Holiday Homes in Cuttyhunk

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Featured Holiday Homes in Cuttyhunk and around

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

6.2 out of 10, (24)
"The property is quiet, spacious and was within a walkable mile of downtown Oak Bluffs. The beds were comfortable. Plenty of clean linens and towels. The house could use some updating. The coffee maker, drinking glasses, and silverware need to be replaced with cleaner ones. And the torn portions of the sectional couch should be fixed. I would definitely stay at the property again."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Private cottage nestled in center of the Vineyard

10.0 out of 10, Exceptional, (49)
"This whole experience was better than I could have imagined. The cottage was beautiful in a perfect setting. my Hosts went the extra distance. I didn't arrive until close to midnight. My hosts had left fruit, salad, yogurt and ice cream for me. Since I was unable to get a rental car this meant I had something to eat in the morning. I will definitely stay there 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

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

8.4 out of 10, Very good, (39)
"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

Beach Lovers Paradise! Cozy 3 bedroom home steps from the beach.

9.8 out of 10, Exceptional, (7)
"Wonderful beach property. Clean home, comfortable beds and close to restaurants."
Beach Lovers Paradise! Cozy 3 bedroom home steps from the beach.

Costal Cottage Retreat minutes from Newport, RI

10.0 out of 10, Exceptional, (1)
"Immaculately clean, one of the best equipped places we have stayed, comfortable, spacious, and the location is near to everything. "
Costal Cottage Retreat minutes from Newport, RI

Beach house walking distance to Second Beach

9.8 out of 10, Exceptional, (17)
"Great location, nice house. Great for a group of friends."
The price is €810
includes taxes & fees
17 Sept - 18 Sept
Beach house walking distance to Second Beach

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

9.6 out of 10, Exceptional, (40)
"Fantastic beach cabin in a nice location, close to Gay Head lighthouse and several beaches, including the dog-friendly Lobsterville. Good views, plenty of land, we had a good time!"
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 Home w/ Guest Cottage

10.0 out of 10, Exceptional, (1)
"I lined the view from the home and the safety in the area! Overall, great place for a big family !"
Waterfront Home w/ Guest Cottage

Third Beach Coastal Retreat - Pet-Friendly – 3Bdr-4Bed - 5min Walk to Beach

9.8 out of 10, Exceptional, (66)
"Very good vacation"
Third Beach Coastal Retreat - Pet-Friendly – 3Bdr-4Bed - 5min Walk to Beach

Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

7.6 out of 10, Good, (4)
"We loved the location. The outdoor shower was a hit with the kids."
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

10.0 out of 10, Exceptional, (198)
"As always, lovely home. Perfect place."
The price is €515
includes taxes & fees
8 Sept - 9 Sept
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Great Location! High-End Coastal Country Retreat

10.0 out of 10, Exceptional, (49)
"The home has everything you need for a very enjoyable and relaxing getaway"
Great Location! High-End Coastal Country Retreat

Best Kept Secret Retreat for Adults with Water & Golf Course Views!

10.0 out of 10, Exceptional, (37)
"The home was beautiful and very well appointed. Easily accommodated our group of 8 adults with room to spare. Minor complaint is that there could’ve been a few more towels available, but the washer and dryer took care of that."
Best Kept Secret Retreat for Adults with Water & Golf Course Views!

Spacious colonial home close to town with AC, porches, & W/D

10.0 out of 10, Exceptional, (5)
Spacious colonial home close to town with AC, porches, & W/D

Middletown Bungalow - RIBryan Property

9.2 out of 10, Wonderful, (11)
"In town for daughter's graduation. Was only there for sleeping but was comfortable. Near stores for breakfast food. Decent overall experience (we had to take shoes off which didn't bother me but my 75 year old mom wasn't happy)"
The price is €697
includes taxes & fees
19 Aug - 20 Aug
Middletown Bungalow - RIBryan Property

DISCOUNT WEEK OF JULY 19-26!! Ocean views, Walk to Beach, Central AC, 4 Car Pk

9.8 out of 10, Exceptional, (139)
"Outstanding location and beautiful home"
DISCOUNT WEEK OF JULY 19-26!! Ocean views, Walk to Beach, Central AC, 4 Car Pk

The Field House - Peaceful Martha’s Vineyard Escape with Serene Field Views

2.0 star property
10.0 out of 10, Exceptional, (1)
"We had such a wonderful stay at this house! The layout was perfect — all the bedrooms were spacious and comfortable for our whole group. We especially loved the bright, open living space and the kitchen, which made gathering together so easy. The house was clean and full of natural light.The back deck with its patio seating was the perfect spot for an early morning coffee, and the large open field was great for a soccer game with our group. Plus, the hot tub was an amazing bonus. It was so much...
The Field House - Peaceful Martha’s Vineyard Escape with Serene Field Views

Quaint 1 Bed 1 bath private beach home. Long term renters welcome for winter!

10.0 out of 10, Exceptional, (16)
"We had a great stay at Oceans 11! The home is beautiful, it was incredibly clean, and very well stocked! We look forward to staying here again!!"
The price is €346
includes taxes & fees
25 Aug - 26 Aug
Quaint 1 Bed 1 bath private beach home. Long term renters welcome for winter!
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 Cuttyhunk Hotel Reviews