Vacation rentals in Cuttyhunk Island

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Top-rated vacation rentals in Cuttyhunk Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

The historic property is displayed from the street level, showcasing its architectural charm with a multi-story design. A covered porch is visible, featuring ornate woodwork. Shops line the street, contributing to a lively town atmosphere. Clear skies and bright sunlight enhance the inviting appearance.

Apartment in Oak Bluffs

4.92 out of 5 average rating, 109 reviews

Absolute Best Location on the Island

DanielleRating, 5 stars5 months ago

My family & I have been vacationing at Larry’s Historic Arcade for the past 7+ years. It is in the most perfect spot located right on Circuit Ave in the heart of Oak Bluffs. There are many stores and restaurants located on this road and it’s super convenient to have a market right across the street for any last minute essentials. We always rent the third floor apartment. It is very spacious and has a full size bed, a loft with 2 twin size beds and a pull out couch. It also has 2 decks. One over looking circuit ave and one on the other side with a grill. The house has WiFi, 2 mini splits (for ac or heat) a tv and a full kitchen. I highly recommend booking Larry’s Historic Arcade. It has everything you need and more. Thank you Larry for providing the perfect vacation spot for me and my family. We are already looking forward to next year!

Guest favorite

Home in Mashpee

4.94 out of 5 average rating, 110 reviews

Newly Renovated! Seconds to sand, fire pit, A/C

EzraRating, 5 stars4 months ago

Very comfortable and cozy, in a great part of the Cape. Kitchen has all you need, good set up for a couple or even small family. One note, not a huge problem: the fireplace is only ornamental. Bed is comfortable, might be too soft for some. Very helpful and friendly host, gave clear instructions but respected privacy. Thanks so much!

Top guest favorite

A serene outdoor area features four black Adirondack chairs arranged around a small fire pit on lush green grass. The cottage's charming exterior, highlighted by a wooden deck and American flag, is visible in the background, surrounded by trees.

Home in Sandwich

5 out of 5 average rating, 28 reviews

The Cape Cottage Fireplace * Kid Friendly * PetsOK

DanielRating, 5 stars5 days ago

Ariana was extremely attentive to any questions - the location was ideal and the home was very cozy and comfortable. I would highly recommend this location for a quick relaxing weekend or an extended stay! Thank you for a wonderful long weekend stay!! Best Dan & Mary

Guest favorite

Home in Mashpee

4.93 out of 5 average rating, 44 reviews

Tranquil Cape getaway#2 with AC Kid & Pet friendly

JennRating, 5 stars3 weeks ago

A wonderful spot filled with Machpee and Cape cod decor. The location was excellent given we travelled up and down the Cape and needed a spot that was centrally located. The house is well appointed and has everything you need ! It looks exactly like the photos. And the neighbourhood is very nice too.

Top guest favorite

A circular arrangement of chairs in various colors surrounds a small stone fire pit. The scene overlooks a serene pond, framed by lush trees and bathed in warm sunlight. Subtle outdoor lighting is positioned along the perimeter.

Cottage in Barnstable

4.99 out of 5 average rating, 142 reviews

Beach Glass Cottage - Pond Front

MaureenRating, 5 stars1 month ago

My friends and I stay at Maureen’s cottage every February for a winter stitching getaway. The house is perfect for the 3 of us. It has 3 comfortable bedrooms and 2 full baths. The living room is spacious. We love the kitchen and dining table. We set up our stitching gear and stitch the days away until it’s time to say goodbye. There are so many great restaurant choices close by. We highly recommend the Keltic Kitchen a short distance away on rte 28. Perfect breakfast place. We also tried for the first time a very small Thai restaurant, Bangkok Kitchen. The food was delicious and very nice people. Back to Maureen’s Beach Glass Cottage…just a perfect place to stay. The amenity list does not even begin to cover what they have available. It’s the perfect getaway home in my opinion. The one floor living is great for us with 1 of us having mobility issues. We cannot wait to come back. Thank You!

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What guests are saying

3BR Modern Home 5 Star, Walk2 Priv Beach, Mktplace

5 out of 5 average rating, 3 reviews35 months ago

Beautiful & comfortable beach house! We have stayed in a lot of short term rentals and this was definitely the best! Settled on a quiet dead end it is also directly next to a wooded path that takes you on a short walk to the Marketplace with mini golf, restaurants, and shops. It is also a short walk to the private beach. The layout of the house was perfect and it is nicely decorated as well as clean. We stayed for a long weekend with our young children to attend a wedding at the Popponesset Inn and the single level space was perfect for them. The convenience of not having to get in the car for food, beach, or activities was also priceless. Don was extremely welcoming and responded quickly with any of our questions. Would definitely stay again!

Home in Mashpee

What guests are saying

11 Drift

4.67 out of 5 average rating, 21 reviews4 months ago

This is a beautiful, old home that has been remodeled nicely. The kitchen amenities are solid. We hosted a Thanksgiving dinner here for my local family and it was absolutely perfect for the occasion. I saw the previous review about heat issues and mold, but we didn't encounter any of those problems. The heat worked very well on the main floor. It was a little chilly in the upstairs bedroom, but nothing that a portable wall heater couldn't take care of. The beds were super comfortable and everything was very clean. The layout of the bedrooms is a little awkward, but nothing insurmountable. There are some hard-to-navigate stairs that lead to the upstairs bedroom that would be impossible for the very old to navigate, but my teenage kids did just fine getting up there. The host was incredibly responsive and even had warm, homemade sourdough bread waiting for us! John is a wonderful host and this home is a true find.

Home in Westport

What guests are saying

In town Cozy-Cottage-Glam w/ Fab backyard 2bd/2B

4.95 out of 5 average rating, 19 reviews7 months ago

The house is lovely! The yard is the real star here, and the location is fantastic. The only small things I would comment on are providing your own linens (not ideal) and no coffee or anything to last a day upon arrival. But overall, I would recommend it for a nice stay on the island!

Cottage in Oak Bluffs

What guests are saying

Top floor with views and steps to private beach!

4.88 out of 5 average rating, 140 reviews20 months ago

We had a wonderful stay! The space was just what our family needed for a peaceful and laid back vacation before the summer comes to a close. We enjoyed the private beach just steps away from the house, and Bob provided us with beach toys for our daughter to play with! It’s a great location to get to some local attractions! Bob was a very friendly, communicative, and helpful host!! Thank you so much for our stay, Bob!

Apartment in Bourne

What guests are saying

2BR Lakefront | Deck | Washer/Dryer

4.55 out of 5 average rating, 31 reviews11 months ago

What a great location. Yes, the pond is closer, but the Vineyard Haven Harbor is right after the pond. So the views are wonderful! We thoroughly enjoyed the deck, overlooking the water, watching and listening to the birds, and star gazing at night. Almost equally distant from "downtown" Oak Bluffs and Vineyard Haven.

Home in Oak Bluffs

What guests are saying

54 - Private forested oasis near town and beach

4.95 out of 5 average rating, 76 reviews6 months ago

We had a horrible experience with our original rental (from another app)... we couldn't stay at the original place.. with a 1 year old in tow and evening approaching, we were scampering to find a place - within 2 hrs we were checking into Clif and Lindsay's place... it saved our holiday. They were super responsive, considerate and helpful if we needed anything! Thank you Clif and Lindsay for your timely responsiveness and wonderful house - great space!

Home in Edgartown

What guests are saying

Salty by the Sea

5 out of 5 average rating, 24 reviews2 days ago

We absolutely loved Nicole’s place. It’s in a quiet neighborhood and very easy to get to. We used it as a starting point on some trips to Plymouth and Newport. The house is set up very well, had all the amenities we needed, and was very comfortable. Our kids loved going to the beach every day, which is only a two minute drive away, and easily walkable. Nicole also shared several recommendations with us and she did not disappoint! I’d highly recommend her cottage.

Home in Mattapoisett

What guests are saying

Coastal Cottage

4.96 out of 5 average rating, 28 reviews2 weeks ago

We had a wonderful stay at Coastal Cottage! The setting was lovely and the house was spotless, very well equipped, and super comfortable with plenty of space for everyone. The outdoor areas were lovely and perfect for relaxing and hanging out. The hosts (Lauren & Mike) were responsive and thoughtful, and the welcome treats were such a nice touch! Great amenities all around—this was an ideal spot for a family and friends gathering. Highly recommend!

Home in Little Compton

What guests are saying

Cape Cod Seaside Getaway, Your Scenic Escape

4.91 out of 5 average rating, 32 reviews7 months ago

Lovely place to stay and unwind. The dwelling is an exquisite property that is clean, relaxing, private, and spacious. Everything you read in the property's description is true. The host (Jannet) is always available for questions or concerns. We feel very blessed to have found this property to rent and spend some time in Falmouth. It looks like this will be our annual place to stay. Paul T.

Home in Falmouth

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Popular amenities for Cuttyhunk Island vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Cuttyhunk Island

Superhost

An outdoor shower is enclosed with wooden panels and a clear curtain, offering privacy. The structure features a natural wood finish and is positioned near a wooden bench and grassy area. Steps lead down from the elevated deck to the yard.

Home in Narragansett

4.94 out of 5 average rating, 49 reviews

Allagash

JenniferRating, 5 stars9 months ago

We had a wonderful time! The place is great and the access to the private beach was so perfect and convenient. The house was perfect for our extended family. Would highly recommend

Guest favorite

A patio area features several white Adirondack chairs arranged around a small table, inviting relaxation. A pergola is visible, with a dining table set for outdoor meals. The pond is seen in the background, framed by trees and a clear sky.

Home in Mashpee

4.94 out of 5 average rating, 18 reviews

25 Menemsha Rd., Popponesset, pond & beach views

LisaRating, 5 stars5 months ago

We absolutely enjoyed our stayed. It's beautiful from the pictures online, but when you walk in it has a feel of being at a getaway even better than expected. The view is gorgeous and the home is very well kept and decorated. A big bonus for us was the spacious outdoor hottub. I would definitely feel comfortable booking with them again!

Top guest favorite

A two-story, light blue house is shown, featuring a well-maintained landscape with shrubs and small trees. A stone wall borders the property, and a concrete walkway with steps leads to a wooden deck at the entryway.

Apartment in Providence

5 out of 5 average rating, 7 reviews

Beautiful and spacious lovely home

ChrisRating, 5 stars3 weeks ago

Place worked out perfect

Superhost

Three turquoise Adirondack chairs are positioned on a grassy area, offering a view of a natural pathway lined with trees. The scene is brightened by natural light filtering through the leaves, creating a serene outdoor environment.

Home in Wareham

4.93 out of 5 average rating, 14 reviews

Private home, secluded 6 acre lot with water view

JaredRating, 5 stars7 months ago

Rebecca’s house in Wareham was a blessing! She is an attentive and responsive host, any concerns I had she was able to resolve immediately. We found ourselves wishing we had booked a longer stay to enjoy everything there was to offer!! Thank you Rebecca!

Superhost

The spacious rooftop deck features outdoor seating arranged around a coffee table, with a light-colored area rug beneath. Greenery from nearby trees adds a natural touch, while the view extends toward Newport Harbor and distant buildings under a clear blue sky.

Condo in Newport

4.73 out of 5 average rating, 60 reviews

Gorgeous Condo w/Roof Deck, Harbor Views on Thames

AlisonRating, 5 stars8 months ago

Our third time staying at this location and we were thrilled with the beautiful updates/renovations both on the roof deck and common corridor carpet.

Superhost

Home in Falmouth

4.8 out of 5 average rating, 25 reviews

5 Bedroom, Central Air, Close to Beaches and MORE!

CarolRating, 5 stars8 months ago

It is a nice house for a large family. We had between 8-12 there at any points. Close to beaches.

Superhost

A sunlit sunroom features multiple large glass panels allowing natural light to fill the space. Two white wicker rocking chairs are accompanied by a matching wicker table on a patterned area rug, enhancing the serene atmosphere. The view of the outdoors is visible through the glass.

Home in Falmouth

4.75 out of 5 average rating, 4 reviews

NEW! 2 Houses, Main House plus Guest House

CassandraRating, 5 stars7 months ago

We stayed here with a large group of friends including toddlers and babies for a friend’s wedding. We loved the space, especially sitting out on the deck together, having two separate spaces so some friends could stay up chatting while the kids slept in the other house was excellent. We would highly recommend this house for a fun and relaxing group trip!

Top guest favorite

A sandy beach extends along the shoreline, leading to calm waters reflecting the clear blue sky. Grassy dunes are visible to one side, while the horizon features distant trees. The beach appears serene and inviting, perfect for leisurely walks and relaxing moments by the water.

Home in Wareham

5 out of 5 average rating, 8 reviews

Amazing views, steps to private beach

SallyRating, 5 stars6 months ago

From the time we stepped into the home we were comfortable. Lots of seating areas. Having 2 kitchens worked perfectly for our large group of women who like to cook. Well stocked kitchens and bathrooms with extras I wouldn’t expect at an Airbnb. The linens and towels were perfect. Lots of pillows. It was chilly out when we arrived but the heater splits took the chill out in less than 20 min. The view is exceptional and walk to beach easy for all age groups. Plenty of parking. I can’t say enough about it and look forward to returning.

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Vacation rentals in Cuttyhunk Island

Top-rated vacation rentals in Cuttyhunk Island

Chadatopia, Quaint cottage retreat at happy hollow

3BR Modern Home 5 Star, Walk2 Priv Beach, Mktplace

11 Drift

The Island Collection MV: Sandy Shores

In town Cozy-Cottage-Glam w/ Fab backyard 2bd/2B

Top floor with views and steps to private beach!

2BR Lakefront | Deck | Washer/Dryer

54 - Private forested oasis near town and beach

Salty by the Sea

Coastal Cottage

Jaws House - Great Harbors

Cape Cod Seaside Getaway, Your Scenic Escape

Vacation rentals for every style

Popular amenities for Cuttyhunk Island vacation rentals

Other great vacation rentals in Cuttyhunk Island

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