Family friendly vacation rentals in South Chatham, MA

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 $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 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

16606 - Chatham Charmer: Game Room Walk to Nantucket Sound! Nestled between Harwich Port and Chatham Center, this charming Cape Cod retreat offers the perfect blend of relaxation and recreation for your family getaway. The home boasts two spacious family rooms and a large backyard, providing ample space for everyone to unwind. The expansive back deck, complete with a convenient outdoor shower, is the ideal spot for morning coffee in the sun or a delicious evening barbecue on the gas grill.<br><br>A short, leisurely 10 minute stroll takes you to two picturesque beaches—Forest and Pleasant Street—where you can soak up the sun and enjoy the coastal breeze. For more beach adventures, Ridgevale and Hardings Beach are just a quick drive away, perfect for family outings. If you’re in the mood for a scenic ride, the Old Colony bike trail is only a few blocks from your door, offering a delightful way to explore the area. Inside, the home is equipped with modern comforts including central air conditioning, Wi-Fi, and three smart TVs, ensuring a comfortable and connected stay. You’ll enjoy a new dining room that seats ten and a lively game room in the basement—perfect for kids and active adults alike. This dog-friendly haven welcomes your furry friends for an additional fee, making it a true family-friendly destination. With beds made upon arrival, fresh linens, and thorough cleaning with hospital-grade disinfectant, you can relax from the moment you step inside. Whether you’re here to create new memories or continue a cherished tradition, this home is the perfect base for your Cape Cod adventures. Home Details: -Dogs Welcomed (w/fee of $40/night per dog) -Sleeps 10 Bedrooms: -Total 4 -1st Floor Bedroom: 1 Full Bed -1st Floor Bedroom: 1 Queen Bed -2nd floor Bedroom: 1 Queen Bed -2nd floor Bedroom: 1 Queen Bed and 1 Bunk Bed (2 Twins) Bathrooms: -Total 2 Full Baths, 2 Half Baths -1st Floor: Half Bathroom -1st Floor: Full Bathroom w/ Shower/Tub combo -2nd Floor Half Bathroom -2nd Floor: Full Bathroom w/ Shower/Tub combo Other Amenities -Gas Grill -Smart TV -WiFi -Central A/C -Private Yard -Outdoor shower -GAME ROOM! -Gas Fire Pit -Sheets and Bath Towels Provided with Beds Made Upon Arrival -Cleaned with Hospital Grade Disinfectant -C0424570550

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

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

17739 - Deja Blue: Heated Pool AC 1/2 Mile to Beach! Accommodations for twenty people, a heated pool, and a prime location? All this and more awaits in immaculate Harwich. All this and more awaits in immaculate Harwich… wait a minute, it’s Deja Blue all over again! Located in a calm neighborhood, this large home is perfect for families looking to escape to the peace and quiet of Cape Cod. <br><br>Upon arrival, you’ll walk towards the backyard and private heated pool, a highlight of your vacation before you even enter the home. Opening the door to this stunning complex, you’ll enter into a convent mudroom, keeping the beach sand outside and the indoors clean. Head to the right, and step into the modern kitchen, with ample counter space. Or, head left off of the mudroom and down into the dining area. Also located here are even two full sets of washer and dryers to keep everyone fresh all vacation long.<br><br>Passing back through the kitchen, you’ll find the large living room. With a sprawling sectional, the living room is a great place to relax, watch a movie, or play some board games on a summer night. Down the hall, the first of the home’s many bedrooms are located. This sleeps 20 home has plenty of space for the whole family, friends, and their family and friends, as well as two dogs! Sleeping arrangements include eight bedrooms, split between the first and second floor. On the first floor, the primary bedroom has a king size bed, while the second and third bedrooms each have a queen size bed. Head up the staircase, with a stunning unique banister, and to the left where you will find three bedrooms. One bedroom has two full size beds, a second bedroom has two twin size beds, and a third bedroom has a queen size bed. Down the hall to the right of the stairs, the remaining two bedrooms preside, one with three twin size beds and fun dog artwork on the walls, and the final bedroom with one twin size bed and one full size bed.<br><br>After a long night’s rest, be sure to relax under the sun on one of eight chaise lounges around the outdoor, heated pool. Or, step outside the pool’s gates to the spacious yard for some fun yard games and room for your pup to roam.<br><br>Other amenities include a roomy outdoor shower, a massive outdoor picnic-banquet table, pool toys and floats, and central A/C. Just down the street from Red River Beach, whether you want the privacy of your own heated pool, or the joy of the Cape Cod salt water, you have a variety of swimming options to choose from. Be sure to bring everyone along this vacation, you’ll be wanting to come back again and again, at Deja Blue.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 20<br>-2 Floors<br>Bedrooms<br>-Total 8 <br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 1 King Bed<br>-2nd Floor Bedroom: 2 Full Beds<br>-2nd Floor Bedroom: 2 Twin Beds<br>-2nd Floor Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom 1 Full Bed & 1 Twin Bed<br>-2nd Floor Bedroom: 3 Twin Beds<br>Bathrooms<br>-Total 2.5 <br>-1st Floor: Half Bathroom<br>-1st Floor: Shower<br>-2nd Floor: Shower/Tub combo<br>Other Amenities<br>-Fully Equipped Kitchen<br>-Central A/C<br>-Smart Lock/Self Check-In<br>-WiFi<br>-Cable TV<br>-2 Washing Machines + 2 Dryers (full size)<br>-Private Heated In-ground Pool (Pool Open from Memorial Day to Labor Day - may be longer but not guaranteed)<br>-Patio w/ Outdoor Seating & Lounging<br>-Propane Grill<br>-Outdoor Shower<br>-Large Private Yard<br>-Lawn Games<br>-Located South of Route 28<br>-Half Mile to Red River Beach<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0371191260

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 $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 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! ®

16700 - The Wind Drifter: Waterfront Escape, Game Room, Dog Friendly! The Wind Drifter awaits your next Cape Cod escape. This spacious, waterfront home is convenient located in Chatham, MA, offering the perfect setting for a relaxing family getaway or a fun trip with friends, accommodating up to 12 guests.<br><br>Start your mornings with coffee on the back deck, taking in sweeping water views, with only the calls of shorebirds in the background. Inside, a bright, open kitchen flows seamlessly into the dining and living areas—perfect for gathering, sharing meals, and enjoying time together. Open the windows to enjoy fresh breezes off the water. The home features 6 bedrooms and 4 bathrooms with flexible sleeping arrangements designed for groups of all sizes. On the first floor, you’ll find a king bedroom with easy access to a nearby walk-in shower. Upstairs offers four additional bedrooms—including 3 queens, a kids room (with 2 twin trundle beds), while a private king suite above the garage provides extra space and privacy. <br><br>The basement game room with a pool table is perfect for friendly competition or to catch up your favorite TV show on the 75" TV, while the deck invites cookouts on the grill or relaxed evenings dining al fresco under the Cape Cod sky. Unwind with s’mores by the wood fire pit or sip your favorite cocktail as the fire crackles and the sun sets. Lounge on any of the plush couches on the first floor and taken in the breathtaking water views, rain or shine.<br><br>Located just a short drive (about 6 minutes) from Harding’s Beach and Ridgevale Beach—and with Lighthouse Beach also nearby—you’ll have easy access to some of Chatham’s most beloved spots. You’re also minutes away from local favorites like Mac’s Chatham Fish & Lobster, Del Mar Bar & Bistro, Mom & Pops Burgers, Hey Joe’s, and Jam Coffee Shop. Spend your days exploring charming downtown Chatham, browsing boutiques, visiting local museums, spotting seals at Chatham Fish Pier, or biking along the Cape Cod Rail Trail. For nature lovers, the Monomoy National Wildlife Refuge is a must.<br><br>Whether you’re here to reconnect, explore, or simply relax by the water, The Wind Drifter captures the essence of a perfect Cape Cod vacation. Book your stay and experience Chatham at its best.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog) <br>-Sleeps 12<br>Bedrooms<br>-Total 6<br>-1st Floor Bedroom: 1 King Bed (ensuite)<br>-2nd Floor Bedroom: 1 Queen Bed <br>-2nd Floor Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom: 2 Twin Trundle Beds<br>2nd Floor Bedroom: 1 King Bed (ensuite)<br>Bathrooms<br>-Total 4<br>-1st Floor: Full Bathroom, Shower (ensuite to King Bed, 1st Floor)<br>-1st Floor: Full Bathroom, Shower<br>-2nd Floor: Full Bathroom, Shower (ensuite to King Bed, 2nd Floor)<br>-2nd Floor: Full Bathroom, Shower/Tub Combo<br>Other Amenities <br>-Mini Split in dining room<br>-Floor/Window Unit ACs in Bedrooms<br>-Game Room<br>-Pool Table<br>-WiFi<br>-Smart TV <br>-Washer/Dryer <br>-Propane Grill<br>-Wood Fire Pit<br>-Please note outdoor amenities are available seasonally<br>-Please note there is a ring doorbell camera at the front door that faces the driveway<br>-Indoor Fireplaces are not for guest use (fines remitted)<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-Parking for 5 cars maximum<br>-C0579370550 Please note there is a ring doorbell camera at the front door that faces the driveway

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 $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 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! ®

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

This property is professionally managed by Pretty Picky Properties New Luxury Home in Chatham with Pool & Hot Tub, Walk to Town Sleeps 8 4 Bedrooms, 3 Bathrooms, 2 Half Bathrooms Rents Friday to Friday during peak season Linens Included, Beds Made Pool is open from Memorial Day through Columbus Day weekend It’s difficult to find a property with all the attributes of “Stepping Stones Sanctuary” completed in 2022, 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 flagstone 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 custom outdoor fireplace for gazing at the stars. There’s also a hot tub for unwinding at the end of an active day. Here, too, you’ll find the obligatory Cape Cod enclosed outdoor shower. 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 vaulted ceiling living room with appealing, comfortable lounge seating and upscale appointments. This home has central air conditioning, high speed Wi-Fi, cable, as well as smart TV’s– all brand new. There are also two convenient half baths on the main level. The first of two master bedroom 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 master suite, this one with a king size bed and full bath included. Two more upper level bedrooms are located up a second staircase, one with a 2 queen size beds, and the other with 2 queen size beds. There is a shared full bath in this area. There are three full baths along with two half baths in all. If you do choose to venture from the property you are about a half mile from the Chatham Anglers baseball field and under a mile to downtown Chatham with plentiful options for entertainment, shopping and dining. You are also under a mile to Oyster Pond where Children’s Beach awaits. “Stepping Stones Sanctuary” offers a refined living experience, all within a mile of one of the most idyllic villages on Cape Cod and a short walk to Chatham’s bike trails and the Chatham Bakery! 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 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 other Pretty Picky Properties - your best selection of prime vacation rental properties on Cape Cod. It’s your vacation. Get Picky! ® Town of Chatham Registration #1208

This property is professionally managed by Pretty Picky Properties Stunning Newly Built Custom Compound in Chatham with a Resort-Style Ambiance NEW Listing for 2026! Rents Friday to Friday during peak season Linens Included, Beds Made Sleeps 12 Pool & Hot Tub open from Memorial Day to Columbus Day Welcome to Three Buoys, a stunning multi-structure home located in picturesque North Chatham, MA. This spacious retreat is perfect for families or groups, comfortably accommodating up to 12 guests across its five beautifully appointed bedrooms and 7.5 bathrooms. With a serene pool view, this property offers a perfect blend of luxury and relaxation. Step inside to discover a chef-inspired kitchen that is fully equipped with modern appliances, including a gas stove, refrigerator, and dishwasher, making meal preparation a delight. The dining area is perfect for gathering around delicious meals, while the living room invites you to unwind with its cozy ambiance and gas fireplace. The outdoor space is a true highlight, featuring a heated private pool, hot tub, and a fire pit, ideal for evening gatherings under the stars. Enjoy the fresh air on the patio, or challenge your friends to a game of pool in the game room. Each bedroom is designed for comfort, with multiple en suite options, including four king beds and three twin singles, ensuring everyone has their own space to relax. Additional amenities include air conditioning, free WiFi, and 2 sets of washers/dryers for your convenience. Located near beautiful beaches and bike trails, Three Buoys is the perfect base for exploring the charming attractions of Chatham. Whether you’re looking to relax by the pool, enjoy a family barbecue, or explore the local area, this property has it all. Book your stay today and create unforgettable memories! 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 your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ® Town of Chatham Registration #1212

16683 - Cherry Blossom: Plunge Pool, Game Barn, AC, 5 Min to Beach! Experience the charm of Chatham in this exquisite vacation home, featuring a total of 5 bedrooms divided between the main house and a quaint guest cottage. Brand new for the 2026 season, bask in the cool refreshing luxury of your own private in-ground heated plunge pool (available Memorial Day - Labor Day). <br><br>Nestled conveniently on Main Street (but without the noise), this newly renovated property welcomes you and the entire family with open arms. Create endless memories in the spacious screened-in game barn, perfect for post-dinner relaxation or a friendly game of ping pong. The private stone patio, adorned with a century-old cherry blossom tree, invites you to savor sunset dining on warm summer nights. With seating for up to 12 and a Weber gas grill, culinary delights unfold in the open air. <br><br>As you step through the front door, a sense of home envelops you. The main house, bathed in natural light, boasts an eye catching living space. Families will find ample space, whether gathering around the dining table or enjoying the living room’s entertainment options.<br><br>Upstairs, the master king bedroom and en suite full bathroom exudes luxury, accompanied by two additional bedrooms. Another full bathroom with a combined shower and bathtub complements the living quarters, offering abundant closet and storage space.<br><br>A charming guest cottage awaits behind the main house for your exclusive use, a fully independent retreat with two bedrooms - one queen, one with two twins - a full bathroom, stocked kitchen, and a cozy living area with a flatscreen TV. An outdoor shower adds to the cottage’s allure. This is a perfect space to invite friends and family to join while still having your own spaces!<br><br>The beautifully landscaped lot, featuring mature gardens, fruit trees, rock walls, and a shell driveway, creates a private oasis. A short stroll leads to Mac’s Seafood Market and other convenient shops, while the beaches of Harding, Ridgevale, and Cockle Cove are just a 5-minute drive away. Cycling enthusiasts will appreciate the quick ten-minute ride to Harding Beach and Chatham village center, with the Monomoy Wildlife Refuge and neighboring villages like Orleans, Brewster, and Harwich waiting to be explored. Welcome to your perfect Chatham getaway!<br><br>Home Details:<br>-No Dogs (Fines Remitted)<br>-Sleeps 10<br>-3 Dwellings<br>Bedrooms<br>-Total 5<br>Main house<br>-2nd Floor Bedroom: 1 King Bed w/ en suite Bathroom<br>-2nd Floor Bedroom: 1 Full Bed<br>-2nd Floor Bedroom: 2 Twin Beds<br>Cottage<br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 2 Twin Beds<br>Bathrooms<br>-Total 3.5 <br>Main House<br>-1st Floor: Half Bathroom<br>-2nd Floor: Full Bathroom w/ Shower (en suite King Bedroom)<br>-2nd Floor: Full Bathroom w/ Shower/Tub Combo<br>Cottage <br>-1st Floor: Full Bathroom w/ Shower/Tub Combo<br>Other Amenities <br>-Heated Pool (Memorial Day - Labor Day)<br>-3rd Dwelling: Finished Barn Game Room<br>-Split System AC <br>-WiFi<br>-Smart TV<br>-Washer/Dryer <br>-Gas Grill <br>-Outdoor Shower<br>-Indoor Fireplaces are not for guest use (fines remitted)<br>-Please note outdoor amenities are available seasonally<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-Parking for 4 cars maximum<br>C0305630550

This property is professionally managed by Pretty Picky Properties Modern Luxury in North Chatham, Heated Pool and Spa, Views of Pleasant Bay NEW Listing for 2025! Sleeps 8 in 3 bedrooms/3.5 baths Rents Friday to Friday in July and August Linens included, beds made Modern elegance and unparalleled luxury encompass Strong Island Manse. Lavishly appointed details from floor to ceiling complement the water views. Wide plank flooring, custom high-end cabinetry & built-ins, Thermador appliances, Quartz countertops, exquisite trim detail & coffered ceilings are a few of the details carefully selected to ensure a perfect blend of comfort and sophistication. The home provides an expansive open concept floor plan with generously apportioned living and bedroom spaces. Each of the residence’s three bedrooms are complete with their own spacious en suite bathroom and walk in closets. There is one bedroom on the main level that features a cozy king-sized bed. Upstairs you’ll find an additional primary suite also with a king-sized bed. The last bedroom has two queen beds in two different rooms providing privacy for both sleeping areas. There are two spacious living areas upstairs and down. The main level is completely open from the kitchen to the dining room to the living area. Upstairs features a billiard table, seating area with TV and a balcony providing water views of Pleasant Bay. The two bedrooms upstairs also have water views. Outside you’ll find a natural gas fire pit, and heated salt water gunite pool & spa with pebble finish to complement the home’s contemporary allure. There is a new outdoor built-in grill station and kitchen being installed for 2025 season as well. You can access the beach at the end of the street at the town landing or head to one of the private association beaches nearby as well. Only a 10 minute car ride brings you to idyllic Chatham center for ample shopping and dining options form which to choose. Experience luxury living within one of North Chatham’s most coveted neighborhoods. 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 and 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 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! ® Chatham #STR-1097

This property is professionally managed by Pretty Picky Properties Sleeps 16 Eight Bedrooms, Nine Baths Rents Friday to Friday during Peak Season Linens Included, beds made Pool is open from Memorial Day through Columbus Day weekend This totally renovated former Bed & Breakfast, known as the Chatham Gables Inn, brings a new level of luxury and comfort to a Chatham vacation for your group of up to 16. Not that you will ever feel the need to leave the property, but should you choose to venture out, it’s good to know you’re close to everything you love about Chatham. Bring or rent bikes! That’s all you’ll need with so much, so close. Bike five minutes to Lighthouse Beach, Chatham’s biggest and best. Or ride two minutes to Oyster Pond Beach (aka Children’s Beach), a smaller, more sheltered beach. Or walk down to the Chatham Pier Fish Market, where you can take home the catch of the day, fresh off the boat. And it’s only a few-minutes’ walk to Main Street, Chatham Village, for shops, restaurants, galleries, concerts, Cape League baseball, playground, tennis courts, ice cream parlors and much more. The 4,200+ square foot house presents the perfect intersection of classic New England charm and leading-edge creature comforts and convenience. Exposed beam ceilings, heated wide plank wood floors and tasteful choices of furnishings, fabrics, paint and wallpaper all combine to create a one-of-a-kind living experience. The home’s centerpiece is the gleaming white farmhouse kitchen with its expansive center island with second sink. All appliances are new and commercial grade. The kitchen flows into the charming conservatory, which in turn, opens to the patio beyond. Your outdoor living will, of course, center on the beautiful, heated pool and adjacent hot tub. There is also a gas fueled fire pit, so your outdoor pleasure extends beyond sunset. The gas grill lives out here, as well, and you’re likely to prepare and serve most meals using the outdoor kitchen-area and patio dining table and chairs. This home offers multiple inviting lounge areas, each as comfortable and appealing as the next. Sleeping accommodations include eight bedrooms, each with its own name such as “Surfside,” “Nantucket” or “Great Point.’ Each has bedding for two. There are five kings, one queen and two bedrooms each with two twins. Each bedroom has its own private full bath en suite, and each has a smart TV. The lower level includes an oversized laundry with two washers and two dryers plus an additional refrigerator. And to complete its resort-like amenities, there is a game room down here as well. There is cable/smart TV and high-speed Wi-Fi, of course. The home is cooled via an ultra quiet system, which allows customized climate control for each bedroom. It also features Lutron Lighting® allowing guests to automatically or manually adjust the level and even the color of the LED light to create the ideal environment for any living space. 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 your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ® Town of Chatham Registration #152

This home is professionally managed by Pretty Picky Properties Gorgeous Chatham Estate with heated pool, walk to Town or Beach Sleeps 15 7 bedrooms, 5.5 baths Rents Friday to Friday during peak season Linens Included, beds made Pool is open from Memorial Day through Columbus Day weekend If you appreciate the timeless charm of a meticulously preserved, spacious home circa 1848, but insist on all the modern comforts and conveniences, your group of up to 15 will be thrilled to spend your Chatham vacation at this property. Here, wood floors with various width planks, Federalist period glass doorknobs and randomly exposed brick from the original home blend appealingly with today’s tile, granite and stainless steel. It’s hard to find a better location anywhere in Chatham. It’s only a 0.3 mile, five minute walk to Oyster Pond Beach (Children’s Beach) for swimming with the kids. Or go the other way and your walk to the shops, restaurants and all the fun of Main Street, Chatham is only 0.4 mile or eight minutes. Even closer to the house: quaint little Chase Park with its Godfrey Windmill and the challenging Chatham Labyrinth. And every time you head out, you’re strolling safely on sidewalks through one of Chatham’s most beautiful, upscale neighborhoods. This property offers the joys of warm weather outdoor living in a variety of spaces. There’s a large covered porch on one side of the house with an adjacent patio with a dining table and chairs. On the opposite side of the house, there’s a small brick patio where you’ll find the large gas grill and outdoor shower. No doubt, the majority of your outdoor time will be spent on the new patio and in the heated pool at the rear of the property. Here you’ll also enjoy soaking in the hot tub and later, star gazing as you gather your group around the gas fire pit. All of these outdoor spaces are hidden from a curb view for your private enjoyment. What about the kids? When they’re not splashing in the pool, they’ll love the game room over the garage with its ping pong, foosball, arcade game and TV lounge all their own. Inside this extraordinary home you’ll be delighted with all 4,500 square feet of comfy upscale living space. Start with the large chef’s kitchen, fully equipped with topline appliances and everything else you’ll need to operate in style. There’s a large kitchen dining table with seating for eight, with the even larger primary dining table in the adjacent dining room. The main level also has multiple lounges, several smart/cable TVs, and a half bath off the kitchen. One of three primary suites is located on this level as well. It offers a king size bed and private full bath ensuite. There are two stairways up to the second level, which makes sense with so much second level to access. There are a total of six bedrooms upstairs. First, there’s the primary suite, unusually spacious with a king size bed and full private bath and views of the pool. The home’s third king primary suite with private full bath is located on the second level as well. Then you will find a king bedroom that shares a full bath with a bedroom that has a pair of comfy twins. Then there are two bedrooms with bunk beds, each with a full size double on the bottom, one with a pull out trundle under the bottom bed. The washer and dryer are upstairs as well. The home has central air conditioning and high speed Wi-Fi. 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 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! ® Town of Chatham Registration #153

This property is professionally managed by Pretty Picky Properties Chatham Landmark Estate, Awesome Barn/Guest House, Pool Sleeps 18 8 Bedrooms, 7.5 Bathrooms Rents Friday to Friday during peak season Linens included, beds made Pets Considered Pool is open from Memorial Day through Columbus Day weekend. As you roll up the extended driveway and catch your first glimpse of the homes, you realize the impressive individuality of this property. From the Federalist style side gambrel roof on the expanded Colonial main house to the thoroughly exposed wood posts, beams and rafters inside, this place retains the unique charm demanded by its original sea captain owner 220 years ago. First, soak in the location and setting. Here you have 1.61 acres of artfully landscaped privacy, abutting the upscale Eastward Ho! private golf course, with beautiful Pleasant Bay beyond. The carefully kept, expansive lawns make a wonderful and safe play space for children. Note the line of grape arbors leading to an unexpected wishing well. Your private, heated pool is a large one, complete with its own freestanding and well equipped cabana. When you need some beach time, it’s only a two-minute drive over to Jackknife Cove Beach on Pleasant Bay. Or go in the opposite direction for a minute more and discover Strong Island Landing Beach. Inside the two story main manor house, centuries’ old charm mingles perfectly with thoughtful renovation for the best of beauty, function and comfort. The completely updated and outfitted kitchen adjoins a handy breakfast nook and flows into one of the most impressive dining rooms you’ll ever experience. There are three separate lounge and gathering places on the main level, a living room, sitting room and family room. Two of the main house’s six bedrooms and 2.5 of its baths are located here as well. The upper level provides another four bedrooms, including two primary suite bedrooms with ensuite baths and two other bedrooms, one with two queens and one with king size bed. There is also another full bath upstairs. Enter the nearby Guest House/Barn, and it’s hard not to gape at the expanse and sheer visual impact of the great room, so aptly named. It’s positively gigantic in every way, accentuated by the soaring ceiling with its dramatic exposed beams and rafters. The rest of the Guest House includes a second fully equipped kitchen, two more bedrooms and two more full baths. ** Please note that the Guest House (Barn) is fully winterized (closed) from Mid-October through April for off-season stays each year. As a result the property only has 6 bedrooms and 5.5 bathrooms sleeping a maximum of 14 guests. ** The 4,350 square feet of the Main House and Guest House combined are centrally air conditioned or serviced by high efficiency split units. There is also high speed Wi-Fi, as well as several smart flat screen TVs with cable. NOTE: the main part of the barn is not air conditioned, just the bedrooms and the kitchen/living room area. 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 and 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 #584

This property is professionally managed by Pretty Picky Properties Luxurious Chatham Home with Expansive Water Views Sleeps 10 in 4 bedrooms, 4.5 baths Rents Friday to Friday during peak season Linens included, beds made Location Water views from almost every room! Walk to two beaches and a shared dock! Located in one of Chatham’s most picturesque neighborhoods, this newly renovated and expanded residence has undergone an amazing transformation that now highlights stunning water views of saltwater Crow’s Pond. Indoor Space Upon entry, you are greeted by an impressive foyer that welcomes you to both the common and private areas of this nearly 4,000 square foot home. Built in 1985 and remodeled in 2023, the open floor plan of this 4-bedroom home is enhanced by gorgeous white oak flooring and professional interior design. The home features a state-of-the-art kitchen with top-of-the-line custom cabinetry, Thermador® appliances, weathered Quartzite® countertops, and custom tile work. A pillar flanked sunroom with skylights and bank of windows perfectly frames westerly views of the water. The living room is adjacent and features more cozy seating with a TV over the fireplace. There’s also a spacious office on the first floor. The main level also presents a laundry room with two washers and two dryers, a powder room, and a California Closet® pantry. The lower level provides a bright family room with custom built-ins, wet bar and billiard table. Outdoor Space Professionally landscaped, the home features an artistic blend of brick walkways, natural stone steps, and native plantings. The home has an enclosed outdoor shower and has easy access to a shared deep-water dock across the street, as well as to two private beaches on Pleasant Bay (8-minute walk) and on Crow’s Pond (across the street). Sleeping Accommodations On the main level you’ll find one of two primary suites with a four poster King bed, offering captivating water views and a spa-like bathroom with high-end fixtures. On the second level there is an additional King bed primary suite showcasing glass sliders leading to a private balcony with wonderful water views. You’ll be delighted by the luxurious, private bathroom with soaking tub and double vanity. The primary suite also has two walk-in closets. Additionally on the second level, another loft area greets you at the landing with views of Crow’s Pond. There is a second bedroom up here with a King bed and an exceptionally appointed full bathroom. There is also a bedroom on the lower level with two twin-over-full bunk beds. There is a full bathroom on this level 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 $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 and 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 your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ® Town of Chatham Registration #956

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>

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! ®

This property is professionally managed by Pretty Picky Properties Updated Chatham Family Compound, Heated Pool with Hot Tub, Walk to Town/Beach 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 If you relish the charm of Chatham but love modern amenities, here’s the resort style vacation destination for your group. The acre-plus property provides two separate structures with sleeping for up to 10. The in-ground heated pool is the focus of summer outdoor living here, further embellished by the hot tub. The property’s location is ideal. You can walk or bike to the restaurants, shops and entertainment unique to Chatham Village. Or slip into your swimsuit, grab a towel and head to nearby Oyster Pond Beach or famous Lighthouse Beach, your choice. Each less than a 15-minute walk. The larger main house features a big covered outdoor patio with a dining table, plenty of seating and a gas grill. The patio overlooks the pool house and pool less than 100 feet away. The pool house adjoins the surprisingly large pool, surrounded by a roomy stone deck with a dining table, plenty of lounge and other seating, an outdoor shower, gas grill and beverage center, fire table and, of course, the tempting spa. Inside the main house, you’ll be delighted by the fully outfitted, renovated kitchen with granite counters and a center island with built-in gas range top. The kitchen walks out to the patio for convenient serving when you dine outside. You’ll also find a handy half bath just off the kitchen. There’s a good sized dining room with a patio view. The large, comfortable living room adjoins the dining room and offers a flat screen TV. The main level also has a small den/office with a another TV seating area for the kids to watch shows/movies. The home has high speed Wi-Fi, a SONOS system, and is centrally air conditioned. The primary bedroom suite is also on the main level and includes a big king size bed and a remodeled full bath en suite. There is also a flat screen TV. On the upper level of the main house, there are two bedrooms, one with a king size bed. The other bedroom has four twins. These two bedrooms share a roomy full bath. The pool house offers rustic, lodge-like charm with exposed beams and vaulted ceiling in the full kitchen and adjoining family room/TV lounge. The kitchen is fully equipped and includes a round dining table and chairs. The pool house has a main level bunk room with four twins. There is also a ping pong table on the main level and a full bath. The upstairs sleeping area has a small lounge area with another TV and a step-up section with a comfortable king size bed. That upper level walks out to a second level deck overlooking a natural vista of undeveloped woodlands. 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 #286

This property is professionally managed by Pretty Picky Properties Alluring Chatham in-town home with pool, walk to it all Sleeps 10 Rents Friday to Friday during peak season Linens included, beds made Pool & Hot Tub open from Memorial Day to Columbus Day Here you’re close to everything that counts in Chatham. Walk 0.4 mile (8 minutes) to popular Oyster Pond Beach. Walk five minutes to the unique shops, restaurants and galleries of Main Street. You can order amazing take-out sushi from Blue Fins and be home with it before the edamame cools off! Consider your outdoor living options at this property. When you’re not splashing with the kids in the large, heated in-ground pool, you’ll be lounging in the shade of several large poolside umbrellas. Or serving appetizers and drinks on the superb screened porch, cooled by a perfectly placed ceiling fan. Maybe you’ll fire up the gas grill, after rinsing off the beach sand and salt in the outdoor shower. Or jump in the hot tub and enjoy the starry evening. It’s amazing how much privacy you have in these outdoor spaces, given your location in the heart of Chatham. Inside, this home provides 2,800 square feet of the most upscale, yet unpretentious accommodations you could ever hope for in a summer vacation home. The well-outfitted chef’s kitchen is big and bright with custom cabinets, stainless steel and granite throughout. There’s highboy seating at the large center island, encouraging a pleasantly social meal prep experience. The kitchen flows into the elegant dining room, embraced by two walls almost entirely comprised of oversized windows, adding to the cheery ambience. The dining area, in turn, flows into the living room and TV lounge with its comfy seating and large flat screen smart TV. There’s one bedroom on the main level. It’s roomy with a generous king size bed. You’ll find a full bath with a combination tub/shower directly across the hall. The rest of the main level is allocated to a mud room back entry, laundry and a second stairway that leads up to a huge primary bedroom over the garage. The primary has a king size bed plus a twin bed with trundle underneath. There’s a luxurious full bath en suite, offering a twin sink vanity and step-in shower. Another second level bedroom has a queen size bed plus a twin with trundle. Down the hall you’ll find a bedroom with two twins, each with a trundle. There is also a loft at the top of the main stairway which features a desk, for those zoom calls, and a queen size sleep sofa. For those days when the weather doesn’t cooperate there is a wonderful game room for kids of all ages in the lower level. Down there you’ll find a foosball table, air hockey, a pop-a-shot hoops game plus comfy seating and a large flat screen TV! There’s even a table for playing cards or board games. Overall the home has four bedrooms and three full baths. It sleeps up to 10. It has central air conditioning, high speed Wi-Fi and cable/smart TVs. 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 your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ® Town of Chatham Registration #151

This property is professionally managed by Pretty Picky Properties. Renovated Chatham Village Farmhouse, Pool, Walk to Beach and Town Sleeps 10 Rents Friday to Friday during peak season Pets Considered Linens Included, beds made Pool open from Memorial Day to Columbus Day Charm, privacy, style, comfort and convenience -- it’s all yours in this one-of-a-kind Chatham in-town farmhouse. The location is ideal. Sandy Lighthouse Beach is a short walk across Main Street. Walk the other way on Main Street for 10 minutes to find the shops, restaurants, movie theatre, galleries and feel-good vibe of Chatham Village town center. Not to mention the Chatham Anglers of the Cape Cod Baseball League. Back at the farmhouse, the secluded, half acre includes a beautiful grassy yard, a large in-ground heated pool, a comfy seating area with umbrella shaded tables, a built-in grill and gas firepit as well. The pool area includes a freestanding pool house where you’ll find a bedroom, private bath and a sitting area. And the garage has been converted into a game room with a flat screen smart TV, couch, extra refrigerator, and ping pong table. Walk into the expansive kitchen and dining area, and you realize that the special allure of this home is its flawless blend of 19th century charm and modern furnishings and features. Contrast the exposed beam ceiling here with the totally cutting edge kitchen with its island seating and Miele appliances. But keep in mind that as an older home, the ceilings are lower in some places than those of a more recently built home. The main level also includes a comfortable living room with a smart TV, den, half bath and laundry. And there is an enclosed outdoor shower. No Cape vacation is complete without an outdoor shower! Upstairs you’ll find a total of three bedrooms, the king primary bedroom with full bath en suite. There is also a queen bedroom upstairs with peaks of the water at Lighthouse Beach. You’ll also find the “bunk room” that houses a bunk bed plus two twin beds. There is another full bath located on the second level. This home has split unit air conditioning and a couple of window units, which effectively cools its 2,400 square feet of living space and allows individual temperatures to be set. There’s also a SONOS sound system and high-speed Wi-Fi, of course. It’s unusual to find a spacious family compound such as this in the heart of Chatham Village, so close to everything that makes Chatham the vacation destination of choice for so many families. 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 three-night minimum stay during select weeks in May – June and 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 your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

Private, Spacious, Pristine with Heated Pool 7-Night minimum for June, July & August Linens Included, Beds Made Rents Friday to Friday in Peak Summer Pool open from Memorial Day to Columbus Day Welcome to Orleans Oasis, a stunning vacation home nestled in the picturesque neighborhood of Pleasant Bay in South Orleans. This spacious house offers a perfect blend of luxury and comfort, making it an ideal retreat for families or groups seeking a memorable getaway. With a generous 3,450 square feet of living space, this property comfortably accommodates up to 10 guests across its four beautifully appointed bedrooms and three bathrooms. As you step inside, you’ll be greeted by an inviting ambiance that features updated interiors and modern amenities. The main level boasts a master bedroom with a king-sized bed, while the second floor offers three additional bedrooms, including another king suite, a room with a double bed and twin singles, and a cozy queen bedroom. Each room is designed for relaxation and comfort, ensuring a restful night’s sleep. The heart of the home is the expansive living area, perfect for gathering with loved ones. Enjoy the convenience of a fully equipped kitchen, complete with a kitchen island, dining table, and modern appliances, including a dishwasher and microwave. The living room is ideal for unwinding, featuring comfortable seating and entertainment options such as a television and games. The lower level unfinished space is home to the ping pong table. Step outside to discover your private oasis. The outdoor space features a heated pool, perfect for a refreshing dip, and a wood fire pit for cozy evenings under the stars. The patio provide ample space for outdoor dining and relaxation, making it easy to soak up the sun or enjoy al fresco meals. For those seeking adventure, the property is conveniently located near a variety of attractions, including beautiful beaches, golf courses, and opportunities for fishing, hiking, and whale watching. Whether you’re looking to explore the local area or simply relax by the pool, Orleans Oasis is the perfect home base for your Cape Cod vacation. Don’t miss out on the chance to experience this exceptional property. Book your stay at Orleans Oasis today and create unforgettable memories with family and friends! Please enter your travel dates in 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 your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

16656 - Decked Out Oyster: Steps to Oyster Pond Private Dock! Calling all water enthusiasts! This stunning home has water views and a floating dock just down the street! Enjoy a swim off of your own personal dock or take one of the home’s paddle boards or inflatable boats for a spin! The perfect place to entertain, this home comes fully equipped for ten people, boasting two balconies, a spacious backyard deck, outdoor grill, fire pit and a large well-manicured lawn. But, the fun does not stop there! The home also has croquet and bocce ball sets, an outdoor ping pong table, and air hockey table in the basement.<br><br>The home’s coastal-inspired interior features sun-drenched living areas and plenty of space. On the first floor there is a formal living room with large sofas and a fireplace; a contemporary kitchen with countertop seating as well as a formal dining area; a master bedroom with a king bed and a full, en suite bath; a second bedroom with a queen bed; plus, a third bedroom with a queen bed and office space perfect for working remotely.<br><br>On the second floor, there is a family room with a smart TV, board games and a deck for sunset and water viewing; a bedroom with a twin bunk bed; and another bedroom with two double beds and a private deck, as well as a Jack-and-Jill bathroom with jacuzzi tub (and upstairs washer/dryer) shared between both the upstairs bedrooms.<br><br>Chatham Main Street is only a 20-minute walk or a 3-minute drive away from the home; here, you’ll find a fabulous selection of local restaurants and one-of-a-kind stores. Some popular places to dine are The Impudent Oyster, Bluefins Saki and Sushi Bar and The Wild Goose Tavern. Nearby attractions also include movies at the historic Chatham Orpheum; guided tours of Chatham Lighthouse and learning about the Atlantic White Sharks at the Chatham Shark Center. <br><br>Home Details:<br>-Dogs Welcomed (w/fee of $30/night per dog)<br>-Sleeps 10<br>-2 Livable Floors <br>-1st Floor Master Bedroom: 1 King Bed w/ en suite Full Bathroom (walk-in shower)<br>-1st Floor Bedroom #2: 1 Queen Bed -1st Floor Bedroom #3: 1 Queen Bed -2nd Floor Bedroom #4: 2 Full Beds -2nd Floor Bedroom #5: 2 Twin Beds (bunk beds) -Central Heat & A/C -Smart TV w/ Cable -DVD Player -WiFi -Washer/Dryer (Basement) -Air Hockey (Basement) -Outdoor Ping Pong Table -Spa Tub in 2nd Floor Bathroom -1st Floor Gas Fireplace (Living Room) for guest use -2nd Floor Gas Fireplace (Not for Guest Use) -Fire Pit -Private Yard -Lawn Games -Propane Grill -Paddle Boards & Inflatable Rafts -Steps to Oyster Pond with a Private Floating Dock -Sheets and Bath Towels Provided with Beds Made Upon Arrival -Cleaned with Hospital Grade Disinfectant