Holiday Homes in Cuttyhunk

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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 Holiday Homes in Cuttyhunk

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

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
Private cottage nestled in center of the Vineyard
Beach nearby

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
Terrace/patio

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
Outdoor dining

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

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
Smart TV

Costal Cottage Retreat minutes from Newport, RI

9.0 out of 10, Wonderful, (2)
"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
Exterior

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 AU$1,168
includes taxes & fees
19 Aug - 20 Aug
Beach house walking distance to Second Beach
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Dining

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
Interior

Family-Friendly Tisbury Escape - Walk to Town

9.8 out of 10, Exceptional, (19)
"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
Smart TV

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
Beach nearby, sun-loungers, beach towels

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
Fridge, microwave, oven, stovetop

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

7.4 out of 10, Good, (3)
"We had a wonderful early-June weekend stay at this charming house minutes walk from town. Highlights were reading on the rocking chair on the deck and playing games in the screened-in porch. Everything looks just like in the listing - charming, warm, like staying at your grandpa's beach house. There were a few bumps - the listed dryer was in a locked shed, a faucet wasn't working - but our sense was this is a new listing and details are still being ironed out. None of that interfered with our...
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
Fridge, microwave, oven, stovetop

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 AU$1,144
includes taxes & fees
29 Aug - 30 Aug
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Great Location! High-End Coastal Country Retreat
Smart TV, fireplace, table football, books

Great Location! High-End Coastal Country Retreat

10.0 out of 10, Exceptional, (47)
"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!
Terrace/patio

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
TV, DVD player, books

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

10.0 out of 10, Exceptional, (3)
"We had such a great stay here. Very clean and super close to town. We would definitely stay here again. Thanks!"
Spacious colonial home close to town with AC, porches, & W/D
Middletown Bungalow - RIBryan Property
Exterior

Middletown Bungalow - RIBryan Property

9.0 out of 10, Wonderful, (10)
"roomy, clean, and lovely outdoor deck. great kitchen and comfortable beds. very near newport sights."
The price is AU$1,521
includes taxes & fees
2 Sept - 3 Sept
Middletown Bungalow - RIBryan Property
DISCOUNT WEEK OF JULY 19-26!! Ocean views, Walk to Beach, Central AC, 4 Car Pk
Smart TV, fireplace

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
Exterior

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!
On the beach, sun-loungers, beach towels

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

10.0 out of 10, Exceptional, (15)
"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 AU$636
includes taxes & fees
3 Sept - 4 Sept
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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