An aerial view of a coastal area with a lighthouse, a sandy beach, and a marina.

Search Chappaquiddick Island Cottage Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Chappaquiddick Island cottages

Outdoor dining

Chappy cottage with private beach

Chappy cottage with private beach
Edgartown
10.0 out of 10, Exceptional, (18 reviews)
"What a gorgeous location, my family and I had a wonderful time on Chappy, will definitely be back!"
United States
Clinton G.
The price is ￥146,259
￥259,216 total
includes taxes & fees
Jul 30 - Jul 31
Chappy cottage with private beach
Exterior

Small One Bedroom Private Cottage on Large Quiet Property.

Small One Bedroom Private Cottage on Large Quiet Property.
Tisbury
10.0 out of 10, Exceptional, (16 reviews)
"Nice, quaint cottage. Perfect for a couple's getaway! Location was convenient for walking to shops and restaurants."
United States
Randy T.
Small One Bedroom Private Cottage on Large Quiet Property.
Property grounds

4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4 Mi to Bristol Beach! Coastal Retreat w/ Pond
East Falmouth
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay at this charming New England home. The house was spotless, beautifully maintained, and full of character. It had all the comforts we needed, inviting spaces to relax in after exploring the area. The location was perfect—close to local shops, scenic spots, and great dining. Our host was friendly, responsive, and made us feel right at home. We honestly couldn’t have asked for a better experience, and we look forward to returning."
United States
Shaun G.
The price is ￥29,378
￥113,385 total
includes taxes & fees
Aug 14 - Aug 15
4 Mi to Bristol Beach! Coastal Retreat w/ Pond
Exterior

1 Mi to Ferry: 'Sea Street Cottage' in Hyannis

1 Mi to Ferry: 'Sea Street Cottage' in Hyannis
Hyannis
8.8 out of 10, Excellent, (19 reviews)
"Perfect weekend getaway- super location. Cozy spot! Loved the area "
United States
Jill S.
1 Mi to Ferry: 'Sea Street Cottage' in Hyannis
Cottage (2 Bedrooms) | Interior

4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4 Mi to Bristol Beach! Coastal Retreat w/ Pond
3.0 star property
East Falmouth
The price is ￥37,215
￥110,850 total
includes taxes & fees
Aug 14 - Aug 15
4 Mi to Bristol Beach! Coastal Retreat w/ Pond
Terrace/patio

WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (50 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is ￥187,692
￥270,725 total
includes taxes & fees
Aug 20 - Aug 21
WATERFRONT Downtown Cottage w/ Beach
Exterior

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Tisbury
10.0 out of 10, Exceptional, (60 reviews)
"We loved the location and place was great!"
United States
Eileen M.
The price is ￥146,726
￥187,228 total
includes taxes & fees
Aug 16 - Aug 17
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Exterior

Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!

Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!
Falmouth
9.4 out of 10, Exceptional, (3 reviews)
"Good location, close to ferry and restaurants. Quiet neighborhood."
United States
Kerry B.
The price is ￥65,004
￥124,616 total
includes taxes & fees
Aug 17 - Aug 18
Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!
Cottage (2 Bedrooms) | Interior

1 Mi to Ferry: 'sea Street Cottage' in Hyannis

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
8.0 out of 10, Very Good, (1 review)
"The cottage is in a great location close to Main Street and the harbor. Easy parking at the cottage and it’s in a walkable area. Decor is cute and nautical, but it does feel like the cottage is missing a few things. It sleeps 4, but there is not enough seating for 4 in the living room. An additional comfortable chair would be nice. A stackable washer and dryer would also be great, but there is very little space for anything- we even had trouble finding spots for our luggage. The fridge door...
United States
Christa
1 Mi to Ferry: 'sea Street Cottage' in Hyannis
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chappaquiddick Island Hotel Reviews

Americas Best Value Inn & Suites Hyannis Cape Cod

Americas Best Value Inn & Suites Hyannis Cape Cod

8/10 Good
"parking lot was a mess. room was ok."
Joe 2-night trip
Posted less than an hour ago
Americas Best Value Inn & Suites Hyannis Cape Cod

Find out more about Chappaquiddick Island

Chappaquiddick Island Cottages information

Number of reviews
150
Accommodation
110 Cottages
Lowest Price
￥110,850
Highest Price
￥270,725

Frequently asked questions

Why book your cottage in Chappaquiddick Island with Expedia?
Reserving a cottage in Chappaquiddick Island is as simple as deciding on your travel dates and picking an ideal place for a getaway in the outdoors. From ritzy retreats to inexpensive stays and cottages that offer amenities like laundry facilities, Expedia has something for all tastes. As for epic deals? We've got your back!
How can I find cheap cottages in Chappaquiddick Island?
Expedia can help you locate cheap cottages in Chappaquiddick Island. To book your perfect stay in just a few clicks, simply use our handy filter tool to tailor your search results by amenities, star rating and budget.

Explore a world of travel with Expedia