Cuttyhunk Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Cuttyhunk holiday rentals

Marina
Charming cottage overlooking the bay in Padanaram Village.

Cottage in Dartmouth

Charming cottage overlooking the bay in Padanaram Village.
2.0 star property
10.0 out of 10, Exceptional, (11)
"Super location, very nice accommodations, very clean, modern and comfortable "
United States
Cathie K.
The price is HK$1,679
HK$3,048 total
includes taxes & fees
2 Jan - 3 Jan 2026
Charming cottage overlooking the bay in Padanaram Village.
Exterior
Seapowet suite

Apartment in Tiverton

Seapowet suite
9.6 out of 10, Exceptional, (5)
"Adequate for one night. Host friendly."
United States
Louise
The price is HK$622
HK$856 total
includes taxes & fees
1 Jan - 2 Jan 2026
Seapowet suite
Fridge, microwave, oven, stovetop
The Charming Gem Near The Water!

Apartment in New Bedford

The Charming Gem Near The Water!
9.6 out of 10, Exceptional, (34)
"I had stayed here last year and it's so close to several of my family members. This is my go to place when I travel to the New Bedford area."
United States
Judy C.
The price is HK$700
HK$1,763 total
includes taxes & fees
18 Jan - 19 Jan 2026
The Charming Gem Near The Water!
Interior
Lovely 4- Bedroom apartment for rent

Apartment in New Bedford

Lovely 4- Bedroom apartment for rent
9.0 out of 10, Wonderful, (2)
"My friend and I were looking for a place to stay for a last minute day-trip to Nantucket. This property was great for that purpose and Angelino was a very responsive host. One thing to note is that while there is plenty of free street parking, there is no onsite parking even though we were told there was one spot available. I think this might have been due to some confusion regarding which property we had actually booked."
United States
Elizabeth C.
The price is HK$979
HK$2,708 total
includes taxes & fees
9 Jan - 10 Jan 2026
Lovely 4- Bedroom apartment for rent
Interior
Ellery Beach Bungalow #47- Relaxed Island Living

Holiday Home in Middletown

Ellery Beach Bungalow #47- Relaxed Island Living
10.0 out of 10, Exceptional, (4)
"Fantastic stay! "
United States
Cristin C.
The price is HK$894
HK$3,498 total
includes taxes & fees
20 Jan - 21 Jan 2026
Ellery Beach Bungalow #47- Relaxed Island Living
TV
Blue Haven Houseboat

Holiday Home in New Bedford

Blue Haven Houseboat
2.0 star property
The price is HK$809
HK$1,077 total
includes taxes & fees
6 Jan - 7 Jan 2026
Blue Haven Houseboat
TV
Ellery Beach Bungalow #45- A Refined Island Escape

Holiday Home in Middletown

Ellery Beach Bungalow #45- A Refined Island Escape
10.0 out of 10, Exceptional, (1)
"Beautiful area, walking distance to the beach and restaurants, nice clean house"
United States
Dana N.
The price is HK$878
HK$3,471 total
includes taxes & fees
4 Jan - 5 Jan 2026
Ellery Beach Bungalow #45- A Refined Island Escape
Interior
Ellery Bungalow #51- Island Calm Near Newport

Holiday Home in Middletown

Ellery Bungalow #51- Island Calm Near Newport
9.6 out of 10, Exceptional, (94)
"My family had an amazing stay at this bungalow. It is very clean and offered everything we needed for our stay in Newport. The beach is very close and there are plenty of restaurants and convenience store within walking distance. "
United States
Tamara C.
The price is HK$886
HK$3,489 total
includes taxes & fees
4 Jan - 5 Jan 2026
Ellery Bungalow #51- Island Calm Near Newport
Exterior
The Beach Estate, Panoramic Ocean Views, 5700 sqft

Holiday Home in Mattapoisett

The Beach Estate, Panoramic Ocean Views, 5700 sqft
9.8 out of 10, Exceptional, (8)
"This was the perfect getaway for our large family. Everything was immaculate and we had all the comforts of home. We had a great week!"
United States
Catherine T.
The price is HK$5,493
HK$14,048 total
includes taxes & fees
13 Jan - 14 Jan 2026
The Beach Estate, Panoramic Ocean Views, 5700 sqft
Fridge, microwave, oven, stovetop
Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

Holiday Home in Dartmouth

Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA
Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA
Outdoor pool, a heated pool
Cozy efficiency apartment/heated pool

Apartment in Chilmark

Cozy efficiency apartment/heated pool
9.6 out of 10, Exceptional, (21)
"We loved this property and would love to return!"
United States
Clifford L.
Cozy efficiency apartment/heated pool
TV
Between Beaches

Holiday Home in Easton's Point

Between Beaches
8.0 out of 10, Very good, (1)
The price is HK$1,252
HK$5,197 total
includes taxes & fees
2 Jan - 3 Jan 2026
Between Beaches
Exterior
Beach house walking distance to Second Beach

Holiday Home in Easton's Point

Beach house walking distance to Second Beach
9.8 out of 10, Exceptional, (26)
"What a great location, well appointed home, and a very professional VRBO host. You know that love and care goes into making guests feel welcomed and special. Lots of amenities and space to make your stay memorable. "
United States
Victoria L.
The price is HK$1,112
HK$4,302 total
includes taxes & fees
1 Jan - 2 Jan 2026
Beach house walking distance to Second Beach
4 bedrooms, desk, iron/ironing board, travel cot
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Holiday Home in Dartmouth

Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
10.0 out of 10, Exceptional, (14)
"Beautiful home, well maintained, incredibly hospitable and responsive host. Kitchen is well equipped and amply stocked with cooking essential and extras for feeding your guests. Wonderful spacious yard great for outdoor fun."
United States
Nick R.
The price is HK$6,584
HK$11,227 total
includes taxes & fees
4 Jan - 5 Jan 2026
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
TV, fireplace, books
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Holiday Home in Oak Bluffs

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
9.4 out of 10, Exceptional, (3)
"This house was perfect for our getaway. Rebecca, the host, was extremely responsive and helpful during our trip. The house was as advertised. It was clean, well equipped, and the location was perfect as well "
United States
Louis R.
The price is HK$2,720
HK$6,944 total
includes taxes & fees
10 Jan - 11 Jan 2026
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
2 bedrooms, desk, iron/ironing board, free WiFi
Middletown Modern Apartment - RIBryan Property

Apartment in Middletown

Middletown Modern Apartment - RIBryan Property
9.6 out of 10, Exceptional, (16)
"Apartment was beautiful in a great location!!!"
United States
cathy g.
The price is HK$1,247
HK$2,987 total
includes taxes & fees
4 Jan - 5 Jan 2026
Middletown Modern Apartment - RIBryan Property
Interior
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Holiday Home in Oak Bluffs

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
10.0 out of 10, Exceptional, (7)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
United States
Swathanthra M.
The price is HK$4,274
HK$9,418 total
includes taxes & fees
3 Jan - 4 Jan 2026
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Fridge, microwave, oven, stovetop
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Holiday Home in Falmouth

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
10.0 out of 10, Exceptional, (211)
"Nicely furnished and very comfortable. Very private, yet convenient location. "
United States
John H.
The price is HK$1,259
HK$3,844 total
includes taxes & fees
4 Jan - 5 Jan 2026
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Fridge, microwave, oven, stovetop
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Holiday Home in Tisbury

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
10.0 out of 10, Exceptional, (16)
"The house is clean, peaceful and perfectly appointed with everything you need for a great week on the Vineyard."
United States
Celeste P.
The price is HK$3,886
HK$8,429 total
includes taxes & fees
9 Jan - 10 Jan 2026
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Property grounds
Double lot walk to beach 5 bed 7 bath, large yard

Holiday Home in Easton's Point

Double lot walk to beach 5 bed 7 bath, large yard
9.8 out of 10, Exceptional, (26)
"We enjoyed our stay at the home. Very well maintained."
United States
Anmol P.
The price is HK$5,084
HK$11,963 total
includes taxes & fees
5 Jan - 6 Jan 2026
Double lot walk to beach 5 bed 7 bath, large yard
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cuttyhunk Hotel Reviews

Mansion House Inn And Spa

Mansion House Inn And Spa

10/10 Excellent
"Our second time staying. Friendly staff, perfect location, great views. Highly recommend."
Kurt 2-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:

  • View our selection of featured holiday rentals in Cuttyhunk
  • Use the map to find apartments and other holiday homes in the Cuttyhunk neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cuttyhunk while they last

Look no further and take a look at our great range of rental properties in Cuttyhunk!

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.