Holiday Homes in Cuttyhunk

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Featured Holiday Homes in Cuttyhunk and around

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

10.0 out of 10, Exceptional, (16)
"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 €346
includes taxes & fees
1 Sept - 2 Sept
Quaint 1 Bed 1 bath private beach home. Long term renters welcome for winter!

Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

The price is €263
includes taxes & fees
1 Sept - 2 Sept
Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

King Bed Standard View

The price is €155
includes taxes & fees
1 Sept - 2 Sept
King Bed Standard View

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 €1,759
includes taxes & fees
1 Sept - 2 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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."
Seapowet suite

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 €441
includes taxes & fees
2 Sept - 3 Sept
Ellery Beach Bungalow #45- A Refined Island Escape

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 €2,061
includes taxes & fees
18 Sept - 19 Sept
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

The FREEDOM HOME FROM HOME

10.0 out of 10, Exceptional, (1)
"Super great communication and easy check in process! Loved the house with everything needed for a short weekend getaway!"
The price is €375
includes taxes & fees
19 Aug - 20 Aug
The FREEDOM HOME FROM HOME

Ellery Bungalow #51- Island Calm Near Newport

9.8 out of 10, Exceptional, (90)
"This was the perfect size and location for our group of 5, would definitely stay again! "
The price is €433
includes taxes & fees
3 Sept - 4 Sept
Ellery Bungalow #51- Island Calm Near Newport

Cozy Oceanfront Room | 2 Beds + Kitchenette

The price is €220
includes taxes & fees
1 Sept - 2 Sept
Cozy Oceanfront Room | 2 Beds + Kitchenette

Stunning, Chic Remodel! Beach House Minutes to Newport!

9.8 out of 10, Exceptional, (15)
"House was great kitchen had everything you would need and more! Beds very comfortable like others have stated. Very close to Newport😃 Would recommend!!"
The price is €1,786
includes taxes & fees
1 Sept - 2 Sept
Stunning, Chic Remodel! Beach House Minutes to Newport!

2 Double Bed Oceanview Stay + Shared Deck

The price is €247
includes taxes & fees
4 Sept - 5 Sept
2 Double Bed Oceanview Stay + Shared Deck

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

10.0 out of 10, Exceptional, (12)
"We so enjoyed our stay! Alexis has thought of everything to make a visit comfortable. Enjoyed the location and was able to walk to the village for coffee! Very convenient location and would highly recommend!"
The price is €1,364
includes taxes & fees
1 Sept - 2 Sept
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!

The price is €676
includes taxes & fees
1 Sept - 2 Sept
Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!

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

10.0 out of 10, Exceptional, (12)
"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 €1,006
includes taxes & fees
15 Sept - 16 Sept
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Little Creek Retreat - RIBryan Property

9.2 out of 10, Wonderful, (11)
"Although my party and I only stayed for 1 night we still had a great time in this lovely house."
Little Creek Retreat - RIBryan Property

Delightful, Charming, Oversized 2 bedroom 2 bath Cottage!

9.8 out of 10, Exceptional, (21)
"We enjoyed our stay and found it a great location for day trips around the area."
Delightful, Charming, Oversized 2 bedroom 2 bath Cottage!

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

10.0 out of 10, Exceptional, (198)
"As always, lovely home. Perfect place."
The price is €515
includes taxes & fees
8 Sept - 9 Sept
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Stunning, Classic Renovated Greek Revival - few mins Walk to Main St & VH Ferry

10.0 out of 10, Exceptional, (41)
"Couldn't have asked for a better place to have as a homebase while I was in town for a wedding! My friends and I loved using the outdoor space and being so close to town. I look forward to coming back for a future vacation. I would highly recommend staying here!"
Stunning, Classic Renovated Greek Revival - few mins Walk to Main St & VH Ferry
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