House vacation rentals in Chappaquiddick Island

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Popular amenities for Chappaquiddick Island house rentals

House rentals with a pool

Superhost
A spacious dining area is showcased from an elevated perspective, featuring a large wooden table surrounded by white woven chairs. Delicate blue plates rest atop the table, with a vibrant green arrangement at the center. Natural light floods the space through large glass doors.
Home in Barnstable
4.8 out of 5 average rating, 20 reviews

Stunning Cape Home - Inground Pool, 5 Min To Beach

KristenRating, 5 stars1 week ago
This house and property were charming and beautiful. The location was extremely close to beaches, restaurants, and stores all while being nestled in a quiet neighborhood. Highly recommend!
Guest favorite
An outdoor deck is visible, featuring a wooden table surrounded by blue cushioned chairs. The light-colored house exterior is complemented by a finished roofline and large glass doors, allowing natural light to brighten the space. Trees provide a natural backdrop.
Home in Mashpee
5 out of 5 average rating, 12 reviews

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

CarolRating, 5 stars1 week ago
We loved are family stay at Paul & Katie’s home for Easter Week. It is a dream home . The neighborhood was beautiful and walkable, with a peaceful path to a private beach. We enjoyed the shops and restaurants in Mashpee Commons about an 8 minute drive away.
Superhost
A comfortable living area is framed by a stylish sectional sofa and wooden accent chair. A dark coffee table contrasts with light-toned walls, while a large screen is mounted above a wooden slatted feature. The open layout offers views of a contemporary kitchen in the background.
Home in Sandwich
4.64 out of 5 average rating, 11 reviews

New Cape Escape for 10 People With Heated Pool

LaurenRating, 5 stars6 months ago
Perfect stay. Pool was amazing. Host was very responsive to everything. Great for families, Just bring socks with friction pads on the bottom so you don’t slide .
Top guest favorite
Home in Oak Bluffs
4.94 out of 5 average rating, 194 reviews

Spectacular beach & pool combo; beautiful sunsets!

JillRating, 5 stars3 weeks ago
The house was beautiful, very comfortable and extremely well equipped. I would highly recommend this home. We had a wonderful stay there!
Superhost
Home in Falmouth
5 out of 5 average rating, 3 reviews

Spacious home with Pool! Close to Beaches & Town!

michaelRating, 5 stars8 months ago
it is a nice comfy house esp for a family. Swimming pool and game room down in the basement would be alot of fun for kids to keep them busy at day time and night time. Beach, restaurants, grocery stores, liquor stores, etc are all right there esp. only like less than 5 to 15 minutes drive and also less than 25 minutes drive to go to north Falmouth or Wood Hole. They have a nice downtown with many stores, restaurants, bowling ally, etc which that is only less than 15 minutes drive from the house Also taking a walk from the house to the beach is so beautiful esp morning time. i walked every morning, and love every bit of the walk. It rained once during our vacation week and rest were sunny days for the rest of the week. We were lucky to have the good weather. Anyway, the house is approximately about less than a mile and half from the beach. Driving to Chetham is about little a hour drive from the house. To Provincetown, about 1 hour and 45 minutes drive.
Guest favorite
The outdoor pool area is surrounded by a black metal fence and features clear blue water. A swan-shaped float is situated on the water, while lounge chairs are positioned nearby. An umbrella provides shade, enhancing the inviting setting.
Home in Falmouth
5 out of 5 average rating, 13 reviews

New Construction Home with Pool in N. Falmouth

MichelleRating, 5 stars7 months ago
Had a great family vacation for my sisters wedding. House was perfect for our toddlers with kids room in basement. Stunning home and amenities, the perfect Cape Cod vacation home!
Guest favorite
A well-maintained swimming pool reflects the greenery surrounding it, bordered by a stone deck. Poolside seating arrangements include a black metal table with chairs and a blue lounge chair. A red umbrella offers shade, while the exterior of the home features a wooden deck and bright lounge furniture.
Home in Yarmouth
4.9 out of 5 average rating, 42 reviews

Winslow Acres [heated] Pool Escape; pool May 15

JeannineRating, 5 stars8 months ago
The house was clean and comfortable. I loved the coffee bar:) my kids loved the pool and hot tub. And it was especially great to be able to bring my dog! We will definitely rent again.
Top guest favorite
A spacious backyard is highlighted by a private, unheated in-ground pool surrounded by paved areas. Colorful lounge chairs and an inflatable float add to the inviting atmosphere. A patio table with patterned cushions is positioned nearby, offering a space for relaxation and outdoor dining.
Home in Barnstable
4.95 out of 5 average rating, 113 reviews

Private Pool, near beaches, 3 BR/3 BA, Central Air

CamilleRating, 5 stars7 months ago
There should be more than 5 stars for this lovely property and its hosts!!! We were three couples vacationing for the first time on the Cape and this charming home was perfect for us. Conveniently located to serve as home base for many excursions we felt immediately at home. We each had our own themed bedroom with en suite bathroom and TV. All common areas including the sun porch and outdoor deck were fantastic places to gather and enjoy our time together. Our hosts were so pleasant and helpful throughout our stay. As only one example, on a rainy day the host proactively contacted us wth suggestions on things to do in the event of rain on the Cape. We so appreciated this thoughtful gesture and there were many more. When I think about it, this really sums up why we had such a wonderful time. Everything about this property speaks to how much these hosts care about their guests! Hope to return one day. Thank you!

Weekly house rentals

Guest favorite
A sandy beach area is captured, featuring soft dunes and gentle ridges formed by the wind. A building with a distinctive cupola is visible in the distance, surrounded by wooden walkways. Clear blue skies complement the serene coastal setting.
Home in Centerville
4.88 out of 5 average rating, 111 reviews

#25 Seasonal Cottage is 200 feet from the Beach

RuthRating, 5 stars6 months ago
A minor communication glitch between host and cleaners meant two of the beds had not been made and probably a general cleaning between guests wasn't done. Fortunately the property was already very clean and the guests before me must have been, too. Everything else was in order. When I let the host know, she immediately contacted the cleaners while I went out for groceries. By the time I got back, the place was perfect and the cleaners were gone. I don't think this is a regular occurrence at all. In October this neighborhood was very quiet, which is a priority for me. And I felt very safe, which is also important. I would definitely return and highly recommend.
Top guest favorite
The spacious kitchen features white cabinetry and a modern layout. A central island with seating is complemented by a dining table nearby. Natural light floods the area through sliding glass doors, enhancing the welcoming ambiance.
Home in Yarmouth
4.95 out of 5 average rating, 151 reviews

Cape Cod Life is Good Rentals

JaredRating, 5 stars4 weeks ago
This was a great place for a large family. The kids especially enjoyed riding bicycles through the neighborhood. The house was spacious and comfortable. We plan to stay again.
Superhost
A spacious living area is highlighted by a large blue sectional sofa, complemented by several accent pillows. Large glass doors provide a view of the deck, while pendant lights hang from a vaulted wooden ceiling, enriching the open atmosphere.
Home in Tisbury
4.69 out of 5 average rating, 158 reviews

Carolyn's Vineyard Haven

JenniferRating, 5 stars1 week ago
We had a wonderful stay at this beautiful Martha’s Vineyard home! It was incredibly spacious - perfect for our family of 5 and could easily fit more. Thoughtfully decorated and stocked with everything a real home has, from quality kitchenware to high-end soaps and shampoos (a rare Airbnb treat!). Our kids especially loved the triple bunk bed. Check-in was a breeze, and the location couldn’t be better. We’d absolutely stay here again!
Guest favorite
A serene bedroom space features a blue quilted bedspread and vibrant accent pillows. Above, decorative sailboat models are displayed against a light wall. Natural light streams in through a window, illuminating wooden furniture, including a dresser and built-in closet doors.
Home in Nantucket
4.86 out of 5 average rating, 22 reviews

Beautiful Custom Nantucket Home

RobertRating, 5 stars4 weeks ago
Perfect Madaket location in a great neighborhood of year around residents. The beach is a 10-minute walk through amazingly beautiful conservation land. Our dogs loved every minute. The house is clean, well-appointed and equipped with all of the amenities you need for a Nantucket holiday. Adam is a top notch communicative host who goes out of his way to ensure your stay is special. We will be returning to the Pineapple House.
Guest favorite
A two-story cape cod home is showcased, featuring a light-colored exterior with blue shutters. A well-maintained driveway leads to a covered entryway, and a lush green lawn surrounds the property. Mature trees provide shade, enhancing the welcoming outdoor space.
Home in Falmouth
4.84 out of 5 average rating, 74 reviews

Expansive & Renovated Teaticket Cape

AnnieRating, 5 stars3 weeks ago
Great house for a larger group. It has all the amenities and lots of beds. Very close to the ocean and Brien was easy to communicate with. Thank you for having us at your home!
Guest favorite
A grassy outdoor space features two blue Adirondack chairs and a small fire pit, surrounded by trees and overlooking a serene pond. A hammock hangs in the distance, while the deck is visible on the right, extending from the house.
Home in Oak Bluffs
4.83 out of 5 average rating, 193 reviews

Waterview, Private, Walk to Beach, Mile to Town

LaurenRating, 5 stars6 months ago
We stayed at Lisa’s place for three nights and it was a 10/10 experience. Lisa was a fantastic host and was very helpful with island recommendations prior to our trip. The property itself is stunning and although we wanted to explore the island, the property also provided a beautiful landscape to just relax. Even given its private, peaceful location, it was still so convenient to town. The house is an adorable converted barn that has incredible, rustic charm and the decor was so beautifully thought out. Before we even left we were talking about booking again in the future. We definitely recommend booking here!
Top guest favorite
A waterfront hot tub is set against a natural backdrop of trees and calm waters. Inside, a dining area features a large window with views of the lake. A cozy living room displays comfortable seating, while an outdoor patio has seating for relaxation and enjoying the scenery.
Home in South Yarmouth
4.95 out of 5 average rating, 230 reviews

Waterfront★ Hot Tub ★ Kayaks ★ Firepit ★ Pet OK

MonicaRating, 5 stars4 weeks ago
From the moment we entered until We packed up we felt a world away from the house selling process. Aruna and Joe have done a beautiful job decorating the house inside and out. It felt so cozy to sit with the gas fireplace and look at the mallards, Canada geese and swans float by. The location was perfectly situated in a very safe neighborhood yet close to route 28. We loved our stay and hope to come back to explore the pond by kayak. Thank you so much!
Superhost
A spacious lower-level room is highlighted by a large sectional sofa facing a wall-mounted flat-screen TV. Light grey walls and new flooring enhance the fresh aesthetic. A staircase is visible in the background, leading to the main level, while a closet is seen on the right.
Home in Dennis
5 out of 5 average rating, 18 reviews

Newly Renovated! Less than 1 mile from the beach.

LindaRating, 5 stars8 months ago
The house was very clean and everything was in working order. There were plenty of towels and space for our family. (It rents for 8 people but we only had 6 for 1 night and 4 for the rest of the nights and a baby.) But even if we had 8 people, there would have been plenty of space.

Private house rentals

Top guest favorite
A spacious outdoor deck is surrounded by greenery and blooming flowers. A table with matching chairs occupies the center, complemented by an outdoor grill nearby. The soft colors of the area rug add warmth to the inviting space, perfect for gatherings.
Home in Falmouth
4.92 out of 5 average rating, 78 reviews

Private home with walkable freshwater beach access

MatthewRating, 5 stars7 months ago
The house was as advertised. In a nice quiet area. The house was well set up and as advertised. We felt right at home for the weekend.
Superhost
The exterior of the home is presented at dusk, featuring soft outdoor lighting and classic blue siding. A pathway of stone leads to the entrance, flanked by neatly manicured shrubs and a lawn. A small porch area and steps provide access to the front door.
Home in Barnstable
4.88 out of 5 average rating, 133 reviews

The Mills Retreat- 3BR/2Bath - Beach pass included

JulieRating, 5 stars4 months ago
This was a family Christmas getaway, and it was perfect.
Top guest favorite
Home in Yarmouth
5 out of 5 average rating, 12 reviews

Spacious Mid-Cape Home 5 Bedrooms, 9 Beds, 3 Bath

HannahRating, 5 stars4 months ago
We absolutely loved our stay at Rachel’s! We kept saying “this place has everything”. It was a wonderful home for a multi generation holiday hang. From a 7 month old to great grand parents. The main floor was easily accessible for family member with a disability. We felt right at home with our 7 month old, the home had a pack n play - all set up with fresh sheets, baby bath tub, high chair, bath toys, monitor, etc. The basement was perfect for the teenagers to hangout and have their space. The backyard was peaceful and extended the hang area. Rachel was incredibly friendly and responsive.
Guest favorite
A charming single-story house is surrounded by well-maintained gardens featuring colorful hydrangeas and tidy shrubbery. A private driveway is visible alongside the house, complemented by a rustic wooden fence that adds to the property's warmth. The front entrance is framed by seasonal blooms.
Home in Dennis
4.96 out of 5 average rating, 68 reviews

Quaint Cape Beach House

SamanthaRating, 5 stars4 months ago
The house was cozy, quaint, and spotless—perfect for our off-season weekend getaway! Adele was incredibly accommodating and flexible with us, and her communication was top-tier. We couldn’t have asked for a better experience and would happily stay again. Highly recommend!
Superhost
An open concept living area features high cathedral ceilings with natural wood finishes. A modern gray sofa with red and black accent pillows is positioned near a vibrant wall art piece. Doorways lead to a dining area and kitchen, enhancing the spacious layout.
Home in Mashpee
4.91 out of 5 average rating, 34 reviews

New Seabury home, private yard, great location

MikeRating, 5 stars6 months ago
Comfortable yet spacious home nestled in the woods of New Seabury. Great location to visit beaches and restaurants. Just minutes from Mashpee Commons and Falmouth for shopping and dining. Beautiful place, Thanks Alex!
Superhost
The exterior of the home is shown, featuring a spacious deck with seating overlooking a large, grassy backyard. The landscape is bordered by trees, with a fenced area visible in the background. A storage shed is located to the left in the distance.
Home in Sandwich
4.77 out of 5 average rating, 26 reviews

Holiday in the sun!

KaylaRating, 5 stars1 week ago
Craig was awesome and extremely nice and understanding! The house was clean and one of the best I have stayed in. The location is quiet and tucked in a small neighborhood. I had the most amazing stay and would suggest this to anyone going to this location!
Guest favorite
The exterior of a two-story house features natural shingle siding and a welcoming front porch. Lush hydrangeas line the walkway, providing a vibrant green and white contrast against the home. Multiple large windows invite natural light into the living spaces.
Home in Tisbury
4.86 out of 5 average rating, 69 reviews

Your home away from home

CristinaRating, 5 stars8 months ago
Patricia was very responsive before and during our stay. She was easy to communicate with and gave great suggestions for beaches to visit. The house is about a 10 minute drive from the closest beach. It’s near water but it’s more for fishing or boating. It’s less than 10 minutes from the center of town where there are great places to eat and shop around. The house is beautiful and spacious. Two bedrooms and a full bathroom on the main level and 2 bedrooms and a full bathroom the second level. Highly recommend.
Superhost
An aerial view of the property reveals two distinct homes set on a half-acre lot. The front house features a gray exterior with a central entryway, surrounded by neatly trimmed greenery. The back house, smaller in size, complements the overall layout, with a spacious gravel area visible between them.
Home in Dennis
5 out of 5 average rating, 3 reviews

Lower County Compound

HeatherRating, 5 stars7 months ago
If you're planning a Cape getaway with a large family, this home is an absolute gem! We had both homes on the property, and it worked out perfectly—one for the early risers and the other for the night owls. The homes were incredibly clean and offered plenty of outdoor space. The property is surprisingly large for the Cape, with expansive outdoor areas to enjoy, and the outdoor shower was the best I've ever experienced—spacious and very private. Both homes were fully stocked with everything we needed to cook in, which we did a few times, and everything worked flawlessly. Even though it's on a main road, the traffic noise was minimal, and we always felt peaceful. I’m very particular about where I stay, but this home checked all the boxes. I can't think of a single negative. Dom, the property manager, was fantastic—super responsive to all our questions and truly a top-notch host! I hope this property continues to be available because I will definitely be back!

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