
House holiday rentals in Chappaquiddick Island
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Top-rated house rentals in Chappaquiddick Island
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Popular amenities for Chappaquiddick Island house rentals
House rentals with a pool

Stunning Cape Home - Inground Pool, 5 Min To Beach
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!

"Cape Escape" luxury home w/pool & beach access.
I can not say enough about how wonderful this house was to stay at for my son's wedding weekend. This house was very clean and organized. The hosts were extremely thoughtful with how everything was laid out. They thought of everything that you would need or might forget. The outdoor space was great!! My grandchildren and kids floated around the pool and played yard games. I did not hear "I am bored" and that was wonderful. We had so much space to get ready for the wedding and were able to get wonderful pictures of my son getting ready for his wedding. There are so many places in the house to either gather together or to go off and do something else. Two kids were playing chess while the younger ones were down playing with the video games and my dad and the men were watching the Masters. We had plenty of space for everyone to hang out. My entire family enjoyed this house and can't wait to go back.

Home in Falmouth ~ 5 min drive to beach
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.

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

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

Beautiful Edgartown Colonial with heated pool.
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!

Dog Friendly Cape Oasis | Pool+Beach |Tennis Court
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.

Yarmouthport house heated pool/hot tub near beach.
Wonderful place to stay! So comfortable and lots of space! Close to lots of restaurants and shopping! Would definitely stay again!
Weekly house rentals

Vineyard Vacation, 3-Bedroom, Hot-tub, Golf course
The home was clean and cozy. Updated decor and well supplied with everything we would need. I would stay again.

Updated Beautiful Cottage in Edgartown AC
Kenneth Is a great host communicates very well and has a genuine concern for his guests Ray

Charming Edgartown Log Cabin with Peloton bike
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

Buzzard Bay Getaway
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.

Sauna I Walk2Beach I Pet Friendly I Fire Pit
We loved our stay here! Spent the weekend with our two young children and the house had everything we could need and more. It was walking distance to the beach and near great restaurants. Victoria also provided a list of local recommendations which we took a few of and loved them all! Would recommend staying here.

Guest House In Edgartown
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.

Walk to downtown Edgartown in a quiet neighborhood
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.

The Seashell Cove - Martha's Vineyard
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!
Private house rentals

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

Grab A Last Minute, Relaxing Summer Beach Getaway!
Our family had a wonderful stay in Falmouth! The home is beautiful with plenty of natural light and a nice breeze coming in through the many windows. The kitchen is the most well stocked of any Airbnb homes we have stayed. The beds are very comfortable, and we felt right at home in the large bedrooms. The entire home is immaculate! The kids enjoyed playing in the yard surrounded by trees and lots of birds. There are tons of parks/hiking trails and restaurants nearby - great central location on Cape Cod. We really enjoyed visits to Skaket beach with tide pools that the kids could explore in the late afternoon during low tide. The Cape Cod Museum of Natural History in Brewster was really neat, with a short boardwalk trail back to Wing’s Island. Jessica is a great host and communicated well. We will definitely be back!

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

Walk to EDG Wharf - Beautiful Home with AC & Grill
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.

Escape to cape/water front home
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!

The Blue Lagoon, Oak Bluffs
Thank you Brian we enjoyed our stay. The home is beautiful and so many amenities. The rooms are large and everything was so neat and clean. The open floor plan allowed us to sit and watch TV as well as cook in that beautiful gourmet kitchen. We will be back!

Idyllic renovated home across from Seth's Pond
We loved our stay, would definitely stay again! Meredith was very helpful and responsive. The house was beautiful and very clean. Highly recommend.

Sea Haven | beach • restaurants • spacious
Excellent location halfway between the beach and main street! Plenty of space and beds to accommodate our whole family, and a big backyard to play in. Sarah and Christin were super responsive to all of our questions and sent us local recommendations for restaurants and farmers markets. Would definitely stay here again!
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Easton Beach
- Sagamore Beach
- Sandwich Glass Museum
- Coast Guard Beach
- Owen Park Beach
- Onset Beach
- Nickerson State Park
- Inman Road Beach
- Pinehills Golf Club
- South Shore Beach
- Fort Adams State Park
- Second Beach
- Oyster Harbors Beach
- White Horse Beach
- Kelly Beach
- Island Park Beach
- Kalmus Park Beach
- Ridgevale Beach