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

Holiday Homes in Cuttyhunk

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Our top choices for Cuttyhunk holiday homes

1. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is AU$1,311
includes taxes & fees
31 Aug - 1 Sept
Walk to Beach! Oak Bluffs Home & Studio

2. Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"I can’t say enough about this beautiful property. pictures don’t do any justice for this piece of heaven. The flowers were everywhere , it’s so apparent that the property owners take such pride in this beautiful property. The place was spotless when we walked in the door. We met the owners on arrival , they surprised us with a beautiful ballon to celebrate my 50th birthday. My family enjoyed the pool and the fun Tiki. The outdoor fireplace was inviting after the sun went down. I was a little...
United States
Miriam D.
The price is AU$6,074
includes taxes & fees
30 Aug - 31 Aug
Beautiful Estate with salt water pool & pond with kayaks

3. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is AU$3,036
includes taxes & fees
23 Aug - 24 Aug
Charming Vacation Home in Oak Bluffs.

4. 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, (6 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is AU$2,036
includes taxes & fees
1 Sept - 2 Sept
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

5. 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 AU$909
includes taxes & fees
2 Sept - 3 Sept
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

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

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (7 reviews)
"This house was perfect for our getaway. Rebecca, the host, was extremely responsive and helpful during our trip. The house was as advertised. It was clean, well equipped, and the location was perfect as well "
United States
Louis R.
The price is AU$2,113
includes taxes & fees
1 Sept - 2 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (10 reviews)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
United States
Swathanthra M.
The price is AU$5,528
includes taxes & fees
3 Aug - 4 Aug
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

8. NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Tisbury
10.0 out of 10, Exceptional, (16 reviews)
"We had an amazing time at this beautiful home. Great, clean space to spend an evening visit with friends and family. Great location with easy access around the island. Would highly recommend! "
United States
Jennifer T.
The price is AU$2,009
includes taxes & fees
17 Aug - 18 Aug
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

9. Sea Captain's Estate in Falmouth Village

Sea Captain's Estate in Falmouth Village
Falmouth
10.0 out of 10, Exceptional, (2 reviews)
"All the current and updated amenities available while retaining the historic charm of the house. We were ideally located for walking into town, over to the Shining Sea Bikeway and to the beach, as well as to the bus to the ferry in Woods Hole to get to Martha’s Vineyard. Hosts were responsive to questions and a concern one guest had that arose. They even messaged me at one point about slow internet that they were already taking care of. The house was clean upon arrival. We found an abundance of...
United States
Judy M.
The price is AU$4,332
includes taxes & fees
22 Aug - 23 Aug
Sea Captain's Estate in Falmouth Village

10. NEW Construction: a Love Letter to Martha's Vineyard

NEW Construction: a Love Letter to Martha's Vineyard
West Tisbury
10.0 out of 10, Exceptional, (2 reviews)
NEW Construction: a Love Letter to Martha's Vineyard

11. Elisa's Cottage - Your Family Vacation Destination

Elisa's Cottage - Your Family Vacation Destination
Woods Hole
10.0 out of 10, Exceptional, (8 reviews)
"We enjoyed the proximity to Woods Hole and Falmouth and the added snack touches. "
United States
Stefanie G.
The price is AU$1,739
includes taxes & fees
5 Aug - 6 Aug
Elisa's Cottage - Your Family Vacation Destination

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

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is AU$1,240
includes taxes & fees
4 Aug - 5 Aug
Backyard Retreat / 5 Min > Beach & Main St

13. World Cup Ocean retreat 40 minute drive from Boston Stadium - Gillette

World Cup Ocean retreat 40 minute drive from Boston Stadium - Gillette
Fairhaven
8.4 out of 10, Very good, (5 reviews)
"The home was beautiful and well equipped. Perfect location in a quiet new england neighborhood. My family enjoyed our stay!"
United States
lea m.
The price is AU$1,681
includes taxes & fees
4 Aug - 5 Aug
World Cup Ocean retreat 40 minute drive from Boston Stadium - Gillette

14. Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
9.6 out of 10, Exceptional, (37 reviews)
"We were looking for a weekend away from home, and we're lucky to find this place available. We got great recommendations for places to eat nearby, and were able to enjoy the area. We'd stay here again!"
United States
Zachary S.
The price is AU$738
includes taxes & fees
3 Aug - 4 Aug
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

15. 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 AU$1,645
includes taxes & fees
1 Sept - 2 Sept
Little Creek Retreat Private hot tub & yard - RIBryan Properties

16. Beach house walking distance to Second Beach

Beach house walking distance to Second Beach
Easton's Point
10.0 out of 10, Exceptional, (32 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 AU$1,817
includes taxes & fees
11 Aug - 12 Aug
Beach house walking distance to Second Beach

17. WALK to BEACH/CLIFF WALK! FANTASTIC Location! July OPENING! Fenced yard! Pets!

WALK to BEACH/CLIFF WALK! FANTASTIC Location! July OPENING! Fenced yard! Pets!
Middletown
10.0 out of 10, Exceptional, (52 reviews)
"Great stay! House was very clean and exactly as described in the listing. The fenced in yard was a huge plus with dogs and kids and getting into Newport was a breeze. "
United States
Tom C.
WALK to BEACH/CLIFF WALK! FANTASTIC Location! July OPENING! Fenced yard! Pets!

18. Double lot walk to beach 5 bed 7 bath, large yard

Double lot walk to beach 5 bed 7 bath, large yard
Easton's Point
9.6 out of 10, Exceptional, (28 reviews)
"We enjoyed our stay at the home. Very well maintained."
United States
Anmol P.
The price is AU$2,664
includes taxes & fees
10 Aug - 11 Aug
Double lot walk to beach 5 bed 7 bath, large yard

19. Spacious Private Cottage Close to Beaches & Newport

Spacious Private Cottage Close to Beaches & Newport
Middletown
10.0 out of 10, Exceptional, (1 review)
"We really enjoyed our stay. Everything was seamless from communication prior to arrival, check-in, and check-out. The team at STAY Newport was super responsive, though there wasn't much we needed, since the cottage was just as we expected and even better! Lots of room for our girls' trip and super close proximity to walk down to the beach. We were there in May, so it wasn’t quite beach season, but still ventured down for a walk, and it was an easy ride into downtown (less than 10 minutes). ...
United States
Amanda H.
The price is AU$1,831
includes taxes & fees
2 Sept - 3 Sept
Spacious Private Cottage Close to Beaches & Newport

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 AU$1,320
includes taxes & fees
9 Aug - 10 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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