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Holiday Rentals in Chilmark

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Holiday Rentals in Chilmark

Holiday Home in Chilmark

7.4 out of 10, Good, (6)
"This place is a nightmare!"
United States
Daniel K.
Water-view home in great location with spacious backyard, grill, kayaks, dogs OK

Condo resort in Mashpee

3.5 star property
9.0 out of 10, Wonderful, (338)
"Very relaxing, loved the different clubs available; beach, pool, tennis, playground for the little ones, bars and food. Some shops were closed due to being off season, but still enjoyed our stay. Looking forward to booking again "
United States
Jose O.
The price is €145
includes taxes & fees
30 Nov - 1 Dec
The Club at New Seabury

Holiday Home in East Falmouth

10.0 out of 10, Exceptional, (88)
"Great stay! "
United States
Michael M.
The price is €789
includes taxes & fees
30 Nov - 1 Dec
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Aparthotel in Mashpee

3.0 star property
8.6 out of 10, Excellent, (142)
"Overall was a wonderful stay. Unit could use a hair dryer."
United States
Susan
Sea Mist Resort

Aparthotel in Falmouth Heights

3.5 star property
9.8 out of 10, Exceptional, (192)
"Great property! Would definitely stay again."
United States
Brad
InnSeason Resorts Captain's Quarters

Apartment in Falmouth

3.0 star property
9.4 out of 10, Exceptional, (101)
"Very clean and quiet place to relax. Very friendly and professional! We will come back!"
United States
Emmanuelle Loriot
Beachside Village Resort

Holiday Home in Oak Bluffs

6.4 out of 10, (31)
"indoor and outdoor comfortable space"
United States
Delores C.
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Holiday Home in Falmouth

9.8 out of 10, Exceptional, (73)
"Great stay"
United States
Michael S.
Newly Renovated Near Amazing Sunset Beach

Holiday Home in West Tisbury

9.0 out of 10, Wonderful, (35)
"Great spot for a get away. Private with easy access to activities."
United States
Philip E.
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

Holiday Home in Falmouth Heights

10.0 out of 10, Exceptional, (187)
"Great house with 4 bedrooms, good for couples. Walking distance to many places in Falmouth. Really enjoyed our stay here. Would stay again. "
United States
christine d.
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

Holiday Home in Edgartown

9.6 out of 10, Exceptional, (40)
"Great family friendly home with lots of living space and activities such as tennis, pickle ball, ping pong, and games all on the property. My family of 10, inclusive of 4 grandchildren had an awesome time."
United States
Bob B.
Sleeps 12, amazing view, tennis court, basketball court, beaches

Holiday Home in Oak Bluffs

10.0 out of 10, Exceptional, (7)
"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 €1,072
includes taxes & fees
30 Nov - 1 Dec
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Holiday Home in Mashpee

9.4 out of 10, Exceptional, (30)
"Beautiful location. We enjoyed every minute of our stay. "
United States
Clayton B.
Breathtaking Views with Private Dock & Pool!

Cottage in Tisbury

10.0 out of 10, Exceptional, (31)
"Perfect for my family of 4. Very walkable to everything Vineyard Haven. "
United States
Dave B.
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

Holiday Home in Falmouth Heights

10.0 out of 10, Exceptional, (53)
"Beautiful home in a great location! "
United States
Maurice R.
Classic Cape Cod - Ocean Views - Steps to Falmouth Heights Beach.

Holiday Home in East Falmouth

10.0 out of 10, Exceptional, (37)
"A perfect location and awesome for a family vacation"
United States
joyce b.
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

Holiday Home in Oak Bluffs

9.6 out of 10, Exceptional, (44)
"We had an amazing time. Kim is fabulous. The loft is beautiful and perfect for the three families. Plenty of room! The kitchen was amazing, outdoor space and a 5 minute walk to down town oak bluffs. I've stayed at a number of places on Martha's Vineyard and this by far is the best! Thank you for a wonderful place to stay!"
United States
chanda f.
Luxury Loft Historic Center Oak Bluffs

Holiday Home in Katama

2.0 star property
10.0 out of 10, Exceptional, (4)
"This property was great for our golf trip. The 3 bedrooms were exceptional "
United States
stephen t.
The Costal Corner - Martha's Vineyard

Holiday Home in Mashpee

9.6 out of 10, Exceptional, (95)
"Loved having the lake outside our door and the pool was great for some rainy evenings. We enjoyed the kayaks, paddle boards and the kids toys."
United States
Kelsy S.
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!

Holiday Home in East Falmouth

10.0 out of 10, Exceptional, (112)
"The location and amenities were perfect. We are looking forward to returning next year."
United States
Trayce H.
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub
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, apart-hotels, 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 favorite 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 depends 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 €145 per night. Entering your travel dates in the search wizard you might find 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?

Newly Renovated Near Amazing Sunset Beach: This holiday home rental outside of Chilmark offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 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 games.

How many holiday rentals are there in Chilmark?

Choose from 76 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 Lucy Vincent Beach 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.