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Compare 570 Vacation Homes in Cuttyhunk with updated reviews, rates, and availability.

Ellery Bungalow #51- Island Calm Near Newport

9.8 out of 10, Exceptional, (83)
"We had a wonderful stay!"
The price is AED 735
AED 1,916 total
includes taxes & fees
5 May - 6 May
Ellery Bungalow #51- Island Calm Near Newport

Little Creek Retreat - RIBryan Property

9.8 out of 10, Exceptional, (10)
"Great location! Quiet area, yet nearby to everything. The property was very spacious, clean and nice amenities. "
The price is AED 884
AED 2,435 total
includes taxes & fees
6 May - 7 May
Little Creek Retreat - RIBryan Property

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

8.8 out of 10, Excellent, (9)
"Private with beach access minutes away."
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry

9.6 out of 10, Exceptional, (49)
"This was a lovely home in a very nice location"
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry

Historic Oak Bluffs home, short walk to town, beach, and harbor.

9.6 out of 10, Exceptional, (28)
"We enjoy it all. "
Historic Oak Bluffs home, short walk to town, beach, and harbor.

Great Location Between First & Second Beach -- Pet Friendly!

9.8 out of 10, Exceptional, (71)
"would definitely recommend this property to family and freinds"
Great Location Between First & Second Beach -- Pet Friendly!

Gorgeous Spacious Victorian Cape Code Beach View Retreat

Gorgeous Spacious Victorian Cape Code Beach View Retreat

Cozy Middletown Home Near Beaches + Newport!

8.8 out of 10, Excellent, (11)
"This was a wonderful house amazing located for the Newport/Middletown area. I would stay here again in a heartbeat. "
Cozy Middletown Home Near Beaches + Newport!

Harbor Landing Resort

10.0 out of 10, Exceptional, (1)
"The kitchen facilities and out door grills made the vacation affordable. Not fancy, but very clean rooms. Would stay again for sure. Li"
Harbor Landing Resort

New Home close to Beach, Bike Path, and Sleeps 10! ☀️ 🏖

9.4 out of 10, Exceptional, (12)
"Perfect for a family of 5! Well equipped and great location. "
New Home close to Beach, Bike Path, and Sleeps 10! ☀️ 🏖

APRIL DISCOUNT NOW, Ocean views/Deck, Walk to Beach, Central AC, 4 Parking Spots

9.8 out of 10, Exceptional, (134)
"Outstanding location and beautiful home"
APRIL DISCOUNT NOW, Ocean views/Deck, Walk to Beach, Central AC, 4 Parking Spots

Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs

10.0 out of 10, Exceptional, (34)
"Great house in a great location! Very clean and well stocked with any kitchen supplies, towels, etc"
Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs

Middletown Bungalow - RIBryan Property

9.0 out of 10, Wonderful, (7)
"Enjoyed our overnight stay. Nice, clean and comfy place."
The price is AED 786
AED 2,091 total
includes taxes & fees
5 May - 6 May
Middletown Bungalow - RIBryan Property

Guest House In Edgartown

10.0 out of 10, Exceptional, (3)
"Everything was great! Very clean, loved the decor! Everything you would ever need in the kitchen. Bed was very comfortable. Porch was lovely with comfortable seating. Living room had a great TV. We ate in a lot and had everything we needed.. Difficult to find. Glad we arrived before it got dark! Very peaceful. Hated to leave"
Guest House In Edgartown

Great Vacation Place Just Steps From The Beach

9.8 out of 10, Exceptional, (26)
"Thank you for a perfect week! Everything was great!"
Great Vacation Place Just Steps From The Beach

Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

8.8 out of 10, Excellent, (30)
"A wonderful spot! Private and secluded. Great area that is close to all parts of the island. Wonderful hosts."
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

The Vienyard Haven Hideaway Apt

9.6 out of 10, Exceptional, (4)
"The property is clean and spacious. Great location and quiet."
The Vienyard Haven Hideaway Apt

Beach house walking distance to Second Beach

9.8 out of 10, Exceptional, (13)
"Great location, nice house. Great for a group of friends."
The price is AED 1,098
AED 2,467 total
includes taxes & fees
5 May - 6 May
Beach house walking distance to Second Beach

5 Blocks to Beach+Town, Stocked Kitchen, Cozy Beds

6.0 out of 10, (1)
"."
The price is AED 514
AED 1,871 total
includes taxes & fees
11 May - 12 May
5 Blocks to Beach+Town, Stocked Kitchen, Cozy Beds

Escape to this charming coastal retreat on Easton's Point, minutes from beaches

10.0 out of 10, Exceptional, (105)
"A perfect home base for our family in the Newport area! We loved the proximity second beach, and the huge yard was perfect for our toddler to run around."
Escape to this charming coastal retreat on Easton's Point, minutes from beaches
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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Other property types in Cuttyhunk

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (168)
"Very peaceful "
InnSeason Resorts Captain's Quarters

Ellery Bungalow #51- Island Calm Near Newport

9.8 out of 10, Exceptional, (83)
"We had a wonderful stay!"
The price is AED 735
AED 1,916 total
includes taxes & fees
5 May - 6 May
Ellery Bungalow #51- Island Calm Near Newport

Dog Friendly Cottages w/ easy access to Newport, beaches, trails and vineyards

9.8 out of 10, Exceptional, (124)
"Wonderful place to stay to enjoy all Newport has to offer. Lots of local places to eat and enjoy. Would definitely stay again!"
The price is AED 511
AED 656 total
includes taxes & fees
5 May - 6 May
Dog Friendly Cottages w/ easy access to Newport, beaches, trails and vineyards
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.