A coastal cliff with a sandy beach and the ocean.

Dukes County holiday rentals

We found 1,996 holiday rentals — enter your dates for availability

Select from 880 houses, 60 apartments 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 historic two-story house with a balcony and a porch, surrounded by a well-maintained garden.

Oak Bluffs

A sandy beach leading to a white lighthouse with a black top, surrounded by grass and a clear sky.

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

Tisbury

West Tisbury

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

Chilmark

Holiday rentals with weekly discounts – Dukes County

Showing deals for:25 Dec - 1 Jan

Exceptional

(6 reviews)

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

Westport Point

8% off

AU$23,979

for 7 nights, 1 room

AU$3,426 per night

includes taxes & fees

Exceptional

(43 reviews)

Reserve for 2027 season, Wraparound Porch, Waterviews, Walk to beach,4 Ensuites

Mattapoisett

8% off

AU$9,042

for 7 nights, 1 home

AU$1,292 per night

includes taxes & fees

Exceptional

(10 reviews)

Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails

Chilmark

8% off

AU$13,683

for 7 nights, 1 home

AU$1,955 per night

includes taxes & fees

Family Room with Panoramic View of the Pool and the Patio

Exceptional

(5 reviews)

Heated Indoor Pool & Spa - Golf Course View

Mashpee

8% off

AU$14,068

for 7 nights, 1 villa

AU$2,010 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$5,971

for 7 nights, 1 cottage

AU$853 per night

includes taxes & fees

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

Exceptional

(25 reviews)

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

Falmouth

7% off

AU$5,383

for 7 nights, 1 home

AU$769 per night

includes taxes & fees

Exceptional

(11 reviews)

The Beach Estate, Panoramic Ocean Views, 5700 sqft

Mattapoisett

13% off

AU$26,722

for 7 nights, 1 home

AU$3,817 per night

includes taxes & fees

Spacious wrap around deck with all day sun and shade

Exceptional

(45 reviews)

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

Chilmark

8% off

AU$7,253

for 7 nights, 1 home

AU$1,036 per night

includes taxes & fees

Exceptional

(17 reviews)

THE PARK ESTATE! Your Martha's Vineyard Getaway!

Oak Bluffs

9% off

AU$79,754

for 7 nights, 1 home

AU$11,393 per night

includes taxes & fees

Exceptional

(28 reviews)

Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.

East Falmouth

8% off

AU$9,024

for 7 nights, 1 home

AU$1,289 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$7,506

for 7 nights, 1 home

AU$1,072 per night

includes taxes & fees

Exceptional

(5 reviews)

Beach Getaway - Spacious Katama Beach House

Edgartown

9% off

AU$35,089

for 7 nights, 1 home

AU$5,013 per night

includes taxes & fees

Exceptional

(7 reviews)

BRAND NEW!

Oak Bluffs

8% off

AU$11,176

for 7 nights, 1 home

AU$1,597 per night

includes taxes & fees

Exceptional

(6 reviews)

WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!

Edgartown

9% off

AU$34,724

for 7 nights, 1 home

AU$4,961 per night

includes taxes & fees

Exceptional

(6 reviews)

Spacious home for entertaining, centrally located to beach, ferry, and airport.

Edgartown

8% off

AU$30,572

for 7 nights, 1 home

AU$4,367 per night

includes taxes & fees

South view to Pond and Atlantic Ocean from master bedroom

Exceptional

(14 reviews)

Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views

Chilmark

8% off

AU$10,024

for 7 nights, 1 home

AU$1,432 per night

includes taxes & fees

Meals on the patio are a daily delight- sparkly mornings to ocean dipped sunsets

Large, farmhouse fireplace perfect for chillier seasons.

Dining area can seat 8-10 and looks onto patio and water views.

Exceptional

(43 reviews)

Sanctuary House: An ocean-view farmhouse retreat

Vineyard Haven

8% off

AU$7,253

for 7 nights, 1 home

AU$1,036 per night

includes taxes & fees

You will create forever memories in this amazing setting.

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

Your closest neighbors are a family of Osprey!

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

Exceptional

(28 reviews)

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

Oak Bluffs

9% off

AU$48,975

for 7 nights, 1 home

AU$6,996 per night

includes taxes & fees

Exceptional

(34 reviews)

Across the street from Old Silver Beach; New house with hot tub. Sleeps 12.

Falmouth

8% off

AU$8,214

for 7 nights, 1 home

AU$1,173 per night

includes taxes & fees

Exceptional

(51 reviews)

Luxury Loft Historic Center Oak Bluffs

Oak Bluffs

19% off

AU$6,789

for 7 nights, 1 home

AU$970 per night

includes taxes & fees

Use of clubhouse heated POOL & tennis courts.

Wonderful

(35 reviews)

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

East Falmouth

8% off

AU$4,445

for 7 nights, 1 home

AU$635 per night

includes taxes & fees

Slate kitchen island & granite dining room table.
Seating for 10.

Kayaks to paddle around Waquoit Bay to Washburn Island

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

Excellent

(68 reviews)

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

East Falmouth

8% off

AU$4,445

for 7 nights, 1 home

AU$635 per night

includes taxes & fees

Exceptional

(97 reviews)

Perfect location for your summer vacation! Newly renovated kitchen & bathrooms!!

Falmouth

8% off

AU$6,016

for 7 nights, 1 home

AU$859 per night

includes taxes & fees

Toasty Fireplace for fall and winter getaways

Exceptional

(76 reviews)

Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!

East Falmouth

8% off

AU$5,261

for 7 nights, 1 home

AU$752 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

Cozy, exceptional view, quiet, high speed WIFI, close to all island attractions

Sleeps 8 · 4 bedrooms · 2 bathrooms

Premier Host

Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach

Sleeps 8 · 3 bedrooms · 2 bathrooms

Premier Host

Walk To Downtown and Beaches

Sleeps 8 · 4 bedrooms · 2 bathrooms

Premier Host

Cozy efficiency apartment/heated pool

Sleeps 2 · 1 bedroom · 1 bathroom

Martha's Vineyard Beachfront Cottage in Oak Bluffs but closer to Vineyard Haven

Sleeps 6 · 3 bedrooms · 1+ bathroom

Private cottage nestled in center of the Vineyard

Sleeps 4 · 1 bedroom · 1 bathroom

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:

Farm Neck Golf Club (4.4 mi / 7.1 km)
Shining Sea Bikeway (14.3 mi / 23.1 km)
Cape Cod Country Club (16.2 mi / 26 km)
Cape Codder Water Park (22.3 mi / 35.8 km)
Water Wizz (26.5 mi / 42.6 km)
Downtown Library Park (12.4 mi / 20 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)
Norton Point Beach (3.1 mi / 5 km)
Katama Beach (4.4 mi / 7.1 km)
Inkwell Beach (4.9 mi / 7.8 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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