A coastal landscape with a sandy beach, grassy areas, and a small island with a lighthouse.

Cuttyhunk Vacation Rentals

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Our top choices for Cuttyhunk vacation rentals

The Charming Gem Near The Water!

The Charming Gem Near The Water!
New Bedford
9.6 out of 10, Exceptional, (44 reviews)
"A lovely apartment, nicely appointed, and conveniently located. One of my nicest stays to date"
United States
Thomas
$199 nightly
The price is $222
Jul 26 - Jul 27
Total with taxes and fees
The Charming Gem Near The Water!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
9.6 out of 10, Exceptional, (35 reviews)
"We were looking for a weekend away from home, and we're lucky to find this place available. We got great recommendations for places to eat nearby, and were able to enjoy the area. We'd stay here again!"
United States
Zachary S.
$463 nightly
The price is $517
Jul 27 - Jul 28
Total with taxes and fees
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi

Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi
New Bedford
9.8 out of 10, Exceptional, (11 reviews)
"We love it here quite neighbors are really nice Angelino is on top of everything great host "
United States
Joann E.
$331 nightly
The price is $369
Jul 29 - Jul 30
Total with taxes and fees
Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi

Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
$706 nightly
The price is $788
Jul 28 - Jul 29
Total with taxes and fees
Backyard Retreat / 5 Min > Beach & Main St

Drift Loft Houseboat

Drift Loft Houseboat
New Bedford
10.0 out of 10, Exceptional, (2 reviews)
"Clean property, great amenities."
United States
Sandra T.
$233 nightly
The price is $260
Aug 4 - Aug 5
Total with taxes and fees
Drift Loft Houseboat

Lovely 4- Bedroom apartment for rent

Lovely 4- Bedroom apartment for rent
New Bedford
6.8 out of 10, (3 reviews)
"Stay was great! "
United States
Zoe D.
$362 nightly
The price is $404
Jul 27 - Jul 28
Total with taxes and fees
Lovely 4- Bedroom apartment for rent

Walk to Beach & Lighthouse: Oak Bluffs Studio!

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
8.4 out of 10, Very Good, (6 reviews)
"Very accommodating early check in and great communication "
United States
Katelyn K.
$358 nightly
The price is $400
Jul 27 - Jul 28
Total with taxes and fees
Walk to Beach & Lighthouse: Oak Bluffs Studio!

Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
9.8 out of 10, Exceptional, (28 reviews)
"Lovely and all brand new accommodation's that are clean and comfy! A quiet location too! "
United States
Nancy K.
$385 nightly
The price is $430
Jul 27 - Jul 28
Total with taxes and fees
Brand new! Lovely apartment-Vineyard Haven

Ellery Beach Bungalow #45- A Refined Island Escape

Ellery Beach Bungalow #45- A Refined Island Escape
Middletown
10.0 out of 10, Exceptional, (1 review)
"Beautiful area, walking distance to the beach and restaurants, nice clean house"
United States
Dana N.
$427 nightly
The price is $487
Jul 28 - Jul 29
Total with taxes and fees
Ellery Beach Bungalow #45- A Refined Island Escape

Ellery Beach Bungalow #47- Relaxed Island Living

Ellery Beach Bungalow #47- Relaxed Island Living
Middletown
9.4 out of 10, Exceptional, (6 reviews)
"Fantastic stay! "
United States
Cristin C.
$427 nightly
The price is $487
Jul 28 - Jul 29
Total with taxes and fees
Ellery Beach Bungalow #47- Relaxed Island Living

Small One Bedroom Private Cottage on Large Quiet Property.

Small One Bedroom Private Cottage on Large Quiet Property.
Tisbury
10.0 out of 10, Exceptional, (16 reviews)
"Nice, quaint cottage. Perfect for a couple's getaway! Location was convenient for walking to shops and restaurants."
United States
Randy T.
$457 nightly
The price is $510
Aug 23 - Aug 24
Total with taxes and fees
Small One Bedroom Private Cottage on Large Quiet Property.

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
West Tisbury
$838 nightly
The price is $936
Jul 25 - Jul 26
Total with taxes and fees
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

Seapowet suite

Seapowet suite
Tiverton
9.2 out of 10, Wonderful, (12 reviews)
"Lovely spot, wonderful host. Had everything we needed, close to town."
United States
Lauren S.
$263 nightly
The price is $300
Aug 4 - Aug 5
Total with taxes and fees
Seapowet suite

World Cup Ocean retreat 40 minute drive from Boston Stadium - Gillette

World Cup Ocean retreat 40 minute drive from Boston Stadium - Gillette
Fairhaven
8.4 out of 10, Very Good, (5 reviews)
"The home was beautiful and well equipped. Perfect location in a quiet new england neighborhood. My family enjoyed our stay!"
United States
lea m.
$1,077 nightly
The price is $1,203
Aug 4 - Aug 5
Total with taxes and fees
World Cup Ocean retreat 40 minute drive from Boston Stadium - Gillette

Middletown Modern Apartment w/ Private Deck - RIBryan Properties

Middletown Modern Apartment w/ Private Deck - RIBryan Properties
Middletown
9.6 out of 10, Exceptional, (17 reviews)
"Apartment was beautiful in a great location!!!"
United States
cathy g.
$422 nightly
The price is $459
Jul 28 - Jul 29
Total with taxes and fees
Middletown Modern Apartment w/ Private Deck - RIBryan Properties

Ellery Bungalow #51- Island Calm Near Newport

Ellery Bungalow #51- Island Calm Near Newport
Middletown
9.6 out of 10, Exceptional, (96 reviews)
"This was the perfect size and location for our group of 5, would definitely stay again! "
United States
toni g.
$610 nightly
The price is $695
Aug 9 - Aug 10
Total with taxes and fees
Ellery Bungalow #51- Island Calm Near Newport

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

Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
Dartmouth
10.0 out of 10, Exceptional, (16 reviews)
"This property is amazing. One of the most thoughtful hosts I have ever had with VRBO. First class all the way. Great location. The view is outstanding. Just a wonderful stay, the kitchen is a dream. Just a fantastic find and I cant wait to return to No Egrets Haven. "
United States
Valerie J.
$1,932 nightly
The price is $2,158
Jul 28 - Jul 29
Total with taxes and fees
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Charming Guesthouse | Walk to Beach | Downtown

Charming Guesthouse | Walk to Beach | Downtown
Falmouth
$658 nightly
The price is $753
Jul 26 - Jul 27
Total with taxes and fees
Charming Guesthouse | Walk to Beach | Downtown

Ellery Bungalow #49 - Minutes from the Sand

Ellery Bungalow #49 - Minutes from the Sand
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Great stay. Very close to the beach. Would highly recommend"
United States
Semo A.
$427 nightly
The price is $487
Jul 28 - Jul 29
Total with taxes and fees
Ellery Bungalow #49 - Minutes from the Sand

NEW Construction: a Love Letter to Martha's Vineyard

NEW Construction: a Love Letter to Martha's Vineyard
West Tisbury
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay at this home in West Tisbury. The house was exactly as described - comfortable, clean, well-appointed, and thoughtfully stocked with everything we needed. The location was perfect for exploring the island while still feeling peaceful and relaxing. Jack was incredibly responsive, helpful, and easy to communicate with throughout our stay. We truly felt at home and would gladly stay here again. Highly recommend!"
United States
Nini D.
$1,935 nightly
The price is $2,161
Aug 3 - Aug 4
Total with taxes and fees
NEW Construction: a Love Letter to Martha's Vineyard
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

Find out more about Cuttyhunk

Everything you need to know about Cuttyhunk vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cuttyhunk vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cuttyhunk vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cuttyhunk vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cuttyhunk. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cuttyhunk in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $400 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cuttyhunk rentals

At Expedia, we put the best Cuttyhunk vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cuttyhunk rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cuttyhunk vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cuttyhunk. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Cuttyhunk?

Yes, there are vacation rentals near popular attractions in Cuttyhunk, or you can select a more remote option if you want a relaxing place to stay. Cuttyhunk is known for its beaches.

What are some of the best vacation home rentals in Cuttyhunk?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This vacation home near Cuttyhunk is located in the city center and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What’s there to see and do in Cuttyhunk?

Explore the area and family-friendly sights such as Buttonwood Park Zoo, or get out into nature at a spot like Aquinnah Cliffs. Gay Head Lighthouse and Horseneck Beach State Reservation are a couple of places you'll find in the larger area.

What’s a vacation rental in Cuttyhunk like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Cuttyhunk. Vacation rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a small group gathering.