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Holiday Rentals in Chilmark

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Holiday Rentals in Chilmark

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

10.0 out of 10, Exceptional, (51)
"We were in town for a wedding in Chilmark and the property was exactly what we needed!"
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (325)
"Great stay! Didn't notice it being dated or dirty at all like some reviews said. We loved it!"
The Club at New Seabury

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (175)
"Just a quick weekend away. Great location for beach lovers. Also excellent retaurants "
InnSeason Resorts Captain's Quarters

Beachside Village Resort

3.0 star property
9.4 out of 10, Exceptional, (96)
"Great location! Nice property! "
The price is €309
includes taxes & fees
14 Aug - 15 Aug
Beachside Village Resort

Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..

8.6 out of 10, Excellent, (40)
"Great place for a summer vacation"
The price is €707
includes taxes & fees
20 Aug - 21 Aug
Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (133)
"Great resort with suites, very cosy with great amenities, close to excellent beach and shopping."
The price is €157
includes taxes & fees
2 Sept - 3 Sept
Sea Mist Resort

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.0 out of 10, (22)
"There were times when the shower in the master bathroom only emitted cold water. The water spigot in the tubs would not turn completely off in bathroom in the hallway. I had trouble with the lockbox. Maybe add more specific directions. It would have been helpful to know that MV transit bus was available at the intersection of the street and County Road."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Southcape Resort Mashpee a Ramada by Wyndham

3.0 star property
8.6 out of 10, Excellent, (200)
"Enjoyed our stay."
Southcape Resort Mashpee a Ramada by Wyndham

Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

8.8 out of 10, Excellent, (33)
"Great spot for a get away. Private with easy access to activities."
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (85)
"Great stay! "
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Renovated 1-bedroom apartment in Downtown Falmouth Located Right on Main Street

2.0 star property
10.0 out of 10, Exceptional, (1)
"I would 100% recommend this apartment! My friends and I had the best experience. The host was so friendly and made himself available for us via text and in person whenever we needed. The listing aligns perfectly with the actual apartment. The apartment was extremely clean and shampoo conditioner etc were provided for us as well as extra bedding. The building is super easy to access with the instructions provided and the location is amazing as it is right on Main Street in Falmouth! Overall we...
Renovated 1-bedroom apartment in Downtown Falmouth Located Right on Main Street

Cape beach house steps to beach, a short walk to town & AC

10.0 out of 10, Exceptional, (4)
"This home is beautiful and a perfect beach retreat with all the amenities. The small, quiet community is perfect for walks and beach access couldn't be more convenient. We loved our stay and can't wait to return!"
Cape beach house steps to beach, a short walk to town & AC

Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

8.4 out of 10, Very good, (20)
"So turn key and perfect for Month, Joy is an exceptional host and I’d recommend her place anytime"
The price is €196
includes taxes & fees
10 Aug - 11 Aug
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

Charming 3-bedroom house with a pool, AC, WiFi in pleasant East Falmouth

9.4 out of 10, Exceptional, (3)
"Really beautiful place with a lot of space and a very helpful host"
Charming 3-bedroom house with a pool, AC, WiFi in pleasant East Falmouth

Water Front DREAM vacation, whole house AC, Free wi-fi, linen&towels, fire pit,

9.6 out of 10, Exceptional, (65)
"Nice house in a beautiful peaceful setting."
Water Front DREAM vacation, whole house AC, Free wi-fi, linen&towels, fire pit,

Relax & Unwind at this Adorable and very private 1 bedroom 1 bath studio

10.0 out of 10, Exceptional, (4)
"A very nice stay. Relaxing and quiet - we would highly recommend!"
Relax & Unwind at this Adorable and very private 1 bedroom 1 bath studio

Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

5.6 out of 10, (24)
"Great location and private beach access. Charming enclave perfect for our weekend getaway."
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

Walking-distance to town, shops, restaurants & ferry!

10.0 out of 10, Exceptional, (18)
"I rented this for my staff, and they said it was the best place they have stayed on Martha's Vineyard."
Walking-distance to town, shops, restaurants & ferry!

Newly Renovated Martha's Vineyard Vacation Rental!

9.6 out of 10, Exceptional, (44)
"Love our stay!"
The price is €683
includes taxes & fees
4 Sept - 5 Sept
Newly Renovated Martha's Vineyard Vacation Rental!

SUMMER RETREAT AWAITS YOU

9.0 out of 10, Wonderful, (24)
"A wonderful visit and a short walk to the beach"
SUMMER RETREAT AWAITS YOU
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

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?

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.: This highly rated holiday home rental in Chilmark is located on the waterfront, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Chilmark?

Choose from 74 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.