Search Chappaquiddick Island Cottage Rentals

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 89 Cottages in Chappaquiddick Island with updated reviews, rates, and availability.

Cape Cod Holiday Estates, a VRI resort
Indoor pool

Cape Cod Holiday Estates, a VRI resort

3.0 star property
9.6 out of 10, Exceptional, (120)
"Nice & clean. The only complaint Would be that the pool closed at 6 PM because they were low on staff so by the time we got back from sightseeing, we weren’t able to get in the pool"
Cape Cod Holiday Estates, a VRI resort
Renovated Cottage off Main Street- Great Location
Exterior

Renovated Cottage off Main Street- Great Location

10.0 out of 10, Exceptional, (143)
"Visiting a niece working on the island for the summer. Planned the trip with this purpose to see family. It was wonderful and met all our expectations. 🥰❤️"
Renovated Cottage off Main Street- Great Location
Martha's Vineyard Getaway Cottage
Exterior

Martha's Vineyard Getaway Cottage

10.0 out of 10, Exceptional, (2)
"Bright, open, clean & cozy. Will return and love the year round option."
Martha's Vineyard Getaway Cottage
Steps to the beach with an ocean view,
Beach nearby, sun loungers, beach towels

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (109)
"We came to visit Nantucket and Martha’s Vineyard and one of the best parts of our trip is this gem. It was the perfect size for 4 of us. Close to the beach and the seashell collecting was amazing. Lots of shops and restaurants close by. We had some questions and the owner was very responsive. We would stay here again!"
Steps to the beach with an ocean view,
Steps to the Ocean! Perfect Location!!!
Beach nearby, sun loungers

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (195)
"I spent the weekend in this adorable cottage after waking up in 5 different states 5 days in a row for a work trip. The location is perfect and the sunrise and sunsets from the beach were some of the most vibrant and colorful I have ever seen. I’m sure this is an amazing place to vacation in the summer but the quiet and solitude of November was its own treasure. And I was able to visit Walden Pond on my way to Boston Airport—-just a quick 30 minute detour and well worth the visit. "
Steps to the Ocean! Perfect Location!!!
12 VINEYARD VIEW - FULLY RENOVATED
Property grounds

12 VINEYARD VIEW - FULLY RENOVATED

9.8 out of 10, Exceptional, (39)
"We had such an amazing time staying here! The location is perfect and has amazing ocean views right from the house. Everything was super clean and well maintained. We will definitely be coming back! "
12 VINEYARD VIEW - FULLY RENOVATED
2 Bedrooms + Loft - sleeps 6 in beds but max 4 adults- 5 Blocks to Town
Property grounds

2 Bedrooms + Loft - sleeps 6 in beds but max 4 adults- 5 Blocks to Town

10.0 out of 10, Exceptional, (85)
"We absolutely LOVED staying here. Close enough to downtown to walk but far out enough to be very quiet and peaceful. The space itself is very open and spacious while still feeling cozy and comfortable. We will definitely be back!"
2 Bedrooms + Loft - sleeps 6 in beds but max 4 adults- 5 Blocks to Town
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Property grounds

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

8.6 out of 10, Excellent, (79)
"Great location but the place was dirty. Need a better cleaning service. "
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Cozy cottage w/ remodeled kitchen - less than a mile from Woods Hole Ferry
Fridge, microwave, oven, stovetop

Cozy cottage w/ remodeled kitchen - less than a mile from Woods Hole Ferry

7.8 out of 10, Good, (26)
" Affordable, clean, enjoyable experience "
The price is ￥18,499
￥58,593 total
includes taxes & fees
Nov 23 - Nov 24
Cozy cottage w/ remodeled kitchen - less than a mile from Woods Hole Ferry
Exquisite Oceanfont Cottage at Madaket Beach!
On the beach, sun loungers, beach towels

Exquisite Oceanfont Cottage at Madaket Beach!

10.0 out of 10, Exceptional, (12)
"Fantastic property well aportioned and great communication. Would highly recommend"
Exquisite Oceanfont Cottage at Madaket Beach!
Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people
Beach nearby, sun loungers, beach towels

Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people

8.8 out of 10, Excellent, (26)
"The property was great and walkable to the beach, but needs a few upgrades. "
Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
Beach nearby, sun loungers, beach towels

Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

9.6 out of 10, Exceptional, (64)
"Great property in great location on Cape Cod. 30 min drive for ferry to Nantucket. 2 minute walk to Beach within neighborhood. Cozy and quiet. Would not hesitate to stay again. "
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
New Rental - 2 bedrooms, 1.5 baths, with magnificent views.
On the beach, sun loungers, beach towels

New Rental - 2 bedrooms, 1.5 baths, with magnificent views.

10.0 out of 10, Exceptional, (19)
"Everything was perfect. Super clean. Location was perfect. House had everything you need. The owner even made sure the weather was great. "
New Rental - 2 bedrooms, 1.5 baths, with magnificent views.
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Terrace/patio

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

10.0 out of 10, Exceptional, (16)
"Warm and inviting property. Everything was perfect, from the solar lights on the patio to the fireplace in the living area. We enjoyed a walk to dinner. Walked to Carboat for coffee in the morning. Fun visit to Martha’s Vineyard and a pleasant stay in this house !"
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Charming Pet Friendly Cottage
Outdoor dining

Charming Pet Friendly Cottage

9.8 out of 10, Exceptional, (16)
"Best time to be on island and this was an amazing location and home. The outside space is some of the best weve had. Deirdre was great and answered all our questions quickly. Would definitely return"
Charming Pet Friendly Cottage
Chappy cottage with private beach
Fridge, microwave, oven, stovetop

Chappy cottage with private beach

10.0 out of 10, Exceptional, (14)
"This cottage was the perfect little getaway for our family to base our first visit on Chappy. We loved being able to walk to the beach and appreciated the cleanliness of the cottage as well as its charm. "
Chappy cottage with private beach
Charming Cottage near Beach and Ferry
Terrace/patio

Charming Cottage near Beach and Ferry

10.0 out of 10, Exceptional, (4)
"We really enjoyed our stay here. Everything you need for a comfortable stay. Cottage is well equipped and very clean. Great location and close to many activities. Looking forward to renting again. "
Charming Cottage near Beach and Ferry
Cozy Beach Cottage
Beach nearby, sun loungers, beach towels

Cozy Beach Cottage

10.0 out of 10, Exceptional, (41)
"We (a party of 3 lifelong friends!) loved this little tucked away cottage. Despite the bad weather cards we were dealt with, (a lot of rain and wind) we easily walked to the Campground and marvelled at the uniqueness of the gingerbread cottages and found some good rainy day hang-out's that I wasn't aware of (especially loved Behind The Bookstore & ventured out on a little bit on a rainy night to listen to live music at Nonan's) The check-in was super easy and we took advantage of the outdoor...
Cozy Beach Cottage
Waterfront Hyannis Port Gem: Walk to Beach
Flat-screen TV, fireplace, video games, DVD player

Waterfront Hyannis Port Gem: Walk to Beach

9.8 out of 10, Exceptional, (20)
"Place was clean and easy to access, lots of amenities and the owner was great to deal with. "
Waterfront Hyannis Port Gem: Walk to Beach
3 Bed Home w/ Free Barnstable Beach Pass!
TV, fireplace, video games

3 Bed Home w/ Free Barnstable Beach Pass!

9.6 out of 10, Exceptional, (5)
"Me and a few friends spent four nights in the house. The beds were comfy, great kitchen for making group meals and nice common spaces. The owners provide a beach pass that helped us visit a few different places. Highly recommended! "
3 Bed Home w/ Free Barnstable Beach Pass!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Chappaquiddick Island
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chappaquiddick Island

The Club at New Seabury
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (304)
"will definitely go back again .. awesome place! "
The price is ￥22,754
￥26,042 total
includes taxes & fees
Nov 26 - Nov 27
The Club at New Seabury
Courtyard Resort
Indoor pool

Courtyard Resort

3.0 star property
8.4 out of 10, Very Good, (43)
"Great for short or extended stay. "
The price is ￥11,129
￥12,737 total
includes taxes & fees
Dec 9 - Dec 10
Courtyard Resort
2 Bedrooms + Loft - sleeps 6 in beds but max 4 adults- 5 Blocks to Town
Property grounds

2 Bedrooms + Loft - sleeps 6 in beds but max 4 adults- 5 Blocks to Town

10.0 out of 10, Exceptional, (85)
"We absolutely LOVED staying here. Close enough to downtown to walk but far out enough to be very quiet and peaceful. The space itself is very open and spacious while still feeling cozy and comfortable. We will definitely be back!"
2 Bedrooms + Loft - sleeps 6 in beds but max 4 adults- 5 Blocks to Town
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Why book your cottage in Chappaquiddick Island with Expedia?
Reserving a cottage in Chappaquiddick Island is as easy as entering your travel dates and choosing an ideal place for outdoor relaxation and recreation. From ritzy retreats to affordable stays and cottages that include amenities like a kitchenette, Expedia has something for all tastes. As for epic deals? We’ve got you covered!
How can I find cheap cottages in Chappaquiddick Island?
Expedia is here to help you easily locate cheap cottages in Chappaquiddick Island. To book your perfect stay in a few quick clicks, use the filter tool to tailor your search results by amenities, budget and star rating.