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

Cuttyhunk Holiday Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Cuttyhunk holiday rentals

Smart TV, stereo

The Charming Gem Near The Water!

The Charming Gem Near The Water!
New Bedford
9.6 out of 10, Exceptional, (43 reviews)
"We really liked the area - quiet - spacious apartment Nice attention to details . Had a full kitchen with dishes etc. one suggestion is for host to provide a muffin pan."
United States
stephen
The price is HK$671
HK$1,748 total
includes taxes & fees
8 Jul - 9 Jul
The Charming Gem Near The Water!
Property grounds

The Sky-High Beach House: Panoramic Waterfront views

The Sky-High Beach House: Panoramic Waterfront views
Fairhaven
The price is HK$1,907
HK$3,917 total
includes taxes & fees
14 Jul - 15 Jul
The Sky-High Beach House: Panoramic Waterfront views
Property grounds

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.
The price is HK$1,318
HK$4,122 total
includes taxes & fees
28 Jul - 29 Jul
Ellery Beach Bungalow #47- Relaxed Island Living
Smart TV

Middletown Modern Apartment w/ Private Deck - RIBryan Properties

Middletown Modern Apartment w/ Private Deck - RIBryan Properties
Middletown
9.6 out of 10, Exceptional, (16 reviews)
"Apartment was beautiful in a great location!!!"
United States
cathy g.
The price is HK$1,745
HK$3,630 total
includes taxes & fees
22 Jul - 23 Jul
Middletown Modern Apartment w/ Private Deck - RIBryan Properties
1 bedroom, iron/ironing board, free WiFi

Convenient and clean studio near the beach and Newport.

Convenient and clean studio near the beach and Newport.
Middletown
9.2 out of 10, Wonderful, (20 reviews)
"Meets basic needs if your staying a night or two. "
United States
Michael M.
The price is HK$1,176
HK$1,922 total
includes taxes & fees
15 Jul - 16 Jul
Convenient and clean studio near the beach and Newport.
Interior

Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is HK$2,561
HK$6,269 total
includes taxes & fees
8 Jul - 9 Jul
Backyard Retreat / 5 Min > Beach & Main St
Beach

Spacious, comfortable rooms near beach & Newport

Spacious, comfortable rooms near beach & Newport
Middletown
8.0 out of 10, Very good, (16 reviews)
"Great stay - great location! "
United States
Jana D.
The price is HK$1,161
HK$1,904 total
includes taxes & fees
15 Jul - 16 Jul
Spacious, comfortable rooms near beach & Newport
Pool

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.
The price is HK$1,843
HK$4,056 total
includes taxes & fees
27 Jul - 28 Jul
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Terrace/patio

Seapowet suite

Seapowet suite
Tiverton
10.0 out of 10, Exceptional, (11 reviews)
"Lovely spot, wonderful host. Had everything we needed, close to town."
United States
Lauren S.
The price is HK$1,729
HK$2,508 total
includes taxes & fees
14 Jul - 15 Jul
Seapowet suite
Interior

Ellery Bungalow #49 - Minutes from the Sand

Ellery Bungalow #49 - Minutes from the Sand
Middletown
10.0 out of 10, Exceptional, (1 review)
"Had a wonderful stay; loved that it was within walking distance to great places to eat and also the beach.Everything was clean and cozy. I highly recommend it if you would like to check out Newport and the surrounding towns.Owners were very responsive if needed. We loved our trip!"
United States
Cheryl H.
The price is HK$1,114
HK$3,813 total
includes taxes & fees
8 Jul - 9 Jul
Ellery Bungalow #49 - Minutes from the Sand
Living area

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.
The price is HK$1,341
HK$3,198 total
includes taxes & fees
13 Jul - 14 Jul
Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi
TV

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, (15 reviews)
"Nice, quaint cottage. Perfect for a couple's getaway! Location was convenient for walking to shops and restaurants."
United States
Randy T.
The price is HK$2,353
HK$4,003 total
includes taxes & fees
27 Jul - 28 Jul
Small One Bedroom Private Cottage on Large Quiet Property.
Smart TV

Lovely 3 bedroom apartment 3rd floor

Lovely 3 bedroom apartment 3rd floor
New Bedford
9.4 out of 10, Exceptional, (13 reviews)
"Nice place for staying when traveling to Massachusetts "
United States
Anonymous traveller
The price is HK$1,416
HK$3,290 total
includes taxes & fees
13 Jul - 14 Jul
Lovely 3 bedroom apartment 3rd floor
Exterior detail

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.
The price is HK$1,416
HK$3,290 total
includes taxes & fees
13 Jul - 14 Jul
Lovely 4- Bedroom apartment for rent
TV

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.
The price is HK$1,741
HK$4,706 total
includes taxes & fees
13 Jul - 14 Jul
Ellery Bungalow #51- Island Calm Near Newport
Interior

Beach house walking distance to Second Beach

Beach house walking distance to Second Beach
Easton's Point
9.8 out of 10, Exceptional, (30 reviews)
"Great house and communication with the owner! We would stay there again!"
United States
Stan C.
The price is HK$2,110
HK$5,803 total
includes taxes & fees
12 Jul - 13 Jul
Beach house walking distance to Second Beach
Exterior

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
The price is HK$3,317
HK$7,341 total
includes taxes & fees
11 Jul - 12 Jul
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
Exterior

Charming Guesthouse | Walk to Beach | Downtown

Charming Guesthouse | Walk to Beach | Downtown
Falmouth
The price is HK$1,713
HK$5,165 total
includes taxes & fees
8 Jul - 9 Jul
Charming Guesthouse | Walk to Beach | Downtown
TV, computer monitors

Pop, Bubble, and sun-drenched Cutie Cottage!

Pop, Bubble, and sun-drenched Cutie Cottage!
Middletown
9.8 out of 10, Exceptional, (21 reviews)
"We loved our stay! The cottage was the perfect size for what we needed and a great location! We would definitely stay again."
United States
Lauren C.
The price is HK$1,876
HK$3,824 total
includes taxes & fees
19 Jul - 20 Jul
Pop, Bubble, and sun-drenched Cutie Cottage!
Beach nearby

Loft Hideaway in Falmouth Village

Loft Hideaway in Falmouth Village
Falmouth
9.6 out of 10, Exceptional, (5 reviews)
"We really enjoyed our visit!! The location can’t be beat and Falmouth was a great place to explore. "
United States
Nancy F.
The price is HK$2,265
HK$4,217 total
includes taxes & fees
22 Jul - 23 Jul
Loft Hideaway in Falmouth Village
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

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

8/10 Good
"Room was clean. We loved being on the 2nd floor. It was a great view of the water and the marina. Great walking distance to everything!"
SANDY 1-night trip
Posted 2 hours ago
Vineyard Harbor Motel - Private Beach

Find out more about Cuttyhunk

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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 garden, a BBQ 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 Gooseberry Island 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.