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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Chappaquiddick Island and around

Charming Seaside Cottage Central to the Beach and New Seabury Resort Community
Stroll through a charming neighborhood lined with classic homes and lush greenery.

Charming Seaside Cottage Central to the Beach and New Seabury Resort Community

2.0 star property
9.2 out of 10, Wonderful, (7)
"Perfect cottage"
Charming Seaside Cottage Central to the Beach and New Seabury Resort Community
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach
Situated in a residential area, this two-story house features a gabled roof and a beautiful garden with mature trees and shrubs.

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

5.6 out of 10, (24)
"Great location and private beach access. Charming enclave perfect for our weekend getaway."
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
Welcome to this charming home with a front door, garage, and cozy porch area.

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

9.6 out of 10, Exceptional, (68)
"Clean property, great location"
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
Cozy family-friendly cottage on beautiful Shining Sea bike trail
Enjoy cooking in this well-lit kitchen with a central island, sink, microwave, and coffee maker.

Cozy family-friendly cottage on beautiful Shining Sea bike trail

10.0 out of 10, Exceptional, (4)
"This cottage is charming and inviting. The hosts have outdone themselves with their attention to detail. This place has everything you could want or need. We hope to return someday! "
Cozy family-friendly cottage on beautiful Shining Sea bike trail
Steps to the Ocean! Perfect Location!!!
Guests can enjoy a serene view of the outdoor area through the window, featuring a garden with plants and flowers, a tree, and a building in the distance.

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (217)
"Perfect for a couple and two kids"
Steps to the Ocean! Perfect Location!!!
Steps to the beach with an ocean view,
Enjoy a traditional home with a front porch and a yard.

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (124)
"We had a wonderful time staying in Hyannis off season (April vacation for CT, but not for MA)! The host provided us with everything we needed and the location can't be beat! It's in a very walkable area, close to Main Street and the beach! We would love to come back again in the warmer weather! "
Steps to the beach with an ocean view,
Gorgeous Cottage steps from the beach
Walk along the serene beach, flanked by tall grasses and dunes.

Gorgeous Cottage steps from the beach

8.4 out of 10, Very good, (16)
"Great place to stay we loved it"
Gorgeous Cottage steps from the beach
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Stunning two-story house with a central entrance, flanked by windows and a charming porch.

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

10.0 out of 10, Exceptional, (53)
"We had a wonderful stay! The place was clean, cute, and very conveniently located. Would definitely return!"
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.
Stunning coastal homes line a scenic road leading to the sea.

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

10.0 out of 10, Exceptional, (28)
"We had a great trip and look forward to staying there again. Location is the best part!"
5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.
Renovated Cottage off Main Street- Great Location
Situated in a quiet suburban neighborhood, this charming house features a front porch and a well-manicured lawn with beautiful flowering plants.

Renovated Cottage off Main Street- Great Location

10.0 out of 10, Exceptional, (155)
"The cabin was perfect. It was on more of a busy road than we anticipated, but everything else was wonderful. We enjoyed ourselves so much!!"
Renovated Cottage off Main Street- Great Location
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Set amidst a serene garden, this charming two-story house offers a peaceful retreat.

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

10.0 out of 10, Exceptional, (25)
"This was the perfect place for a weekend on the island. Great location and my son loved the upstairs rooms to play in. "
The price is €904
includes taxes & fees
19 Aug - 20 Aug
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Cozy Beach Cottage
Charming single-story home with a gabled roof and covered porch, set amidst a well-manicured lawn and a large tree.

Cozy Beach Cottage

10.0 out of 10, Exceptional, (48)
"The property was prepared, very thoughtful and had everything you could think of for a wonderful beach Island stay. The only downside was cable because I’m addicted to TV and I would’ve appreciated at least a smart TV that I could connect my own Netflix. "
Cozy Beach Cottage
Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower
Relax in a serene outdoor space surrounded by lush greenery, complete with a deck and storage shed.

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

9.8 out of 10, Exceptional, (27)
"This is our 2nd time at this property and we loved it again. The location is great. The property was super clean and inviting. Everything we needed to enjoy our stay. Just excellent across the board."
Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower
Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach
Situated in a grassy yard, this charming house features a gabled roof and a welcoming front porch.

Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach

9.6 out of 10, Exceptional, (4)
"The Pinkletink was a quaint home for a wonderful visit to Martha's Vinyard. It is in a quiet neighborhood and a nice walk from both the beach and the town of Oak Bluffs. Perfect location for a couple wanting to visit Martha's Vinyard and enjoy the island."
Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach
Family Cottage Big yard w\Fire Pit & Outside Shower Walk to beaches 1PVT Pets OK
Exterior

Family Cottage Big yard w\Fire Pit & Outside Shower Walk to beaches 1PVT Pets OK

9.6 out of 10, Exceptional, (4)
"Drew was there to meet us at check-in and explained all aspects of the property. The location is perfect, a short walk to the private beach and Seagull Beach. The home is quintessential Cape Cod and located in a quiet neighborhood. We definitely plan to return next Summer! "
Family Cottage Big yard w\Fire Pit & Outside Shower Walk to beaches 1PVT Pets OK
Charming 1 Bedroom Cottage Close To Beautiful Craigville Beach
Stunning home with a gabled roof and dormer window, featuring a combination of siding and brickwork.

Charming 1 Bedroom Cottage Close To Beautiful Craigville Beach

9.8 out of 10, Exceptional, (110)
"Comfortable cottage. Great location. "
Charming 1 Bedroom Cottage Close To Beautiful Craigville Beach
Charming Post and Beam Cottage! Walk to the beach, Tennis, Bike Path, & Shuttle
Traditional two-story house with a gabled roof and porch, set amidst lush greenery.

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

9.8 out of 10, Exceptional, (29)
"We had a lovely time. Charming cottage"
The price is €1,284
includes taxes & fees
10 Aug - 11 Aug
Charming Post and Beam Cottage! Walk to the beach, Tennis, Bike Path, & Shuttle
Make Lasting Memories In This Adorable Vineyard Cottage!
Relax on the deck surrounded by lush greenery and enjoy the serene atmosphere.

Make Lasting Memories In This Adorable Vineyard Cottage!

9.8 out of 10, Exceptional, (145)
"Absolutely loved this place. Had everything we needed. Such cute decor. Perfect cute little rental in convenient location. "
Make Lasting Memories In This Adorable Vineyard Cottage!
Craigsville beach cottage located .4 walking distance to the Beach!
Relax in a comfortable outdoor space with a sofa, chairs, and table, perfect for al fresco dining and socializing.

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

9.6 out of 10, Exceptional, (15)
"bed rooms are cramped"
Craigsville beach cottage located .4 walking distance to the Beach!
12 VINEYARD VIEW - FULLY RENOVATED
Relax under the covered patio with a beautiful garden view.

12 VINEYARD VIEW - FULLY RENOVATED

9.8 out of 10, Exceptional, (43)
"Definitely would stay again!"
12 VINEYARD VIEW - FULLY RENOVATED
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.
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Top Chappaquiddick Island Hotel Reviews

The Beachside

The Beachside

10/10 Excellent
"Absolutely loved this hotel - perfect location close to the beach and town center with all restaurants and shops. Cute interior design. "
Irina 3-night trip
Posted 1 day ago
The Beachside

Frequently asked questions

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