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

A modern kitchen with a marble countertop, a central island, and a hanging light fixture.

1. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
9.8 out of 10, Exceptional, (30 reviews)
"Lovely and all brand new accommodation's that are clean and comfy! A quiet location too! "
United States
Nancy K.
The price is AU$614
includes taxes & fees
27 Aug - 28 Aug
Brand new! Lovely apartment-Vineyard Haven
A gravel driveway leading to a house surrounded by trees and a garden.

2. Lovely two bedroom apartment with indoor fireplace

Lovely two bedroom apartment with indoor fireplace
Oak Bluffs
10.0 out of 10, Exceptional, (8 reviews)
"Great stay, flexible and responsive host. Difficult location, however, as it was not centrally located or easy to access transportation, etc."
United States
Aviva M.
The price is AU$1,011
includes taxes & fees
7 Sept - 8 Sept
Lovely two bedroom apartment with indoor fireplace
A wooden deck with a white railing, two chairs, and a small table.

3. Make Lasting Memories In This Adorable Vineyard Cottage!

Make Lasting Memories In This Adorable Vineyard Cottage!
Oak Bluffs
9.8 out of 10, Exceptional, (155 reviews)
"Cute, compact, and had everything we needed for ourstay. I'd definitely stay there again."
United States
Karen C.
The price is AU$698
includes taxes & fees
2 Sept - 3 Sept
Make Lasting Memories In This Adorable Vineyard Cottage!
A living room with a flat-screen TV on a stand, a black leather chair, and a sofa. There are two windows with curtains, one of which offers a view of the sea.

4. 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)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
The price is AU$722
includes taxes & fees
20 Sept - 21 Sept
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
A modern kitchen with white cabinets, a central island with blue drawers, and stainless steel appliances.

5. Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (6 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$1,375
includes taxes & fees
7 Sept - 8 Sept
Brand New Guest house
A spacious living area with a high ceiling, a dining table, and a kitchen area.

6. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (9 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is AU$1,163
includes taxes & fees
11 Sept - 12 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A two-story house with a swimming pool, a covered patio, and a fenced backyard.

7. Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool
Chilmark
9.6 out of 10, Exceptional, (25 reviews)
"This is a great property for an individual or a couple looking to explore the island!"
United States
Jillian G.
The price is AU$688
includes taxes & fees
15 Sept - 16 Sept
Cozy efficiency apartment/heated pool
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

8. Walk to Beach & Lighthouse: Oak Bluffs Studio!

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
8.4 out of 10, Very good, (9 reviews)
"Very accommodating early check in and great communication "
United States
Katelyn K.
The price is AU$867
includes taxes & fees
30 Aug - 31 Aug
Walk to Beach & Lighthouse: Oak Bluffs Studio!
A circular stone patio with Adirondack chairs and a small table in a forested area.

9. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.2 out of 10, (10 reviews)
"We had a perfect pre-/off-season stay with plenty of sleeping space. The location is fantastic—right between Vineyard Haven and Edgartown—making it easy to bike to both, plus there’s a beach across the street. The WiFi wasn’t working when we first arrived, but the owner was incredibly responsive and went above and beyond to fix it quickly. We’ll definitely be back!"
United States
Bethann N.
The price is AU$998
includes taxes & fees
25 Aug - 26 Aug
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A residential area with a well-maintained lawn, a stone retaining wall, and a two-story house with a blue door.

10. 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, (8 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is AU$1,947
includes taxes & fees
7 Sept - 8 Sept
New 4 BR house near center and beaches with bikes
A modern kitchen with white cabinets, a wooden dining table, and black chairs.

11. Walk to Town/Golf Club - Renovated Edgartown Home

Walk to Town/Golf Club - Renovated Edgartown Home
Edgartown
10.0 out of 10, Exceptional, (47 reviews)
"Great house in a great location—just a short, easy walk to downtown Edgartown"
United States
Steven M.
The price is AU$1,420
includes taxes & fees
2 Sept - 3 Sept
Walk to Town/Golf Club - Renovated Edgartown Home
A view through a window with a wooden frame, overlooking a garden with various plants and a body of water in the background.

12. 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, (7 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$863
includes taxes & fees
1 Sept - 2 Sept
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
A cozy living room with a wooden ceiling, a stone fireplace, a leather sofa, and a dining area with a table and chairs.

13. < 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
Oak Bluffs
7.4 out of 10, Good, (3 reviews)
"House was neat architectural wise and family history of home ownership was very cool. However, listing noted there was a washer/dryer and there was not. House also noted that there was a fire pit and it was rusted through. Screen door handles were broken, windows need repair, and house has animals living in the downstairs bathroom wall. House needs updates to charge what was being charged a night. In addition, there was a Nor’easter that hit the island and we attempted to contact the host to let...
United States
Kate K.
The price is AU$1,097
includes taxes & fees
31 Aug - 1 Sept
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

14. 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, (8 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is AU$1,884
includes taxes & fees
7 Sept - 8 Sept
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

15. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is AU$1,286
includes taxes & fees
8 Sept - 9 Sept
Charming Vacation Home in Oak Bluffs.
A two-story house with a brick chimney, a wooden deck, and a wooden fence.

16. 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$1,118
includes taxes & fees
12 Sept - 13 Sept
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
A wooden deck with wicker furniture, a table with a vase of flowers, and a view of a marina with boats.

17. WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (54 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is AU$1,939
includes taxes & fees
8 Sept - 9 Sept
WATERFRONT Downtown Cottage w/ Beach
A waterfront marina with boats docked, buildings with gabled roofs, and a clear blue sky.

18. Walk to downtown Edgartown in quiet neighborhood - Perfect Location!

Walk to downtown Edgartown in quiet neighborhood - Perfect Location!
Edgartown
10.0 out of 10, Exceptional, (5 reviews)
"One of the most well equipped vacation rentals I’ve stayed in. A simple, but well curated place. Thank you to our hosts!"
United States
Anonymous traveller
The price is AU$1,741
includes taxes & fees
31 Aug - 1 Sept
Walk to downtown Edgartown in quiet neighborhood - Perfect Location!
A spacious living area with wooden beams, a dining table, and a sofa.

19. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (29 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is AU$1,629
includes taxes & fees
6 Sept - 7 Sept
The Seashell Cove - Martha's Vineyard
A modern kitchen with white cabinetry, a central island with stools, a blue sofa, and a round coffee table.

20. 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, (40 reviews)
"Great place, awesome location!"
United States
Connor B.
The price is AU$1,458
includes taxes & fees
6 Sept - 7 Sept
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
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

The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

10/10 Excellent
"The helpfulness of staff; Ely was amazing"
Joann 3-night trip
Posted 1 hour ago
The Franklin Hotel Martha's Vineyard

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$614 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.