantucket Sound wash your worries away! -- THE PROPERTY -- C0369050750 | Outdoor Shower | Furnished Deck Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Twin Beds | Family Room: Queen Futon | Additional Sleeping: Pack ‘n Play INDOOR LIVING: 6 Smart TVs, board games, books OUTDOOR LIVING: Private yard, beach cart & towels, beach umbrella, fire pit, gas grill, beach chairs KITCHEN: Blender, coffee maker, cooking basics, microwave, refrigerator, stovetop/oven GENERAL: Dog waste bags, free WiFi, central A/C, washer/dryer FAQ: Pet fee (paid pre-trip), steps required to access, 2 bedrooms and 1 bathroom on the 1st floor PARKING: Driveway (2 vehicles), EV charger in garage -- THE LOCATION -- BEACHES: Sea Street Beach (0.8 miles), Raycroft Beach (0.8 miles), Belmont Road Beach (1.0 miles), Pleasant Road Beach (1.6 miles), Bank Street Beach (3.5 miles), Veterans Park Beach (10.3 miles), Sandy Neck Beach (19.1 miles) GOLF: Blue Rock Golf Course (4.0 miles), Cranberry Valley Golf Course (5.1 miles), The Captains Golf Course (10.4 miles), Olde Barnstable Fairgrounds Golf Course (17.1 miles), The Ridge Club (20.2 miles) EXPLORE CAPE COD: The Cape Playhouse (7.0 miles), Cape Cod Museum of Art (7.1 miles), Nauset Lighthouse (20.1 miles), Wellfleet Cinemas (20.4 miles), Sandwich Glass Museum (23.9 miles), Heritage Museums & Gardens (24.6 miles), Pilgrim Monument and Provincetown Museum (40.9 miles) DINING: The Ocean House Restaurant (0.7 miles), Clancy’s Restaurant (1.3 miles), Clean Slate Eatery/ La Tacodilla (1.9 miles), Sesuit Harbor Cafe (7.5 miles), Mac's Shack (25.9 miles), Moby Dick's Restaurant (26.6 miles), The Glass Onion (30.4 miles) AIRPORT: Boston Logan International Airport (81.2 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $100 fee (+ fees & taxes, max 2 dogs) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: There are 2 steps to access the front door and stairs to access the yard. There are 2 bedrooms and 1 bathroom on the 1st floor

Luxurious Estate, Private Heated pool!

Harwich, MA, US
6 Bedrooms 12 Guests
Sep 17 - 19
$1,853 night

17718 - The Secret Garden: Luxurious Estate with Private Heated pool! Indulge in a world of enchantment at the Secret Garden in Harwich, where every detail exudes whimsical charm and luxurious comfort. Step into this stately home and prepare to be mesmerized by its meticulous design, where each room is a testament to craftsmanship and artistic flair.<br><br>Begin your journey in the exquisite mudroom, a vibrant oasis of color and warmth, complete with heated floors and captivating artwork. Follow the path to the heart of the home, where a thoughtfully designed kitchen awaits, seamlessly blending elegance and functionality. Adjacent to the dining room, an expansive sun porch beckons with its panoramic views and inviting ambiance, perfect for poolside gatherings and al fresco dining under the Cape Cod skies.<br><br>Venture upstairs to discover three sumptuous bedrooms, each boasting en suite full bathrooms and private viewing porches offering breathtaking ocean vistas and refreshing sea breezes. The remaining bedrooms, including a delightful kids’ retreat with a twin-over-full bunk bed, promise restful nights and tranquil escapes.<br><br>Outside, the wonders continue with an outdoor oasis that rivals the home’s interior splendor. Delight in morning espresso amidst the lush gardens or channel your inner chef in the outdoor kitchen, complete with a pizza oven and full prep station, where gourmet delights come to life in the open air.<br><br>But the pièce de résistance awaits with the heated pool, nestled within immaculate gardens, inviting you to bask in the sunshine and indulge in moments of relaxation and rejuvenation. With amenities such as a washer and dryer, propane grill, and central A/C ensuring comfort and convenience, every moment at the Secret Garden is a celebration of luxury and serenity.<br><br>Experience the epitome of Cape Cod elegance and hospitality, where every day is a fairy tale come true. With luxury service provided throughout your stay, including daily cleaning and towel exchange, your vacation dreams are about to unfold at the Secret Garden.<br><br>Home Details:<br>-No pets (fines remitted)<br>-Sleeps 12<br>-3 Floors (1st Floor, 2nd Floor + 3rd Floor)<br>Bedrooms<br>-Total: 6<br>-Bedroom #1: 1 Queen Bed w/ En Suite Full Bathroom, 2nd Floor <br>-Bedroom #2: 1 Queen Bed w/ En Suite Full Bathroom, 2nd Floor   <br>-Bedroom #3: 2 Twin Beds w/ En Suite Full Bathroom, 2nd Floor <br>-Bedroom #4: 1 Queen Bed, 3rd Floor <br>-Bedroom #5: 2 Twin Beds - Twin Bed with twin Trundle, 3rd Floor<br>-Bedroom #6: 1 Twin-over-Full Bunk Bed, 3rd Floor<br>Bathrooms<br>-Total: 5.5<br>-Bathroom #1: En Suite Full Bathroom with Shower, 2nd Floor<br>-Bathroom #2: En Suite Full Bathroom with Shower, 2nd Floor<br>-Bathroom #3: En Suite Full Bathroom with Shower and Tub, 2nd Floor<br>-Bathroom #4: En Suite Full Bathroom with Shower, 3rd Floor<br>-Bathroom #5: En Suite Full Bathroom with Tub, 3rd Floor<br>-Bathroom #6: Half Bathroom, 1st Floor<br>Other Amenities<br>-Central A/C<br>-TV with Cable<br>-Smart Lock/Self Check-In<br>-WiFi<br>-Washer and Dryer<br>-Heated Pool (Pool Open from Memorial Day to Oct 1)<br>-Outdoor Kitchen with Pizza Oven<br>-Stunning Outdoor Spaces<br>-Propane Grill<br>-please note outdoor amenities are available seasonally<br>-please note there are exterior cameras on the entrance door and driveway that are not recording during the rentable season<br>-Water Views<br>-2-minute Walk to Beaches<br>-There is parking for a maximum of 4 cars<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-C0434931260 -please note there are exterior cameras on the entrance door and driveway that are not recording during the rentable season

Sophisticated Luxury Home 1 Mi from Downtown!

Harwich, MA, US
7 Bedrooms 14 Guests
Sep 14 - 16
$575 night

17754 - Summer’s Crown: Sprawling, Sophisticated Luxury Home 1 Mi from Downtown w/ Pool and Game Room! From the moment you arrive at Summer’s Crown, you’ll know you just stepped into a new kind of Cape Cod vacation. This sprawling luxury home, just a mile from downtown Harwich Port has all you could need and more to make the most of your time on Cape Cod. Immediately, this home stands out with it’s crisp architectural silhouette and expansive grounds. With multiple gathering spaces across the estate and three private living spaces, this expansive home offers refined comfort, generous space, and flexibility--ideal for multigenerational vacations, milestone celebrations, or guests attending events at nearby Wychmere Beach Club. Inside, three distinct living spaces allow your group to gather with ease while still enjoying meaningful privacy. Multiple kitchens and independent quarters make it simple to vacation together without ever feeling crowded. The Main House spans two floors and features two inviting sitting areas and four well-appointed bedrooms, each with its own ensuite bath. The spacious kitchen and dining area are designed for connection, whether you’re preparing a favorite family recipe or lingering over dinner while recounting the day’s adventures. The Pool House, set just below the main home with its own private entrance, includes a bedroom with ensuite bath, kitchenette, TV area, card table, and ping pong table. It’s an inviting space for teens, friends, or anyone seeking a little extra independence. Above the garage, the In-Law Apartment offers two bedrooms, a full kitchen, dining area, and comfortable TV lounge-- perfect for grandparents, another family, or guests who appreciate their own retreat within the estate. Throughout all three residences, high-end furnishings and clean coastal design create a cohesive, elevated feel.<br><br>Indoor entertainment is thoughtfully woven throughout the property. A dedicated kids’ game and TV room in the Main House is stocked with board games, while the Pool House adds lively competition with ping pong and table games. Whether you’re escaping a summer shower or taking a break from the sun, there’s always a comfortable place to unwind. Outdoors, the experience continues. The 10’ x 16’ heated plunge pool with hydrotherapy jets (open Memorial Day through Thanksgiving) offers a soothing place to relax after the beach. Newly completed hardscaping surrounds the pool, complemented by a fire pit for evening gatherings under the stars. An outdoor shower makes it easy to rinse off after a day in the sand. Multiple balconies offer ample opportunity to enjoy the fresh, Cape Cod air. The expansive front lawn invites a casual game of wiffle ball, while the welcoming front porch is the ideal spot to enjoy cocktails as the sun sets on another idyllic Cape Cod day. When you’re ready to explore, Harwich Port’s Main Street is just a mile away, offering locally loved restaurants, boutique shops, and ice cream stops perfect for an evening stroll. Enjoy a round of mini golf or go-karts at Bud’s, catch a Cape Cod Baseball League game at Whitehouse Field, or plan a memorable dinner at Wequassett Resort. Every day offers a balance of activity and relaxation. At Summer’s Crown, space, comfort, and thoughtful design come together to create a seamless Cape Cod stay—an inviting setting for gathering, celebrating, and savoring time well spent. Book Summer’s Crown today, and secure the backdrop to your perfect vacation, designed for those who appreciate the finer details of modern seaside living. Home Details: -No Pets (Fines Remitted) -Sleeps 12 Bedrooms -Total 7 Main House -1st Floor Bedroom: 1 King Bed w/ En-Suite Full Bathroom -2nd Floor Bedroom: 1 King Bed w/ En-Suite Full Bathroom -2nd Floor Bedroom: 1 Queen Bed w/ attached Jack & Jill Bathroom -2nd Floor Bedroom: 1 Queen and 1 Twin w/ attached Jack & Jill Bathroom In-Law Suite -2nd Floor Sleeping Space: 1 King Bed -2nd Floor Sleeping Space: 1 Queen Bed Pool House -Ground Floor Bedroom (separate from main house and garage apartment): Queen Bed Bathrooms -Total 6.5 Main House -1st Floor: Full Bathroom w/ Shower (En suite King Bedroom) -1st Floor: Half Bathroom -2nd Floor: Full Bathroom w/ Shower (En suite King Bedroom) -2nd Floor: Full Bathroom w/ Tub and Shower (Jack & Jill style) -2nd Floor: Full Bathroom w/ Tub and Shower In-Law Suite -2nd Floor: Full Bathroom w/ Shower (In-Law Suite) Pool House -Ground Floor: Full Bathroom w/ Shower Other Amenities -Heated Plunge Pool (available Memorial Day to Thanksgiving) -Game Room w/ Ping Pong -Central Air Conditioning -WiFi -Smart TV -Washer/Dryer (3 sets) -Propane Grill -Outdoor Shower -Fire Pit -Please note outdoor amenities are available seasonally -Sheets and Bath Towels Provided with Beds made Upon Arrival -Cleaned with Hospital Grade Disinfectant -Parking for 4 cars maximum -EV Charger -C0499561260

Wychmere Heights: 003-HK Magnificent Harwich Port Estate, Heated Pool, Walk to Beach & Village

Harwich Port, MA, US
9 Bedrooms 20 Guests
Oct 12 - 15
$2,223 night

This property is professionally managed by Pretty Picky Properties Magnificent Harwich Port Estate, Heated Pool, Walk to Wychmere Harbor and Village Sleeps 20 Linens Included, beds made Rents Friday to Friday during peak season Pets considered Pool is open Memorial Day weekend through Columbus Day weekend Just across the street from picturesque Wychmere Harbor, “Wychmere Heights” offers unique and private accommodations in the heart of Harwich Port. The 6800+ square foot property is located on a large acre lot and features tremendous indoor and outdoor living spaces for your group of up to 20. Featuring 9 bedrooms, 7 full baths, and 2 half baths there is ample room for groups to spread out and have their own space inside. Outside your focus will no doubt be the heated 20x40 saltwater pool and surrounding spacious patio. The property also has a lush, irrigated lawn for recreation or relaxation. Interior Living Space The property’s main level is comprised of a spacious living and dining room. There is seating for 18-20 at two dining tables. The living room has a TV, ample seating and has a slider out to the pool area. The updated kitchen is adjacent to the dining rooms and features new appliances, 2 full size refrigerators, 2 ovens, 2 dishwashers, a waterfall granite counter, and a spacious bar area. The roomy kitchen area is ideal for entertaining and has a slider to the pool area. There are two primary bedroom suites on this level as well. Both rooms have private baths and king-size beds. Finally, there is a private wing off the other side of the kitchen that has a small den, two bedrooms with a queen bed in each plus a full bath. This area may be ideal for a young family or anyone who may need some extra privacy from the rest of the group. In all, the main level has four bedrooms. The lower level is set up with a King bedroom suite with a spa-like private bath, a secondary TV lounge plus a game room. There is also a half bath down here. Upstairs, you’ll find 4 additional bedrooms. There are two primary suites (Orleans Room & Brewster Room) each with a king size bed. The Dennis Room features a double bed plus a twin. The final bedroom upstairs is the "bunk room" and in here you will find 3 XL twin beds plus a queen size bed. There is a full bath in the hallway up here as well. Outdoor Space The heated pool is surrounded by a spacious patio with plentiful lounging and seating. The dining area has seating for up to 18-20 and features chaise lounges to soak up the sun. The pool includes an auto safety cover that can be closed with a flick of a switch. This keeps the pool safe for any young ones and also helps to keep debris out and heat in the pool. You will also find a stand alone hot tub and a gas firepit. There is a playset on the side yard for the kids to enjoy. Harwich Port From the house, you can head west into Harwich Port Village, about a 7-minute walk. The village has several dining and bar options to choose from. There’s also ice cream, boutiques, and art studios to browse. It’s a charming village center that features Port Summer Nights on Wednesdays in the summer. The streets are closed to vehicle traffic and the area is festive with live music, food trucks and other attractions. Saquatucket Harbor You can also head just east to Saquatucket Harbor. There are waterfront dining options here as well as a great selection of charter boats on which to get out on the water with a rod and reel. Or, head out to Nantucket for the day! The Freedom Ferry will have you over to the island in just over an hour. Don’t forget the beach! You can walk across the street and down Snow Inn Road to Merkel Beach, about a 10-minute walk from the house (half a mile). Here you have an expansive Nantucket Sound beach with the calm warm waters of the sound massaging the shoreline. Wychmere Harbor Wychmere Harbor is a stone’s throw from the property and is one of the most photographed vistas on the Cape. Wychmere is also home to the Wychmere Beach Club. The club is private but is very popular for weddings and events. “Wychmere Heights” is uniquely set up to welcome guests of events for long weekends in the shoulder seasons. Though large events are not permitted at “Wychmere Heights”, modest dinner gatherings or the like are considered with approval. Experience the best of Cape Cod at “Wychmere Heights” with all your favorite people! Please enter in your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $255.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. This property offers a 3-night minimum stay outside of the peak season. Guests are charged a cleaning fee for all stays less than 7 nights. Stay 7-nights or more and the cleaning fee is waived. Be sure to search this site for your best selection of prime vacation homes available for rental on Cape Cod. It’s your vacation. Get Picky! ®

Stony Brook Sanctuary: 095-B Brand New Custom Built Luxury Home, Heated Pool, Close to Bay Beaches

Brewster, MA, US
5 Bedrooms 10 Guests
Dec 31 - Jan 3
$1,292 night

This property is professionally managed by Pretty Picky Properties New Custom Built Luxury Home, Heated Pool, Close to Bay Beaches “Stony Brook Sanctuary” 95-B Rents Saturday to Saturday during peak season Linens Included, Beds Made Sleeps 10 Location In 2022, the owners turned a vacant wooded lot into a tasteful luxury home. The lot is just under two acres and offers plenty of privacy and ample outdoor yard space. When you’re ready for the beach, you won’t have to go far. It’s less than a five-minute drive to Sea Street Beach and the intriguing Brewster Flats. It’s also about a 25-minute walk along an appealing path through the scenic marshlands leading to the beaches on Cape Cod Bay. You have your choice of several sandy beaches along the Bay in East Dennis, including the exceptional Corporation and Mayflower Beaches. You can also drive a few more minutes to Paine’s Creek Beach in Brewster for some of Cape Cod’s most beautiful sunsets. You’re also near excellent dining at several highly rated restaurants scattered along Main Street (Route 6A). Check out the Brewster Fish House, Scargo Café and the Sesuit Harbor Café, to name just a few favorites. Outside Living Space The centerpiece, of course, is the extra long heated pool, ideal for swimming laps as well as for splashing around with the kids. The superb outdoor living space behind the house features a large patio with an umbrella shaded oversized picnic table. The kids will make good use of the playscape/swing set as well! You’ll also take advantage of the enclosed outdoor shower and handy gas grill. Fire up the grill and serve dinner outside. Off the front side of the house you’ll enjoy a generous screened porch with comfy seating and a full-scale wood burning fireplace. Inside Living Space This home has 3,700 sq ft of interior living space, not counting the large screened porch and the finished lower level. You’ll be impressed by the combination of taste and quality the owners have brought to bear on all three levels of the house for your vacation enjoyment. And in case you have any office work to be done, the home has two offices equipped with high speed Wi-Fi. The extraordinary kitchen features a large center island with counter seating for five. The new, top of the line appliances are a pleasure to use, including the induction range. There is also a custom wood topped wet bar island in the kitchen with a wine fridge included. Immediately adjacent is the dining area with seating for eight, which can be expanded to 12, at a table lovingly crafted from reclaimed 17th century red pine. And just off that, the living room is light and bright with comfortable lounge seating and a gas fireplace. The finished lower level offers a comfy TV lounge, a recreation room with a regulation size pool table and another full bath. In all, the house has 5.5 baths. Sleeping Accommodations Start with the primary bedroom on the main level. It has a king size bed and a full private bath and a large TV. On the second level there are four more bedrooms. Two have queen size beds. One has a bunk bed with a full-size double under a twin on top. Finally, the fifth bedroom has a king size bed plus a sleep sofa with a fold out twin. It also has an adjacent full bath. For more information on bedrooms and baths, please click on the Room Details tab above. Amenities This amenity-rich home has two laundries, central air conditioning, high speed Wi-Fi, a Sonos® Sound System, cable/smart TV and much more. For a complete list of amenities please click on the Amenities tab above. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Damage Protection fee totaling $245.00 In addition, there are state and local taxes applied to all reservations of l 31 days or less that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

1 Mi to South Village Beach: BBQ-Ready Retreat

Dennis, MA, US
3 Bedrooms 6 Guests
Aug 29 - Sep 1
$578 night

Dine Al Fresco | Private Green Space | Near Kayaking & Boating | Swan River Views Beach days, boating, and classic Cape Cod charm await at this 3-bedroom, 3-bathroom West Dennis vacation rental. Located along the Swan River, which leads to Nantucket Sound, this home offers a relaxing space to unwind after exploring the coast. Rinse off sand in the outdoor shower, then gather around the fire pit. Later, catch a stunning sunset or explore local shops and seaside dining. -- THE PROPERTY -- C0139500750 SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Bedroom 3: 2 twin beds - Additional Sleeping: 1 portable crib OUTDOOR LIVING - Deck w/ water views - Patio, private yard  - Outdoor shower - Gas grill, fire pit, outdoor dining area INDOOR LIVING - Flat-screen TV - Board games, books - Shower/tub combo, 2 walk-in showers KITCHEN - Stove/oven, refrigerator, microwave - Drip coffee maker, toaster, toaster oven - Dishware & flatware - Paper towels, trash bags - Dining table GENERAL - Free WiFi - Keyless entry - Central heating & A/C - Linens & towels, washer & dryer, iron & board - Complimentary toiletries, hair dryer FAQ - 1 Ring doorbell camera (facing out) ACCESSIBILITY - Single-story home - 3 exterior steps to enter PARKING - Driveway (2 vehicles) -- THE LOCATION -- - 2 miles to West Dennis Beach & Bass River Cruises - 6 miles to Scargo Tower & Cape Cod Museum of Art - 9 miles to Cape Cod Rail Trail - 8 miles to Cape Cod Gateway Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome--because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story home requires 3 exterior steps to enter - This property runs on a septic system; it is critical no items (feminine products, floss, food, toys, etc) other than toilet paper be flushed down the toilet - Your safety matters. This property features a Ring doorbell device with an exterior security camera on the front exterior facing the front outdoor entry. The camera does not look into any interior spaces. The camera records video and sound when activated by motion Licence number: C0139500750

Olivia’s Oasis: 006-HL - Stunning New Construction with Heated Pool & Hot Tub in Harwich

Harwich, MA, US
5 Bedrooms 12 Guests
Sep 19 - 26
$1,280 night

This property is professional managed by Pretty Picky Properties Stunning New Construction with Heated Pool & Hot Tub in Harwich NEW Listing for 2026! Sleeps 12 Linens provided, beds made Rents Saturday to Saturday during peak season 7 night minimum stay required for all seasons Pool is open Memorial Day weekend through Columbus Day weekend Welcome to Olivia’s Oasis! Tucked away in East Harwich and crafted with fresh, modern elegance, this brand-new five-bedroom retreat sets the tone for an effortless Cape Cod escape. Thoughtfully designed and impeccably furnished, the home blends clean coastal style with the comforts of a true luxury stay. The layout offers privacy and flexibility for families or groups traveling together, with five spacious bedrooms—each featuring its own ensuite bath. The first-floor primary suite is a serene sanctuary with a king bed, while three upstairs bedrooms also offer king accommodations. A fifth bedroom, accessed by a separate staircase, features two twin beds with trundles, making it ideal for children or younger guests seeking their own space. At the heart of the home, the chef’s kitchen showcases high-end appliances and sleek finishes, opening seamlessly to inviting living and dining areas perfect for gathering. A second living space upstairs includes a wet bar, creating a relaxed lounge for evening cocktails or movie nights, while a private office provides a quiet place to check in—if you must. Outside, the experience continues with a heated saltwater pool, hot tub, and gas fire pit, all set within a private outdoor setting designed for long summer days and cool Cape evenings. Whether you’re returning from the beach or lingering under the stars, this outdoor oasis invites you to unwind in style. Ideally located, the home is just a 10-minute drive to several beautiful beaches including expansive Red River Beach (1.5 miles) and downtown Chatham, offering easy access to dining, shopping, and classic Cape Cod charm—while still enjoying the tranquility of East Harwich. Polished, private, and perfectly appointed, this exceptional home is a refined base for making lasting Cape memories. Please enter in your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $255.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. This property offers a 3-night minimum stay outside of the peak season. Guests are charged a cleaning fee for all stays less than 7 nights. Stay 7-nights or more and the cleaning fee is waived. Be sure to search this site for your best selection of prime vacation homes available for rental on Cape Cod. ​​​​​​​ It’s your vacation. Get Picky! ®

Quivett Compound 419-B Magnificent Mansion, Privacy, Pool, Water Views in Brewster

Brewster, MA, US
10 Bedrooms 20 Guests
Aug 30 - Sep 2
$2,411 night

This property is professionally managed by Pretty Picky Properties Magnificent Mansion, Privacy, Pool, Water Views in Brewster Come for July 4th! Arrive on Thursday July 2 or Friday July 3rd and enjoy the holiday! Sleeps 22 in 10 Bedrooms, 9.5 Baths Linens and Bed Making Included The newly constructed Quivett Compound is the perfect summer retreat for your discerning group of up to 22. The property is secluded on seven-plus acres and set far back from the historic Old King’s Highway in beautiful West Brewster by the bay, the property serves up sweeping views of Quivett Creek and Cape Cod Bay beyond. Launch an owner-provided kayak or canoe and explore the creek. Watch the kids frolic in the in-ground heated pool, which provides continuous entertainment when they come off the nearby bay side beaches in both Brewster and Dennis. You’ll spend a lot of time on the expansive shaded deck or outdoor patio with its built-in gas grill, fire pit and large dining table. Set up the net provided and organize a volley ball or badminton tournament. You certainly have plenty of space to do it! Inside, you’ll roam through 6,300 square feet of modern luxury, exquisitely designed and superbly furnished and appointed. The main level common living space includes an immense living room with two seating areas, one with a large flat screen, wall mounted TV. There is also a separate TV lounge with wet bar upstairs. The kitchen is big, bright and totally social. It is equipped with everything you could ask for, including two dishwashers, a beverage center and a Keurig coffee maker. The adjacent dining room offers a great place to gather inside, although you’ll likely choose to eat outside most summer days on the deck and patio. The lower level has a very cool game room, ready for action with a pool table, ping pong table, air hockey, video games and more. Then, it’s show time in the home theater, with its huge movie screen and comfy recliner chair seating. The laundry lives on this level, as well, with not one but two new washers and dryers. The ten bedrooms break down as follows: six kings, three queens, one full size double and two twins. The 9.5 baths sort out this way: one half bath on the main level, six bedrooms with en suite baths plus two full baths on the lower level. Finally, there is a room above the detached garage withe a King bed and a full bath. Of course, the home is centrally air conditioned and has high-speed Wi-Fi and Cable TV. **Please note that the bedroom and bathroom over the garage is fully winterized from 11/1 - 5/1 each year. As a result the property only has 9 bedrooms and 7.5 baths from November through April sleeping a maximum of 20 guests*** *** Pool is open and heated from Memorial Day (late May) through Columbus Day (early October)*** ****The Quivett Creek Compound does consider small events (with a maximum of 50 attendees including guests staying at the property) on site on a case by case basis in May, June, September and October. There are no events allowed in July and August. Please contact us for more details.**** Please enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

Walk to Haigis Beach: Cape Cod Retreat w/ Deck!

Dennis, MA, US
4 Bedrooms 9 Guests
Sep 25 - 28
$334 night

Book your trip to Dennis and discover year-round destinations and activities in the heart of Cape Cod! This 4-bedroom, 2-bath vacation rental is equipped with modern appliances, cozy furnishings, and spacious living areas to host your crew. Spend your days lounging on the deck, or walk less than .5 miles from this home to catch some rays on Haigis Beach. The fun continues just a day trip away at Provincetown or Martha's Vineyard - prime spots for shopping, dining, hiking, fishing, and more! -- THE PROPERTY -- C0479270750 | 1,500 Sq Ft | Off-Street Parking | Outdoor Living Space Whether you're a group of friends or family looking to discover relaxation and entertainment in Cape Cod, this home has you covered with its ideal location near beaches, trails, historic sites, and family-friendly attractions! Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: 2 Twin Bunk Beds INDOOR LIVING: 2 Smart TVs, dining table, wood-burning fireplace, vaulted ceilings KITCHEN: Well-equipped w/ stainless steel appliances, cooking basics, drip coffee maker, toaster oven, blender, teapot OUTDOOR SPACE: Deck, patio, dining table, gas grill, outdoor shower, beach chairs, bikes GENERAL: Free WiFi, central A/C & heating, linens/towels, complimentary toiletries, washer/dryer, hair dryer FAQ: Stairs required, Ring doorbell camera PARKING: Driveway (2 vehicles), home front (2 vehicles) -- THE LOCATION -- BEACHES: Haigis Beach (0.3 miles), Glendon Road Beach (0.6 miles), West Dennis Beach (1.9 miles), Seagull Beach (7.0 miles), Cape Cod National Seashore (11.9 miles) OUTDOOR ACTIVITIES: Cape Cod Waterways Kayak Rentals (1.0 miles), Holiday Hill Miniature Golf (1.5 miles), Bass River Golf Course (3.3 miles), Chatham Lighthouse (11.5 miles), Cape Cod Rail Trail (11.5 miles), Nickerson State Park (12.5 miles), Dolphin Whale Watch (42.5 miles) THINGS TO SEE & DO: Cape Cod Museum of Art (8.1 miles), Cape Cod Children's Museum (22.1 miles), Heritage Museums & Gardens (22.6 miles), Woods Hole Science Aquarium (33.2 miles) DAY TRIPS: Hyannis Cruise Terminal-Nantucket and Martha's Vineyard Ferries (8.2 miles), Provincetown (41.6 miles) FOOD + DRINK: Sundae School Ice Cream (1.1 miles), Kream 'n Kone (1.2 miles), First Crush Winery (4.8 miles), Brax Landing Restaurant (4.7 miles), Cape Cod Beer (10.4 miles) AIRPORT: Boston Logan International Airport (80.6 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - Massachusetts Tax ID: ROC-13071594-003 | C0247210750 - NOTE: The property requires stairs and may be difficult for guests with limited mobility - NOTE: Your safety matters. This property features a Ring Doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device or when the video doorbell button is pressed Licence number: C0247210750;C0479270750

Close to Beach, Fire Pit, and Hot Tub!

Dennis, MA, US
4 Bedrooms 8 Guests
Sep 22 - 24
$288 night

19945 - Octopus’s Garden: Close to Beach, Fire Pit, and Hot Tub! Welcome to Octopus’s Garden, a completely remodeled stylish vacation home featuring a newly designed fire pit area, perfect for cozy evenings under the stars. This inviting space offers a private deck where you can savor alfresco dinners and unwind in a serene atmosphere.<br><br>The home also features an air hockey table, perfect for kids. Enjoy multiple sitting areas, where you can relax with a cup of coffee in a high back chair, or lounge and watch TV on one of the many comfortable couches throughout the home. The upstairs loft bedroom also has a window seat, perfect for enjoying a cat nap or reading a book in the sun. <br><br>Just 2 miles from West Dennis Beach and other Nantucket Sound Beaches, you can spend your days in the sand and surf and come home to enjoy the evening breeze off the deck. Located conveniently near local favorites, you’ll find delightful dining options like the Chapin’s Fish & Chips for a casual meal, Sundae School Ice Cream Parlor for a sweet treat, and Good Friends Cafe for a delightful breakfast. <br><br>At Octopus’s Garden, you’ll experience the perfect blend of modern comfort and Cape Cod charm, making it an ideal getaway for families and friends alike. Your unforgettable coastal escape awaits!<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 8<br>Bedrooms<br>-Total 4<br>-2nd Floor Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom: 1 King<br>-3rd Floor Bedroom: 1 King<br>Bathrooms<br>-Total 4.5: 4 Full Bathrooms, 1 Half Bathroom<br>-Ground Floor Bathroom: Full Bathroom w/ Shower<br>-1st Floor Bathroom: Half Bathroom<br>-2nd Floor Bathroom: Full Bathroom w/ Shower (en suite King Bedroom)<br>-2nd Floor Bathroom: Full Bathroom w/ Tub/ Shower Combo<br>-3rd Floor Bathroom: Full Bathroom w/ Shower (en suite King Bedroom)<br>Other Amenities <br>-Game Room with Air Hockey<br>-Hot Tub (available year round!)<br>-Air Conditioning via Mini-Splits<br>-Central Heat<br>-WiFi<br>-Smart TV <br>-Washer/Dryer <br>-Propane Gas Grill<br>-Fire Pit<br>-Outdoor Shower<br>-Indoor Fireplaces are not for guest use(fines remitted)<br>-Please note outdoor amenities are available seasonally<br>-Please note there is an exterior ring camera on the property that records the entry door<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Please note there are exterior cameras on the property that record the driveway and basement door<br>-Cleaned with Hospital Grade Disinfectant<br>-Parking for 4 cars maximum Please note there are exterior cameras on the property that record the driveway and basement door

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

Dennis, MA, US
3 Bedrooms 8 Guests
Aug 29 - 31
$517 night

Escape to this newly remodeled open-concept stunner, located right next the Cape Cod Rail Trail bikepath. Quick access to great bayside & oceanside beaches - w/ all the beach essentials provided! Enjoy an evening under the stars in our huge backyard with a firepit, outdoor seating & tables + a grill. Plenty of space in the house to spread out w/ numerous living rooms and dining areas. Books, games & ping pong for rainy days. Ideal for families or groups seeking classic Cape Cod charm & comfort. HIGHLIGHTS: ★ 3 Bedrooms + 5 Beds + 3 Baths ★ Less than 10 minutes to both bay & oceanside Beaches ★ Beach essentials provided such as towels, chairs & beach toys ★ Direct access to the Cape Cod Rail Trail - perfect for biking, walking & running ★ Massive backyard and terrace with a BBQ Grill, outdoor seating & tables, and a fire pit ★ Game Room in the basement with a Ping Pong table ★ 3 Living Room areas to hang out in, including a huge sunroom filled with books + games ★ Expandable dining table with seating for 8-10, plus additional dining table in the kitchen that seats 6-8 ★ Fully stocked kitchen with a granite island, barstools, and all the appliances & utensils you would need ★ Piano ★ Smart HD TV with all the Streaming Apps available ★ Washer/Dryer ★ AC available through central air and wall units ★ High-speed WiFi ★ 5 min to Stop & Shop or Ring Bro’s Marketplace for groceries ★ Minutes to downtown Dennis Port restaurants & shopping ★ Desk to work from ★ Very secluded & private property ★ Free parking in the driveway ★ Near Breweries such as Devil’s Purse Brewing Company ★ Walking distance to a Bike Rental shop ★ Stroll across the path into the Indian Lands, with beautiful paths along Bass River ★ Close to the ferries that go to Nantucket & Martha’s Vineyard BEDS: Bedroom 1: King Bed + toddler bed Bedroom 2: King Bed Bedroom 3: Twin-over-Full Bunk Bed + Twin Daybed BATHROOMS: Bathroom 1: Full size bathroom attached to Bedroom #1 with a standing shower Bathroom 2: Full size bathroom with a standing shower and the washer / dryer Bathroom 3: Full size upstairs bathroom with a bathtub / shower combo BEACH DETAILS: The town of Dennis has easy access to plenty of beautiful bayside, oceanside, and freshwater beaches. ★ West Dennis Beach: a popular 2-mile long beach on Cape Cod known for its calm, salt-water swimming and various recreational activities. ★ Mayflower Beach: Kid-friendly bay-side beach with a concession stand and restrooms. ★ Corporation Beach: Big bay-side beach, with concession stand and swing set. Great place to watch the sunset. ★ South Village Beach: Oceanside (Nantucket Sound) beach. Lots of seashells and horseshoe crabs on the beach. Walk east to where the Swan River meets the ocean, for some fun swimming and beautiful scenery. ★ Scargo Lake. Freshwater, shallow and good for young children. There are a few entry points, including one off of Route 6a. NEARBY TRANSPORTATION: 20 minutes from the following places: ★ Cape Cod Gateway Airport ★ Hy-Line Cruises (ferries to Martha’s Vineyard and Nantucket) ★ The Steamship Authority (ferries to Martha’s Vineyard and Nantucket) We are located on the Cape Cod Rail Trail and near lots of restaurants, activities, family attractions, hiking trails, golfing, and shopping. You will love this cozy, classic home, and will thoroughly enjoy staying in this area! NEARBY PLACES (Alphabetical Order): ★ Barb’s Bike Shop ★ Bass River Beach + Picnic Area ★ Bass River Golf Course ★ Captain Frosty’s ★ Captain Parkers ★ Clancy’s Restaurant ★ Devil’s Purse Brewing Company ★ Great Western Deli ★ Haigis Beach ★ Harvest Gallery Wine Bar ★ Ocean House Restaurant ★ Pleasant Road Beach ★ Raycroft Beach ★ Red Cottage Restaurant ★ Red Nun Bar & Grill ★ Ring Bro’s Marketplace ★ Sea Street Beach ★ Sesuit Harbor Cafe ★ Solstice Fly Fishing Charter ★ Stop & Shop Groceries ★ Sundae School Ice Cream ★ The Ocean House ★ The Oyster Company ★ The Sailing Cow ★ The Ocean House ★ Three Fins Coffee Roasters ★ Woolfie’s Coffee & Breakfast Bakery ★ Yarmouth Pizza by Evan We are located in the heart of South Dennis, a charming and historic village in the town of Dennis on Cape Cod. Our neighborhood blends classic Cape character with modern convenience. We’re right next to the famous Cape Cod Rail Trail bike path, which leads for miles in either direction. The Indian Lands Conservation Area is on the other side of the CCRT, with paths through evergreen groves along the Bass River. Bring a picnic to watch the sunset from picnic tables overlooking the water. South Dennis is full of quiet, tree-lined streets and boasts a central location between the bay and the sound. Come stay for a relaxed, family-friendly atmosphere perfect for vacationers and year-round visits. You’ll have the whole home to yourself! Please note we do not provide propane for the BBQ grill or wood for the fire pit, but there may be some leftover from a previous guest. If not, propane is readily available from Breakaway (one block away) or Ace Hardware. The fireplaces are not usable.

Eileen’s Escape: 021-C Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated

Chatham, MA, US
5 Bedrooms 12 Guests
Sep 7 - 10
$1,065 night

This home is professionally managed by Pretty Picky Properties Luxurious Chatham Home, Heated Saltwater Pool, Newly Renovated Rents Friday to Friday during peak season Linens Included. Beds made. Sleeps 12 Pool & Hot Tub open from Memorial Day to Columbus Day Be one of the first to stay in this masterfully renovated home with a brand-new saltwater pool under a mile (.7 mile) to Ridgevale Beach in Chatham. The 5-bedroom home plus bonus room has been totally updated from top to bottom and features brand new furniture throughout. The focal point of course is the custom saltwater pool with a built-in hot tub. The outdoor living space is stunning with an expansive travertine patio, plenty of lounge seating and an outdoor kitchen set up with a grill and granite counter. Don’t forget to use the outdoor shower after the beach! Inside, the attention to detail is evident from the coffered ceilings to custom local art on the walls. The main living area is open to the kitchen and dining area. The kitchen is of course fully equipped with all you’ll need to prepare any meal. The main level is also home to the primary bedroom with a King-sized bed and exquisite private bathroom. There are two additional bedrooms on the main level: one with a queen and one with 2 twins. There is a full bath for these rooms as well. Finally there is a second vaulted living area with additional lounge seating and a TV. Upstairs features a classic Cape set up with a full bathroom at the top of the stairs. There are bedrooms on either side. Both bedrooms feature custom ship-lapped walls and ceilings and have King beds with a twin trundle. Even more living space awaits on the fully finished lower level! There is another TV lounge area plus a workspace and an exercise area. There is a flex sleeping area down here which houses 2 queen beds. A brand-new full bath on the lower level completes the space. A 15 minute walk or a very short bike ride brings you down to one of Nantucket Sound’s most desirable beaches: Ridgevale Beach. Relax on the beach, have the little ones play in the creek flowing into the Sound and grab a bite to eat at the snack bar. A 6-8 minute drive brings you to both Chatham and Harwich Port Villages for pedestrian friendly shopping and dining. There are ample dining and shopping opportunities along Route 28 closer to the house as well. Please enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $255.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. This property offers a 3-night minimum outside of the peak season. Guests are charged a cleaning fee for all stays less than 7 nights. Stay 7-nights or more and the cleaning fee is waived. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Lower Cape Cod. It’s your vacation. Get Picky! ® Town of Chatham Registration #STR-562

Water Views Private Pool, Hot Tub, Access to Cove!

Dennis, MA, US
4 Bedrooms 10 Guests
Sep 22 - 24
$433 night

19908 - Grand Cove: Water Views Private Pool, Hot Tub, Access to Cove! This gorgeous West Dennis home, located on Grand Cove in Bass River, is the perfect place for your next luxury vacation! Two huge wrap around decks offer spectacular water views of the cove, and with direct water access, you are just steps from being able to kayak, paddleboard, or swim in this beautiful body of water. After your adventures on the cove, walk back to our private fenced in yard, which features an in-ground pool complete with a waterfall, as well as a poolside patio. If the backyard wasn’t spectacular enough, the large front yard is grassy and a great place to play a classic game of summer whiffle ball. <br><br>Inside, you will find an eat-in kitchen with brand new appliances, and a large formal dining area that opens into a family room (with a large, sectional leather couch and flat screen TV) with a slider out to a large deck - perfect for summer cookouts. The top level master suite features a king size bed under a vaulted, pine planked ceiling with bright skylights, and a slider leading to another large, wrap around deck with panoramic views of the cove. There are two more bedrooms upstairs, one with a king bed and en suite full bathroom and the other with two full beds, as well as another full bathroom. The fourth bedroom is located on the first floor and has a queen bed, with a third full bathroom down the hall.<br><br>Downstairs is the Game Room with a foosball table, couches, flat screen TV, and slider that steps out to the pool and the private yard. Other amenities include smart TV, WiFi, washer/dryer in the basement, air conditioning, an outdoor shower, and linens and bath towels provided for each guest. Take your next vacation in style and book our gorgeous vacation home now!<br><br>Home Details:<br>-Sleeps 10<br>-3 Floors<br>-3,624 Sq Ft<br>Bedrooms<br>-Total 4<br>-Bedroom #1: 1 Queen Bed, 1st Floor<br>-Bedroom #2: 1 King Bed, 2nd Floor<br>-Bedroom #3: 1 King Bed w/ en suite Full Bathroom,, 2nd Floor<br>-Bedroom #4: 2 Queen Beds 2nd Floor<br>Bathrooms<br>-Total 3<br>-Bathroom #1: Full Bath w/ Shower, 1st Floor<br>-Bathroom #2: Full Bath w/ Shower, 2nd Floor<br>-Bathroom #3: Full Bath w/ Tub/Shower Combo, en suite, 2nd Floor<br>-Fully Equipped Kitchen<br>-Central A/C & Mini-Split A/C Systems<br>-Smart Lock/Self Check-In<br>-Smart TV<br>-WiFi<br>-Washer/Dryer<br>-NO Pets (fines remitted)<br>-Hot Tub (Open from Memorial Day to Labor Day - may be longer but not guaranteed)<br>-Outdoor Shower <br>-Private Yard<br>-Private Saltwater Pool (no heat) (Pool Open from Memorial Day to Labor Day - may be longer but not guaranteed)<br>-Gas Grill<br>- Fire Pit<br>-Game Room!<br>-Air Hockey<br>-Pack Man<br>-Water Views<br>-Multiple Decks<br>-Direct Access to Grand Cove<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0346480750

Bayside Dunes: 023-D Dennis Bayside: Just Renovated, Pool, Hot Tub, Walk to Beaches

Dennis, MA, US
4 Bedrooms 12 Guests
Dec 31 - Jan 3
$1,191 night

This property is professionally managed by Pretty Picky Properties Dennis Bayside: Updated, Pool, Hot Tub, Walk to Beaches Sleeps 12 5 Bedrooms, 4.5 Baths Rents Saturday to Saturday during Peak Season Linens Included, Beds Made You won’t have to worry about parking at the beach. You can walk there, and not in the road, either. Here you have private paths to two of the best beaches on Cape Cod Bay. You’ll have your feet in the sand at either Mayflower or Bayview Beach in five minutes or less. You’ll want to come back for sunset. It can be absolutely stunning over the Bay. And after sunset, take a short walk to Chapin’s - an excellent spot for dinner and cocktails! You’ll also enjoy a beautiful sunset back at the house, where you’ll quickly understand why the road is called Dunes View, as you look out over the sandy dunes that shape this part of the bay’s coast. After leaving the beach, rinse off the sand and salt in the outdoor shower, then unwind by the stunning heated pool. Alternatively, have the kids start a game of “Marco Polo" while you relax in the calming hot tub. The outdoor living areas are exceptional, and the pool is just the start. Beyond the gate lies a separate outdoor space with a large dining table, chairs, a hot tub, a gas fire pit, and a large gas grill. A new pool cabana features an additional bar area that opens to the pool deck, along with extra seating to watch the ball game while staying connected to the poolside activities. The upper decks offer a captivating elevated view of the well-kept, private yard and gardens, with the beach dunes visible beyond. The large upstairs deck features shaded seating under an awning. Inside, you’ll be captivated by the cheerful, bright, open floor plan. The modern kitchen features top-tier stainless steel appliances, extensive granite countertops, and a wet bar with a wine fridge, offering more than you could imagine. Next to the kitchen, a spacious dining table seats twelve, with three additional seats at the kitchen island, which includes a second sink for easier meal preparation. The kitchen and dining space seamlessly connect to the living room, furnished with lounge seating and a large wall-mounted TV. Sleeping arrangements include 12 beds, starting with two main-level bedrooms, each furnished with a comfortable queen-sized bed. These share a beautifully renovated, spacious full bathroom. Upstairs, there are two additional bedrooms, each a primary suite with a generous king-sized bed and a private full bath, one featuring a two-person shower. The house also offers a large bonus space above the pool cabana, featuring a great room with a large TV, a full bath, and ample lounge seating. Four XL single beds are located here, two of which are built-in trundle beds, increasing the total sleeping capacity to 12. The pool cabana provides another area with a TV and a half bath nearby for poolside use. This home has four full baths and one half bath. There’s central air conditioning, high-speed Wi-Fi, smart/cable TV, a Sonos® Sound System, and a ping-pong table for guest use. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $255.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

Serenity by the Sea: 162-C Chatham Waterfront w/heated Pool, Stunning Views of Oyster Pond

Chatham, MA, US
4 Bedrooms 8 Guests
Dec 31 - Jan 3
$1,146 night

This property is professionally managed by Pretty Picky Properties Chatham Waterfront with Pool, Stunning Views of Oyster Pond, Chatham Villa Sleeps Eight Four Bedrooms, Four Baths Rents Friday to Friday during Peak Season Linens Included Pool operational from Memorial Day to Columbus Day ​​​​​​​ The pool is great, the house is lovable, but what truly sets this property apart is its location directly on picturesque Oyster Pond. Sit back in your lounge chair overlooking the pool and marvel at the sails in the foreground, with the one-of-kind view of Chatham Village beyond. Bring your kayak and take a tour of the pond and river. Another nice thing you’ll notice when you’re hanging out at the pool: it’s quiet and very private, because you’re at the end of a neighborhood road with no outlet and next to no traffic. The large new deck provides another special outdoor living space with water views, especially thanks to its built-in fire pit where you’ll gather when the sun goes down for gazing at the stars. There’s also a good sized dining table here that seats eight for meals al fresco, and an awning to provide shade when needed. Inside, you’ll quickly discover that the floorplan was created with the water views in mind, especially noteworthy from the dining table which seats eight. The open kitchen is spacious, very social and nicely equipped (including a Nespresso Machine!). The living room provides plenty of comfy lounge seating, and there’s a bathroom here where you’ll find a small washer and dryer. There’s another full bath just off the pool deck which essentially serves as an outdoor shower. Sleeping quarters on the main level include one bedroom with a queen size bed and another with twin beds. Walk upstairs to discover a second, lounge area with a large TV. There are two more bedrooms on this level, including the spacious master suite with a King size bed, full bath en suite and amazing elevated views of the water. The home’s fourth bedroom provides a queen size bed. There’s another full bath off the upstairs hall that’s used by the occupants of the queen bedroom and has been recently upgraded. You’ll also find another laundry here with a full-size washer and dryer. The home has central air-conditioning, high-speed Wi-Fi and cable/smart TV. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for more Pretty Picky Properties - your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ® Town of Chatham Registration #778

Estate w/ Private pool, tennis court, playground!

Harwich, MA, US
9 Bedrooms 18 Guests
Aug 30 - Sep 1
$1,201 night

17757 - Bride of the Sea: Estate with Private pool, tennis court, and playground! Experience coastal luxury at its finest at Bride of the Sea, where your dream vacation awaits with luxury service provided throughout your stay which includes daily cleaning and towel exchange. Nestled in the heart of picturesque Harwich Port, Bride of the Sea is a one-of-a-kind estate offering 9 bedrooms, 7.5 baths, and sweeping views of Wychmere Harbor (please note the studio with 1 bedroom and 1 bath is only available May 1st - October 31st). Set on 2.1 lush acres, this meticulously renovated historic home combines timeless elegance with modern amenities, making it an ideal retreat for multigenerational families or groups of friends. The grounds include the main home, garage apartment, studio apartment (available May 1st - October 31st), and pool house for your use. <br>Step out onto the breezy wrap-around porch for a glimpse of the harbor or unwind by the private 900 sq. ft. in-ground pool, surrounded by a beautifully appointed pool house perfect for lunch or afternoon cocktails. The entertainment continues with a commercial-grade children’s playground, tennis court, and a stunning new outdoor kitchen—ideal for alfresco dining or evenings by the built-in gas fire pit. Inside, the home’s charm is elevated by original woodwork and built-ins. For rainy days or friendly competition, enjoy a game of billiards in the spacious game room. A separate, heated 3-car garage houses a charming 2-bedroom guest apartment, offering a private sanctuary for visitors.<br>Located just a short stroll from Merkle Beach and Wychmere Beach Club, this estate offers easy access to Harwich Port’s vibrant dining scene, including local favorites like Perks Coffee Shop, Brax Landing, and Cape Sea Grille.<br><br>Whether you’re lounging poolside, exploring the harbor, or indulging in local cuisine, Bride of the Sea offers the perfect blend of relaxation and adventure. Plus, with nearby fishing charters and all that Harwich Port has to offer, you’ll never run out of things to do. <br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 18 (16 November 1st - April 30th)<br>Bedrooms<br>-Total 9 (8 November 1st - April 30th)<br>Main House<br>-1st Floor Bedroom: 1 King Bed<br>-2nd Floor Bedroom: 1 King Bed<br>-2nd Floor Bedroom: 1 Queen Bed <br>-2nd Floor Bedroom: 1 King Bed w/ensuite<br>-2nd Floor Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom: 2 Twin Beds<br>Carriage House<br>-2nd Floor Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom: 1 Full Bed<br>Studio (Only available between May 1st and October 31st)<br>-1st Floor Bedroom: 1 Queen <br>Bathrooms<br>-Total 7 ½ (6 1/2 November 1st - April 30th)<br>Main House<br>-1st Floor: Tub only<br>-1st Floor: Tub/Shower Combo<br>-2nd Floor: Shower Only Ensuite<br>-2nd Floor: Tub/Shower Combo<br>-2nd Floor: Tub only<br>Carriage House<br>-2nd Floor: Tub/Shower Combo<br>Studio (Only available May 1st - October 31st)<br>-1st Floor: Tub only<br>Pool House<br>-1st Floor: ½ Bath<br>Other Amenities <br>-Central AC<br>-WiFi<br>-Smart TV<br>-Streaming Service<br>-Washer/Dryer Main House<br>-Washer/Dryer Carriage House<br>-Propane Gas Grill<br>-Gas fire pit<br>-Tennis<br>-Volleyball Net<br>-Playground<br>-Heated pool (Open Memorial Day to Labor Day)<br>-Indoor Fireplaces are not for guest use(fines remitted)<br>-Please note outdoor amenities are available seasonally<br>-Please note there is/are an exterior camera(s) on the property that records front of house/driveway/entry door<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-Parking for 8 cars maximum<br>-C0509501260<br>

Heated Pool, Outdoor Kitchen, Luxury Living!

Harwich, MA, US
5 Bedrooms 10 Guests
Sep 7 - 9
$664 night

17765 - Royal’s Hideaway: Heated Pool, Outdoor Kitchen, Luxury Living! Step into Royal’s Hideaway, where elegance meets escapism. This Harwich retreat is designed for discerning guests who crave luxury, calm, and unforgettable Cape Cod moments. Bathed in natural light, each room reveals meticulous design, with sumptuous finishes and high-end amenities throughout.<br><br>On the main level, revel in spacious, open living where a large Smart TV pairs with a whole-home Sonos sound system—stream your favorite playlists anywhere inside or out, all controlled from your phone. Culinary dreams come alive in the chef’s kitchen, outfitted with a gas Thermador oven and stovetop, a wine refrigerator, and a restaurant-grade ice maker. <br><br>Retire to one of five beautifully styled bedrooms—one nestled in the separate carriage house, an idyllic escape with its own half bath and loft. The primary suite elevates comfort with a spacious private balcony for morning coffee or evening cocktails, plus a spa-like ensuite bathroom for the ultimate retreat.<br><br>Outside, your own sanctuary waits. The heated saltwater pool, complete with a cascading waterfall, sets a serene tone, while the gas fire table beckons for cozy evenings, or cook in the full outdoor kitchen—ideal for clambakes, barbecues, or sunset dinners. The carriage house acts as a tranquil guest haven, while the main estate remains the beating heart of luxury.<br><br>Location is part of the charm: just 2 miles from Bank Street Beach, a quarter mile from Harwich Center and only 1.5 miles to Downtown Harwichport. Dining gems such as Ruggie’s Breakfast & Lunch and Seal Pub & Cafe are just a short walk down the road. Feel like going out for dinner? Just a short drive away are dining gems such as Twenty-Eight Atlantic and Cape Sea Grill. Whether your aim is luxurious relaxation or Cape beach adventures, Royal’s Hideaway offers a flawless base. <br><br>With its unmatched amenities, graceful design, and superb locale, this property invites you to make lasting memories. Reserve your stay at Royal’s Hideaway now and step into a world of Harwich luxury.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 10<br>Bedrooms<br>-Total 5<br>-2nd Floor Bedroom: Queen Bed<br>-2nd Floor Bedroom: King Bed<br>-2nd Floor Bedroom: Queen Bed<br>-2nd Floor Bedroom: King Bed<br>-1st Floor Carriage House Bedroom: Queen Bed<br>Bathrooms<br>-Total 3.5<br>-1st Floor: Full Bathroom w/ Shower<br>-2nd Floor: Full Bathroom w/ Shower/Tub Combo<br>-2nd Floor: Full Bathroom w/ Shower (master ensuite)<br>-Carriage House: ½ bathroom<br>Other Amenities <br>-Central AC with ventilation fan system<br>-WiFi<br>-Smart TVs<br>-Streaming Services<br>-Washer/Dryer <br>-Propane AND Natural Gas Grill<br>-Fire table with surrounding seating<br>-Outdoor Shower<br>-Full outdoor kitchen<br>-Outdoor Games, corn hole and outdoor ping pong<br>-Heated saltwater pool<br>-Indoor gas fireplace<br>-Please note outdoor amenities are available seasonally<br>-Please note the Piano is not for guest use<br>-Please note there are exterior cameras on the property that record the front of house/driveway/entry door. There are interior cameras, but are shut off. <br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-Parking for 5 cars maximum<br>-C0559661260 Please note there are exterior cameras on the property that record the front of house/driveway/entry door. There are interior cameras, but are shut off.

Breakwater Acres 164-B Luxurious Estate by the Bay in Brewster

Brewster, MA, US
8 Bedrooms 18 Guests
Aug 29 - Sep 1
$1,757 night

This property is professionally managed by Pretty Picky Properties Luxurious Estate by the Bay in Brewster: Sleeps 20 with Expansive New Pool, Walk to Beach, Walk to Town Rents Saturday to Saturday in Peak Summer Off-Season Weekends and Partial Weeks Available Choose this vacation headquarters and give your group of up to 20 the best of all options. A main house plus separate guest house on nearly an acre and a half of level yard for play space. A stunning new 20’ X 60’ heated saltwater pool with large stone patio. A three-minute walk to Brewster’s Breakwater Beach. And an eight-minute walk to the iconic Brewster Store and Main Street/Route 6A, where you’ll discover some excellent restaurant choices. The main house, just completed in 2020, offers elegance without pretense, centered on its spacious, thoughtfully outfitted chef’s kitchen. Here you’ll appreciate the large center island with high boy seating, beautiful granite and tile, as well as abundant counter space bathed in natural light. The kitchen opens to a TV lounge, which walks out to the expansive patio and pool. There is also a good-sized dining room here, as well as a handy half bath and laundry. The main house has sleeping for up to 12 in five bedrooms, two of which are king masters, one on the main level, the other upstairs. Each master has its own private full bath en suite. The separate guest house offers single level living and sleeps up to eight in three bedrooms with a full bath. You have a full eat-in kitchen here, as well as a TV lounge. Your outdoor summer living is optimized on the oversized patio which envelops the big pool. There’s also a hot tub, a large gas grill, a fire pit and an enclosed outdoor shower. Each house is centrally air conditioned, has cable TV, a SONOS Sound system and high speed Wi-Fi. Please enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for more Pretty Picky Properties - your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

Shore Daze: 096-C Luxury Living in Chatham with Pool and Hot Tub

Chatham, MA, US
3 Bedrooms 6 Guests
Sep 28 - Oct 1
$919 night

This property is professionally managed by Pretty Picky Properties Luxury Living in Chatham with Pool and Hot Tub Pool open for the season as of May 1st till Columbus weekend Sleeps 8 3 Bedrooms plus flex bonus room, 3.5 Bathrooms ​​​​Rents Friday to Friday during peak season Linens Included, Beds Made Small Dogs Considered Here’s your Chatham summer home --- for a week, a month or possibly all summer long! Built in 2020, everything here is fresh, new and top of the line. Outdoor warm weather living doesn’t get any better. Whether you’re lounging on the expansive deck or travertine patio watching the kids splash in the heated saltwater pool, or firing up the built-in gas grill with granite counters to enjoy a perfect dinner al fresco. Later on, you’ll want to gather around the handsome fire table for gazing at the stars. You’ll also find a handy outdoor shower plus a sizable pool cabana. Drive just four minutes to popular Oyster Pond Beach and 2 miles to Hardings Beach. Or leave the car at the house and take a short, easy walk up to Main Street – only six minutes to Mac’s Fish & Lobster. Inside this home you’ll be charmed by the open floor plan with all brand new high-end furnishings, appliances and appointments. The sparkling chef’s kitchen is right out of a magazine feature story, where practical functionality and beautiful design join forces to create a meal preparation experience you will long treasure. The adjacent dining area elevates the cheery, open impression still more, as does the large living room with appealing, comfortable lounge seating and upscale appointments. This home has central air conditioning, high speed WiFi, cable, as well as smart TV and a Sonos® sound system – all brand new. The first of two primary room suites is on the main level. It is spacious and luxurious with a new king size bed. There’s a roomy private full bath en-suite. The upper level serves up the other king master suite, full bath included. Upper level guest room with a king size bed. A flex bonus room has a private balcony with water views equipped with twin beds in addition to the king. There are 3.5 baths in all at the house. Please enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. This property offers a three-night minimum stay during select weeks in May – June & September – November. Guests are charged a cleaning fee for all stays less than seven nights. Stay seven nights or more and the cleaning fee is waived. Be sure to search this site for more Pretty Picky Properties - your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ® Town of Chatham Registration #675

Queen’s Perch: 051-C Spacious Custom Chatham Home w/Pool, Guest Cottage & Water Views

Chatham, MA, US
5 Bedrooms 12 Guests
Aug 29 - Sep 1
$1,310 night

This property is professionally managed by Pretty Picky Properties. Spacious Custom Chatham Home w/Pool, Guest Cottage & Water Views Sleeps 12 Heated salt-water pool, outdoor kitchen and spa! Linens included, beds made Rents Friday to Friday in peak season To view a slide show with captions, click on icon in upper right corner of the photo. Pool is open from Memorial Day through Columbus Day weekend This immaculate custom home features three primary en suite bedrooms and is close to everything to love about Chatham. The property is centrally located just 0.75 miles from the popular restaurants, shops and live entertainment of Chatham Village. The Cape Cod Rail Trail is a scant 0.3 miles up the road. The location is close to several fan-favorite beaches as well. Set on scenic Perch Pond, the outdoor living and dining space is superb. With a large deck, heated salt-water pool with built in spa, gas grill and outdoor kitchen all overlooking the pond for relaxing days and amazing sunsets. The deck table can seat 12 for relaxing meals while viewing the wildlife that calls Perch Pond home. The ever changing sounds and mix of birds makes for a relaxing environment. Featuring plenty of private yard area to enjoy outdoor lawn games there is even an official sized bocce court for extended outdoor fun. In total, the 3,300+ sq. ft. home, plus separate cottage, has at total of five bedrooms and 4.5 baths and includes all the modern amenities including central air conditioning. The main level of the house offers a generous, bright and cheerful open-plan living space with a fully loaded kitchen, seating and dining area, breakfast room, and one of four lounge areas in the house. The main level also features a primary bedroom suite, including a comfy king size bed and a private luxury bath. There’s also a cozy TV lounge area just off the kitchen as well as a half bath/laundry room. On the upper level, you’ll find a second primary suite with a king bed and en suite bathroom. This primary bedroom has a small adjacent room that can serve as extra sleeping space for young children or a quiet getaway for reading and relaxing. Also on the second level, there is a bedroom with a queen size bed and a bunk room with four twin size beds. Those two bedrooms share a full bath. The unfinished basement includes a small workout area with exercise flooring, yoga mats, hand weights, a TV for casting your workouts and a Peleton (please bring your own shoes and subscription). You can also play a rousing game of ping pong or darts in case the weather isn’t cooperating! Finally, there is a bonus living area over the garage that is accessed by a separate stairway. Here you’ll find a large TV with surround sound, ample lounge seating and a card/game table. Just out the back door of the main house is the freestanding, very well-appointed separate guest cottage with a queen bed, TV/sitting area, coffee bar, full bath with shower and a wraparound deck overlooking the pond. The deck at the "Perch Pond Yacht Club", as the cottage is named, is a perfect place to relax with morning coffee or a glass of wine while enjoying the sunsets. The house is close to Chatham Bars Inn and Wequassett for those attending events or simply eager for an extraordinary dining experience. The home is ideally suited for summer or off-season relaxation. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. This property offers a 3-night minimum stay during select weeks in May – June & September – November. Guests are charged a cleaning fee for all stays less than 7-nights. Stay 7-nights or more and the cleaning fee is waived. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ® Town of Chatham Registration #155

Beam Reach: 137-O Orleans Oasis on Pleasant Bay, Estate with 2 homes & heated pool

Orleans, MA, US
6 Bedrooms 14 Guests
Sep 1 - 4
$1,433 night

This property is professionally managed by Pretty Picky Properties. Orleans Oasis on Pleasant Bay, 2 Homes and Heated Pool; "Beam Reach" Sleep up to 14 Rents Friday to Friday in Peak Season Linens Included, Beds Made Pets Under 25 Pounds Considered Pool is open from Memorial Day to Columbus Day weekend Welcome to your private oasis on Pleasant Bay. At the end of the road you will find this private setting which features 2 homes located right on the water. Windward and Leeward are two wonderful homes that will provide you and your family of up to 14 with great Cape Cod memories. There is a beach area just outside the back door of the Windward home. And there is a heated pool between the two houses for those who prefer a pool to the Bay. Windward was completely remodeled recently. All new furnishings and a brand new kitchen. Sit in the living room and enjoy tremendous views of Pleasant Bay. There are a total of 3 bedrooms in Windward. The first features a queen size bed with an ensuite bath. The views are amazing from here! The second bedroom has a comfy king size bed along with an ensuite bath. The third bedroom is located through the walk-in closet and offers a twin-over-full bunk bed. There is a private entrance to this room off of the front porch. These two bedrooms are set up perfectly for a family with kids. There is also a half bath, brand new kitchen and laundry. And of course the home is outfitted with central AC and Wi-Fi. Leeward is on the other side of the pool and features 3 more bedrooms. On the main level you will find a cozy living room, full kitchen and a large screened in porch. There is also a dining room, full bath and two bedrooms on this level. The first bedroom features two twin beds. The other bedroom has a queen size bed and an ensuite bath. Upstairs you’ll find a suite perfect for a family with kids. There is a king size bed plus two twin beds up there in addition to a full bath. The Leeward home also features a wonderful media room in the lower level. A brand new 75” TV is ready for movie night! There is a cozy sectional sofa, a kitchenette, small refrigerator and a popcorn machine making this the best spot for movie night or in case the weather doesn’t cooperate. There is also a full bath, exercise equipment and laundry facilities down stairs. And while the homes are beautiful on the inside you will undoubtedly spend most of your time enjoying the outdoors. The pool (12’x24’), which has a fence around the outside for safety, is heated so it’s a great option even in June or September (pool is heated from Memorial Day – Columbus Day). There is a large table inside the pool area for dining al fresco! And the views from the pool area are awesome. There is an outdoor fire-table for enjoying the evenings under the stars listening to the water against the shoreline. And of course no Cape vacation home is complete without an outdoor shower! In addition, the owners provide kayaks and stand-up-paddle boards. This property offers a wonderful Cape escape. You will feel like you’ve gone back to a simpler time but thanks to all the modern amenities you’ll still enjoy today’s creature comforts. A SONOS system, central AC, heated pool, flat screen TV’s and Wi-Fi throughout will allow you to enjoy your vacation in comfort. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 245.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 17.45%. This property offers a 3-night minimum stay during select weeks in May – June & September – November. Guests are charged a cleaning fee for all stays less than 7-nights. Stay 7-nights or more and the cleaning fee is waived. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

Front n’ Center: 121-C Immaculate on Chatham’s Prestigious Stage Island, New Saltwater Pool

Chatham, MA, US
4 Bedrooms 10 Guests
Sep 8 - 11
$1,294 night

This property is professionally managed by Pretty Picky Properties. Immaculate on Chatham’s Prestigious Stage Island, New Saltwater Pool Sleeps 8 3 Bedrooms, 3.5 Baths Rents Friday to Friday in peak season Linens Included, Beds Made Pool & Hot Tub open from Memorial Day to Columbus Day Front n’ Center, located on Chatham’s Stage Island provides a luxury vacation experience on every level. You’ll no doubt spend the majority of your outdoor time in or around the new heated saltwater pool and the exquisite flagstone patio. You could also relax in the screened in porch or head up to the roof deck to take in distant views of the Atlantic Ocean. Inside, the home features spacious, exquisite gourmand’s kitchen with vaulted ceiling, exposed beams and skylights fostering a marvelous sense of light and space. Granite counters and new stainless-steel appliances, including a big six burner gas range, Keurig and drip coffee makers, and lobster pot. The center island adds workspace, and the peninsula has counter seating for three. Right off the kitchen you’ll find the handsome wood dining room table and chairs. Sleeping Arrangements: One bedroom on the main level with queen size bed, TV and full private bath ensuite. Second level has two bedrooms, one has a queen plus two twins and two trundle beds. Third bedroom, also on second level, is the primary suite, featuring a king size bed, TV and private full bath, as well as peeks of Chatham Harbor. Living Spaces: This home has several lounge areas, including the main level living room, which walks out to the patio and in-ground pool. There is also a sitting room on the second level with still more lounge seating including a convertible sleep sofa. There is also a large three-season room on the main level, which functions as a screened porch in the warm weather. Outdoor Spaces: The patio includes two umbrella shaded picnic tables, several pool-side padded lounge chairs and a spiral staircase which takes you to the upper open deck with yet more seating and limited, but beautiful elevated views of Chatham Harbor. Owners have thoughtfully provided kayaks for guest use. There is also a wood burning firepit, enclosed outdoor shower and gas grill. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Damage Protection fee totaling $245.00 In addition, there are state and local taxes applied to all reservations of 31 days or less that total 14.45%. Be sure to search this for more Pretty Picky Properties - your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

Vacation Rentals in West Harwich by Amenities & Features

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Vacation Rentals Near West Harwich

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