Holiday Homes in Cuttyhunk

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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Holiday Homes in Cuttyhunk

Cozy Middletown Home Near Beaches + Newport!
Enjoy meals at the central island or dining table, which seats four.

Cozy Middletown Home Near Beaches + Newport!

8.8 out of 10, Excellent, (15)
"This was a wonderful house amazing located for the Newport/Middletown area. I would stay here again in a heartbeat. "
Cozy Middletown Home Near Beaches + Newport!
Spacious home in central location with beautiful patio, pool table, W/D, & AC
Stroll out to the front porch and enjoy the serene surroundings.

Spacious home in central location with beautiful patio, pool table, W/D, & AC

10.0 out of 10, Exceptional, (1)
"We loved our stay. This is the first time I have rented a house without a prior review. So glad we did! The house seemed brand new or very recently remodeled. The pool table and media area downstairs made the rainy day we had on the island a great one. We had a party of seven and plenty of space to spread out and relax. It was easy to walk to town but we also rented bikes to get around. I would highly recommend this home to anyone looking for a relaxing stay on Martha's Vineyard."
Spacious home in central location with beautiful patio, pool table, W/D, & AC
Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C
Relax on the deck with a view of the surrounding landscape and trees, featuring a glass-top table and comfortable seating for four.

Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C

6.2 out of 10, (17)
"This property has not been well cared for or cleaned. Arrived to a very musty/moldy smell, trash outside, the walls were streaked with dead bug guts and then the stove didn't work!! It was a step above camping. You get what you pay for!"
Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Enjoy dining or socializing on the patio surrounded by lush greenery.

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
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
Victorian cottage overlooking downtown Oak Bluffs and the Harbor.
Property grounds

Victorian cottage overlooking downtown Oak Bluffs and the Harbor.

2.0 star property
10.0 out of 10, Exceptional, (1)
"Nice nostalgic home Needs minor work (Toilet seats)(Middle room mirror )AC "
Victorian cottage overlooking downtown Oak Bluffs and the Harbor.
Beach house walking distance to Second Beach
Stunning two-story home with a charming front porch and beautifully manicured lawn.

Beach house walking distance to Second Beach

9.8 out of 10, Exceptional, (16)
"Great location, nice house. Great for a group of friends."
The price is NZ$2,134
includes taxes & fees
13 Aug - 14 Aug
Beach house walking distance to Second Beach
Beautiful Country Setting Near Newport
Enjoy cooking in this well-equipped kitchen with an oven, microwave, and refrigerator.

Beautiful Country Setting Near Newport

10.0 out of 10, Exceptional, (1)
"Beautiful townhouse, very well kept with clear attention to detail. "
Beautiful Country Setting Near Newport
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Residents can stroll along the walking path and enjoy the serene atmosphere of this well-maintained neighborhood.

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
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, (2)
"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
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator, oven, and dishwasher.

Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry

9.6 out of 10, Exceptional, (52)
"This was a lovely home in a very nice location"
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
Great Location! High-End Coastal Country Retreat
Cozy living area with a staircase leading to a balcony.

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
Private cottage nestled in center of the Vineyard
Enjoy a serene beach experience with gentle waves lapping onto the shore.

Private cottage nestled in center of the Vineyard

10.0 out of 10, Exceptional, (46)
"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
Quaint 1 Bed 1 bath private beach home. Long term renters welcome for winter!
Guests can enjoy a serene beach scene with sailboats anchored offshore.

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

10.0 out of 10, Exceptional, (14)
"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 NZ$645
includes taxes & fees
5 Aug - 6 Aug
Quaint 1 Bed 1 bath private beach home. Long term renters welcome for winter!
The Field House - Peaceful Martha’s Vineyard Escape with Serene Field Views
Guests can enjoy a spacious balcony and a large front porch with outdoor seating and a barbecue grill.

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
Family Friendly 5 Bedroom, Walk to Town, Beach & Ferry
Relax on the deck with a comfortable seating area, featuring a sofa, chairs, and a coffee table.

Family Friendly 5 Bedroom, Walk to Town, Beach & Ferry

10.0 out of 10, Exceptional, (6)
"Nice, newly renovated place. Very well equipped with easy access to either ferry terminals."
Family Friendly 5 Bedroom, Walk to Town, Beach & Ferry
Charming 2-bd Home Steps to Falmouth Heights Beach w/ Fab Fenced Patio & Yard
Enjoy cooking in this well-equipped kitchen with a central island, gas stove, refrigerator, and microwave.

Charming 2-bd Home Steps to Falmouth Heights Beach w/ Fab Fenced Patio & Yard

Charming 2-bd Home Steps to Falmouth Heights Beach w/ Fab Fenced Patio & Yard
Dog-friendly home with beautiful deck & AC - close to 3 towns & great beaches
Relax in this inviting living area with a comfortable sofa set and a modern kitchen in the background.

Dog-friendly home with beautiful deck & AC - close to 3 towns & great beaches

3.8 out of 10, (7)
"We enjoyed our stay here and loved having the big open kitchen to the living room to all hang out in!"
Dog-friendly home with beautiful deck & AC - close to 3 towns & great beaches
Stunning Tisbury Retreat with Pool
Outdoor pool

Stunning Tisbury Retreat with Pool

10.0 out of 10, Exceptional, (3)
"Wonderful home to stay with family and friends. The pool is a perfect addition. Plenty of space for everyone to relax after a long beach day. The host was great to deal with also. Highly recommend! "
Stunning Tisbury Retreat with Pool
Top-Rated Vineyard Retreat: Hot Tub + Private Lambert’s Cove Beach Access!
Enjoy a leisurely day on this wide, calm beach with ample space for relaxation.

Top-Rated Vineyard Retreat: Hot Tub + Private Lambert’s Cove Beach Access!

10.0 out of 10, Exceptional, (11)
"We had a wonderful stay in the home."
Top-Rated Vineyard Retreat: Hot Tub + Private Lambert’s Cove Beach Access!
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

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

10/10 Excellent
"Staff were amazing and helpful! Beautiful view and private beach "
Brody McCoy 3-night trip
Posted 1 day ago
Vineyard Harbor Motel - Private Beach