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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Featured Cottages in Cuttyhunk

Idyllic Newport Area Cottage - Walk to First Beach
Enjoy cooking in this kitchen with an oven, stainless steel range hood, and granite countertop.

Idyllic Newport Area Cottage - Walk to First Beach

3.0 star property
Idyllic Newport Area Cottage - Walk to First Beach
Coastal Abode w/ Beach Views, Walk to Beach & Bars
Interior

Coastal Abode w/ Beach Views, Walk to Beach & Bars

3.0 star property
Coastal Abode w/ Beach Views, Walk to Beach & Bars
Family-friendly Tisbury Escape - Walk to Town
Relax in this serene outdoor seating area with a wooden ceiling and large windows offering a view of the surrounding trees and landscape.

Family-friendly Tisbury Escape - Walk to Town

3.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect. Great."
Family-friendly Tisbury Escape - Walk to Town
Vineyard Haven House - Easy Access to Beaches
Front of property

Vineyard Haven House - Easy Access to Beaches

3.0 star property
Vineyard Haven House - Easy Access to Beaches
Cozy Vineyard Haven Cottage < 1 Mi to Beach!
Cozy cabin kitchen with a stove, refrigerator, and dining table for four.

Cozy Vineyard Haven Cottage < 1 Mi to Beach!

3.0 star property
Cozy Vineyard Haven Cottage < 1 Mi to Beach!
Charming MV Cottage: Walk to Dtwn Oak Bluffs!
Relax and unwind in this serene outdoor space, featuring a TV for entertainment, a dining table, and comfortable seating.

Charming MV Cottage: Walk to Dtwn Oak Bluffs!

3.0 star property
Charming MV Cottage: Walk to Dtwn Oak Bluffs!
Mattapoisett Home on 7 Acres w/ Private Beach!
Cozy cabin with a high ceiling, wooden bench, and sofa, perfect for relaxation and quiet reading.

Mattapoisett Home on 7 Acres w/ Private Beach!

3.0 star property
4.0 out of 10, (1)
"One bathroom was updated, only 3 of the bedrooms had a/c. Sunken living room and 1st floor br had ants and bugs crawling around. All the prongs I saw (other than the bathroom) were 2 prong outlets, no light switches in bedrooms. The whole house smelled like mold and mildew. I had to get 2 air purifiers due to smell. We left 2 days early. Just wasn’t enjoyable. Good news - great private property and very close to beach. Owner did respond quickly to initial queries."
Mattapoisett Home on 7 Acres w/ Private Beach!
9 Mi to Beach: Home w/ Private Yard in Westport
Interior

9 Mi to Beach: Home w/ Private Yard in Westport

3.0 star property
9 Mi to Beach: Home w/ Private Yard in Westport
Birders Paradise Beachhouse < 2 Miles to Winery!
Property grounds

Birders Paradise Beachhouse < 2 Miles to Winery!

3.0 star property
Birders Paradise Beachhouse < 2 Miles to Winery!
Coastal Home: 1 Mi to Beach, 2 Mi to Dtwn Newport!
Interior

Coastal Home: 1 Mi to Beach, 2 Mi to Dtwn Newport!

3.0 star property
Coastal Home: 1 Mi to Beach, 2 Mi to Dtwn Newport!
Fairhaven Harbor-front Gem - Steps From the Water!
Interior

Fairhaven Harbor-front Gem - Steps From the Water!

3.0 star property
Fairhaven Harbor-front Gem - Steps From the Water!
Martha's Vineyard Home: Walk to Oak Bluffs Beach!
Interior

Martha's Vineyard Home: Walk to Oak Bluffs Beach!

3.0 star property
Martha's Vineyard Home: Walk to Oak Bluffs Beach!
Falmouth Retreat w/ Deck & Grill, Walk to Beaches!
Guests can store bicycles and a small boat in this well-organized garage with ample shelving.

Falmouth Retreat w/ Deck & Grill, Walk to Beaches!

3.0 star property
Falmouth Retreat w/ Deck & Grill, Walk to Beaches!
Vineyard Gem < 2 Mi to Beach & Oak Bluffs!
Microwave, oven, stovetop, dishwasher

Vineyard Gem < 2 Mi to Beach & Oak Bluffs!

3.0 star property
Vineyard Gem < 2 Mi to Beach & Oak Bluffs!
Oak Bluffs 3-Bed Cottage, Walk to Town
Compact kitchen with oven, stainless steel range hood, microwave, and modern sink.

Oak Bluffs 3-Bed Cottage, Walk to Town

3.5 star property
Oak Bluffs 3-Bed Cottage, Walk to Town
Serene Mattapoisett Home w/ Private Beach Access!
Interior

Serene Mattapoisett Home w/ Private Beach Access!

3.0 star property
Serene Mattapoisett Home w/ Private Beach Access!
Cape Cod Cottage w/ Deck, Grill, & Games!
Interior

Cape Cod Cottage w/ Deck, Grill, & Games!

3.0 star property
Cape Cod Cottage w/ Deck, Grill, & Games!
Peaceful Chilmark Farmhouse by Menemsha Beach
Enjoy a serene beach experience with large boulders and a tranquil ocean.

Peaceful Chilmark Farmhouse by Menemsha Beach

3.0 star property
Peaceful Chilmark Farmhouse by Menemsha Beach
Beautiful Aquinnah Home: Ocean View, Walk to Beach
Enjoy cooking in this well-equipped kitchen with microwave, refrigerator, and various appliances.

Beautiful Aquinnah Home: Ocean View, Walk to Beach

3.0 star property
Beautiful Aquinnah Home: Ocean View, Walk to Beach
Sunny Beach House Getaway - Steps From Water!
Interior

Sunny Beach House Getaway - Steps From Water!

3.0 star property
Sunny Beach House Getaway - Steps From Water!
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

The East Island Reserve Hotel

The East Island Reserve Hotel

10/10 Excellent
"Wonderful place to stay-clean, many amenities. Nice pool and beautiful landscaping. Close to restaurants, stores and beaches. One of the best hotels I’ve ever stayed at."
Brenda 3-night trip
Posted 10 hours ago
The East Island Reserve Hotel

Frequently asked questions

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How can I find cheap cottages in Cuttyhunk?
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What is there to do in Cuttyhunk near my cottage?
The ideal travel accessory is a well-planned to-do list. Barges Beach is a terrific place to kick off your sightseeing in Cuttyhunk.