Holiday Homes in Cuttyhunk

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Featured Holiday Homes in Cuttyhunk and around

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

9.0 out of 10, Wonderful, (2)
"The house was lovely. Very clean and orderly. Beautiful back porch that we enjoyed very much. The beds were very comfortable. Our only complaint was the Master bathroom needs some updating. The shower head desperately needs to be changed and the lighting is extremely poor. Also, only 1 half size mirror on the whole first floor. Other than that, it was perfect."
The price is €587
includes taxes & fees
5 Oct - 6 Oct
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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

10.0 out of 10, Exceptional, (17)
"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 €272
includes taxes & fees
8 Oct - 9 Oct
Quaint 1 Bed 1 bath private beach home. Long term renters welcome for winter!

Seapowet suite

10.0 out of 10, Exceptional, (1)
"The property is located in a beautiful little setting set back off the road with a huge lawn and outside patio area. Alan, the owner was very accommodating. Inside was two bedrooms, a bathroom and a nice big living room with a table. Also was a mini fridge along with a microwave and a Keurig coffee maker. A great little hiking area about 200 feet down the road. Beds were comfortable and very clean. I would highly recommend this place."
The price is €140
includes taxes & fees
7 Oct - 8 Oct
Seapowet suite

Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

2.0 star property
The price is €263
includes taxes & fees
17 Oct - 18 Oct
Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

Ellery Beach Bungalow #45- A Refined Island Escape

10.0 out of 10, Exceptional, (1)
"Beautiful area, walking distance to the beach and restaurants, nice clean house"
The price is €396
includes taxes & fees
3 Nov - 4 Nov
Ellery Beach Bungalow #45- A Refined Island Escape

Stunning, Chic Remodel! Beach House Minutes to Newport!

9.8 out of 10, Exceptional, (18)
"The house was convientky close to Newport There were 6 adults with us plenty of space for everyone. Host was very responsive And accommodating. "
The price is €1,727
includes taxes & fees
6 Oct - 7 Oct
Stunning, Chic Remodel! Beach House Minutes to Newport!

Ellery Bungalow #51- Island Calm Near Newport

9.6 out of 10, Exceptional, (94)
"This was the perfect size and location for our group of 5, would definitely stay again! "
The price is €398
includes taxes & fees
29 Oct - 30 Oct
Ellery Bungalow #51- Island Calm Near Newport

Little Creek Retreat - RIBryan Property

9.4 out of 10, Exceptional, (13)
"Although my party and I only stayed for 1 night we still had a great time in this lovely house."
The price is €584
includes taxes & fees
5 Oct - 6 Oct
Little Creek Retreat - RIBryan Property

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

10.0 out of 10, Exceptional, (7)
"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."
The price is €1,061
includes taxes & fees
5 Oct - 6 Oct
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

10.0 out of 10, Exceptional, (12)
"Extremely well designed extremely comfortable and well appointed. Beautiful scenery, and very relaxing."
The price is €1,177
includes taxes & fees
15 Oct - 16 Oct
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Entire house minutes from Newport, RI. Near beaches.

10.0 out of 10, Exceptional, (12)
"I stayed over Thanksgiving holiday to celebrate with my daughter attending school in Boston. The house was pristine, has a well stocked kitchen, thoughtfully decorated, conveniently located and Chadd was a terrific host! I will definitely stay here again, highly recommend the home!"
The price is €454
includes taxes & fees
20 Oct - 21 Oct
Entire house minutes from Newport, RI. Near beaches.

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

10.0 out of 10, Exceptional, (200)
"Loved this spot. So easy to get to downtown and Surf Beach. It was fabulous and clean!"
The price is €410
includes taxes & fees
7 Oct - 8 Oct
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

The Beach Estate, Panoramic Ocean Views, 5700 sqft

9.8 out of 10, Exceptional, (6)
"This was the perfect getaway for our large family. Everything was immaculate and we had all the comforts of home. We had a great week!"
The price is €1,595
includes taxes & fees
4 Nov - 5 Nov
The Beach Estate, Panoramic Ocean Views, 5700 sqft

Half mile to beach, Family & Pet Friendly, Newly Renovated Full House

10.0 out of 10, Exceptional, (17)
"Great property in a convenient location. Highly recommend this home. Property manager was great at getting back to us. "
Half mile to beach, Family & Pet Friendly, Newly Renovated Full House

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

10.0 out of 10, Exceptional, (15)
"The house is beautiful and conveniently located. The host, Melissa, was accessible and super helpful. We thoroughly enjoyed our time here and hope to be back in the future."
The price is €972
includes taxes & fees
3 Nov - 4 Nov
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Beautiful Home in Falmouth Village

10.0 out of 10, Exceptional, (9)
"Great house and good location. "
Beautiful Home in Falmouth Village

Stones Throw Waterfront

8.8 out of 10, Excellent, (6)
"We've selected this place for two main reasons - 1) Kayaks included, and 2) pets are welcome (at least, a dog - check the rules). Apart from the two kayaks, three standup boards (SUB) were also available. The property is located near a small cove, so it's perfect for SUB beginners, as there are no waves due to power motorboats, jet skis, etc. Note that launching the boats ISN'T a walk in the park. You'll have to deal with a narrow and relatively steep path, dealing with shrubs, rocks, and...
The price is €676
includes taxes & fees
5 Oct - 6 Oct
Stones Throw Waterfront

Beach house walking distance to Second Beach

9.8 out of 10, Exceptional, (20)
"Great location, nice house. Great for a group of friends."
The price is €755
includes taxes & fees
5 Oct - 6 Oct
Beach house walking distance to Second Beach

Middletown Bungalow - RIBryan Property

9.4 out of 10, Exceptional, (13)
"In town for daughter's graduation. Was only there for sleeping but was comfortable. Near stores for breakfast food. Decent overall experience (we had to take shoes off which didn't bother me but my 75 year old mom wasn't happy)"
The price is €537
includes taxes & fees
6 Oct - 7 Oct
Middletown Bungalow - RIBryan Property

The Wolcott... Walk To Beach!

10.0 out of 10, Exceptional, (8)
"House was great, plenty of bedrooms and living space and very clean. The location to Newport was great and very easy to get into and out of town. I would definitely recommend this to anyone who wants a house to relax in and one near NewPort!"
The Wolcott... Walk To Beach!
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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