A coastal cliff with a sandy beach and the ocean.

Dukes County holiday rentals

We found 2,020 holiday rentals — enter your dates for availability

Select from 914 houses, 25 flats and other holiday rentals to find the perfect place for your stay in Dukes County. Whether you're travelling with family, friends or just your furry companion, holiday homes have the best amenities for spending time at your holiday home, which might include Wi-Fi and a fireplace. No matter what you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Popular Dukes County destinations on Stayz

A row of large, historic houses with a well-maintained lawn and a flag.

Oak Bluffs

A marina with docked boats, a lighthouse, and residential houses along the waterfront.

Edgartown

A coastal landscape with a curved shoreline, a pier extending into the water, and a building with a balcony overlooking the beach.

Vineyard Haven

A coastal landscape with a lighthouse, sandy cliffs, and a beach.

West Tisbury

A white lighthouse with a red roof, an American flag, and a view of the ocean.

Tisbury

A dock with boats, a small wooden structure, and a forested shoreline.

Chilmark

Holiday rentals with weekly discounts – Dukes County

Showing deals for:13 Nov - 20 Nov

Exceptional

(5 reviews)

Relax by the sea! Bed & Breakfast room near Horseneck State Beach

Westport Point

8% off

AU$23,845

for 7 nights, 1 room

AU$3,406 per night

includes taxes & fees

Exceptional

(17 reviews)

THE PARK ESTATE! Your Martha's Vineyard Getaway!

Oak Bluffs

9% off

AU$79,306

for 7 nights, 1 home

AU$11,329 per night

includes taxes & fees

Exceptional

(5 reviews)

WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!

Edgartown

9% off

AU$34,974

for 7 nights, 1 home

AU$4,996 per night

includes taxes & fees

Butlers panty with wet bar and drinks fridge.

Exceptional

(41 reviews)

August dates AVAILABLE, Wraparound Porch, Waterviews, Walk to beach,4 Ensuites

Mattapoisett

8% off

AU$8,636

for 7 nights, 1 home

AU$1,234 per night

includes taxes & fees

Exceptional

(16 reviews)

New 4-bedroom House with Swimming Pool–Just a 10-minute Walk to Town

Edgartown

5% off

AU$11,843

for 7 nights, 1 home

AU$1,692 per night

includes taxes & fees

Spacious wrap around deck with all day sun and shade

Exceptional

(43 reviews)

Striking 5BR/4BA Chilmark Contemporary with Views of the Sound

Chilmark

8% off

AU$10,722

for 7 nights, 1 home

AU$1,532 per night

includes taxes & fees

Exceptional

(34 reviews)

Walk to Town! Beautiful, Private Edgartown Home

Edgartown

8% off

AU$10,082

for 7 nights, 1 home

AU$1,440 per night

includes taxes & fees

Dining table with view of ocean in the sunroom

Exceptional

(39 reviews)

Maushop Village Getaway with Ocean Views, Steps to Private Beach

Mashpee

8% off

AU$5,938

for 7 nights, 1 cottage

AU$848 per night

includes taxes & fees

Open concept living space on the second floor with custom octagonal ceiling

Kitchen with panoramic west-facing window

Exceptional

(30 reviews)

Luxury Chappaquiddick Getaway with Oceanviews

Edgartown

8% off

AU$7,509

for 7 nights, 1 home

AU$1,073 per night

includes taxes & fees

Very good

(5 reviews)

Beautiful Custom Home In Oak Bluffs

Oak Bluffs

8% off

AU$16,926

for 7 nights, 1 home

AU$2,418 per night

includes taxes & fees

Exceptional

(7 reviews)

BRAND NEW!

Oak Bluffs

8% off

AU$11,261

for 7 nights, 1 home

AU$1,609 per night

includes taxes & fees

Very good

(38 reviews)

The Cabin on Chappy!

Edgartown

8% off

AU$3,504

for 7 nights, 1 cottage

AU$501 per night

includes taxes & fees

Front of main house at 47 Cooke St Edgartown MA

Exceptional

(55 reviews)

Edgartown close to beach and town 6BD with Pool and Hot Tub

Edgartown

8% off

AU$21,342

for 7 nights, 1 home

AU$3,049 per night

includes taxes & fees

Choose from a variety of seating areas
overlooking the ocean and harbor.

This unique home was
carefully renovated to maintain its original character.

Your closest neighbors are a family of Osprey!

You will create forever memories in this amazing setting.

Exceptional

(26 reviews)

Oceanfront, Private Dock and Harthaven Private Beach - Walk to Noman's, Inkwell

Oak Bluffs

9% off

AU$56,117

for 7 nights, 1 home

AU$8,017 per night

includes taxes & fees

Exceptional

(35 reviews)

Cozy New TimberFrame Vineyard Haven!

Vineyard Haven

8% off

AU$5,753

for 7 nights, 1 cottage

AU$822 per night

includes taxes & fees

Loaded with glass sliders and skylights.

Exceptional

(30 reviews)

Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.

Chilmark

11% off

AU$3,754

for 7 nights, 1 home

AU$536 per night

includes taxes & fees

Exceptional

(50 reviews)

Luxury Loft Historic Center Oak Bluffs

Oak Bluffs

15% off

AU$8,789

for 7 nights, 1 home

AU$1,256 per night

includes taxes & fees

Nice deck right off the kitchen with a grill and exterior furniture

Exceptional

(23 reviews)

New Home close to Beach, Bike Path, and Sleeps 10! ☀️ 🏖

Falmouth

7% off

AU$4,384

for 7 nights, 1 home

AU$626 per night

includes taxes & fees

Deck with outdoor dining & plenty of flowers.

Kayaks to paddle around Waquoit Bay to Washburn Island

Open floor plan of Living Room/ Dining room & Kitchen.

Wonderful

(64 reviews)

Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.

East Falmouth

8% off

AU$4,420

for 7 nights, 1 home

AU$631 per night

includes taxes & fees

3 sided deck with outdoor couch, table, lounge chairs for sun or shade.

New Minisplit for heat / AC in each room. Slider leads to outdoor shower.

Exceptional

(63 reviews)

Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger.

Chilmark

12% off

AU$3,030

for 7 nights, 1 home

AU$433 per night

includes taxes & fees

Exceptional

(7 reviews)

6bedroom, 4bath, chefs kitchen, central air, ping pong, walking distance to town

Vineyard Haven

8% off

AU$18,310

for 7 nights, 1 home

AU$2,616 per night

includes taxes & fees

Use of clubhouse heated POOL & tennis courts.

Great kayaking down the street to Washburn Island & Waquoit Bay.

Wonderful

(33 reviews)

Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.

East Falmouth

8% off

AU$4,420

for 7 nights, 1 home

AU$631 per night

includes taxes & fees

Excellent

(35 reviews)

A Vineyard Home Perfect For Family Gatherings

Vineyard Haven

8% off

AU$6,908

for 7 nights, 1 home

AU$987 per night

includes taxes & fees

Exceptional

(38 reviews)

Walk to private beach from beautiful Abels Hill house

Chilmark

8% off

AU$7,362

for 7 nights, 1 home

AU$1,052 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Chalet

Find the best place to stay - Dukes County

Premier Host

Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach

Sleeps 8 · 3 bedrooms · 2 bathrooms

Cozy efficiency apartment/heated pool

Sleeps 2 · 1 bedroom · 1 bathroom

The Cabin on Chappy!

Sleeps 4 · 2 bedrooms · 2 bathrooms

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

Sleeps 4 · 1 bedroom · 1 bathroom

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

Sleeps 4 · 1 bedroom · 1 bathroom

New Custom Built Home With A Pool In Edgartown

Sleeps 14 · 5 bedrooms · 5 bathrooms

Find the perfect holiday rental for your Dukes County getaway

Learn about the unique charm of Dukes County with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Dukes County

Are you searching for things to do while you're in the area? Venture out of your holiday home and experience everything that makes Dukes County a fun spot to go on holiday. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

Shining Sea Bikeway (14.3 mi / 23.1 km)
Cape Codder Water Park (22.3 mi / 35.8 km)
Water Wizz (26.5 mi / 42.6 km)
Farm Neck Golf Club (4.4 mi / 7.1 km)
Cape Cod Winery (13.4 mi / 21.6 km)
Cape Cod Country Club (16.2 mi / 26 km)

Exploring the natural features in Dukes County

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Dukes County. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

Lighthouse Beach (0.7 mi / 1.1 km)
Edgartown Beach (2.6 mi / 4.1 km)
South Beach (2.8 mi / 4.6 km)
Katama Beach (4.4 mi / 7.1 km)
Inkwell Beach (4.9 mi / 7.8 km)
Ocean Park (5.1 mi / 8.1 km)

Transport options to and around Dukes County

The nearest airport is in Vineyard Haven, MA (MVY-Martha's Vineyard), located 5.1 mi (8.2 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Dukes County?

Houses are the most popular type of holiday home in Dukes County, according to our data. Even if you have something a little different in mind, Stayz has properties in a variety of sizes and shapes. Browse our many options to find your perfect pad.

How much does it cost to rent a holiday home in Dukes County?

Season, length of stay and property type are some of the things that can determine the price of a holiday home. Simply click on your travel dates to find your dream escape. From cosy chalets to sprawling villas, all Stayz holiday homes provide incredible value.

How much does it cost to rent a beach house in Dukes County?

When you travel and the style and size of the property will help determine the cost of your beachside holiday home. Click on your Dukes County travel dates to see your options on Stayz. Did someone just say "private pool"? Use our filters to choose the features and amenities you want in your home.

What are popular home amenities in Dukes County?

The most popular home amenities people prefer in Dukes County are off-street parking options, a microwave oven and a fridge. Whether you're on a trip with buddies, family or even pets, Stayz holiday homes provide the best amenities for hanging out with the people who matter most.

Are there large group holiday homes in Dukes County?

There are 202 holiday homes in Dukes County that can accommodate a group of 10 or more guests. Whether you're planning a holiday with extended family or a special event, there's ample space to get your group together under one roof.

What are the top attractions for families in Dukes County?

There are plenty of cool things to see and do with the family in Dukes County, such as:

Oak Bluffs Harbour
Inkwell Beach
Oak Bluffs Town Beach

Can I find two-bedroom holiday homes in Dukes County?

Gather your nearest and dearest and enjoy peace, privacy and comfort in one of the 136 two-bedroom holiday homes Dukes County has to offer.

Are there holiday homes with WiFi in Dukes County?

Dukes County has 336 holiday homes with WiFi, so you can stay connected during your trip. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming TV shows with the family to sending emails, these Stayz homes make it a cinch to go online.

How old do you have to be to rent a holiday home in Dukes County?

The minimum required age is typically 16, 18 or 21. It can differ from property to property on Stayz, so check the rules of your chosen Dukes County holiday home before you book.

How long can I rent a holiday home in Dukes County for?

The amount of time you can stay in a Dukes County holiday home for varies depending on the property. Just enter your dates of travel to see available options that offer extended stays. They have the things you need to make your extended holiday more comfortable and enjoyable, like kitchens and laundries. Some properties may also offer discounted weekly or monthly prices, so you can have a longer stay for less.

More holiday ideas

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