Vacation Rentals in Dukes County

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Top Cities in Dukes County

Top Vacation Rentals in Dukes County

Our top choices for Dukes County vacation rentals

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

9.4 out of 10, Exceptional, (86)
"We loved our stay! It was the perfect location, loved the view, it was sparce but clean. Check in/out was easy and owner was responsive. "
$536 nightly
The price is $599
Oct 1 - Oct 2
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

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

9.4 out of 10, Exceptional, (84)
"Close to buses, restaurants and ferries. 10/10, we would stay again."
$479 nightly
The price is $535
Oct 1 - Oct 2
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

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

6.4 out of 10, (26)
"The property is quiet, spacious and was within a walkable mile of downtown Oak Bluffs. The beds were comfortable. Plenty of clean linens and towels. The house could use some updating. The coffee maker, drinking glasses, and silverware need to be replaced with cleaner ones. And the torn portions of the sectional couch should be fixed. I would definitely stay at the property again."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Classic Cape home with full kitchen, W/D, firepit & gas grill - walk to beach

5.2 out of 10, (5)
"The living room was moldy, the door doesn’t lock, the insects were in every room; including the bed, the kitchen tools were rusty, the floors were dirty, the place is a mess. The post states a gas grill; there’s only a charcoal grill without any charcoal, the post states resident beach parking pass; there was none, the post states a queen size bed; there wasn’t one. The kitchen floor was completely stripped of tile. Overall the house was dirty and a complete waste of money. The only nice thing...
Classic Cape home with full kitchen, W/D, firepit & gas grill - walk to beach

Walking to the beach. Bars and Restaurants.

9.6 out of 10, Exceptional, (4)
"The home was very nice and in a convenient location. Ana was very helpful and quick with communications during our stay. Would highly recommend for anyone traveling to Oak Bluffs! "
Walking to the beach. Bars and Restaurants.

Cozy cottage 3/4 mile from Oak Bluffs harbor

9.8 out of 10, Exceptional, (47)
"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

Lambert's Cove Beach Getaway - NEW LISTING Private Beach Access!

10.0 out of 10, Exceptional, (61)
"The most magical place, thank you for the prefect stay."
Lambert's Cove Beach Getaway - NEW LISTING Private Beach Access!

The Costal Corner - Martha's Vineyard

2.0 star property
10.0 out of 10, Exceptional, (2)
"This property was great for our golf trip. The 3 bedrooms were exceptional "
The Costal Corner - Martha's Vineyard

Newly Renovated Apartment in the heart of Edgartown on the Bike Path!

8.8 out of 10, Excellent, (32)
"This was a great apartment in a great location!"
Newly Renovated Apartment in the heart of Edgartown on the Bike Path!

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

10.0 out of 10, Exceptional, (53)
"We were in town for a wedding in Chilmark and the property was exactly what we needed!"
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

Sanctuary House: An ocean-view farmhouse retreat

10.0 out of 10, Exceptional, (32)
"Property was as presented and the attention to detail throughout the house to ensure we enjoyed the stay was noticed and appreciated! Will definitely recommend Dan and Havens Sanctuary Farm to others!"
Sanctuary House: An ocean-view farmhouse retreat

Beautiful Carriage House on the Chop

10.0 out of 10, Exceptional, (24)
"Great location, well outfitted, great kitchen, comfortable beds. Would stay again."
Beautiful Carriage House on the Chop

Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

8.0 out of 10, Very Good, (5)
"We had a wonderful early-June weekend stay at this charming house minutes walk from town. Highlights were reading on the rocking chair on the deck and playing games in the screened-in porch. Everything looks just like in the listing - charming, warm, like staying at your grandpa's beach house. There were a few bumps - the listed dryer was in a locked shed, a faucet wasn't working - but our sense was this is a new listing and details are still being ironed out. None of that interfered with our...
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

Charming 2-bedroom house on Chappy with pool, Tennis, pickleball, WiFi and AC

8.0 out of 10, Very Good, (2)
"Awesome house, very comfortable and a lot of fun. Thanks so much for the hospitality!!"
Charming 2-bedroom house on Chappy with pool, Tennis, pickleball, WiFi and AC

The Field House - Peaceful Martha’s Vineyard Escape with Serene Field Views

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great location, walking distance to the fairgrounds, well appointed home, great house for our family. Large great room with windows to view the amazing property . The best outdoor shower I’ve ever been in."
The Field House - Peaceful Martha’s Vineyard Escape with Serene Field Views

Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

8.4 out of 10, Very Good, (39)
"Close to the beach , clean and a wonderful Vineyard stay"
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

Spacious Waterview Condo - Steps To The Beach, Right Across The Street!

9.4 out of 10, Exceptional, (72)
"This was both a spacious and cozy home away from home unit directly across from the beach and very easy walking distance to numerous restaurants, shops, and the ferry. "
Spacious Waterview Condo - Steps To The Beach, Right Across The Street!

Walk to Beach & Lighthouse: Oak Bluffs Studio!

7.4 out of 10, Good, (3)
"Very accommodating early check in and great communication "
$369 nightly
The price is $412
Sep 14 - Sep 15
Total with taxes and fees
Walk to Beach & Lighthouse: Oak Bluffs Studio!

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

8.0 out of 10, Very Good, (14)
"This place is perfect, My girlfriend and I stayed there for Memorial Day weekend. It’s a quiet little cottage nestled in the wood we loved the privacy and getting away from the hustle and bustle of Oak bluffs at night. I’ve read some other reviews saying that the electricity doesn’t work but it worked for us the whole time. I personally plan on staying there again"
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)
"House was in a great location for easy access to Edgartown. Lots of room in the house."
Tranquil 5 BR House, Heated Saltwater Pool Near Downtown Edgartown
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 $412 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.