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

Holiday Homes in Cuttyhunk

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Cuttyhunk holiday homes

1. 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 €703
includes taxes & fees
12 Sept - 13 Sept
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

2. Ellery Bungalow #49 - Minutes from the Sand

Ellery Bungalow #49 - Minutes from the Sand
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Great stay. Very close to the beach. Would highly recommend"
United States
Semo A.
The price is €442
includes taxes & fees
14 Sept - 15 Sept
Ellery Bungalow #49 - Minutes from the Sand

3. Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is €912
includes taxes & fees
23 Aug - 24 Aug
Backyard Retreat / 5 Min > Beach & Main St

4. 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 €723
includes taxes & fees
11 Sept - 12 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

5. 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 €477
includes taxes & fees
26 Aug - 27 Aug
Ellery Bungalow #51- Island Calm Near Newport

6. 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 €435
includes taxes & fees
7 Sept - 8 Sept
Ellery Beach Bungalow #47- Relaxed Island Living

7. Little Creek Retreat Private hot tub & yard - RIBryan Properties

Little Creek Retreat Private hot tub & yard - RIBryan Properties
Middletown
9.4 out of 10, Exceptional, (15 reviews)
"Best stay "
United States
Justin R.
The price is €800
includes taxes & fees
24 Aug - 25 Aug
Little Creek Retreat Private hot tub & yard - RIBryan Properties

8. 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 €605
includes taxes & fees
3 Sept - 4 Sept
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

9. 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 €813
includes taxes & fees
8 Sept - 9 Sept
Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties

10. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is €814
includes taxes & fees
17 Sept - 18 Sept
Charming Vacation Home in Oak Bluffs.

11. 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 €688
includes taxes & fees
17 Sept - 18 Sept
Ellery Beach Bungalow #45- A Refined Island Escape

12. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (8 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is €1,223
includes taxes & fees
7 Sept - 8 Sept
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

13. Beach house walking distance to Second Beach

Beach house walking distance to Second Beach
Easton's Point
10.0 out of 10, Exceptional, (34 reviews)
"This is a hidden gem, off the beaten path, yet accessible to all the splendors of this beautiful area. The home is spacious and welcoming. The kitchen offers the opportunity to cook all meals comfortably if wanted. The fire pit is a definite bonus."
United States
Kelley
The price is €1,137
includes taxes & fees
1 Sept - 2 Sept
Beach house walking distance to Second Beach

14. Stepping Stone

Stepping Stone
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"This vacation place was clean, beautiful and comfortable with easy access to downturn Newport, the beaches and all the area has to offer. Perfect stay for our family wedding weekend."
United States
George
Stepping Stone

15. Beautiful Home in Falmouth Village

Beautiful Home in Falmouth Village
Falmouth
10.0 out of 10, Exceptional, (15 reviews)
"We had a family reunion and 75 Locust Street was the central hub of the four night stay. The house is beautiful, clean and we had family from all over stay there. We'd go back in a heartbeat. Easy access to downtown and the hosts were communicative and informative."
United States
Melissa L.
The price is €1,008
includes taxes & fees
16 Sept - 17 Sept
Beautiful Home in Falmouth Village

16. MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.8 out of 10, Exceptional, (12 reviews)
"TLDR: House is nice,"
United States
Rachel
The price is €1,895
includes taxes & fees
8 Sept - 9 Sept
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

17. A View Fit for Royalty! Top Compliments: so clean! fab hot tub! best view!

A View Fit for Royalty! Top Compliments: so clean! fab hot tub! best view!
Tisbury
10.0 out of 10, Exceptional, (31 reviews)
"Host was very informative before the arrival, house was spotless and everything was easy to find "
United States
Anonymous traveller
The price is €1,267
includes taxes & fees
24 Aug - 25 Aug
A View Fit for Royalty! Top Compliments: so clean! fab hot tub! best view!

18. Luxury Newport Home on Upscale Indian Ave. Close to Downtown Newport & Beaches!

Luxury Newport Home on Upscale Indian Ave. Close to Downtown Newport & Beaches!
Portsmouth
10.0 out of 10, Exceptional, (6 reviews)
"We stayed here for my wedding weekend, and it was absolutely perfect for me and my friends. The house is beautiful, in a great location, and had everything we needed. The yard and deck were such a wonderful spot to relax and enjoy our time together. We couldn’t have asked for a better place to stay and had a fantastic experience. Highly recommend!"
United States
Cara P.
The price is €2,142
includes taxes & fees
23 Aug - 24 Aug
Luxury Newport Home on Upscale Indian Ave. Close to Downtown Newport & Beaches!

19. Third Beach Road

Third Beach Road
Middletown
6.0 out of 10, (1 review)
"Renovated house, very cute. Kitchen was definitely a highlight as it was a good space for cooking and gathering together. Some amenities of house were not exactly as listed in description. Location of house was nice-close to beach and park with pickleball courts, easy access to Newport wharves and restaurants "
United States
Janet S.
Third Beach Road

20. Solo Fish - Family home, walk to beach and pool!

Solo Fish - Family home, walk to beach and pool!
Middletown
9.0 out of 10, Wonderful, (2 reviews)
"Everything about our stay was perfect. The house was extremely clean and very spacious! We were there celebrating my wedding and hosting many people. All the girls got ready there in the morning and we had so much room! Taking pictures in the home that will last us a lifetime made is super easy due to how clean and modern the home was. We all felt so comfortable there and really enjoyed the backyard as well. We will definitely be coming back!Lastly, the management team was 10/10. They answered...
United States
Jenna M.
The price is €2,267
includes taxes & fees
17 Sept - 18 Sept
Solo Fish - Family home, walk to beach and pool!
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

Top Cuttyhunk Hotel Reviews

Find out more about Cuttyhunk

Cuttyhunk Holiday Homes information

Number of reviews
247
Accommodation
474 Holiday Homes
Lowest Price
€435
Highest Price
€2,267

Explore a world of travel with Expedia