Dukes County holiday homes

We found 2,032 holiday rentals — enter your dates for availability
Select from 911 houses, 61 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 Bookabach

Holiday rentals with weekly discounts – Dukes County

Showing deals for:27 Nov - 4 Dec

the lounge, small event
back of the house, from the our dock
Paquachuck Inn
our dock
Exceptional
(5 reviews)

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

Westport Point

8% off
NZ$28,504
for 7 nights, 1 room
NZ$4,072 per night
includes taxes & fees
Relax by the sea! Bed & Breakfast near Horseneck State Beach
Living area
Private kitchen
Interior
Exterior
Very good
(41 reviews)

The Cabin on Chappy!

Edgartown

8% off
NZ$4,261
for 7 nights, 1 cottage
NZ$609 per night
includes taxes & fees
The Cabin on Chappy!
Outdoor Shower
Town Beach, across the street
Butlers panty with wet bar and drinks fridge.
Remodeled Kitchen
Exceptional
(42 reviews)

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

Mattapoisett

8% off
NZ$10,432
for 7 nights, 1 home
NZ$1,490 per night
includes taxes & fees
Reserve for 2027 season, Wraparound Porch, Waterviews, Walk to beach,4 Ensuites
Entering from the driveway
Living room  with loft space above
Spacious wrap around deck with all day sun and shade
West wing with futon/sleeper
Exceptional
(43 reviews)

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

Chilmark

8% off
NZ$9,942
for 7 nights, 1 home
NZ$1,420 per night
includes taxes & fees
Striking 5BR/4BA Chilmark Contemporary with Views of the Sound
Living area
Living area
Rose covered flower arch next to unit
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
NZ$7,150
for 7 nights, 1 cottage
NZ$1,021 per night
includes taxes & fees
Maushop Village Getaway with Ocean Views, Steps to Private Beach
Private kitchen
Terrace/patio
Interior
Exterior
Exceptional
(7 reviews)

BRAND NEW!

Oak Bluffs

8% off
NZ$13,760
for 7 nights, 1 home
NZ$1,966 per night
includes taxes & fees
BRAND NEW!
Interior
Living area
Exterior
Room
Very good
(5 reviews)

Beautiful Custom Home In Oak Bluffs

Oak Bluffs

8% off
NZ$16,413
for 7 nights, 1 home
NZ$2,345 per night
includes taxes & fees
Beautiful Custom Home In Oak Bluffs
Living area
Terrace/patio
Interior
Family Room with Panoramic View of the Pool and the Patio
Exceptional
(5 reviews)

Heated Indoor Pool & Spa - Golf Course View

Mashpee

5% off
NZ$14,791
for 7 nights, 1 villa
NZ$2,113 per night
includes taxes & fees
Heated Indoor Pool & Spa - Golf Course View
Living area
Living area
Outdoor dining
Exterior
Exceptional
(17 reviews)

THE PARK ESTATE! Your Martha's Vineyard Getaway!

Oak Bluffs

9% off
NZ$94,366
for 7 nights, 1 home
NZ$13,481 per night
includes taxes & fees
THE PARK ESTATE! Your Martha's Vineyard Getaway!
Dining
Living area
Room
Pool
Exceptional
(26 reviews)

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

East Falmouth

8% off
NZ$10,829
for 7 nights, 1 home
NZ$1,547 per night
includes taxes & fees
Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.
Dining Room
Living area
Exterior
Screened-in porch
Exceptional
(8 reviews)

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

Chilmark

8% off
NZ$16,118
for 7 nights, 1 home
NZ$2,303 per night
includes taxes & fees
Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails
Interior
Interior
Private kitchen
Outdoor dining
Exceptional
(51 reviews)

Luxury Loft Historic Center Oak Bluffs

Oak Bluffs

17% off
NZ$9,199
for 7 nights, 1 home
NZ$1,314 per night
includes taxes & fees
Luxury Loft Historic Center Oak Bluffs
Games room
Property grounds
Dining
Living area
Exceptional
(31 reviews)

Cape Cod New Seabury Family Compound private pool near beach/dining/shopping

Mashpee

6% off
NZ$13,643
for 7 nights, 1 home
NZ$1,949 per night
includes taxes & fees
Cape Cod New Seabury Family Compound private pool near beach/dining/shopping
Double sinks for busy kitchens.
Exterior
Sun room off the kitchen.
Outdoor relaxing!
Exceptional
(5 reviews)

WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!

Edgartown

8% off
NZ$46,221
for 7 nights, 1 home
NZ$6,603 per night
includes taxes & fees
WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!
Laughter and stories are guaranteed as you
get together on the West Porch.
This unique home was
carefully renovated to maintain its original character.
Choose from a variety of seating areas
overlooking the ocean and harbor.
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
NZ$66,773
for 7 nights, 1 home
NZ$9,539 per night
includes taxes & fees
Oceanfront, Private Dock and Harthaven Private Beach - Walk to Noman's, Inkwell
Private kitchen
Living area
Living area
Living area
Excellent
(36 reviews)

A Vineyard Home Perfect For Family Gatherings

Vineyard Haven

8% off
NZ$8,287
for 7 nights, 1 home
NZ$1,184 per night
includes taxes & fees
A Vineyard Home Perfect For Family Gatherings
Interior
Dining
Exterior
Living area
Exceptional
(5 reviews)

Beach Getaway - Spacious Katama Beach House

Edgartown

8% off
NZ$46,112
for 7 nights, 1 home
NZ$6,587 per night
includes taxes & fees
Beach Getaway - Spacious Katama Beach House
Pet Friendly Cape House.
Kayaks to paddle around Waquoit Bay to Washburn Island
Slate kitchen island & granite dining room table.
Seating for 10.
Deck with outdoor dining & plenty of flowers.
Wonderful
(66 reviews)

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

East Falmouth

8% off
NZ$5,372
for 7 nights, 1 home
NZ$767 per night
includes taxes & fees
Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.
Pool
Private kitchen
Private kitchen
Dining
Exceptional
(53 reviews)

Luxurious & Spacious 6 Bed/5 Bath Home with Ocean Views, New Seabury, Cape Cod

Mashpee

5% off
NZ$14,963
for 7 nights, 1 home
NZ$2,138 per night
includes taxes & fees
Luxurious & Spacious 6 Bed/5 Bath Home with Ocean Views, New Seabury, Cape Cod
Terrace/patio
The garden gate
Exterior
Living area
Exceptional
(39 reviews)

Walk to private beach from beautiful Abels Hill house

Chilmark

8% off
NZ$8,899
for 7 nights, 1 home
NZ$1,271 per night
includes taxes & fees
Walk to private beach from beautiful Abels Hill house
Kitchen
Kitchen
Kitchen
front of house at dusk
Exceptional
(7 reviews)

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

Vineyard Haven

8% off
NZ$21,589
for 7 nights, 1 home
NZ$3,084 per night
includes taxes & fees
6bedroom, 4bath, chefs kitchen, central air, ping pong, walking distance to town
Living room / Dining area
Approach to our home
Loft area
Kitchen
Exceptional
(16 reviews)

Katama Edgartown... bike to South Beach, bike to Town

Edgartown

8% off
NZ$6,169
for 7 nights, 1 home
NZ$881 per night
includes taxes & fees
Katama Edgartown... bike to South Beach, bike to Town
Dining
Exterior
Private kitchen
Exterior
Exceptional
(10 reviews)

The Beach Estate, Panoramic Ocean Views, 5700 sqft

Mattapoisett

12% off
NZ$16,004
for 7 nights, 1 home
NZ$2,286 per night
includes taxes & fees
The Beach Estate, Panoramic Ocean Views, 5700 sqft
Brand new kitchen with stainless & quartz.
Use of clubhouse heated POOL & tennis courts.
Out door seating for 8 & gas grill.
Open dining room, living room, kitchen (brand new) 
 & deck.
Wonderful
(35 reviews)

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

East Falmouth

8% off
NZ$5,372
for 7 nights, 1 home
NZ$767 per night
includes taxes & fees
Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.

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:

  • 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)
  • Oak Bluffs Town Beach (5.3 mi / 8.6 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, Bookabach 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 Bookabach 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 Bookabach. 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, Bookabach 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 Bookabach 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 Bookabach, 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