Vacation Rentals in Dukes County

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Top Cities in Dukes County

Top Vacation Rentals in Dukes County

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

6.4 out of 10, (31)
"The weather was perfect and our crew made the best of our trip."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

9.4 out of 10, Exceptional, (88)
"The location of this property cannot be beat! Our second time staying here."
$480 nightly
The price is $536
Nov 1 - Nov 2
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts

9.8 out of 10, Exceptional, (80)
"Central property with all essentials!"
Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts

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

9.4 out of 10, Exceptional, (91)
"Close to buses, restaurants and ferries. 10/10, we would stay again."
$446 nightly
The price is $498
Oct 8 - Oct 9
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

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

10.0 out of 10, Exceptional, (64)
"The house was well stocked and had everything you could need. "
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

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

8.8 out of 10, Excellent, (33)
"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."
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

Spacious colonial home close to town with AC, porches, & W/D

10.0 out of 10, Exceptional, (5)
Spacious colonial home close to town with AC, porches, & W/D

Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!

10.0 out of 10, Exceptional, (71)
"Large home with plenty of room for extended family. Located in quiet neighborhood close to Oak Bluffs, would highly recommend."
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!

Spacious home in central location with beautiful patio, pool table, W/D, & AC

2.0 star property
10.0 out of 10, Exceptional, (4)
"Absolutely loved our stay at this Oak Bluffs home! The location was perfect—just a 20-minute walk to downtown—and the house itself was warm, inviting, and beautifully laid out with an open-air feel. The kitchen was fully stocked, the beds were super comfortable, and the outdoor shower was a wonderful bonus. We felt completely relaxed and free during our stay. Can’t wait to come back next summer!"
Spacious home in central location with beautiful patio, pool table, W/D, & AC

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

10.0 out of 10, Exceptional, (29)
"Perfect for my family of 4. Very walkable to everything Vineyard Haven. "
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

The Costal Corner - Martha's Vineyard

2.0 star property
10.0 out of 10, Exceptional, (3)
"This property was great for our golf trip. The 3 bedrooms were exceptional "
The Costal Corner - Martha's Vineyard

Heart of VH, walk to ferry, shops & restaurants. Pool, AC & beach gear provided!

9.4 out of 10, Exceptional, (26)
"We had a lovely time, everything was very clean and Matthew was very welcoming. Everything that we needed was right at hand!"
Heart of VH, walk to ferry, shops & restaurants. Pool, AC & beach gear provided!

Cozy cottage 3/4 mile from Oak Bluffs harbor

9.8 out of 10, Exceptional, (49)
"Stayed here with 3 friends as we were running the marathon. Better than the photos! So cute, everything was thoughtfully set up, we had anything we needed and having a washer dryer was a huge bonus! Flexible check in as well. Secluded, but easily walkable to many great places to eat and shop. Would 100% stay here again, highly recommend."
Cozy cottage 3/4 mile from Oak Bluffs harbor

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

9.0 out of 10, Wonderful, (15)
"Had a lovely stay for a week in September with our dog! House is clean, well stocked and in a very private location. The house is perfect for a couple or small family. We could not have asked for a better stay! Highly recommend!"
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

New construction Edgartown home with AC, new furnishings, o/d shower, bike path.

10.0 out of 10, Exceptional, (147)
"Really nice comfortable home. Very well outfitted. We loved the fireplace and Stephen was super accommodating to our ever changing plans. "
New construction Edgartown home with AC, new furnishings, o/d shower, bike path.

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

9.0 out of 10, Wonderful, (2)
"The house was lovely. Very clean and orderly. Beautiful back porch that we enjoyed very much. The beds were very comfortable. Our only complaint was the Master bathroom needs some updating. The shower head desperately needs to be changed and the lighting is extremely poor. Also, only 1 half size mirror on the whole first floor. Other than that, it was perfect."
$600 nightly
The price is $670
Oct 7 - Oct 8
Total with taxes and fees
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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."
$1,085 nightly
The price is $1,212
Oct 7 - Oct 8
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette

8.0 out of 10, Very Good, (16)
"Well maintained. Very quiet. No TV. Doubt if there is any air conditioning. "
Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette

Tranquil 5 BR House, Heated Saltwater Pool Near Downtown Edgartown

9.4 out of 10, Exceptional, (11)
"wonderful house, location, pool, and experience. would stay here again!"
Tranquil 5 BR House, Heated Saltwater Pool Near Downtown Edgartown

The quintessential MV home. Now booking for 2026!

9.8 out of 10, Exceptional, (54)
"Just a quick 4 minute drive to downtown. Listing was accurate and place was clean!"
The quintessential MV home. Now booking for 2026!
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

Find out more about Dukes County

Discover your perfect Dukes County vacation rental with Expedia

How many vacation rentals are available in Dukes County?


Expedia has plenty of vacation rentals to choose from in and around  Dukes County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Dukes County?


The selection of Dukes County vacation rentals we have selected for you start as low as $498 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Dukes County?


Vacation rentals in Dukes County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Dukes County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Dukes County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Dukes County vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Dukes County?


Find vacation rentals in Dukes County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Dukes County.  


What amenities are available in a vacation rental in Dukes County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Dukes County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Dukes County?   


Everytime is a great time to head to Dukes County! Staying in a Dukes County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Dukes County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Dukes County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Dukes County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Dukes County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.