Cuttyhunk Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Cuttyhunk Vacation Homes

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

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
Outdoor dining

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
Beachfront 3 bedroom house in Mattapoisett
Sun loungers, beach towels

Beachfront 3 bedroom house in Mattapoisett

10.0 out of 10, Exceptional, (1)
"What an amazing place! Perfect location.Beach is basically in your back yard and views from almost every window. Close to everything and far enough for privacy. Shayna was responsive and a great host! Thank you for letting me stay in this gem!"
Beachfront 3 bedroom house in Mattapoisett
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
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
Exterior

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 CA $412
CA $932 total
includes taxes & fees
Aug 19 - Aug 20
Beach house walking distance to Second Beach
Beautiful Country Setting Near Newport
Fridge, microwave, oven, stovetop

Beautiful Country Setting Near Newport

10.0 out of 10, Exceptional, (2)
"Great meeting you, great place we will be back next year. "
Beautiful Country Setting Near Newport
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
Fridge, microwave, oven, stovetop

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
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
Great Location! High-End Coastal Country Retreat
Smart TV, fireplace, foosball, 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
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
Private cottage nestled in center of the Vineyard
Beach nearby

Private cottage nestled in center of the Vineyard

10.0 out of 10, Exceptional, (47)
"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!
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, (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 CA $247
CA $562 total
includes taxes & fees
Sep 3 - Sep 4
Quaint 1 Bed 1 bath private beach home. Long term renters welcome for winter!
Recent Construction, Fire Pit, Kayaks, Close to Town, and Beach. Easton’s Point.
Fridge, microwave, oven, stovetop

Recent Construction, Fire Pit, Kayaks, Close to Town, and Beach. Easton’s Point.

10.0 out of 10, Exceptional, (94)
"The property was amazing and the host was so easy to communicate with! We love to the location and would definitely stay again"
Recent Construction, Fire Pit, Kayaks, Close to Town, and Beach. Easton’s Point.
Family Friendly 5 Bedroom, Walk to Town, Beach & Ferry
Terrace/patio

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
Fridge, microwave, oven, stovetop

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
TV, video games, DVD player, books

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
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
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cuttyhunk Hotel Reviews

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

10/10 Excellent
"Staff were attentive, kind and very helpful. We loved having a kitchen and the on site parking made our trip easier. "
Mari 3-night trip
Posted 2 days ago
Vineyard Harbor Motel - Private Beach