Search Cottages in Chappaquiddick Island

  • 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
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 101 Cottages in Chappaquiddick Island with updated reviews, rates, and availability.

Renovated Cottage off Main Street- Great Location

10.0 out of 10, Exceptional, (145)
"We spent about a month in this absolutely wonderful home on Nantucket. When we arrived, it was clear the house has been professionally cleaned and was spotless. The kitchen is great for cooking for meals in. The tv room has a ton of natural light & was a great place to hang out as a family. There are 2 bedrooms, one on main floor which is easily accessible and 1 in the loft which is a steep staircase (fine for us as we have no mobility issues but bear this in mind). The little patio on the side...
Renovated Cottage off Main Street- Great Location

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (109)
"To stay a block from the beach and look out the window at the water is the ultimate vacation! Even in winter this place is warm and inviting! The hosts are caring and communicative - just the best! This cottage lets you do just that"
Steps to the beach with an ocean view,

Craigsville beach cottage located .4 walking distance to the Beach!

9.8 out of 10, Exceptional, (7)
"My friend and I stayed at this cute cottage for nearly a week. It was immaculately clean, cozy, well equipped, and convenient to everything! Town, restaurants, big box shopping, and a beautiful beach!The back yard is private with plenty of outdoor seating. Unfortunately, the weather did not cooperate while we were there so we couldn't take advantage of relaxing on the back patio...but it would be wonderful if the sun was out!If I have the opportunity to return to the Cape, I would stay here...
Craigsville beach cottage located .4 walking distance to the Beach!

Gorgeous Cottage steps from the beach

9.0 out of 10, Wonderful, (12)
"Perfect getaway"
Gorgeous Cottage steps from the beach

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

5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.

10.0 out of 10, Exceptional, (20)
"Maushop is the perfect place for a family getaway right on the ocean. The property was clean and spacious for a tiny cottage. We had a wonderful time."
The price is AED 1,466
AED 3,287 total
includes taxes & fees
21 May - 22 May
5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.

Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

6.2 out of 10, (17)
"We did not stay. Place was a dump No one has called us We are not paying It is illegal not to have carbon / smoke detectors We went to condos at new seabury"
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower

10.0 out of 10, Exceptional, (23)
"This is our second time at this property. It is as described. Beautifully updated. Location could not be better!! One street away from where my grandparents used to live. Such great memories!"
Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower

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!

2-bdrm Cottage | Close to Everything | Pet Friendly

9.8 out of 10, Exceptional, (9)
"Beautiful cottage, very clean and comfortable. Very peaceful and quiet! Weather wasn't the best for sitting outside to enjoy nature, but it was beautiful nonetheless. Bonnie is an excellent host! We definitely will return!"
2-bdrm Cottage | Close to Everything | Pet Friendly

★The Islander | Steps From Water, Fire Pit, AC★

10.0 out of 10, Exceptional, (46)
"Our host, Matt was attentive and responsive. The house and neighborhood were exactly what we were looking for our brief getaway. It was off the beaten path, quiet and beautiful. Whatever we needed, we found within a short distance. "
★The Islander | Steps From Water, Fire Pit, AC★

Charming 1 Bedroom Cottage Close To Beautiful Craigville Beach

9.8 out of 10, Exceptional, (102)
"Comfortable cottage. Great location. "
Charming 1 Bedroom Cottage Close To Beautiful Craigville Beach

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

Chappaquiddick, Cozy 2 Bedroom, Spring and Fall Derby availability

10.0 out of 10, Exceptional, (25)
"we stayed on Chappy for a family wedding. The cottage was great. No issues, very comfortable and close proximity to the festivities! Thanks!"
Chappaquiddick, Cozy 2 Bedroom, Spring and Fall Derby availability

12 VINEYARD VIEW - FULLY RENOVATED

9.6 out of 10, Exceptional, (40)
"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

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (205)
"Perfect for a couple and two kids"
Steps to the Ocean! Perfect Location!!!

2 Bedrooms + Loft - Sleeps 6 in Beds but max 4 adults- 5 Blocks to Town

10.0 out of 10, Exceptional, (97)
"The best time to visit. Quiet and relaxing. Our accommodations were perfect "
2 Bedrooms + Loft - Sleeps 6 in Beds but max 4 adults- 5 Blocks to Town

Cozy New TimberFrame Vineyard Haven!

10.0 out of 10, Exceptional, (19)
"As advertised. Photos are accurate, as is description. Short walk to town/supermarket, cafes and more. Accommodations are clean, well-kept, and basically brand new. Thanks! Brett Star"
Cozy New TimberFrame Vineyard Haven!

One Bedroom Private Cottage on Large Quiet Property.

9.6 out of 10, Exceptional, (5)
"Absolutely perfect, right down to the brands of soaps and shampoos! Beautiful artwork everywhere. I wouldn't change a thing!"
One Bedroom Private Cottage on Large Quiet Property.

Charming Post and Beam Cottage! Walk to the beach, Tennis, Bike Path, & Shuttle

9.8 out of 10, Exceptional, (28)
"We loved our stay. The cottage was very well equipped, clean and private (even though it is a guest cottage on the back of the property). The owners were so nice and willing to help with dinner recommendations and island suggestions. We’ve been coming to Nantucket for 25 years and would highly recommend this property! We loved our family vacation in this beautiful location close to walking trails, 40th Pole, Madaket beach (Millies) and public transportation to town."
Charming Post and Beam Cottage! Walk to the beach, Tennis, Bike Path, & Shuttle
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

Other property types in Chappaquiddick Island

Sleeps 12, amazing view, tennis court, basketball court, beaches

9.6 out of 10, Exceptional, (37)
"It was a great place to hangout with family members. I lot of places to plop down with a book, a lot of things to do to keep people busy - just a great time."
Sleeps 12, amazing view, tennis court, basketball court, beaches

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (166)
"Enjoyed walking on the beach across the street from the property."
InnSeason Resorts Captain's Quarters

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (315)
"Tired unit. Primary bath water closet leaked around base. No soap or paper towels. "
The price is AED 740
AED 847 total
includes taxes & fees
29 Apr - 30 Apr
The Club at New Seabury
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.