Chilmark Holiday Rentals

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Our top choices for Chilmark holiday rentals

Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool
Chilmark
9.6 out of 10, Exceptional, (21 reviews)
"We loved this property and would love to return!"
United States
Clifford L.
The price is AU$702
includes taxes & fees
19 June - 20 June
Cozy efficiency apartment/heated pool

New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (83 reviews)
"Host was super organized with clear instructions and easy check-in. The condo was well appointed and beautifully decorated. We enjoyed our brief stay!"
United States
Gina P.
The price is AU$475
includes taxes & fees
17 June - 18 June
New Seabury Cape Condo + Pool & Beach Escape

Open all year! Relaxation & privacy at this cozy 1 bedroom 1 bath studio.

Open all year! Relaxation & privacy at this cozy 1 bedroom 1 bath studio.
Falmouth
10.0 out of 10, Exceptional, (10 reviews)
"A very nice stay. Relaxing and quiet - we would highly recommend!"
United States
David C.
The price is AU$558
includes taxes & fees
1 June - 2 June
Open all year! Relaxation & privacy at this cozy 1 bedroom 1 bath studio.

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
New Seabury
8.6 out of 10, Excellent, (91 reviews)
"This was the perfect home for our weekend getaway! Joyce was wonderful to work with. Perfect location and beautiful home, just what we needed!"
United States
Courtney R.
The price is AU$859
includes taxes & fees
1 June - 2 June
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
9.8 out of 10, Exceptional, (25 reviews)
"Lovely and all brand new accommodation's that are clean and comfy! A quiet location too! "
United States
Nancy K.
The price is AU$667
includes taxes & fees
21 June - 22 June
Brand new! Lovely apartment-Vineyard Haven

Trendy Great Pond Escape! HotTub Open! Sleeps 9!

Trendy Great Pond Escape! HotTub Open! Sleeps 9!
Falmouth
10.0 out of 10, Exceptional, (13 reviews)
"Very happy with our stay and definitely would rebook again in the future. "
United States
Reed W.
The price is AU$1,201
includes taxes & fees
1 June - 2 June
Trendy Great Pond Escape! HotTub Open! Sleeps 9!

Near Old Silver Beach Falmouth-Two bedroom, private bathroom and kitchenette

Near Old Silver Beach Falmouth-Two bedroom, private bathroom and kitchenette
Falmouth
8.4 out of 10, Very good, (26 reviews)
"Very nice location in North Falmouth where things feel timeless. The only disadvantage was there is no living/sitting room. You can sit in the kitchen or be in the bedrooms. Host was attentive and available."
United States
Michelle
The price is AU$387
includes taxes & fees
1 June - 2 June
Near Old Silver Beach Falmouth-Two bedroom, private bathroom and kitchenette

Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
The price is AU$294
includes taxes & fees
7 June - 8 June
Charming studio in tranquil Falmouth with AC

Walk to Beach & Lighthouse: Oak Bluffs Studio!

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
7.6 out of 10, Good, (4 reviews)
"Very accommodating early check in and great communication "
United States
Katelyn K.
The price is AU$475
includes taxes & fees
1 June - 2 June
Walk to Beach & Lighthouse: Oak Bluffs Studio!

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
The price is AU$1,685
includes taxes & fees
1 June - 2 June
4-bedroom house in lovely Edgartown..Centrally located

Edgartown Designer Cottage between Town & Beach.

Edgartown Designer Cottage between Town & Beach.
Katama
10.0 out of 10, Exceptional, (25 reviews)
"Wonderful week in MV! The cottage had everything we needed and was a great location to bike into town or to the beach. Would love to come back and stay again!"
United States
Lauren B.
The price is AU$1,070
includes taxes & fees
2 June - 3 June
Edgartown Designer Cottage between Town & Beach.

LUX on Main | Downtown | Parking | Sleeps 6, #201

LUX on Main | Downtown | Parking | Sleeps 6, #201
Falmouth
The price is AU$929
includes taxes & fees
2 June - 3 June
LUX on Main | Downtown | Parking | Sleeps 6, #201

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Falmouth
10.0 out of 10, Exceptional, (9 reviews)
"A beautiful home conveniently located-very clean Nd comfortable for 6 long time friends."
United States
Linda W.
The price is AU$896
includes taxes & fees
21 June - 22 June
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
10.0 out of 10, Exceptional, (11 reviews)
"Super location, very nice accommodations, very clean, modern and comfortable "
United States
Cathie K.
The price is AU$724
includes taxes & fees
2 June - 3 June
Charming cottage overlooking the bay in Padanaram Village.

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
Falmouth
9.6 out of 10, Exceptional, (11 reviews)
"Really beautiful place with a lot of space and a very helpful host"
United States
Gokul K.
The price is AU$1,169
includes taxes & fees
7 June - 8 June
Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

4-bedroom waterfront house in E. Falmouth with WiFi, AC, Hot Tub, Private Beach

4-bedroom waterfront house in E. Falmouth with WiFi, AC, Hot Tub, Private Beach
Falmouth
The price is AU$1,126
includes taxes & fees
16 June - 17 June
4-bedroom waterfront house in E. Falmouth with WiFi, AC, Hot Tub, Private Beach

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.0 out of 10, Wonderful, (4 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is AU$1,326
includes taxes & fees
4 June - 5 June
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
10.0 out of 10, Exceptional, (8 reviews)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
United States
Swathanthra M.
The price is AU$1,880
includes taxes & fees
2 June - 3 June
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Spring Escape in Hatchville – Sleeps 6 + Dogs!

Spring Escape in Hatchville – Sleeps 6 + Dogs!
Falmouth
10.0 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay. Everything was clean and well kept. "
United States
Lynn S.
The price is AU$1,079
includes taxes & fees
1 June - 2 June
Spring Escape in Hatchville – Sleeps 6 + Dogs!

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Tisbury
10.0 out of 10, Exceptional, (58 reviews)
"We loved the location and place was great!"
United States
Eileen M.
The price is AU$919
includes taxes & fees
14 June - 15 June
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
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 Chilmark Hotel Reviews

Find out more about Chilmark

Everything you need to know about Chilmark holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chilmark holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chilmark holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chilmark holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chilmark. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chilmark holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chilmark holiday rentals we have selected for you start as low as AU$387 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chilmark rentals

At Expedia, we put the best Chilmark holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chilmark rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chilmark holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chilmark. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Chilmark?

Yes, there are holiday rentals in Chilmark close to Chilmark Chocolates, or you can select a more secluded option if you're looking for a relaxing stay. Chilmark is known for its beaches and wineries. Make sure you have time to check out the festivals and local tours during your trip.

What are some of the best holiday rentals that Chilmark has to offer?

Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool. : This holiday home rental outside of Chilmark is located near the beach, and has a patio, a private garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books.

How many holiday rentals are there in Chilmark?

Choose from 66 Expedia holiday rentals in Chilmark for a memorable holiday.

What’s there to see and do in Chilmark?

Family-friendly attractions include Chilmark Chocolates and Fulling Mill Brook Preserve, whereas Menemsha Beach and Edys Island are a couple of great spots to enjoy the outdoors. While here, Chilmark Town Hall and Chilmark Public Library are other places worth a visit.

What’s a holiday rental in Chilmark like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chilmark. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.