House vacation rentals in Chappaquiddick Island

Find and book unique houses on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Chappaquiddick Island house rentals

House rentals with a pool

Top guest favorite
Home in Sandwich
4.99 out of 5 average rating, 82 reviews

"Cape Escape" luxury home w/pool & beach access.

JanelleRating, 5 stars3 weeks ago
We have stayed in multiple houses / penthouses throughout the U.S. , however, this home surpassed them all. Jennifer was amazing from the beginning of the booking with answering my questions and went above and beyond to make this special occasion memorable. The house is well equipped! The sounds of birds chirping in the morning , the breeze, and the view of the pond when drinking coffee was so serene. The space in the house was more than I expected with everyone having lots of space to enjoy all the designated areas for playing board games, Video game room( so cool) , reading , watching tv - there was a room for everyone’s enjoyment from our 12 year old, 17, 25, to my 78 year old parents. The well thought out toiletries in every bathroom, spa slippers and robes in each bedroom, ear plugs located by the bedside, laundry room that has labeled racks of beach items and games , kitchen with all its wonderful amenities- I can do on and on. We WILL be back !
Guest favorite
The charming exterior of the newly renovated home is highlighted by a sloping roof and a welcoming front door. Framing the entrance are neatly trimmed bushes and a small pathway leading to the door. A garage is located on the side, complemented by grassy green surroundings.
Home in Falmouth
5 out of 5 average rating, 15 reviews

Home in Falmouth ~ 5 min drive to beach

AnnieRating, 5 stars10 months ago
This rental is exactly as described with accurate pictures. It was recently renovated with all new furnishings, new kitchen, appliances and baths. Our family enjoyed the brand new outdoor deck, picnic tables, gas grill, swing and s’mores by the fire pit. Unfortunately it was too chilly to use the pool. The kitchen had all supplies to make a large pasta meal. Our daughter ran the Falmouth Road race and so Sunday was a bit chaotic and the owner gave us flexibility to check out a bit later, which was a huge help!!. A wonderful family vacation!! Highly recommend.
Guest favorite
The spacious outdoor area features a heated saltwater pool surrounded by paver stones. Lounge chairs are positioned around the pool, accompanied by blue umbrellas. A nearby cabana is visible, along with vibrant landscaping, providing a relaxing atmosphere for guests.
Home in Mashpee
5 out of 5 average rating, 12 reviews

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

CarolRating, 5 stars1 month 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.
Guest favorite
An outdoor pool area showcases a heated inground pool with clear water, surrounded by a wooden deck. Sun loungers are placed nearby, and patio umbrellas provide shade. Lush greenery and trees line the background, offering a serene environment. A beach ball floats in the water.
Home in Mashpee
5 out of 5 average rating, 20 reviews

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

AriannaRating, 5 stars2 weeks ago
We had a wonderful stay here in New Seabury! The house is beautiful, spacious and just as described. The heated pool was an added bonus! Michael provided prompt and clear communication when needed. I would absolutely stay here again!
Top guest favorite
A spacious colonial house is framed by lush green grass and mature trees. The exterior features dark shingles with multiple windows reflecting natural light. A winding driveway leads to the entrance, while a wooden fence provides privacy at the rear.
Home in Edgartown
4.92 out of 5 average rating, 49 reviews

Beautiful Edgartown Colonial with heated pool.

DavidRating, 5 stars2 weeks ago
We had such a fantastic stay at Sue’s beautiful Edgartown home! The house was charming, spotless, and well-stocked with everything we needed—from kids’ toys and extra keys to cozy spaces for the whole family. Even with some chilly weather, we made great memories thanks to Sue’s warmth and hospitality. One huge highlight was the car rental—what a convenient bonus! It was clean, reliable, and made exploring the island a breeze. Sue was responsive and thoughtful throughout our stay, checking in with helpful suggestions and going above and beyond. She truly made us feel at home. From shell picking at Felix Neck to relaxing in the playroom and enjoying everything the Vineyard has to offer, our family had a wonderful time. We’re already talking about our next trip back—and hoping Sue’s hot tub addition is ready by then! Highly recommend!
Guest favorite
A view from the deck reveals a well-maintained pool area surrounded by lounge chairs and umbrellas. Adjacent to the pool is a tennis court, framed by greenery, providing a serene backdrop. The water sparkles under a clear blue sky, inviting relaxation.
Home in Falmouth
4.95 out of 5 average rating, 38 reviews

Dog Friendly Cape Oasis | Pool+Beach |Tennis Court

SydneyRating, 5 stars5 days ago
Emily was so kind and responsive and the house was exactly as expected. The walk to the beach was lovely and doable with the toddlers thanks to the wagon provided. It was a quick drive into all things Falmouth and a great home base for us. The stand outs for everyone were how comfy the beds were and we were all obsessed with the outdoor shower. Loved all the thoughtful amenities, such as games and kids dinnerware. Overall very stylish and comfortable. Highly recommend.
Top guest favorite
An outdoor space features a landscaped area with lush greenery and a fenced backyard. A heated plunge pool is surrounded by stone patio tiles. Comfortable seating is arranged under a shaded umbrella, inviting relaxation in a peaceful setting.
Home in Yarmouth
5 out of 5 average rating, 9 reviews

Yarmouthport house heated pool/hot tub near beach.

AngeliqueRating, 5 stars1 week ago
Wonderful place to stay! So comfortable and lots of space! Close to lots of restaurants and shopping! Would definitely stay again!
Top guest favorite
A private, gated pool is surrounded by a concrete deck and bordered by lush greenery. The sparkling blue water is enhanced by a bright yellow floating ring. In the background, a spacious sunroom and outdoor seating areas are visible, offering convenience and leisure options.
Home in Barnstable
4.95 out of 5 average rating, 114 reviews

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

ZackRating, 5 stars8 months ago
Awesome stay! Great house/location and Sandy is an awesome host. Highly recommend

Weekly house rentals

Guest favorite
A modern kitchen features a spacious island with four bar stools and stylish pendant lighting above. Sleek white cabinetry complements the elegant quartz countertop. Large windows provide natural light, and stainless steel appliances, including a gas range and refrigerator, are visible in the background.
Home in Oak Bluffs
5 out of 5 average rating, 26 reviews

Vineyard Vacation, 3-Bedroom, Hot-tub, Golf course

JayneRating, 5 stars1 month ago
The home was clean and cozy. Updated decor and well supplied with everything we would need. I would stay again.
Guest favorite
A spacious outdoor deck features comfortable, cushioned seating with a view of the ocean. A table is positioned centrally, inviting gatherings. The tranquility of the scene is enhanced by natural grass and the serene waters in the background, creating an ideal relaxing space.
Home in Yarmouth
4.95 out of 5 average rating, 56 reviews

Oceanfront Vacation Home with Private Beach for 6

JeffreyRating, 5 stars6 days ago
This is a true hidden gem. A stones throw from one of the best raw bars in Yarmouth (or Cape Cod for that matter), literally steps (like 5 steps right out the slider) from the beach, stunning views and sunsets. Very clean and cozy cottage, and our host was excellent. The value was also incredible. Very central in Cape Cod, meaning anything you want to do besides Provincetown is 30 mins or less in any direction. Yarmouth had a charm of its own, especially for a family with young children. Lots of kids activities within 5 minutes. A+++
Guest favorite
The exterior of a charming shingled cottage is displayed, featuring a welcoming front porch with steps leading to the entrance. Green shutters flank the windows, and an American flag adds a patriotic touch. The surrounding grassy lawn enhances the home's inviting appearance.
Home in Edgartown
4.91 out of 5 average rating, 54 reviews

Updated Beautiful Cottage in Edgartown AC

RayRating, 5 stars7 months ago
Kenneth Is a great host communicates very well and has a genuine concern for his guests Ray
Superhost
The log cabin is surrounded by greenery, featuring a spacious patio area designed with stone flooring. A wooden picnic table sits in the foreground, while the cabin's deck provides a warm, welcoming entrance with steps leading up to it.
Home in Edgartown
4.83 out of 5 average rating, 12 reviews

Charming Edgartown Log Cabin with Peloton bike

DianaRating, 5 stars9 months ago
This is our second time staying here and we wouldn’t stay anywhere else! Conveniently located on the island but our favorite part is the tranquil, peaceful setting. The property abuts a wooded park which is perfect for walking and bird watching. We love the relaxing atmosphere. We will definitely be back again! Diana and Frank
Guest favorite
A bright living room features large windows offering views of the beach. Light-colored furnishings are complemented by a patterned area rug. A coffee table is centrally positioned, with decorative items placed atop. Two chairs provide additional seating, enhancing the open space.
Home in Fairhaven
4.94 out of 5 average rating, 32 reviews

Lovely Day Oceanside

KathleenRating, 5 stars3 weeks ago
Tina's BnB is so peaceful and in a beautiful setting with a beach. The cottage is right on the bay - sunsets are stunning. The bed is very comfortable, which is unusual for most BnBs. It is in a quiet neighborhood, and I slept well each night! Everything was clean. Even though I ate out nightly, the kitchen had all that you need to prepare a dinner. There is also a shed with beach toys and chairs. Tina checked in a few times through the message app and offered assistance, but I had everything I needed. I loved my stay and will return in the future!
Top guest favorite
A bright living space features two orange chairs and a large blue ottoman. A wall-mounted smart TV is visible, and a dining area with colorful chairs and a chandelier is located nearby. A ladder leads to a loft area above the seating.
Home in Falmouth
5 out of 5 average rating, 62 reviews

Waterfront-Kayaks & SUPs-Firepit-Pet OK-Kingbed

JudithRating, 5 stars1 month ago
Beautifully remodeled home, lovely setting on a large pond. Everything was clean, the kitchen was well stocked. I am an avid cook/home chef and appreciate the decent cookware. So many places have understocked kitchens and wounded cookware. Comfortable King bed. Thoughtfully decorated. Nice quiet neighborhood. We travel with our 13 year old boxer who has traveled the country and we appreciated the one level living. We did not mind being farther from town, we love the wildlife and the beautiful swan swimming on the pond! The host, Benjamin, was easy to get ahold of, though we had no issues with anything at all. The booklet on Salt Crystal that was sent ahead to us was extremely helpful to us! We would definitely stay here again!
Guest favorite
The exterior of a two-unit house is displayed, featuring a central white door framed by two symmetrical windows. Flowering shrubs in vibrant pink and white enhance the landscape, while a gravel yard stretches out in front. The structure is surrounded by trees providing shade.
Home in Edgartown
5 out of 5 average rating, 15 reviews

Walk to downtown Edgartown in a quiet neighborhood

SamanthaRating, 5 starstoday
Katie was an excellent and responsive host. She was proactive and sent clear check in instructions without having to ask and the space was very clean. We also loved how close to Edgartown the home is located.
Guest favorite
An enclosed front porch features multiple windows providing a view of the surrounding greenery. Two rocking chairs are positioned on a patterned rug, alongside a wooden table and lamp. Natural light fills the space, creating a bright and open atmosphere.
Home in West Tisbury
5 out of 5 average rating, 47 reviews

Idyllic renovated home across from Seth's Pond

PaulineRating, 5 stars7 months ago
We loved our stay, would definitely stay again! Meredith was very helpful and responsive. The house was beautiful and very clean. Highly recommend.

Private house rentals

Top guest favorite
A bright living area features a gray sectional sofa facing large windows, allowing natural light to fill the space. The vaulted wood ceiling adds warmth, while the kitchen is equipped with stainless steel appliances and a wooden dining table, enhancing the open-concept design.
Home in Tisbury
5 out of 5 average rating, 17 reviews

Family Friendly 5 BR, Walk to Town, Beach & Ferry!

LindsayRating, 5 stars6 days ago
What a wonderful stay we had! The house was stocked with anything you could think of and the host Caroline was readily available for any questions. Will absolutely come back and recommend to all!
Guest favorite
A spacious, modern home is set against a vibrant sunset, featuring a large patio area with lounge chairs. Glass doors provide a view of the outdoor hot tub and well-maintained yard, highlighting a welcoming atmosphere for relaxation and enjoyment.
Home in Yarmouth
5 out of 5 average rating, 15 reviews

Gorgeous Renovation - Boat Dock, Hot Tub, 5 Beds!

NoahRating, 5 stars1 month ago
This property is on another level. It’s the four seasons of Airbnb. It’s such an immaculate place to stay and we loved every part of it. The cleanliness, the high quality of the essentials, the coziness, ambience and so much more was truly worth the stay.
Guest favorite
The exterior of a cape style home is presented, featuring a dark wood shingle facade and multiple gabled rooflines. A white front door is flanked by evergreen shrubs, while a stone path leads to the entrance. Lush green grass surrounds the property, complemented by a wooden fence.
Home in Edgartown
4.93 out of 5 average rating, 92 reviews

Walk to EDG Wharf - Beautiful Home with AC & Grill

HillaryRating, 5 stars4 days ago
Wonderful place for my large family to stay for a wedding weekend! Definitely located close by things so easy walk but also large driveway so we could bring cars and drive to things. The master bedroom is unbelievably huge! Amazing if you have a baby/pack and play.
Guest favorite
A coastal retreat is presented with a light gray exterior and large windows on the ground level. A wooden deck sits atop the structure, providing additional outdoor space. The surrounding area features gravel and sparse vegetation, with nearby buildings visible in the background.
Home in Mattapoisett
4.9 out of 5 average rating, 10 reviews

Buzzard Bay Getaway

AnnaRating, 5 stars8 months ago
While the weather did not cooperate (it rained the entire time) the cottage and views made up for the weather. From the table to the couch the views are wonderful. The cottage is very well stocked from towels and blankets to the kitchen. We did not need anything that wasn't supplied. The bathroom is small but functional. The shower might not work well for a larger person. The neighborhood is quiet and feels very safe and peaceful. We enjoyed our long weekend and would book this cottage again.
Top guest favorite
A bright and airy dining area features large windows that invite natural light, showcasing scenic views. A round wooden table is surrounded by four chairs, while the ceiling displays striking vaulted beams. A cozy blue seating area is nearby, enhancing the openness of the space.
Home in Woods Hole
5 out of 5 average rating, 63 reviews

Modern Marvel in Woods Hole - Walk to town & ferry

DoreenRating, 5 stars1 week ago
We traveled with 4 couples who have know each other since HS, 40 years ago. It was a great home to relax and catch up. The house is lovely and we loved that we each had our full bath! I highly recommend this home and this location.
Top guest favorite
A spacious deck is overlookng a serene body of water, surrounded by trees. The area features white railings and a wooden floor, with soft sunlight illuminating the scene. In the distance, a small boat dock is partially visible, adding to the peaceful ambiance.
Home in Mashpee
5 out of 5 average rating, 10 reviews

Escape to cape/water front home

BrendanRating, 5 stars1 week ago
The house and Tam were fantastic! Tam's attention to detail in both the house and how it was prepared for us made it super easy and stress-free to get settled. We had an amazing time!
Superhost
The bedroom features a spacious layout, showcasing a large bed alongside a bunk bed. Soft green walls complement the coastal-themed bedding. Natural light is provided by two window fixtures, with a wooden dresser and a mirror adding to the functional decor.
Home in Edgartown
4.93 out of 5 average rating, 15 reviews

Guest House In Edgartown

SamanthaRating, 5 stars8 months ago
Rodrigo‘s place was excellent. It is spacious and clean and has everything that you would need for a Vineyard visit. You are in someone’s backyard but it is still very quiet - except for the roosters - but even that was more charming than irritating. I would absolutely stay there again.
Guest favorite
A charming Cape-style house features a welcoming front porch with decorative railings and two red doors. Lush greenery and colorful flower beds surround the home, while a pebble driveway leads to the entrance. The exterior is complemented by a clear blue sky.
Home in Edgartown
4.99 out of 5 average rating, 80 reviews

The Seashell Cove - Martha's Vineyard

ShraddhaRating, 5 stars2 weeks ago
Charle's was an amazing host! His home was beautiful, well-maintained, and had clear instructions for everything. It was fully stocked with all the amenities we needed for a comfortable stay. He was also very responsive and quick to answer any questions we had. Highly recommend!

Destinations to explore