Holiday Homes in Chappaquiddick Island

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Featured Holiday Homes in Chappaquiddick Island and around

Chappy - Family Beach House

10.0 out of 10, Exceptional, (14)
"Very nice property. We were comfortable and had everything we needed. "
Chappy - Family Beach House

Charming Cape 🌞 With Beach Pass Included, Close to Beaches and Downtown

9.4 out of 10, Exceptional, (10)
"Very beautiful and clean house and yard. The house is on a busy street but backyard is quite a nice oasis."
Charming Cape 🌞 With Beach Pass Included, Close to Beaches and Downtown

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

The price is €551
includes taxes & fees
1 Sept - 2 Sept
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

10.0 out of 10, Exceptional, (2)
"Mike & Olya's house is even more beautiful in person, both inside and out.The house is equipped with everything needed for a peaceful stay. The décor and contemporary style made us want to live there — very tasteful.Check-in and check-out were easy to access. We were authorized to enter the house starting at 4 p.m.The cleaning crew was delayed by just a few minutes (maybe 5 minutes), and I immediately received a message saying I had been refunded for the inconvenience. Although such a gesture...
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

9.0 out of 10, Wonderful, (2)
"The house was lovely. Very clean and orderly. Beautiful back porch that we enjoyed very much. The beds were very comfortable. Our only complaint was the Master bathroom needs some updating. The shower head desperately needs to be changed and the lighting is extremely poor. Also, only 1 half size mirror on the whole first floor. Other than that, it was perfect."
The price is €1,744
includes taxes & fees
15 Sept - 16 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

10.0 out of 10, Exceptional, (29)
"Good location, pretty spot on pond. Nice deck plenty of room for family of 12"
The price is €861
includes taxes & fees
15 Sept - 16 Sept
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

10.0 out of 10, Exceptional, (7)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
The price is €2,098
includes taxes & fees
1 Sept - 2 Sept
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Love Sand, Madaket on the Beach , Lovely Seaside Home

10.0 out of 10, Exceptional, (52)
"We thoroughly enjoyed our two nights and are sad to leave. The property is iconically Nantucket. Its location - and the views- is spectacular. It is well equipped for a relaxing family or couples vacation. Hope we can make it back. "
The price is €1,474
includes taxes & fees
16 Sept - 17 Sept
Love Sand, Madaket on the Beach , Lovely Seaside Home

Cape Cod Getaway - close to beaches, shopping and more

10.0 out of 10, Exceptional, (17)
"We had a wonderful stay! Nice property."
Cape Cod Getaway - close to beaches, shopping and more

Island Inn - 2 Bedroom & 2 Bath Townhouse - 44G - Oak Bluffs, MA

9.0 out of 10, Wonderful, (2)
"Great location. Very nice property. The unit was clean but dated in a few areas. Overall, it was perfect for 4 of us visiting for the wknd. "
Island Inn - 2 Bedroom & 2 Bath Townhouse - 44G - Oak Bluffs, MA

Beautiful Private Beach House

10.0 out of 10, Exceptional, (48)
"The property was lovely with amazing views and a comfortable atmosphere. The host was very responsive. It was a great long weekend retreat for a multi-generational family."
Beautiful Private Beach House

Charming studio in tranquil Falmouth with AC

The price is €166
includes taxes & fees
15 Sept - 16 Sept
Charming studio in tranquil Falmouth with AC

Remodeled historical Gosnold Cottage.300 yards to the beach.

10.0 out of 10, Exceptional, (3)
"We had a great stay at this property! It was very clean and spacious for our family of 4. Veterans Beach was within walking distance. The shower was great and my 2 year old loved to run around the property l would definitely stay here again"
Remodeled historical Gosnold Cottage.300 yards to the beach.

Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C

10.0 out of 10, Exceptional, (178)
"The property had all the amenities and features to make guests feel right at home. We appreciated all the details in the decor and we appreciated the suggestions for local restaurants. TheTheviewwdrdreadream!amademade"
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

8.8 out of 10, Excellent, (5)
"Perfect to walk to the beach"
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Charming 4-bedroom house with AC and WiFi in enchanting Barnstable

2.0 star property
Charming 4-bedroom house with AC and WiFi in enchanting Barnstable

Cozy Oceanfront Room | 2 Beds + Kitchenette

Cozy Oceanfront Room | 2 Beds + Kitchenette

New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

10.0 out of 10, Exceptional, (28)
"Great location and nice house! "
The price is €1,209
includes taxes & fees
15 Sept - 16 Sept
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

Spacious Lake House for Large Groups w Private Acre+ short path to Lake

10.0 out of 10, Exceptional, (1)
"The home was clean, spacious, and very private. It was a great fit for our large group of friends. On/off street parking was plentiful and half of the bedrooms were spacious and light filled. Some of the smaller, downstairs rooms were less luxurious, but they got the job done. The best part was the spacious backyard and back deck, which was great for hosting a large dinner and barbecue outside. Very private, sun filled, and plenty of seating.We had an issue with the dishwasher not working...
The price is €1,230
includes taxes & fees
17 Aug - 18 Aug
Spacious Lake House for Large Groups w Private Acre+ short path to Lake
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