Chilmark holiday rentals

We found 517 holiday rentals — enter your dates for availability
Select from 66 homes, 12 cottages and other holiday rentals in Chilmark to find one that's perfect for your trip. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as cable TV and a washer and dryer. At the end of the day, you're sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Chilmark

Showing deals for:6 Nov - 13 Nov

Living area
Living area
Exterior
Dining
Exceptional
(17 reviews)

THE PARK ESTATE! Your Martha's Vineyard Getaway!

Oak Bluffs

8% off
S$72,600
for 7 nights, 1 home
S$10,371 per night
includes taxes & fees
THE PARK ESTATE! Your Martha's Vineyard Getaway!
Private kitchen
Spacious great room and kitchen
Brand new landscaping
Interior
Exceptional
(16 reviews)

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

Edgartown

5% off
S$11,303
for 7 nights, 1 home
S$1,615 per night
includes taxes & fees
New 4-bedroom House with Swimming Pool–Just a 10-minute Walk to Town
Outdoor relaxing!
Exterior
Double sinks for busy kitchens.
Sun room off the kitchen.
Exceptional
(5 reviews)

WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!

Edgartown

8% off
S$32,243
for 7 nights, 1 home
S$4,606 per night
includes taxes & fees
WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!
Dining
Living Room with view to kitchen
Interior
Kitchen
Exceptional
(34 reviews)

Walk to Town! Beautiful, Private Edgartown Home

Edgartown

7% off
S$9,547
for 7 nights, 1 home
S$1,364 per night
includes taxes & fees
Walk to Town! Beautiful, Private Edgartown Home
Entering from the driveway
Living room  with loft space above
Kitchen slider and herb garden
West wing with futon/sleeper
Exceptional
(43 reviews)

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

Chilmark

8% off
S$10,032
for 7 nights, 1 home
S$1,433 per night
includes taxes & fees
Striking 5BR/4BA Chilmark Contemporary with Views of the Sound
Entryway
Front of main house at 47 Cooke St Edgartown MA
Front view of main entrance
Hot tub and heated pool
Exceptional
(55 reviews)

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

Edgartown

8% off
S$20,217
for 7 nights, 1 home
S$2,888 per night
includes taxes & fees
Edgartown close to beach and town 6BD with Pool and Hot Tub
Exterior
Terrace/patio
Private kitchen
Interior
Exceptional
(7 reviews)

BRAND NEW!

Oak Bluffs

7% off
S$10,574
for 7 nights, 1 home
S$1,511 per night
includes taxes & fees
BRAND NEW!
Private kitchen
Expansive sun deck with dining set, loungers, and seating area.
Living area
Recently updated kitchen, quartz counters, tons of light.
Exceptional
(30 reviews)

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

Chilmark

10% off
S$3,564
for 7 nights, 1 home
S$509 per night
includes taxes & fees
Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
Dining
The garden gate
Living area
Exterior
Exceptional
(38 reviews)

Walk to private beach from beautiful Abels Hill house

Chilmark

7% off
S$6,955
for 7 nights, 1 home
S$994 per night
includes taxes & fees
Walk to private beach from beautiful Abels Hill house
Interior
Property grounds
Outdoor dining
Room
Exceptional
(92 reviews)

Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach

Aquinnah

7% off
S$5,261
for 7 nights, 1 home
S$752 per night
includes taxes & fees
Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach
New Minisplit for heat / AC in each room. Slider leads to outdoor shower.
3 sided deck with outdoor couch, table, lounge chairs for sun or shade.
Quartz counters, recently updated fully stocked kitchen.
Living area
Exceptional
(63 reviews)

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

Chilmark

12% off
S$2,848
for 7 nights, 1 home
S$407 per night
includes taxes & fees
Unwind in Guest House overlooking Menemsha Pond. Dogs ok+ Lv-2 EV charger.
Living area
Outdoor dining
Interior
Exterior
Exceptional
(13 reviews)

Guest House In Edgartown

Edgartown

7% off
S$3,881
for 7 nights, 1 home
S$554 per night
includes taxes & fees
Guest House In Edgartown
Interior
Property grounds
Living area
Dining
Exceptional
(53 reviews)

Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

Aquinnah

8% off
S$3,021
for 7 nights, 1 home
S$432 per night
includes taxes & fees
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Exterior
Meals on the patio are a daily delight- sparkly mornings to ocean dipped sunsets
Dining area can seat 8-10 and looks onto patio and water views.
Large, farmhouse fireplace perfect for chillier seasons.
Exceptional
(40 reviews)

Sanctuary House: An ocean-view farmhouse retreat

Vineyard Haven

7% off
S$6,302
for 7 nights, 1 home
S$900 per night
includes taxes & fees
Sanctuary House: An ocean-view farmhouse retreat
Living Room
Front of house
Breakfast Bar
Hidden behind picket fence and privet hedges
Exceptional
(117 reviews)

Marthas Vineyard Edgartown Cottage - Easy walk to village, outdoor shower, linen

Edgartown

7% off
S$5,588
for 7 nights, 1 home
S$798 per night
includes taxes & fees
Marthas Vineyard Edgartown Cottage - Easy walk to village, outdoor shower, linen
Extra seating areas throughout the property
Over head views all over the property
Beautiful Landscapes every where throughout the yard
Endless hallway with new flooring in the garden space
Exceptional
(55 reviews)

Beautiful Landscaped Grounds and Pond & Kayaks

Oak Bluffs

5% off
S$7,111
for 7 nights, 1 apartment
S$1,016 per night
includes taxes & fees
Beautiful Landscaped Grounds and Pond & Kayaks
Rear view of our home
Approach to our home
Living room / Dining area
Kitchen
Exceptional
(15 reviews)

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

Edgartown

7% off
S$4,790
for 7 nights, 1 home
S$684 per night
includes taxes & fees
Katama Edgartown... bike to South Beach, bike to Town
Bedroom with queen bed
House exterior
Kitchen
House exterior and front yard
Exceptional
(17 reviews)

Charming Family Home in the Heart of Martha's Vineyard

Vineyard Haven

8% off
S$6,049
for 7 nights, 1 home
S$864 per night
includes taxes & fees
Charming Family Home in the Heart of Martha's Vineyard
Dining
Living area
Living area
Outdoor dining
Exceptional
(28 reviews)

The Seashell Cove - Martha's Vineyard

Edgartown

12% off
S$8,088
for 7 nights, 1 home
S$1,155 per night
includes taxes & fees
The Seashell Cove - Martha's Vineyard
Morning Glory Farm is 1 mile away
Furnished screened-in porch
Grounds include lilacs, hydrangeas and other beautiful plantings
Living area has cathedral ceilings, hardwood floors and high-end furnishings
Exceptional
(112 reviews)

Idyllic Vineyard House in Desirable Katama/Edgartown – Walk/Bike to Town/Beaches

Edgartown

7% off
S$5,147
for 7 nights, 1 home
S$735 per night
includes taxes & fees
Idyllic Vineyard House in Desirable Katama/Edgartown – Walk/Bike to Town/Beaches
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Explore the beachside setting in Chilmark

The area's wineries and festivals are just some of the reasons to come on holiday to Chilmark. Revered for its beaches, hiking and local tours, this city is both relaxing and scenic. 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 Chilmark

Do you want to find things to do in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Chilmark a fun place to get away to. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Farm Neck Golf Club (11.2 mi / 18 km)
  • Shining Sea Bikeway (17.2 mi / 27.7 km)
  • Cape Cod Winery (18.4 mi / 29.6 km)
  • Chilmark Chocolates (0.1 mi / 0.2 km)
  • Fulling Mill Brook Preserve (2.5 mi / 4 km)

Exploring the natural landscape of Chilmark

Whether you're an adventurous traveller or just want to take in the scenery, Chilmark is a great place to get outside. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Menemsha Beach (1.4 mi / 2.3 km)
  • Aquinnah Cliffs (4.8 mi / 7.8 km)
  • Lambert's Cove Beach (8 mi / 12.9 km)
  • Katama Beach (8.6 mi / 13.9 km)
  • Edgartown Beach (11.4 mi / 18.3 km)
  • South Beach (11.4 mi / 18.3 km)

Transport options to and around Chilmark

The nearest airport is in Vineyard Haven, MA (MVY-Martha's Vineyard), located 7.6 mi (12.2 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to New Bedford, MA (EWB-New Bedford Regional), which is 25.4 mi (40.8 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Chilmark?
Houses are the most popular type of holiday rental in Chilmark, according to our data. Even if you have a different idea about what you want, Vrbo has properties in many sizes and shapes. Browse our options to find your ideal fit.
How much does it cost to rent a holiday rental in Chilmark?
Property type, length of stay and season are some factors that can affect the price of a holiday home. Simply add your dates of travel to find your perfect fit. From quaint country cottages to plush villas, all Vrbo holiday rentals offer incredible value.
How much does it cost to rent a beach house in Chilmark?
Prices for beach houses in Chilmark differ depending on the size and type of the property and when you're travelling. Simply enter your dates of travel into Vrbo and the number of guests to view your rental options and prices. From there you can use the filters to tailor your search by amenities, nearby activities, ratings and more.
Are there pet-friendly holiday rentals in Chilmark?
Yes. There are. You'll have your pick of 63 holiday rentals that cater to pets in Chilmark. Several of our pet-friendly holiday rentals have a garden for your fur baby to play in, doggie beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find your pawfect pad on Vrbo.
Can I rent a house with a pool in Chilmark?
Check the "pool" box in our handy filter tool and you'll find eight houses with private pools in Chilmark on Vrbo. Morning dip, sunset soak or midnight swim? Leisure time is up to you when your holiday home comes with its own pool.
What are popular rental amenities in Chilmark?
When it comes to rental amenities that people are on the lookout for in Chilmark, a chef, a water view and tennis rank the highest. With Vrbo holiday homes, you'll have options to suit your taste and style, whether you're taking a trip with your partner, your friends or even pets.
Are there large group holiday rentals in Chilmark?
With 14 properties that can host 10 guests or more in Chilmark, you don't have to limit the invite list. From fun family get-togethers to special events like birthday parties and weddings, Vrbo will help you find a large group rental that fits the occasion.
Are there holiday rentals in Chilmark that welcome kids?
Bring the whole group together for the adventure of a lifetime in Chilmark at one of our 61 family-friendly holiday rentals. A lot of these stays feature amenities that are suitable for getaways with the little ones, such as laundry facilities, living rooms and swimming pools. Simply check the "Properties good for families" filter and choose your favourite.
What are the top attractions for families in Chilmark?
Keeping the kids entertained during your holiday in Chilmark is simple with these leading family-friendly attractions:
  • Lamberts Cove Beach
  • Menemsha Beach
  • Lucy Vincent Beach
Are there one-bedroom holiday rentals in Chilmark?
Chilmark has two one-bedroom rentals on offer. Usually situated in sought-after areas thanks to their smaller size, a one-bedroom holiday rental is great if you're travelling with a pal or your partner. And with home comforts like kitchens and more privacy than a standard hotel, you'll be able to kick back while sightseeing around this fabulous destination.
Can I find two-bedroom holiday rentals in Chilmark?
You can pick from 10 two-bedroom homes in Chilmark. Settle the kids into the second room or fill it with a couple of your besties. There's enough space for whoever's fortunate enough to be coming along for the ride.
Are there holiday rentals with WiFi in Chilmark?
Choose from 26 holiday rentals with WiFi in Chilmark. If you want to disconnect from daily life on your holiday, but still want to be connected to the internet, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Chilmark?
Pick your travel dates and then use the filter tool to find holiday rentals with air conditioning in Chilmark on Vrbo. With 45 air-conditioned properties on offer here, you can enjoy a cool and comfortable trip.
How old do you have to be to rent a holiday rental in Chilmark?
The minimum age allowed can vary across properties on Vrbo, so check the rules of the holiday home in Chilmark you're interested in. But in general, it's 16, 18 or 21.
How long can I rent a holiday rental in Chilmark for?
The amount of time you can rent a Chilmark holiday home for differs depending on the property. Just enter your travel dates to view options that offer extended stays. They come with all the things you need to make your extended holiday more comfortable such as laundries and air conditioning. Some holiday homes may also offer discounted weekly or monthly prices, so you can stick around for longer for less.

More holiday ideas