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Search Holiday Rentals in Chilmark

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Top Holiday Rentals in Chilmark

Water-view home in great location with spacious backyard, grill, kayaks, dogs OK

8.0 out of 10, Very good, (3)
"This small house provided a big relief in our trip. Located steps from the best lobster roll in town and about a block from the water, this is a FANTASTIC spot for getting away."
Water-view home in great location with spacious backyard, grill, kayaks, dogs OK

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

10.0 out of 10, Exceptional, (50)
"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.

Cozy efficiency apartment/heated pool

9.8 out of 10, Exceptional, (17)
"This is a great property for an individual or a couple looking to explore the island!"
Cozy efficiency apartment/heated pool

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (323)
"A great unique and quiet place, very close to Boston."
The Club at New Seabury

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (173)
"Excellent location! Close to the Ferry and downtown !"
InnSeason Resorts Captain's Quarters

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (124)
"Great place just had another family staying above our room that was very noisy the last night we were there"
The price is £195
includes taxes & fees
7 Jul - 8 Jul
Sea Mist Resort

Southcape Resort Mashpee a Ramada by Wyndham

3.0 star property
8.6 out of 10, Excellent, (199)
"Enjoyed our stay."
Southcape Resort Mashpee a Ramada by Wyndham

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (93)
"Wonderful location, nice staff!"
The price is £253
includes taxes & fees
1 Jul - 2 Jul
Beachside Village Resort

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

9.6 out of 10, Exceptional, (78)
"Close to buses, restaurants and ferries. 10/10, we would stay again."
The price is £523
includes taxes & fees
29 Jun - 30 Jun
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Historic Oak Bluffs home, short walk to town, beach, and harbor.

9.6 out of 10, Exceptional, (29)
"We enjoy it all. "
Historic Oak Bluffs home, short walk to town, beach, and harbor.

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

10.0 out of 10, Exceptional, (84)
"Great stay! "
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Charming Seaside Cottage Central to the Beach and New Seabury Resort Community

2.0 star property
9.6 out of 10, Exceptional, (5)
"Perfect cottage"
Charming Seaside Cottage Central to the Beach and New Seabury Resort Community

Newly renovated 2BR house, FREE CAR w/beach sticker, pet friendly, sleeps 8

Newly renovated 2BR house, FREE CAR w/beach sticker, pet friendly, sleeps 8

Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

9.6 out of 10, Exceptional, (64)
"Clean property, great location"
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace

Oak Bluffs - Quiet neighborhood

9.2 out of 10, Wonderful, (37)
"Very nice property, cute backyard set up. Close to downtown OB and Tony's market for grocery needs. Second time staying here and would stay again"
Oak Bluffs - Quiet neighborhood

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

6.2 out of 10, (18)
"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

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

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

Spacious 2 Double Bed Suite w/ Ocean Deck

The price is £272
includes taxes & fees
21 Jul - 22 Jul
Spacious 2 Double Bed Suite w/ Ocean Deck

STEP DIRECTLY ONTO YOUR PRIVATE MAUSHOP VILLAGE BEACH AT THIS SEASIDE TOWNHOME

2.0 star property
10.0 out of 10, Exceptional, (9)
"This beach town home is elegant and charming. The location is unbeatable; we enjoyed easy access to the beach, as well as nearby shops and restaurants. We spent our days beaching it up, and exploring the local area (all fun stuff within walking distance). From the moment we booked to the day we departed, the host always had prompt, friendly and helpful communication, and provided us with great recommendations for things to do for the whole family. THANK YOU FOR AN UNFORGETTABLE vacation, we just...
The price is £902
includes taxes & fees
28 Jun - 29 Jun
STEP DIRECTLY ONTO YOUR PRIVATE MAUSHOP VILLAGE BEACH AT THIS SEASIDE TOWNHOME

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

6.0 out of 10, (21)
"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
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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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?

Water-view home in great location with spacious backyard, grill, kayaks, dogs OK: This highly rated holiday home rental in Chilmark offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Chilmark?

Choose from 67 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.