
House vacation 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

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

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!

Private Pool, near beaches, 3 BR/3 BA, Central Air
Awesome stay! Great house/location and Sandy is an awesome host. Highly recommend
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.

Oceanfront Vacation Home with Private Beach for 6
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+++

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

Lovely Day Oceanside
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!

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

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.

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.
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!

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.

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.

Modern Marvel in Woods Hole - Walk to town & ferry
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.

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!

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.

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!
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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
- Owen Park Beach
- Coast Guard Beach
- Onset Beach
- Inman Road Beach
- South Shore Beach
- Nickerson State Park
- Fort Adams State Park
- Second Beach
- Oyster Harbors Beach
- Pinehills Golf Club
- Scusset Beach
- Cahoon Hollow Beach
- Island Park Beach
- Kalmus Park Beach
- White Horse Beach