A coastal cliff with a sandy beach and the ocean.

Dukes County Holiday Rentals

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Our top choices for Dukes County holiday rentals

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.
The price is AU$729
includes taxes & fees
27 July - 28 July
Small One Bedroom Private Cottage on Large Quiet Property.

Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (4 reviews)
"This is a new, beautiful and tastefully decorated 2 bedroom one bathroom house with a really nice big yard. Owner was very responsive and We had everything we needed for an enjoyable stay!"
United States
Elizabeth O.
The price is AU$2,967
includes taxes & fees
9 Aug - 10 Aug
Brand New Guest house

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely incredible stay! The host is so kind and helpful. House was very clean. Truly everything you need inside for cooking and beach fun! PERFECT location really centrally located to both edgartown and oak bluffs. Located in a quiet neighborhood near Felix Neck with lots of walking trails, which was very nice! Could not recommend this place more!"
United States
Katelyn W.
The price is AU$2,004
includes taxes & fees
21 July - 22 July
4-bedroom house in lovely Edgartown..Centrally located

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Oak Bluffs
9.4 out of 10, Exceptional, (92 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
The price is AU$1,057
includes taxes & fees
21 July - 22 July
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

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 AU$1,327
includes taxes & fees
13 July - 14 July
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt

Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
Oak Bluffs
10.0 out of 10, Exceptional, (46 reviews)
"Great accommodations and a perfect location for the beach, shopping and great food."
United States
Hugh M.
The price is AU$1,043
includes taxes & fees
12 July - 13 July
Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.4 out of 10, Exceptional, (6 reviews)
"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 AU$1,818
includes taxes & fees
30 July - 31 July
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Chappy - Family Beach House

Chappy - Family Beach House
Edgartown
9.8 out of 10, Exceptional, (16 reviews)
"Sun-filled, comfortable, and perfectly located!"
United States
Carmin R.
The price is AU$1,891
includes taxes & fees
26 July - 27 July
Chappy - Family Beach House

Book your stay for Summer 2026 in this charming 2-bedroom house in Edgartown!

Book your stay for Summer 2026 in this charming 2-bedroom house in Edgartown!
Katama
Book your stay for Summer 2026 in this charming 2-bedroom house in Edgartown!

Walking-distance to town, shops, restaurants & ferry!

Walking-distance to town, shops, restaurants & ferry!
Tisbury
10.0 out of 10, Exceptional, (25 reviews)
"I rented this for my staff, and they said it was the best place they have stayed on Martha's Vineyard."
United States
else r.
The price is AU$1,469
includes taxes & fees
22 July - 23 July
Walking-distance to town, shops, restaurants & ferry!

New 4 BR house near center and beaches with bikes

New 4 BR house near center and beaches with bikes
Katama
10.0 out of 10, Exceptional, (7 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is AU$2,862
includes taxes & fees
15 July - 16 July
New 4 BR house near center and beaches with bikes

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Tisbury
10.0 out of 10, Exceptional, (34 reviews)
"Great place, awesome location!"
United States
Connor B.
The price is AU$1,354
includes taxes & fees
14 July - 15 July
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (26 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is AU$1,847
includes taxes & fees
29 July - 30 July
The Seashell Cove - Martha's Vineyard

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (10 reviews)
"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 AU$3,109
includes taxes & fees
22 July - 23 July
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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)
NEW Construction: a Love Letter to Martha's Vineyard

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Tisbury
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful view of the lagoon; ideal place for a couple or single. Leisurely walk to town and close to public transportation."
United States
Adrienne W.
The price is AU$1,279
includes taxes & fees
19 July - 20 July
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!

Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!
Oak Bluffs
9.8 out of 10, Exceptional, (58 reviews)
"Property was well taken care of, very clean with great location!"
United States
Stephanie
The price is AU$1,211
includes taxes & fees
11 July - 12 July
Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Tisbury
10.0 out of 10, Exceptional, (58 reviews)
"We loved the location and place was great!"
United States
Eileen M.
The price is AU$1,432
includes taxes & fees
18 July - 19 July
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (6 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is AU$3,165
includes taxes & fees
17 July - 18 July
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"I can’t say enough about this beautiful property. pictures don’t do any justice for this piece of heaven. The flowers were everywhere , it’s so apparent that the property owners take such pride in this beautiful property. The place was spotless when we walked in the door. We met the owners on arrival , they surprised us with a beautiful ballon to celebrate my 50th birthday. My family enjoyed the pool and the fun Tiki. The outdoor fireplace was inviting after the sun went down. I was a little...
United States
Miriam D.
The price is AU$5,577
includes taxes & fees
22 July - 23 July
Beautiful Estate with salt water pool & pond with kayaks
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 Dukes County Hotel Reviews

Find out more about Dukes County

Everything you need to know about Dukes County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Dukes County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Dukes County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Dukes County holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Dukes County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Dukes County holiday rentals we have chosen for you start as low as AU$811 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Dukes County rentals

At Expedia, we put the best Dukes County holiday 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 Dukes County 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 Dukes County holiday.

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