Cuttyhunk Holiday Rentals

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Check prices for these dates

Tonight
15 Nov - 16 Nov
Tomorrow
16 Nov - 17 Nov
Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov

Holiday Rentals in Cuttyhunk

Seasonal outdoor pool
Beachside Village Resort

Beachside Village Resort

3.0 star property
Falmouth
9.4 out of 10, Exceptional, (101)
"Very clean and quiet place to relax. Very friendly and professional! We will come back!"
United States
Emmanuelle Loriot
Beachside Village Resort
Terrace/patio
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

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

West Tisbury
9.0 out of 10, Wonderful, (35)
"The peaceful woodland setting is just beautiful! Enjoyed a quiet stay in this spacious one bedroom house. The porch wraps around entire house and gave our morning coffee and breakfast a very special vacation feel."
United States
Maryann B.
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
Exterior detail
Quaint Cottage On Christmas Tree Farm in SE coastal Rhode Island

Quaint Cottage On Christmas Tree Farm in SE coastal Rhode Island

Tiverton
10.0 out of 10, Exceptional, (185)
"This is the fifth year that I’ve rented this place and I love it. It’s very private simple all on one floor."
United States
Debbie I.
Quaint Cottage On Christmas Tree Farm in SE coastal Rhode Island
Exterior
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Oak Bluffs
6.4 out of 10, (31)
"indoor and outdoor comfortable space"
United States
Delores C.
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Outdoor dining
Walk to beach, Huge deck off spacious new kitchen, roof-deck, king master

Walk to beach, Huge deck off spacious new kitchen, roof-deck, king master

Middletown
10.0 out of 10, Exceptional, (126)
"Great beach house for families!"
United States
Joanne M.
Walk to beach, Huge deck off spacious new kitchen, roof-deck, king master
Terrace/patio
Stones Throw Waterfront

Stones Throw Waterfront

Dartmouth
8.8 out of 10, Excellent, (6)
"According to the listing, the property has AC. That is not true. It had a tiny portable unit that wasn't on when we entered and didn't cool once it was turned on. It also had a window unit that had no place to plug in. There were bugs in multiple areas. The property was not habitable, so we ended up booking a hotel room in a nearby town. VRBO compensated us partially but the owner was unwilling to refund any of our money even though we did not stay in the property. "
United States
Ashley R.
The price is HK$2,762
HK$5,013 total
includes taxes & fees
16 Nov - 17 Nov
Stones Throw Waterfront
Exterior
Seapowet suite

Seapowet suite

Tiverton
9.6 out of 10, Exceptional, (5)
"Adequate for one night. Host friendly."
United States
Louise
The price is HK$874
HK$1,465 total
includes taxes & fees
18 Nov - 19 Nov
Seapowet suite
Interior
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Oak Bluffs
10.0 out of 10, Exceptional, (7)
"This home is truly that, a welcoming escape nestled in the woods. It’s elevated beach-style furnishings feel hand-picked. We traveled with a 14 month old — the house had high-quality baby must haves, pack and play and high chair. We had the pleasure of a responsive host and caretaker. Close to trails, YMCA and the island’s top attractions … !highly recommend!"
United States
Kerry-Ann H.
The price is HK$4,274
HK$9,418 total
includes taxes & fees
18 Nov - 19 Nov
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Marina
Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.

2.0 star property
Dartmouth
10.0 out of 10, Exceptional, (10)
"Beautiful property. The cottage is beautifully decorated and well maintained. Amazing location. Host was very good at communicating. "
United States
christine l.
The price is HK$1,574
HK$2,912 total
includes taxes & fees
20 Nov - 21 Nov
Charming cottage overlooking the bay in Padanaram Village.
Exterior
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

Tisbury
10.0 out of 10, Exceptional, (67)
"The house was well stocked and had everything you could need. "
United States
ROBYN M.
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
Exterior
Middletown Bungalow - RIBryan Property

Middletown Bungalow - RIBryan Property

Middletown
9.4 out of 10, Exceptional, (13)
"Great location. House is renovated and fit our family perfectly. Backyard is fully fenced in and allowed our dog to roam and be safe. Hot tub is a fun plus! "
United States
Claire T.
The price is HK$1,663
HK$4,449 total
includes taxes & fees
16 Nov - 17 Nov
Middletown Bungalow - RIBryan Property
Beach
Cozy getaway in a central location w/ a full kitchen & furnished deck

Cozy getaway in a central location w/ a full kitchen & furnished deck

Oak Bluffs
6.6 out of 10, (25)
"The home was nice, a little outdated, but great for a family. Unfortunately it does not have AC and when we arrived we found 2 fans were broken. We immediately contacted Vacasa who said they would send maintenance. While waiting for maintenance, we also noticed within the first hour that one of the dining chair backs was broken/not attached, one of the bed posts fell off as it was not attached, and the fan in one of the bathrooms was stuck on. We planned to notify maintenance when they came but...
United States
Dawn R.
Cozy getaway in a central location w/ a full kitchen & furnished deck
Outdoor dining
Be on the Beach! Awesome Oceanfront Living Close to Downtown Dining Amazing View

Be on the Beach! Awesome Oceanfront Living Close to Downtown Dining Amazing View

Easton's Point
10.0 out of 10, Exceptional, (170)
"Fantastic beach house. Thoughtfully stocked with everything you may need. Great location and convenient to all beaches and Newport. We highly recommend a stay at this beautiful spot."
United States
Sally C.
Be on the Beach! Awesome Oceanfront Living Close to Downtown Dining Amazing View
Interior
Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach

Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach

2.0 star property
Falmouth
10.0 out of 10, Exceptional, (1)
"The location was great and the pullouts were comfortable. The only downside is the walk through bathroom."
United States
Matthew
Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach
Smart TV, fireplace
DISCOUNTS for FALL/WINTER! Ocean views, Walk to Beach, Central AC, 4 Car Parking

DISCOUNTS for FALL/WINTER! Ocean views, Walk to Beach, Central AC, 4 Car Parking

Easton's Point
9.8 out of 10, Exceptional, (148)
"We enjoyed our stay. Location especially was fantastic - walkable to the beach and very easy to get in and out of downtown Newport."
United States
Alana M.
DISCOUNTS for FALL/WINTER! Ocean views, Walk to Beach, Central AC, 4 Car Parking
Beach nearby, beach towels
Gorgeous Spacious Victorian Cape Cod Beach View Retreat

Gorgeous Spacious Victorian Cape Cod Beach View Retreat

Falmouth
10.0 out of 10, Exceptional, (16)
"The house is a wonderful place for a slow and relaxing holiday! Close to everything but tucked away from anything too busy. "
United States
Alexandra M.
Gorgeous Spacious Victorian Cape Cod Beach View Retreat
Outdoor dining
Surfside! Fantastic Beach House, Near Restaurants, Cliff Walk, Close to Downtown

Surfside! Fantastic Beach House, Near Restaurants, Cliff Walk, Close to Downtown

Easton's Point
10.0 out of 10, Exceptional, (101)
"Great location and home. Julie is great to work with! "
United States
Matt R.
Surfside! Fantastic Beach House, Near Restaurants, Cliff Walk, Close to Downtown
Property grounds
By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound

By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound

Falmouth
9.8 out of 10, Exceptional, (23)
"Amazing place. Definitely steps from the beach . Also the walk into town was not bad at all. we enjoyed doing that. The house was spacious and clean. Communications were great with the owner Joe. We really enjoyed our stay there. highly recommend the place."
United States
Anonymous traveller
By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound
Fridge, microwave, oven, stovetop
Charming newly renovated home in Little Compton.

Charming newly renovated home in Little Compton.

Little Compton
10.0 out of 10, Exceptional, (6)
"This house is an absolute gem – a perfect blend of old New England charm but completely newly renovated. Pamela has thought of everything that a guest could need to make your stay comfortable and relaxed. The house is sparkling clean with spacious bedrooms, beautiful bathrooms, a fully stocked kitchen and lots of room for a family to spread out and enjoy your time in the lovely town of Little Compton. We also appreciated that it is equidistant to points in Westport and Tiverton, which made for...
United States
Sarah C.
Charming newly renovated home in Little Compton.
Terrace/patio
Private Spacious Pet Friendly Studio / Loft

Private Spacious Pet Friendly Studio / Loft

Little Compton
10.0 out of 10, Exceptional, (79)
"Easy checkin and very comfortable - nice, friendly hoats"
United States
Susan T.
Private Spacious Pet Friendly Studio / Loft
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

Mansion House Inn And Spa

Mansion House Inn And Spa

10/10 Excellent
"Our stay at The Mansion Inn was nothing short of fabulous. The décor strikes that perfect balance between historic charm and modern chic — every corner feels thoughtfully designed. Our room was impeccable, the bedding unbelievably soft, and the whole experience exuded quiet luxury without pretension. The staff deserves special mention — warm, attentive, and genuinely eager to make your stay seamless. One note for future guests: parking can be tight on busy days. There is a lot, but it’s best to drop your luggage first; the team is more than happy to help you with the process. We left feeling rested, spoiled, and already planning our return. The Mansion Inn captures everything that makes Martha’s Vineyard so special — timeless elegance, effortless comfort, and a touch of magic."
Warren 1-night trip
Posted 3 days ago
Mansion House Inn And Spa

Find out more about Cuttyhunk

Search for holiday rentals in Cuttyhunk on Expedia! You can easily find your home rentals, villas, holiday apartments in Cuttyhunk using one of the methods below:

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Frequently asked questions

Can I find a holiday rental in Cuttyhunk?

Yes, there are holiday rentals close to the most popular sights in Cuttyhunk, or you can select a more secluded option if you're looking for a relaxing stay. Cuttyhunk is known for its beaches.

What are some of the best holiday rentals that Cuttyhunk has to offer?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This holiday home rental outside of Cuttyhunk is located in the city centre, and has a patio, a garden and a BBQ 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 wider area.

What’s a holiday rental in Cuttyhunk like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cuttyhunk. Holiday rentals feature extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.