Family friendly vacation rentals in Sandwich, MA

Explore 125 family-friendly vacation rentals, homes, and villas in Sandwich, 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 $75 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.

125 Family-Friendly Homes in Sandwich

Point of Happiness - Bourne

Bourne, MA, US
3 Bedrooms 8 Guests
Aug 25 - 27
$500 night

Welcome to Point of Happiness – Your Peaceful Cape Escape in Bourne, MA Tucked away in Taylor’s Point at the gateway to Cape Cod, Point of Happiness is your next favorite vacation rental. This bright and serene home invites you to slow down, breathe deep, and soak in the natural beauty of coastal Massachusetts. Whether you’re sipping your morning coffee on the deck, strolling to the sand across the street, or enjoying a cozy game night inside, you’ll feel right at home here. The house is thoughtfully designed for families, couples, or friends seeking a peaceful getaway with all the comforts of home, featuring: - 3 spacious bedrooms designed for restful sleep - Pullout sofa queen bed in living room - 2 full and 1 half bathrooms with fresh linens and coastal charm - Fully enclosed outdoor shower to rinse off after a day at the beach - Amazing kitchen, stocked kitchen perfect for family meals - Cozy living area with comfy seating, books, and board games for rainy day fun - Expansive outdoor deck with propane grill - Ping pong table in the shed in the backyard - Private yard for kids to play or for evening stargazing under the trees Easy access to the Cape Cod Canal bike path, beaches, local markets, and more! - Just minutes to the canal bike path, boat launch, and Buzzards Bay shops - A short drive to Cape Cod’s best beaches and attractions - Easy access without crossing the bridge—ideal for quick weekend escapes Whether you’re planning a romantic weekend, a family getaway, or a solo recharge, this home wraps you in comfort and ease. Located in beautiful Bourne, you’re minutes from sandy shores, seafood shacks, and the slower pace we all crave. Come find your joy at the Point of Happiness — where memories are made and peace comes easy. ------------------------- HOUSE RULES: ------------------------- - Primary renter must be 25 years or older - No pets are allowed in this home - No smoking/vaping indoors - Charging of electric vehicles is not permitted on the property - Please NO PARTIES, EVENTS, PERFORMING ARTISTS, OR BANDS ARE ALLOWED AT ANY TIME. Please be respectful of the neighbors at all times! - These are all separate causes for eviction with no refund and may damage our ability to offer the home for future guests exposing you to liability. License: C0537440360

Walk to Monument Beach: Cape Cod Cottage w/ Grill

Bourne, MA, US
3 Bedrooms 5 Guests
Aug 23 - 25
$303 night

Beach Chairs & Umbrella | In-Unit Laundry | Mid-Century Modern Decor | Quiet Neighborhood Escape to the Cape and unwind at this 3-bedroom, 1-bathroom vacation rental! Blending mid-century modern decor with cozy comforts, this delightful cottage features a well-equipped kitchen, a flat-screen TV, and a serene outdoor space complete with a gas grill and hammock. Cast a line at Monument Beach, explore the Cape Cod Canal Bikeway & Walking Path trails, or ice skate at the Gallo Ice Arena. -- THE PROPERTY -- PIT#16379182-002 SLEEPING ARRANGEMENTS - Bedroom 1: 1 full bed - Bedroom 2: 1 full bed - Bedroom 3: 1 twin daybed OUTDOOR LIVING - Spacious yard - Gas grill, outdoor dining area - Hammock - Outdoor shower - 4 Adirondack chairs INDOOR LIVING - Flat-screen TV - Hardwood floors - Desk KITCHEN - Stove/oven, refrigerator, microwave - Keurig coffee maker, Crockpot - Spices - Paper towels, trash bags - Dining table w/ chairs GENERAL - Free WiFi - Central heating, A/C unit - Linens & towels, laundry detergent FAQ - 5 exterior security cameras (facing out) ACCESSIBILITY - Single-story home - 2 steps to enter PARKING - Driveway (2 vehicles) - Free street parking (first-come, first-served) - No EV charging -- THE LOCATION -- - Walking distance to cafe, ice cream shop, playground, and corner store - Less than 1 mile to Monument Beach: sunning, swimming, public access boat ramp, and fishing - 2 miles to Cape Cod Canal - 3 miles to Pocasset Golf Club - 9 miles to Scusset Beach State Reservation - 63 miles to Boston Logan International 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 2 steps to enter - Your safety matters. This property features 5 exterior security cameras. Camera 1 is located above the front door facing the yard; camera 2 is located at the kitchen door facing the road, camera 3 is located at the front breezeway door facing the driveway/road, camera 4 is located at the back breezeway door facing the garage and back door, and camera 5 faces the garage and driveway. All cameras are outward facing and do not look into interior spaces. The cameras record video when activated by motion. The cameras will record when they first sense motion and 30 seconds after the last motion is detected Licence number: C0280370360

Spacious Retreat With Pool, Game Room & Fireplace | Sleeps 10 | Backyard Oasis & Screened Gazebo | Family-Friendly Getaway | 24/7 Hospitality

Plymouth, MA, US
4 Bedrooms 9 Guests
Sep 12 - 14
$561 night

Unwind at your private Plymouth retreat, made for slow mornings, family time, and easy outdoor living. • Sleeps up to 10 across 4 comfortable bedrooms • Private backyard oasis with in-ground pool (closing end of Sept) • Fully screened gazebo • Game room for fun, rain or shine • Wood-burning fireplace for cozy nights in • Outdoor grill • 2 Car garage and ample parking for 8 vehicles • Family-friendly with baby gates and children’s books • Work-ready with high-speed WiFi Step inside and feel the immediate sense of calm in this charming, family-friendly home, filled with bright, natural light. The beautifully styled living room, with its high ceilings and decorative wood-burning fireplace, invites you to unwind. A modern, spacious kitchen is fully equipped for preparing family meals, which you can enjoy together in the ample dining space. Amenities: Games: Pop-A-Shot, skeeball, arcade games, cornhole, and board games Music: Upright piano for the musician in the group Outdoor Pool: Large, in-ground swimming pool (seasonal) Fireplace: Wood burning fireplace in the living room Grill: Propane grill on the back patio with a fully enclosed gazebo for al fresco dining WiFi: High speed internet Children Friendly: Safety features like baby gates and a high chair, dinnerware and a selection of children’s books Parking: Comes with free parking in a 2-car garage and a driveway for 8+ Sleeping Arrangements (Sleeps 10): Primary Suite: 1 King Bed Bedroom 2: 1 Queen Bed Bedroom 3: 1 Full-over-Full Bunk Bed and 1 Twin Trundle Bedroom 4: 1 Twin Bed Living Room: 1 Sleeper Sofa Den: 1 Queen Sleeper Sofa Permit: 03566_followedby_32390 Guests will have exclusive and private access to the entire home and its grounds. This includes all bedrooms, the kitchen, living areas, the detached game room, the private backyard, the pool (OPEN FOR THE 2026 SEASON!), and the screened gazebo. Entry is seamless and secure with a keyless entry system; you will be provided with a unique door code for the duration of your stay. You’ll appreciate having a car to explore the beauty of the area. Pool Season: The in-ground pool is temperature-controlled (80-85°F weather dependent) and IS OPEN for 2026 until late September. Family-Friendly: The home is equipped with safety features like baby gates, a high chair, children’s dinnerware, and books. We can also provide a link to rent additional baby equipment through Babyquip. 24/7 Support: Our hospitality team is available around the clock to assist with any questions or provide local recommendations. License number: C0356632390

Spacious Stone Fire Pit Game Room!

Barnstable, MA, US
4 Bedrooms 8 Guests
Aug 25 - 27
$328 night

21009 - Perfect Peach: Spacious Stone Fire Pit Game Room! Marston’s Mills is one of the many Barnstable Villages world famous for their quaint New England downtowns, access to beautiful beaches and bringing the beauty of Cape Cod to your fingertips. You’ll be elated by all you can experience this vacation, at the Perfect Peach! <br><br>The sunshine yellow front facade welcomes you into the u-shaped driveway, bringing immediate warmth to your vacation. Walking through the navy blue front door, you’ll notice the beautiful formal living room to your left, with a dining seating area in the back awaiting your morning coffee. To the right of the front door, the formal dining room gives access to the large kitchen, with a breakfast bar center island and a cut through window to the living room at the rear of the home. The home’s second living room is past the kitchen, with large sectional, exposed wood beams and vaulted ceiling with large skylight and patio doors to back deck. Head down to the basement of the home, where you’ll find a game room with poker table, a private office area and a half bathroom, as well as access to the backyard through sliding glass doors.<br><br>Upstairs in the home, you will find 4 bedrooms to choose from to refuel for your next vacation day. The primary bedroom is located to the right of the staircase, with a king bed and an ensuite bathroom with shower. To the left of the stairs is a queen bedroom. The third bedroom is also on this side of the home, with a queen sized bed, overlooking the backyard. A final bedroom with two twin beds and built-in cabinetry can be found to the right of the stairs. Straight ahead from the staircase is a full bathroom with double vanities and a shower/ tub combo. There is also an additional sleeping space with a queen bed and separate entrance above the garage. (Please note there is no AC in above the garage - heat only). <br><br>Outdoors, the home’s massive backyard provides lots of space and privacy. Huddle around the fire pit and watch the stars, or let your pups run around in the summer sun. You can even enjoy a meal outdoors at the outdoor dining table on the elevated deck. <br><br>Other amenities include a washer and dryer, propane grill, and an outdoor shower. See what a true Cape Cod vacation is all about, at the Perfect Peach!<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 8<br>-3 Floors (1st Floor + 2nd Floor + Walkout Ground Floor)<br>-2,436 Sq Ft<br>Bedrooms<br>-Total 4<br>-2nd Floor Bedroom: 1 King Bed w/ en suite Bathroom<br>-2nd Floor Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom: 2 Twin Beds<br>-There is an additional queen bedroom above the garage with Heat only. No AC. <br>Bathrooms<br>-Total 3.5<br>-1st Floor: Half Bathroom<br>-2nd Floor: Full Bath room w/ Shower (en suite King Bedroom)<br>-2nd Floor: Full Bathroom w/ Tub/Shower Combo<br>-Ground Floor: Full Bathroom w/ Shower<br>Other Amenities<br>-Fully Equipped Kitchen w/ Island<br>-Central A/C in bedrooms only<br>-Smart Lock/Self Check-In<br>-WiFi<br>-Smart TV<br>-Washer/Dryer (1st floor)<br>-Home Office<br>-Game Room w/ Ping Pong Table (ground floor)<br>-Deck w/ Outdoor Dining<br>-Propane Grill<br>-Stone Fire Pit<br>-Outdoor Shower<br>-Indoor Fireplaces are not for guest use (fines remitted) <br>-Private Yard<br>-Located South of Route 28 in Desirable Neighborhood<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0407190200

Walk to Buzzards Bay Beach: Spacious Onset Home

Bourne, MA, US
5 Bedrooms 8 Guests
Aug 23 - 26
$425 night

Lazy beach days and beautiful bike rides are just some of the activities that await at this spacious Onset home! With 5 bedrooms, 2 full bathrooms, 2 half bathrooms, and a 2,100-square-foot interior, this vacation rental is ready for a group stay! This property offers Cape Cod vacationing without the Bourne Bridge traffic. Located just outside Cape Cod proper, it’s the ideal location to enjoy a view of Buzzards Bay from the neighborhood beach and quickly hop over the bridge for day trips. -- THE PROPERTY -- 3-Minute Walk to Beach | Free WiFi | Central A/C | Laundry Machines | Cape Cod Living Without the Traffic Bedroom 1: King Bed (Converts to 2 Twins) | Bedroom 2: 2 Twin Beds | Bedroom 3: 2 Twin Beds | Bedroom 4: Twin Daybed w/ Twin Trundle | Bedroom 5 (Office): Twin Daybed | Game Room: Twin Daybed w/ Twin Trundle OUTDOOR SPACE: Furnished deck, 6-person table w/ umbrella, spacious yard, yard games, basketball hoop in cul-de-sac KITCHEN: Fully equipped, stainless steel appliances, wraparound counters, toaster, tea kettle, blender, 8-10-person dining table, 4-person dining table INDOOR LIVING: 2 flat-screen cable TVs, gas fireplace, finished basement w/ ping pong table, jetted tub, hardwood floors, nautical decor, 2 full bathrooms, 2 half bathrooms GENERAL: Washer/dryer, linens/towels, family-friendly, central air conditioning, central heating, complimentary toiletries, hair dryer FAQ: 1 exterior security camera (facing out), internal motion detectors PARKING: Garage (2 vehicles), driveway (4 vehicles) -- THE LOCATION -- BEACHES/BOATING: Neighborhood beach (0.2 miles), Point Independence Yacht Club (0.8 miles), Safe Harbor Onset Bay (0.8 miles), Onset Beach (1.4 miles), Shell Point Beach (1.8 miles), Buzzards Bay Marina (1.7 miles) RECREATION: Cape Cod Canal bike path - Buzzards Bay (2.2 miles), The Bay Pointe Club (0.6 miles), Myles Standish State Forest (13.8 miles) ATTRACTIONS: Onset Village (1.3 miles), Water Wizz of Cape Cod (3.2 miles), Heritage Museum (11.1 miles), Scusset Beach State Reservation (9.3 miles), Cape Cod Canal Railroad Bridge (5.9 miles), Edaville Family Theme Park (14.6 miles), Sandwich Glass Museum (14.3 miles) DAY TRIPS: Cape Cod National Seashore (53.0 miles), Woods Hole (23.8 miles), Martha's Vineyard (23.8 to ferry terminal) SEAFOOD: Lobster Pot (1.8 miles), Barnacle Bill's Seafood (2.1 miles), Bailey's Surf N Turf (2.8 miles), Lobster Trap Restaurant (6.4 miles), Kool-Kone (6.9 miles), Gateway Tavern (6.9 miles) AIRPORT: Boston Logan International Airport (61.4 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 -- - Massachusetts Tax ID: C0078543100 - 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 - NOTE: Please note that guests must walk up 3 steps to get to the first floor. it is not a step-less entry - NOTE: Please note this property has 2 full bathrooms and 2 half bathrooms - NOTE: This property features an ADT-powered video/audio doorbell and security system for protection and monitoring only of the property when not occupied and for random spot checks otherwise - NOTE: Your safety matters. This property features 1 exterior security camera on the front of the house facing the driveway. The camera is outward facing and does not look into interior spaces. The camera records video and sound when activated by motion - NOTE: This property features motion detectors inside the home in the kitchen and front hallway. These devices do not record sound or video Licence number: C0078543100

Oceanfront Cottage on Cape Cod Bay w/ Game Room

Plymouth, MA, US
3 Bedrooms 6 Guests
Sep 27 - 29
$271 night

Seaside Stargazing | Beach Access On-Site Kick back Cape-Cod style at this Plymouth vacation rental! Steps from Cape Cod Bay, this 3-bedroom, 2-bath cottage offers on-site beach access, ocean views, and a deck made for unwinding. Launch a boat from Plymouth Yacht Club or browse downtown shops, seafood shacks, and harbor cruises within 10 miles — then wind down with some friendly competition in the game room. Book your bayside stay today! -- THE PROPERTY -- C0369492390 SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 full bed - Bedroom 3: 1 full bed - Game Room: 1 full bed INDOOR LIVING - Game room w/ ping-pong table & Ms. Pac-Man machine - Flat-screen TV - Books - Open floor plan OUTDOOR LIVING - Beach access - Furnished deck w/ fire pit (propane not provided) - Ocean views KITCHEN - Refrigerator, stove/oven, dishwasher (dishwasher liquid not provided) - Keurig, blender, toaster, microwave - Dishware & flatware, trash bags & paper towels - Dining table, wet bar w/ seating GENERAL - Free WiFi - Central A/C & heating - Washer, dryer - Linens & towels - Toilet paper (starter supply) FAQ - 1 exterior security camera (facing front entry) ACCESSIBILITY - 2-level cottage, 3 steps to enter - All bedrooms & full bathrooms on main floor PARKING - Driveway (3 vehicles) -- THE LOCATION -- - Resting on Cape Cod Bay w/ beach access on-site - 7 miles to Plymouth Long Beach - 9 miles to Plymouth Yacht Club - 10 miles to Downtown Plymouth - 53 miles to Boston Logan International 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 2-level cottage requires 3 steps to enter; all bedrooms and full bathrooms are on the main floor - Your safety matters. This property features 1 exterior security camera on the front of the cottage facing the front outdoor entry. The camera does not look into any interior spaces. It records video and sound when activated by motion Licence number: C0369492390

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
$1,197 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 $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! ®

Mashpee River Adventures! Serene Family Retreat

Mashpee, MA, US
4 Bedrooms 8 Guests
Sep 30 - Oct 7
$273 night

Dogs Welcome w/ Fee | 2 Mi to Shops & Eateries Embark on an epic family getaway and book this 4-bedroom, 2-bathroom vacation rental home in Mashpee, MA. The charming property boasts a can't-beat location on the riverfront, so bring a kayak and explore the waterways, or take a scenic walk down to the shore. Afterward, gather on the deck for a hearty dinner and play board games in the game room. Cape Cod is calling! -- THE PROPERTY -- C0518721720 SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 queen bed - Bedroom 3: 1 full bed - Bedroom 4: 2 twin beds MAIN FEATURES - Gas grill (natural gas provided) - Furnished deck, private yard - Outdoor shower, beach gear, life vests - Piano, 2 Smart TVs - Fireplace (decorative only) - Board games & books - Dining table, high chair - Dock KITCHEN  - Stove/oven, refrigerator, dishwasher - Microwave, toaster - Drip coffee maker - Cooking basics - Dishware/flatware - Trash bags & paper towels GENERAL  - Free WiFi (laptop friendly) - Washer & dryer, iron/board - Central A/C & heating (forced gas) - Linens/towels, complimentary toiletries - Hair dryer FAQ - 2 exterior security cameras (facing out) - Pet fee (paid pre-trip) - No swimming on-site ACCESSIBILITY - 2-level home, 4 steps to enter - All bedrooms & full bathrooms on 1st floor PARKING - Driveway (8 vehicles) - RV/trailer parking allowed on-site -- THE LOCATION -- - Quiet location w/ direct access to Mashpee River - Across the street from Mashpee River Woodlands: bird watching & hiking - 1 mile to Cape Cod Children's Museum - 2 miles to Mashpee Commons - 3 miles to Popponesset Island - 27 miles to Martha's Vineyard Airport & 70 miles to Boston Logan Int'l 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 Electric Vehicle Charging - Pet friendly w/ $100 fee (+ fees & taxes, 2 dogs max) - No events, parties, or large gatherings - Must be at least 30 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 2-level home requires 4 steps to enter; all bedrooms and full bathrooms are on the 1st floor - Swimming is prohibited on-site - The fireplace is decorative only and not for guest use - The garage is not available for guest parking - Your safety matters. This property features 2 exterior security cameras. There is a Ring doorbell device with an exterior security camera on the garage facing the driveway and another one on the back of the house facing the deck. The cameras are outward facing and do not look into interior spaces. The cameras record video and sound when activated by motion or when the video doorbell buttons are pressed Licence number: STR-25-0005

Swing Set, Plunge pool, and large yard await!

Barnstable, MA, US
3 Bedrooms 8 Guests
Aug 29 - 31
$553 night

21012 - Oyster Circle: Swing Set, Plunge pool, and large yard await! Over the bridge to Osterville, just a stone’s throw away from the picturesque East Bay, lies a meticulously maintained vacation home awaiting the arrival of discerning vacationers. This haven has been artfully renovated from top to bottom, thoughtfully curated with the comfort and enjoyment of guests in mind. A newly built plunge pool invites you to bask in the warmth of the sun and indulge in moments of leisure. For the little ones, a charming swing set awaits, ensuring endless hours of joy while parents orchestrate a delightful BBQ feast, crafting memories along with delicious meals. As twilight descends, retreat indoors to the embrace of the spacious sofa, tailor-made for cozy movie nights or streaming your favorite shows, providing the perfect den for relaxation and unwinding after a day of exploration. Strategically located just a mile from the pristine shores of Craigville Beach and a mere 1.4 miles from the allure of Dowses Beach, sun-seekers and beach enthusiasts alike will delight in this convenient and stylish location. Meanwhile, Main Street in Osterville awaits, offering an array of culinary delights to tantalize the taste buds, with renowned eateries such as CRISP and Five Bays Bistro a mere 0.7 miles away. Embark on a journey of tranquility and rejuvenation in this meticulously curated home, where every detail is crafted to elevate your stay into an unforgettable experience of comfort, leisure, and cherished moments. Please note there is a pool house on the property that is unavailable to guests due to a small fire. Home Details: -No Dogs (Fines remitted) -Sleeps 8 Bedrooms -Total 3 -1st Floor Bedroom: 1 King Bed -1st Floor Bedroom: 1 Full Daybed with 1 Twin Trundle, 1 Twin Bed -1st Floor Bedroom: 2 Twin Beds Bathrooms -Total 2 -1st Floor: Shower -1st Floor: Tub and Shower Other Amenities -Outdoor rinse station (Cold water only) -Central AC -WiFi -Smart TV -Streaming Service (Apple TV) -Unheated Plunge Pool (Available from Memorial Day - Labor Day) -Washer/Dryer -Propane Grill -Fire Pit -Indoor Fireplace is not for guest use(fines remitted) -Please note outdoor amenities are available seasonally -Sheets and Bath Towels Provided with Beds made Upon Arrival -Cleaned with Hospital Grade Disinfectant -Parking for 3 cars maximum -C0468350200 Please note there is a pool house on the property that is unavailable to guests due to a small fire.

Steps to Beach: Cape Cod Family Retreat w/ Patio

Bourne, MA, US
4 Bedrooms 10 Guests
Aug 23 - 26
$889 night

Treat the family to a quintessential summer vacation on the Cape when you stay at this spacious home in Bourne, Massachusetts. Located just steps away from the peaceful waters of Squeteague Harbor, this 4-bedroom, 2.5-bathroom vacation rental offers the ideal home base for exploring New England. Spend your days lounging on the salty shores, make a day trip to Martha's Vineyard for unforgettable scenery, or stay in town and savor fresh lobster rolls while the sun sets over the bay! -- THE PROPERTY -- C0477250360 | Comunity Playground | Walk to Squeteague Harbor | Family-Friendly Home | 2,336 Sq Ft Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: 2 Queen Beds | Bedroom 4: Queen Bed | Additional Sleeping: Cribs OUTDOOR LIVING: Huge wraparound porch, fenced-in backyard, outdoor shower INDOOR LIVING: Smart TVs, group-friendly dining table, large sectional sofa, ceiling fans KITCHEN: Cooking basics, 6-burner gas range stove/oven, drip coffee maker, dishwasher, toaster oven, knife block, dishware & flatware, high chair GENERAL: Free WiFi, keyless entry, complimentary toiletries, linens & towels, in-unit washer & dryer, central heating & air conditioning, trash bags & paper towels FAQ: 1 exterior security camera (facing out), quiet hours (10:00 PM-8:00 AM) ACCESSIBILITY: Steps required for access, 2-story home PARKING: Driveway (4 vehicles) -- THE LOCATION -- OUTDOOR FUN: Squeteague Harbor (on-site), Fachetti Beach (0.5 miles), Eustis Beach (1 Minute walk to the water), Megansett Beach (1 mile), Sunrise Beach (2 miles), Hen's Cove Public Beach (2 miles), Mashpee National Wildlife Refuge (11 miles), Myles Standish State Forest (21 miles) - hiking, mountain biking, boating, fishing STATE PARKS: Monument Beach (4 miles), Scusset Beach State Reservation (13 miles), South Cape Beach State Park (14 miles), Ellisville Harbor State Park (16 miles) LOCAL ATTRACTIONS: Mashpee Commons (8 miles), Heritage Museums & Gardens (13 miles), Woods Hole Science Aquarium (13 miles), Cape Cod Beer (20 miles), Martha’s Vineyard (27 miles) FESTIVALS/EVENTS: Barnstable County Fair (6 miles), Brewster Summer Arts & Crafts Festival (35 miles) AIRPORTS: Barnstable Municipal Airport (20 miles), Boston Logan International Airport (65 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 - NOTE: Your safety matters. This property features 1 external security camera. This camera is outward facing and does not look into any interior spaces. The camera is located on the garage and faces the driveway and street. It actively records video when motion is detected and will be turned on during your stay - NOTE: Please observe quiet hours from 10:00 PM-8:00 AM - NOTE: This property runs on a septic system - NOTE: This 2-story home requires stairs to access Licence number: C0477250360

Center Of It All: 454-Cv Sea Captain’s Estate with Heated Pool and Pickle Ball Court

Centerville, MA, US
8 Bedrooms 20 Guests
Sep 7 - 10
$1,776 night

This property is professionally managed by Pretty Picky Properties. Sea Captain’s Estate with Heated Pool and Pickle Ball Court Sleeps 20 in 8 Bedrooms, 4.5 Baths Linens Included and Beds Made Rents Saturday to Saturday during the summer months Pets considered up to 40lbs. Pool Heating Fee Prior to June 22 and after September 13 Labor Day Weekend 4-night minimum stay From its rooftop Victorian cupola perfect for stargazing to its classically coffered ceilings and gleaming hardwood floors, this one-of-a-kind, historic grand manor warms your heart the minute you step onto the property and pass under the towering linden trees that define the expansive front yard. Originally built in 1856 for Sea Captain Russell Marston, the 5,600-square-foot property has been fully renovated and modernized over the past decade, retaining the character of a grand estate while featuring tasteful décor and elegant finishes. The result is the perfect balance of historic charm and modern amenities, comfortably and memorably accommodating up to 20 guests. The home’s central location in mid-Cape puts it in the charming Centerville Historic District, less than a mile from Craigville Beach, known for its wide sandy shore and stunning views of Nantucket Sound. Owners offer a beach pass if you prefer to drive to other area beaches! It’s a short walk along the sidewalk to the water, or a quick two-minute drive. Just five minutes down Main Street, you can enjoy award-winning Four Seas Ice Cream, perfect for a treat at any time or after dinner. Nearby, you’ll find the 1856 Country Store, which still sells “penny candy" along with gifts and souvenirs, as well as the library and a new playground. While your group may prefer staying on the grounds, the home offers easy access to all parts of Cape Cod. It’s just 5 minutes to upscale shopping and dining in Osterville, 10 minutes to the variety of options in downtown Hyannis and the ferries to the Islands, and 15 minutes to trendy Mashpee Commons. You’re also close to excellent local markets, bakeries, and coffee shops, along with convenient stores like Whole Foods and Trader Joe’s. It truly offers the best of everything! The main level of this home offers a common space that is remarkably open for a home of this vintage, including a bright, thoughtfully equipped kitchen with high-end appliances and an impressive great room with plush seating and a large smart TV for movie nights. There’s a full dining room and an additional dining area just off the great room and kitchen, which could easily host family game nights. In addition, several living spaces complete the expansive first floor and are ideal for your large group to spread out. There is an elegant lounge perfect for reading by day or for hosting cocktails by night, as well as a more contemporary family room, ideal for kids and teens, with a large smart TV, an Xbox gaming system, and a selection of board games. The main level also includes a sunroom with access to the spacious grounds, a half bath, and a mudroom with two sets of washers and dryers. The home offers various sleeping arrangements across eight bedrooms on three levels. The main level features a spacious bedroom with a King bed and an ensuite bathroom with a step-in shower. Ascending the grand, winding staircase, the second level includes several sleep areas. There is a luxurious King suite with an ensuite bath that has a soaking tub and a large shower. This primary bathroom also has a second door for direct hall access, ensuring privacy for the master suite occupants. Adjacent are two tastefully decorated bedrooms—one with a King bed and the other with a Queen bed—that share a hall bath with a step-in shower. In a separate wing of the second floor, there’s another large King suite with its own private exterior entrance, ideal for a family. This suite includes a bedroom with a comfy King bed, a kitchenette, a full bath with a step-in shower, and an additional sleeping area with two twin beds. From this suite, you can step out onto a spacious deck overlooking the pool and grounds. The third level features three cozy bedrooms: one with a Queen bed, another with two twin beds, and a third with four twin beds. This level also has a smart TV and a PlayStation gaming system. Overall, the house contains four full bathrooms and one half bath. Your outdoor summer experience here will be truly unforgettable! Picture sunny days relaxing by the spacious, secluded heated pool (gated for safety!). This beautiful area will become a favorite spot, featuring resort-style lounge chairs and a dining table perfect for outdoor lunches. There’s also a pool cabana equipped with a fridge/freezer, an outdoor rinse station, and a convenient half bath. Your group will appreciate the many outdoor living options available! On the opposite side of the house, accessible from the great room, is another spacious outdoor entertaining area. It’s a large stone courtyard with premium lounge seating around a gas fire pit, a large gas grill, and a whole-home generator. Additionally, two expansive sundecks with lounge seating and a table with an umbrella—perfect for lunch or cocktails — overlooking the pool are located on the second level. A unique amenity, a private pickleball court. Ideal for family tournaments! This home will be your private resort on the Cape! The house is set on 1.37 acres of private, professionally landscaped, park-like grounds with ample flat yard space for kids to run and play safely. You can enjoy family soccer matches, cornhole games, or basketball at the driveway hoop. The home is equipped with central air conditioning, high-speed Wi-Fi, multiple smart TVs, and a Sonos sound system. 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! ®

Families Welcome! Home 2 Mi to Craigville Beach

Barnstable, MA, US
3 Bedrooms 7 Guests
Aug 30 - Sep 1
$334 night

Escape for a while and enjoy the calm atmosphere of this Hyannis vacation rental! Boasting 3 bedrooms, 1.5 bathrooms, a well-appointed interior with a full kitchen, a spacious backyard, and easy access to local beaches and golf courses, this charming home is an ideal getaway. Ready to explore? Tour the area with Hyannis Whale Watcher Cruises, stroll through the Heritage Museums & Gardens, or take a day trip to Martha's Vineyard. No matter how you spend your trip, a tranquil retreat awaits! -- THE PROPERTY -- MassTaxConnect ID C0420760200 | Dog Friendly w/ Fee | Spacious Yard w/ Fire Pit | Close to Golf Courses Bedroom 1: King Bed | Bedroom 2: Full Bed | Bedroom 3: Queen Bed, Twin Bed | Additional Sleeping: Twin Air Mattress INDOOR LIVING: Smart TVs, fireplace (decorative only), breakfast bar, board games OUTDOOR LIVING: Deck, outdoor seating & dining areas, gas grill, hammock KITCHEN: Dishwasher, stove/oven, fridge, stainless steel appliances, Keurig coffee maker, microwave, toaster, blender, tea kettle, ice maker, dishware/flatware, spices, basic cooking essentials GENERAL: Free WiFi, keyless entry, central A/C & heating, iron/ironing board, towels/linens, hair dryer, complimentary toiletries, trash bags/paper towels FAQ: Steps required to enter, pet fee (paid pre-trip) PARKING: Driveway (4 vehicles) -- THE LOCATION -- ESCAPE TO NATURE: Craigville Beach (2 miles), Keyes Memorial Beach (3 miles), Hyannis Harbor Light Beach (3 miles), Kalmus Park Beach (3 miles), Hyannis Whale Watcher Cruises (4 miles), Cape Cod National Seashore (21 miles), Martha's Vineyard (38 miles w/ ferry) HISTORY BUFFS: John F. Kennedy Hyannis Museum (2 miles), Whydah Pirate Museum (5 miles), Heritage Museums & Gardens (14 miles), Atwood Museum (21 miles) HIT THE LINKS: Twin Brooks Golf Course (2 miles), Hyannis Golf Course (2 miles), Hyannisport Club (2 miles), Old Barnstable Fairgrounds Golf Course (6 miles) AIRPORTS: Cape Cod Gateway Airport (2 miles), Boston Logan International Airport (71 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, 1 dog max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires steps to enter - NOTE: The fireplace is not available for guest use Licence number: C0420760200

Private Saltwater Pool, Game Room, near Beaches!

Barnstable, MA, US
4 Bedrooms 8 Guests
Sep 21 - 23
$214 night

21017 - Salt Wind: Private Saltwater Pool, Game Room, near Beaches! Your Cape Cod escape begins here, where sun-drenched days by your private saltwater pool and evenings of laughter in the finished game room create unforgettable memories. Located in the charming village of Osterville, this spacious four-bedroom retreat is perfectly positioned between three stunning beaches—Craigville Beach (3.8 mi), Dowses Beach (3.9 mi), and Wianno Beach (4.3 mi)—offering endless seaside adventures.<br><br>The heart of the home is the main mid-floor living space, where rustic wood floors, exposed ceilings, and inviting décor set the scene for relaxed gatherings. A fireplace warms the comfortable seating area, while the open-concept chef’s kitchen—complete with a gas range, modern appliances, and dishwasher—makes dining effortless.<br><br>Downstairs, the finished basement transforms into an entertainment hub, featuring soft seating, a TV, and a billiards table for friendly competition. With high-speed WiFi, remote workers and students can stay connected when needed.<br><br>Beyond the home’s welcoming interiors, the expansive deck invites al fresco dining and poolside picnics in your private backyard oasis. When you’re ready to explore, indulge in local flavors just over three miles away—sip a famous Mudslide at The Chart Room at Crosby’s or savor an authentic seafood feast at Wimpy’s Seafood Cafe.<br><br>Designed for multigenerational families and groups, this home offers comfort for everyone, with a first-floor bedroom featuring a wheelchair-accessible sink and shower. The second floor hosts three additional bedrooms, including a bunk room with a private entrance.<br><br>Cape Cod’s coastal magic is calling—book your stay today and create lasting memories by the shore!<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 8<br>Bedrooms<br>-Total 4<br>-1st Floor Bedroom: 2 Twin Beds<br>-2nd Floor Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom: 1 Full Bed, 1 Bunk (Twin over Full)<br>Bathrooms<br>-Total 2<br>-1st Floor: Shower<br>-2nd Floor: Tub/Shower Combo<br>Other Amenities <br>-Game Room w/Billiards<br>-Window A/C<br>-WiFi<br>-Smart TV<br>-Streaming Service<br>-Washer/Dryer <br>-Propane Grill<br>-Saltwater Pool (Unheated) (available Memorial Day to Labor Day)<br>-Gas Fireplace <br>-Please note outdoor amenities are available seasonally<br>-Please note there is/are an exterior camera 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 3 cars maximum<br>-C0368660200<br> Please note there is/are an exterior camera on the property that records front of house/driveway/entry door

Waterfront Falmouth Home w/ Dock on Jenkins Pond!

Falmouth, MA, US
3 Bedrooms 6 Guests
Jan 30 - Feb 6
$395 night

Experience a match made in heaven during your Cape Cod getaway, where swimming and kayaking await just steps from your door! This 3-bed, 2-bath vacation rental pairs a large deck overlooking spring-fed Jenkins Pond and luxury master en-suite bathroom with jetted tub. Wake up to gorgeous views and enjoy dining and drinks on the large deck overlooking the pond. Venture out to walk along any of 11 beautiful nearby ocean beaches or spend a day shopping and dining in Falmouth Center. -- THE PROPERTY -- C0485190960 | Private Dock | 2,200 Sq Ft | Walk to Community Pond Beach Spend quality family bonding time in the coastal town of Falmouth or even spend a day on Martha’s Vineyard a short ferry ride away - both quaint Cape Cod destinations that promise fun, adventure, and relaxation. Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Family Room: Sleeper Sofa OUTDOOR AREA: Deck w/ lounge furniture, gas grill, floating dock, kayak, outdoor shower, direct pond access INDOOR LIVING: 2 flat-screen TVs, dining table, foosball table, Smart speaker, jetted tub, vaulted ceilings, skylights KITCHEN: Fully equipped w/ stainless steel appliances, cooking basics, drip coffee maker, toaster, teapot GENERAL: Free WiFi, air conditioning, central heating, linens & towels, complimentary toiletries, hair dryer, ceiling fans PARKING: Garage (2 vehicles), driveway (4 vehicles) -- THE LOCATION -- BEACHES: Chapoquoit Beach (4.3 miles), Bristol Beach (4.8 miles), Wood Neck Beach (5.8 miles), Old Silver Beach (6.5 miles), Megansett Beach (6.7 miles), Shining Sea Bikeway (6.8 miles), South Cape Beach State Park (10.5 miles) OUTDOOR DESTINATIONS: Goodwill Park (3.7 miles), Mass Audubon's Ashumet Holly Wildlife Sanctuary(4.1 miles), Mashpee National Wildlife Refuge (5.3 miles), The Knob (7.1 miles) THINGS TO DO + SEE: Cape Cod Winery (2.5 miles), Bad Martha Farmer's Brewery (4.0 miles), Downtown Falmouth (4.3 miles), Falmouth Museums On The Green (4.9 miles), The Cape Club (5.5 miles), Falmouth Golf Course (6.4 miles), Nobska Lighthouse (8.4 miles), Woods Hole Oceanographic Institute & Science Aquarium (8.9 miles), Cape Cod Children's Museum (9.0 miles) AIRPORTS: Barnstable Municipal Airport (18.5 miles), Boston Logan International Airport (76.9 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 Licence number: C0242630960;R-23-1180;C0485190960;R-25-0035

Family Tides: Private Retreat with Pool & Hot Tub

Barnstable, MA, US
4 Bedrooms 6 Guests
Aug 29 - Sep 1
$993 night

4 Bedroom - 3 Baths - Sleeps 7 with additional sleep space A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of our homes offer flexible stays with a 3 night minimum in the off season - ask our Reservation Specialists for more details. Complimentary Linens Service Provided: This includes bedsheets, bath, beach, and dish towels for total home occupancy We offer a 4 pm Check-In and 9 am Check-Out Welcome to Family Tides! Renovated and updated home with central AC sleeps 6 in 4 bedrooms and one more in additional sleeping space. This home has a lower level living space including a bedroom, full bathroom, kitchenette/bar, living room and laundry room with dedicated work space and separate entry. The outdoor space includes a kitchen/bar, in ground pool, hot tub and basketball hoop. Gather the whole family in this welcoming home while exploring the Cape from its central location! BONUS: Linens and towels included! Let Us Tell You About This Home: Plenty of parking space in the long driveway as you approach this unassuming home. Enter through the front door into a sun-filled open floorplan of living and kitchen areas draped in hues of local sand and shells. Leave your shoes and your worries by the door on the large storage bench that lines the entryway. Make your way into the living room and take a seat on the large sectional to enjoy your favorite show on the flat screen TV. Beneath it is a gas fireplace that welcomes you with an adjacent comfortable chair. Adjoining the living space is the kitchen that begins its defined space with an oversized island accented by waterfall marble ends and serving the occupants of four bar height chairs. The white cabinetry, appliances and countertops achieve a complimentary flow with lines and swirls of copper colored hues utilized throughout. A sliding glass door on the side of the kitchen will bring you to the impressive outdoor living spaces which are introduced with the enclosable and heated patio and outdoor kitchen/bar surrounded by lounge furniture and game tables. Outside of this covered area you will find a large, fenced lot containing an above ground hot tub, an in ground pool, an area of grass for lawn games and a basketball hoop contained in the end of the driveway which continues beside the house to greet the back yard. Back inside the home, you pass through the open living spaces into a hallway that first leads to full Bathroom #1 with shower/tub combination. Across the hall is Bedroom #1 which has a Twin sized bed, flat screen TV and built in desk/work area with comfortable gaming chair. Bedroom #2 has a Full (Queen?) sized bed, flat screen TV and built in desk/work area also with comfortable gaming chair. At the end of the hall is Bedroom #3, the primary bedroom, offering a King sized bed, flat screen TV, large closet with barn door and full en suite Bathroom #2 with shower. Heading back to the living space/entry, next to the hall bathroom is the door leading to the lower level. At the bottom of the stairs, you find an auxiliary refrigerator, high end full sized washer/dryer in a laundry area and a desk/work space near the doorway that leads into the living spaces of the lower level. You first encounter Bedroom #4 with a built in desk/work area as well as a Twin sized bed. Accompanying this bedroom in the same hallway is full Bathroom #3 with shower. At the end of the hallway, you enter an open area with full kitchen (including refrigerator in laundry room) and bar, entertainment center with flat screen TV, couch and chair near another flat screen TV as well as a Twin sized bed with trundle. From this living space, you can exit to the backyard area near the driveway and basketball hoop by utilizing a stairway leading up to ground level. With a central location in Hyannis Woods as well as a pool, hot tub, well-appointed outdoor area and numerous living and entertaining spaces within, this home offers all that you need for a week of family fun on the Cape. You may never leave! Guest Welcome Starter Bag Included: A large reusable tote with: 2 rolls of toilet paper, tissues, hand soap, sponge, 2 trash bags, dish soap, dishwashing detergent, a roll of paper towels, laundry detergent and hand sanitizer (subject to change based on guest needs and marketplace availability). Free Tickets and Complimentary Activities! Create unforgettable memories and experience Cape Cod like a local! Enjoy $750 worth of daily exclusive free tickets to exciting local attractions through our partnership with Xplorie. Your amenities include activities such as Island Cruises, Whale Watch, Bike Rentals and admission to Whydah Pirate Museum. When you’re not soaking up the sun on the beach, enjoy daily rounds of golf at Cranberry Valley or Chequessett Golf Courses and mini-golf for family fun. This home has Keyless Entry for your convenience. NO SMOKING of anything containing tobacco, any other substance, and e-cigarettes, inside or outside of the home. PET FRIENDLY HOMES are for a DOG only. This home allows 1 dog with a $25 per night fee. With owner approval, a second dog may be considered for an additional $25 per night fee. A Pet Registration form must be completed upon reservation confirmation. Max parking of cars at property: 4 - No parking on lawn anytime. Additional Information to Assist You: Our calendars are updated in real-time and are accurate. Departure cleaning is included with your reservation at no additional charge. Simply follow our basic check-out instructions at your departure. State and local taxes are charged if applicable. For Reservations made over 60 days away, you will make two payments - 50% initial payment with reservation and the final balance will be auto billed to your credit card 60 days prior to arrival. We accept Mastercard and Visa for payments. A confirmed reservation is non refundable--please consider purchasing trip cancellation insurance. Ask our guest specialist for more details regarding cancel options and trip insurance. ***Linens - bed sheets, bath/dish/beach towels and bath mats ARE INCLUDED with this home. Please ask our guest specialist for details. You must be 25+ years old unless accompanied by a parent or guardian to book one of our Vacation Rental Homes. An ID must be furnished upon request. Area Info: *Mileage is approximate 2.1 Miles to Eugenia Fortes Beach 2.2 Miles to Keyes Memorial Beach 2.8 Miles to Craigville Beach 4 Miles to Wequaquet Lake boat ramp 0.8 Mile to nearest grocery and pharmacy stores Short 2 mile drive into the town of Hyannis where you will find : Shopping Restaurants Ferries to the Nantucket /Martha’s Vineyard Whale Watch Tours *Mileage is approximate Licence number: C0420370200

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! ®

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 $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! ®

Pool & Screened Deck! Home 2 Mi to Mashpee Commons

Mashpee, MA, US
4 Bedrooms 8 Guests
Sep 18 - 22
$425 night

Relax in this upscale escape that you and your family will adore no matter the time of year. Gather around the fire pit, have some fun in the pool, and pick from 5 Smart TVs when you’re not sightseeing. Boat or fish at John’s Pond, watch the waves come in at South Cape Beach State Park, shop and dine in style at Mashpee Commons, and take a ferry to Martha’s Vineyard. No matter how you choose to enjoy this 4-bedroom, 2-bath home, there’s something for everyone! -- THE PROPERTY -- MassTaxConnect ID C0447261720 | Charcoal Grill (Bring Your Own Charcoal) | Outdoor Shower | Wine/Beverage Fridge Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: Queen Bed | Bedroom 4: Twin Bunk Bed | Additional Sleeping: Crib OUTDOOR LIVING: Private outdoor pool & garden, 6 poolside deck chairs, fire pit (propane provided), screened deck INDOOR LIVING: 5 Smart TVs w/ cable, DVD player, gas stove, board games, high chair, ceiling fan, central A/C, electric heat KITCHEN: Fridge, stove & oven, dishwasher, microwave, toaster oven, cooking basics, dishware & flatware, Nespresso Vertuo Next w/ welcome pack of capsules, Cuisinart electric kettle, ice maker, water filter, trash bags, paper towels GENERAL: Free WiFi, washer & dryer, laundry detergent, clothes steamer, iron & board, hair dryer, towels & linens, hangers FAQ: Ring doorbell camera (facing out), beach access currently unavailable SUITABILITY: 2 stairs to access, 1st-floor bedroom & bathroom PARKING: 43’ driveway (3 vehicles), RV/trailer parking w/ backup generator, EV charger -- THE LOCATION -- SAND & WATER: John's Pond Park (4 miles), Loop Beach (6 miles), South Cape Beach State Park (8 miles), Falmouth Heights Beach (9 miles), Old Silver Beach (9 miles) TO DOS: Mashpee Commons (2 miles), Cape Cod Fairgrounds (2 miles), Quashnet Golf Course (2 miles), Cape Cod Children's Museum (5 miles) NEAR THE COAST: Mashpee National Wildlife Refuge (6 miles), Hyannis Port (14 miles), Martha’s Vineyard (14 miles to Woods Hole Terminal), Nantucket & Martha's Vineyard (15 miles to Hyannis Cruise Terminal) AIRPORT: Cape Cod Getaway Airport (14 miles), Boston Logan International Airport (72 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 - NOTE: Access to this home requires 2 stairs; there is a bedroom and full bathroom available on the 1st floor - NOTE: Your safety matters. This property features 1 exterior security camera. The camera is a Ring doorbell device with an exterior security camera facing the front outdoor entry. It does not look into any interior spaces. The camera actively records video and sound when motion is detected by the devices (including devices linked to the cameras such as the alarm system’s motion detector) or when the video doorbell button is pressed - NOTE: Access to John's Pond Beach is currently unavailable; however, there is a public access beach on the north shore of the pond, just a short drive away Licence number: C0447261720;STR-24-0011;STR-25-0007;STR-26-0010

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

Brewster, MA, US
10 Bedrooms 20 Guests
Aug 30 - Sep 2
$2,425 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! ®

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
$1,323 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

Brewster Barefoot Bliss: 3447-BMH Luxury Brewster Estate – Pool, Hot Tub, & Steps to Nature

Brewster, MA, US
6 Bedrooms 12 Guests
Aug 29 - Sep 1
$2,365 night

This home is professionally managed by Pretty Picky Properties Luxury Brewster Estate – Pool, Hot Tub, Steps to Bike Trail "Brewster Barefoot Bliss" 3447-BMH Rents Saturday to Saturday in Peak Season Linens Included, Beds Made Six bedrooms, Seven Full Baths Sleeps Twelve Pets Considered **Additional separate two bedroom cottage available to rent next door, total occupancy of sixteen possible** Discover the perfect blend of classic Cape Cod charm and modern luxury at this stunning six bedroom vacation home in Brewster. With four private bedroom suites and space to sleep 12 guests, this expansive retreat is designed for relaxation and adventure alike for groups of any size. Location Nature lovers will appreciate the home’s prime location—adjacent to the popular Cape Cod Rail Trail bike path and just across the street from Nickerson State Park. Spend your days exploring the park’s scenic trails or take a short stroll (under a mile) to Crosby Landing Beach, considered Brewster’s best by many. You can be in downtown in Orleans in about two miles via the bike path. Outside Living Space No doubt most of your lounging and living will be done out on the spacious pool patio with a covered cabana area, gorgeous outdoor kitchen, a large dining table and chairs, a full bathroom and, of course, the heated pool. There’s also a hot tub and gas fire pit, ideal for gathering under the stars. You can whip up a feast in the cabana’s completely outfitted outdoor kitchen. The large, manicured yard is bordered by a tasteful variety of flowering plantings and makes a perfect place to throw a Frisbee ® or whack a Whiffleball ® And here’s an unusual extra amenity: your own private hockey rink! The special synthetic surface accommodates both roller blades and ice skates. Inside Living Space This home seamlessly blends classic coastal elegance with modern finishes, offering stylish and comfortable living spaces. The main level consists of a spacious and elegant kitchen, complete with everything you’ll need to prepare any meal and entertain any group. There’s seating for 12+ at the main dining table and adjacent round table plus there’s additional counter seating at the immense kitchen island. This part of the main level includes a wet bar, pantry and parlor. Fitness enthusiasts will appreciate the fully equipped gym. Then there’s the “Great Room,” which is nothing short of awe inspiring. Original to the structure, this room with soaring ceilings exudes old world charm in stunning fashion. The wood paneled walls are from a French chateau, the circular stairs from a British ship. Sleeping Accommodations The main level rounds out with two bedrooms, one with a queen, the other with a pair of twins, plus a full bath and a half bath. There are three, count ’em, three sets of stairs to the second level bedrooms. The first is off the small parlor and features a vintage narrow staircase to a queen bedroom with a private full bath. The second, more modern staircase leads to a second level area with two queen-bedroom suites, each with a private full bath. The final upstairs area is the most recent renovation and is essentially a self-contained apartment with a living area, kitchenette, king bedroom and a luxurious bathroom with a step-in shower, soaking tub and dual vanity. For a summary of bedrooms and bed configurations, use the Room Details tab above. Amenities This home has high speed WiFi, a Sonos® Sound System and central air conditioning. For a complete list of amenities, please click on the Amenities tab above. The owners reside in a smaller home on the grounds. so you can be sure that any issues that may arise will be quickly addressed. But you won’t see them unless you need them. Book now and experience the best of Brewster in this extraordinary vacation retreat. 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 vacation rental on Cape Cod. It’s your vacation. Get Picky! ®

2 Mi to Beach: Falmouth Group Getaway w/ Game Room

Falmouth, MA, US
4 Bedrooms 8 Guests
Aug 31 - Sep 3
$517 night

Get the most out of your next exciting Atlantic getaway when you stay at this charming East Falmouth vacation rental! With a fully stocked game room, serene covered patio, and great location just minutes from the coast, this 4-bedroom, 3-bath house is perfect for keeping everyone entertained while in town. Relax on the shores of South Cape Beach, check out local fishing charters, or explore shopping and dining options at Mashpee Commons before heading home to end the day with a game of 8-ball! -- THE PROPERTY -- C0424120960 | Covered Patio | In-Unit Laundry | 4 Mi to Downtown Falmouth | 8 Mi to Woods Hole Ferry Terminal Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Full Bed, Twin Bed | Bedroom 4: Twin/Full Bunk Bed w/ Twin Trundle, Twin Bed | Game Room: Queen Sleeper Sofa | Mudroom: Full Futon INDOOR LIVING: Smart TVs, dining table, walk-in closet, en-suite bathroom, walk-in shower, ceiling fans GAME ROOM: Pool table, foosball table, dartboard, board games OUTDOOR LIVING: Outdoor seating, patio heater, outdoor shower, gas grill (propane provided) KITCHEN: Refrigerator, Keurig & drip coffee makers, stove/oven, microwave, toaster oven, blender, dishwasher, dishware & flatware, cooking basics, spices GENERAL: Self check-in, free WiFi, central heating, window A/C units, washer & dryer, laundry detergent, iron/board, towels/linens, trash bags/paper towels, complimentary toiletries, hair dryer ACCESSIBILITY: 3-story house, 2 steps required to enter, interior stairs required to reach all bedrooms on upper & lower levels PARKING: Driveway (8 vehicles) -- THE LOCATION -- AREA BEACHES: Menauhant Beach (2 miles), Old Silver Beach (8 miles), South Cape Beach State Park (9 miles) ON THE WATER: Patriot Party Boats - fishing charters (4 miles), Rideaway Adventures - kayak & canoe rentals (8 miles) NEARBY ATTRACTIONS: Cape Cod Winery (2 miles), Downtown Falmouth (4 miles), Highfield Hall & Gardens (5 miles), Mashpee Commons (6 miles), Cape Cod Children's Museum (7 miles), Nobska Lighthouse (8 miles) AIRPORTS: Boston Logan International Airport (75 miles), Rhode Island T.F. Green International Airport (78 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 - NOTE: While this 3-story house only requires 2 steps to enter, additional interior stairs are required to reach all of the home's bedrooms on the upper and lower levels Licence number: C0424120960

Three Buoys: 739-C Stunning Newly Built Custom Compound in Chatham with a Resort-Style Ambiance

North Chatham, MA, US
5 Bedrooms 11 Guests
Sep 27 - Oct 4
$1,565 night

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

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

Chatham, MA, US
5 Bedrooms 12 Guests
Sep 7 - 10
$1,078 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 $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

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Vacation Rentals Near Sandwich

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