Holiday Homes in Chappaquiddick Island

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Featured Holiday Homes in Chappaquiddick Island and around

Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach

8.2 out of 10, Very good, (37)
"Perfect for one or two people, was great for myself and my dog to stay."
Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

10.0 out of 10, Exceptional, (160)
"Beautiful cottage , great location. Would love to stay again "
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

Hyannis Hideaway in Cape Cod

10.0 out of 10, Exceptional, (2)
"Awesome private property, close to Main Street and Craigsville beach. My friends and I stay in Hyannis every 4th of July and this home was super accommodating for groups and close to everything. Great stay would recommend. "
The price is €613
includes taxes & fees
8 Sept - 9 Sept
Hyannis Hideaway in Cape Cod

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.0 out of 10, (22)
"There were times when the shower in the master bathroom only emitted cold water. The water spigot in the tubs would not turn completely off in bathroom in the hallway. I had trouble with the lockbox. Maybe add more specific directions. It would have been helpful to know that MV transit bus was available at the intersection of the street and County Road."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Beautifully Renovated Main Street Cottage- Great Location

10.0 out of 10, Exceptional, (117)
"We were thrilled to arrive at our property with everything as pictured but actually more charming in person. It is easily walkable to town and restaurants. Communication with the owner was easy and I can recommend it to anyone who wants to stay on Nantucket. "
Beautifully Renovated Main Street Cottage- Great Location

Cape beach house steps to beach, a short walk to town & AC

10.0 out of 10, Exceptional, (4)
"This home is beautiful and a perfect beach retreat with all the amenities. The small, quiet community is perfect for walks and beach access couldn't be more convenient. We loved our stay and can't wait to return!"
Cape beach house steps to beach, a short walk to town & AC

Totally Renovated Central AC Dog Friendly Near Golf

9.6 out of 10, Exceptional, (7)
"Was a great house!! Clean, comfortable, and inviting. Close to Falmouth to get the ferry, close to Hyannis for dinner. Several great restaurants nearby! "
Totally Renovated Central AC Dog Friendly Near Golf

3 Min Walk to Beach! Large Fenced Yard!

9.8 out of 10, Exceptional, (9)
"Charming cottage in a quiet neighborhood. Perfect long weekend getaway for our family of 6."
3 Min Walk to Beach! Large Fenced Yard!

Private cottage nestled in center of the Vineyard

10.0 out of 10, Exceptional, (48)
"The property worked perfect for our family of 3 along with our dog. It was centrally located, really clean, and Jess was wonderful to deal with as she was very responsive throughout the whole process. We would definitely stay here again."
Private cottage nestled in center of the Vineyard

Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

8.8 out of 10, Excellent, (33)
"Great spot for a get away. Private with easy access to activities."
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (85)
"Great stay! "
Coastal chic meets French Provençal in this newly renovated oceanfront home.

3 Mi to Beaches & Golfing: Family Gem in Cotuit

9.2 out of 10, Wonderful, (5)
3 Mi to Beaches & Golfing: Family Gem in Cotuit

Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

8.6 out of 10, Excellent, (38)
"Close to the beach , clean and a wonderful Vineyard stay"
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

Popponesset, Exclusive, 3-Bdrm, 4-Bths, heated pool, hot tub, firepit, and A/C

10.0 out of 10, Exceptional, (79)
"Loved the house. Enjoyed our walk to the beach "
Popponesset, Exclusive, 3-Bdrm, 4-Bths, heated pool, hot tub, firepit, and A/C

Maushop - Perfect for your Vacation

9.8 out of 10, Exceptional, (30)
"Perfect fall getaway"
Maushop - Perfect for your Vacation

Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

9.8 out of 10, Exceptional, (39)
"The house has great historical charm, is immaculate with and incredible view from the roof-deck. My favorite room is the dining/livingroom. Huge room with full view of the outdoors and a fabulous stone fireplace. The location was just what i was hoping; quiet, beautiful and spacious.Loved it!"
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

Family-Friendly Tisbury Escape - Walk to Town

9.8 out of 10, Exceptional, (20)
"We were surprised by the amount of wild turkeys in the area, but other than that we really enjoyed our stay."
Family-Friendly Tisbury Escape - Walk to Town

Waterfront Mashpee 5Bed/3Bath house with AC and WiFi w/ Private Beach

Waterfront Mashpee 5Bed/3Bath house with AC and WiFi w/ Private Beach

Charming 3-bedroom house with a pool, AC, WiFi in pleasant East Falmouth

9.4 out of 10, Exceptional, (3)
"Really beautiful place with a lot of space and a very helpful host"
Charming 3-bedroom house with a pool, AC, WiFi in pleasant East Falmouth

Spacious home with tree-lined yard, deck, Ping-Pong, air hockey & washer/dryer

6.4 out of 10, (5)
"Great location!"
Spacious home with tree-lined yard, deck, Ping-Pong, air hockey & washer/dryer
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