A coastal landscape with a sandy beach, grassy areas, and a small island with a lighthouse.

Cuttyhunk Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Cuttyhunk vacation rentals

Terrace/patio

1. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is AED 1,429
AED 3,520 total
includes taxes & fees
31 Aug - 1 Sep
Walk to Beach! Oak Bluffs Home & Studio
Smart TV, stereo

2. The Charming Gem Near The Water!

The Charming Gem Near The Water!
New Bedford
9.6 out of 10, Exceptional, (45 reviews)
"A lovely apartment, nicely appointed, and conveniently located. One of my nicest stays to date"
United States
Thomas
The price is AED 314
AED 823 total
includes taxes & fees
26 Aug - 27 Aug
The Charming Gem Near The Water!
Outdoor pool, a heated pool

3. Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool
Chilmark
9.6 out of 10, Exceptional, (23 reviews)
"This is a great property for an individual or a couple looking to explore the island!"
United States
Jillian G.
The price is AED 1,194
AED 1,875 total
includes taxes & fees
15 Sep - 16 Sep
Cozy efficiency apartment/heated pool
Interior

4. Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
10.0 out of 10, Exceptional, (15 reviews)
"Super location, very nice accommodations, very clean, modern and comfortable "
United States
Cathie K.
The price is AED 1,157
AED 1,924 total
includes taxes & fees
24 Aug - 25 Aug
Charming cottage overlooking the bay in Padanaram Village.
Interior

5. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
9.8 out of 10, Exceptional, (30 reviews)
"Lovely and all brand new accommodation's that are clean and comfy! A quiet location too! "
United States
Nancy K.
The price is AED 734
AED 1,657 total
includes taxes & fees
27 Aug - 28 Aug
Brand new! Lovely apartment-Vineyard Haven
Exterior detail

6. Lovely 4- Bedroom apartment for rent

Lovely 4- Bedroom apartment for rent
New Bedford
6.8 out of 10, (3 reviews)
"Stay was great! "
United States
Zoe D.
The price is AED 611
AED 1,482 total
includes taxes & fees
17 Aug - 18 Aug
Lovely 4- Bedroom apartment for rent
Smart TV

7. Lovely 3 bedroom apartment 3rd floor

Lovely 3 bedroom apartment 3rd floor
New Bedford
9.4 out of 10, Exceptional, (13 reviews)
"Nice place for staying when traveling to Massachusetts "
United States
Anonymous traveler
The price is AED 785
AED 1,693 total
includes taxes & fees
24 Aug - 25 Aug
Lovely 3 bedroom apartment 3rd floor
TV

8. Ellery Bungalow #51- Island Calm Near Newport

Ellery Bungalow #51- Island Calm Near Newport
Middletown
9.6 out of 10, Exceptional, (97 reviews)
"We had a wonderful stay!"
United States
Stacey
The price is AED 613
AED 1,926 total
includes taxes & fees
2 Sep - 3 Sep
Ellery Bungalow #51- Island Calm Near Newport
Property grounds

9. Lovely two bedroom apartment with indoor fireplace

Lovely two bedroom apartment with indoor fireplace
Oak Bluffs
10.0 out of 10, Exceptional, (7 reviews)
"Great stay, flexible and responsive host. Difficult location, however, as it was not centrally located or easy to access transportation, etc."
United States
Aviva M.
The price is AED 724
AED 2,728 total
includes taxes & fees
7 Sep - 8 Sep
Lovely two bedroom apartment with indoor fireplace
Exterior detail

10. Ellery Beach Bungalow #45- A Refined Island Escape

Ellery Beach Bungalow #45- A Refined Island Escape
Middletown
10.0 out of 10, Exceptional, (1 review)
"Beautiful area, walking distance to the beach and restaurants, nice clean house"
United States
Dana N.
The price is AED 613
AED 1,926 total
includes taxes & fees
2 Sep - 3 Sep
Ellery Beach Bungalow #45- A Refined Island Escape
Exterior

11. serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
West Tisbury
The price is AED 1,157
AED 2,884 total
includes taxes & fees
15 Sep - 16 Sep
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
Property grounds

12. Ellery Beach Bungalow #47- Relaxed Island Living

Ellery Beach Bungalow #47- Relaxed Island Living
Middletown
8.6 out of 10, Excellent, (7 reviews)
"Fantastic stay! "
United States
Cristin C.
The price is AED 617
AED 1,931 total
includes taxes & fees
2 Sep - 3 Sep
Ellery Beach Bungalow #47- Relaxed Island Living
TV, fireplace, books

13. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (9 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is AED 1,157
AED 3,118 total
includes taxes & fees
11 Sep - 12 Sep
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Terrace/patio

14. Seapowet suite

Seapowet suite
Tiverton
9.0 out of 10, Wonderful, (13 reviews)
"Lovely spot, wonderful host. Had everything we needed, close to town."
United States
Lauren S.
The price is AED 900
AED 1,277 total
includes taxes & fees
26 Aug - 27 Aug
Seapowet suite
Interior

15. Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Tisbury
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful view of the lagoon; ideal place for a couple or single. Leisurely walk to town and close to public transportation."
United States
Adrienne W.
The price is AED 1,377
AED 2,322 total
includes taxes & fees
1 Sep - 2 Sep
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Smart TV

16. Middletown Modern Apartment w/ Private Deck - RIBryan Properties

Middletown Modern Apartment w/ Private Deck - RIBryan Properties
Middletown
9.6 out of 10, Exceptional, (17 reviews)
"Apartment was beautiful in a great location!!!"
United States
cathy g.
The price is AED 1,242
AED 2,229 total
includes taxes & fees
13 Sep - 14 Sep
Middletown Modern Apartment w/ Private Deck - RIBryan Properties
Coffee/tea maker, fridge, microwave, oven

17. Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (6 reviews)
"This is a new, beautiful and tastefully decorated 2 bedroom one bathroom house with a really nice big yard. Owner was very responsive and We had everything we needed for an enjoyable stay!"
United States
Elizabeth O.
The price is AED 1,506
AED 3,750 total
includes taxes & fees
7 Sep - 8 Sep
Brand New Guest house
Property grounds

18. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.8 out of 10, (9 reviews)
"We had a perfect pre-/off-season stay with plenty of sleeping space. The location is fantastic—right between Vineyard Haven and Edgartown—making it easy to bike to both, plus there’s a beach across the street. The WiFi wasn’t working when we first arrived, but the owner was incredibly responsive and went above and beyond to fix it quickly. We’ll definitely be back!"
United States
Bethann N.
The price is AED 1,161
AED 2,626 total
includes taxes & fees
25 Aug - 26 Aug
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Sun loungers, beach towels

19. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is AED 1,833
AED 3,512 total
includes taxes & fees
9 Sep - 10 Sep
Charming Vacation Home in Oak Bluffs.
Exterior

20. Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties

Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties
Middletown
9.6 out of 10, Exceptional, (17 reviews)
"We enjoyed our stay at this lovely home. The hot tub was very fun and huge kitchen table was nice for our family. It was conveniently located and well cleaned before our arrival. We recommend this fun spot in Newport."
United States
Michelle N.
The price is AED 1,753
AED 3,320 total
includes taxes & fees
17 Aug - 18 Aug
Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties
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

ShoreWay Acres Inn & Cape Cod Lodging

ShoreWay Acres Inn & Cape Cod Lodging

8/10 Good
"The location and price are great. Indoor and outdoor pools. One block to Main Street to restaurants and shopping. You could walk to beach."
Helen 2-night trip
Posted 16 hours ago
ShoreWay Acres Inn & Cape Cod Lodging

Frequently asked questions

Can I find a vacation rental in Cuttyhunk?

Yes, there are vacation rentals near popular attractions in Cuttyhunk, or you can select a more remote option if you want a relaxing place to stay. Cuttyhunk is known for its beaches.

What are some of the best vacation home rentals in Cuttyhunk?

Gorgeous Spacious Victorian Cape Cod Beach View Retreat: Located near Cuttyhunk, this vacation home rental is located near the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Cuttyhunk?

Explore the area and family-friendly sights such as Buttonwood Park Zoo, or get out into nature at a spot like Aquinnah Cliffs. Gay Head Lighthouse and Demarest Lloyd State Park are a couple of places you'll find in the larger area.

What’s a vacation rental in Cuttyhunk like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Cuttyhunk. Vacation rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a small group gathering.