Photo by Wen C.

Search Resorts in Chilmark

Compare 7 Resorts in Chilmark with updated reviews, rates, and availability.

Captain's Quarters Resort Oceanfront suite, beautiful ocean view, swimming pool
Pool

Captain's Quarters Resort Oceanfront suite, beautiful ocean view, swimming pool

10.0 out of 10, Exceptional, (1)
"The Inn was beautiful and very accommodating. The staff was great and the location perfect."
Captain's Quarters Resort Oceanfront suite, beautiful ocean view, swimming pool
Deluxe suite at the oceanfront Surfside Resort
Exterior

Deluxe suite at the oceanfront Surfside Resort

Deluxe suite at the oceanfront Surfside Resort
Cozy History Resort Located in the center of the city
Exterior

Cozy History Resort Located in the center of the city

4.8 out of 10, (3)
"Lovely community. No restaurant onsite but the location is in the center of plenty of shopping and places to dine. Excellent staff."
Cozy History Resort Located in the center of the city
Studio Villa directly across from beach. Sleeps 4
Pool

Studio Villa directly across from beach. Sleeps 4

Studio Villa directly across from beach. Sleeps 4
Spacious one bedroom getaway resort on Falmouth Harbor. Sleeps 4 comfortably.
Room

Spacious one bedroom getaway resort on Falmouth Harbor. Sleeps 4 comfortably.

Spacious one bedroom getaway resort on Falmouth Harbor. Sleeps 4 comfortably.
Martha’s Vineyard Waterfront 1 Bedroom King Bed - Available October 9-16
Room

Martha’s Vineyard Waterfront 1 Bedroom King Bed - Available October 9-16

Martha’s Vineyard Waterfront 1 Bedroom King Bed - Available October 9-16
Coastal Family Haven: Spacious Retreat Near Old Silver Beach
Exterior

Coastal Family Haven: Spacious Retreat Near Old Silver Beach

Coastal Family Haven: Spacious Retreat Near Old Silver Beach
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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Other property types in Chilmark

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

8.6 out of 10, Excellent, (22)
"We didn't realize how beautiful and unique the architecture of this residence was before we arrived. It is a gorgeous place and we were please by the cleanliness and simplicity of it. "
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Beautiful dog-friendly home with water view, balcony & washer/dryer

Beautiful dog-friendly home with water view, balcony & washer/dryer

7.8 out of 10, Good, (14)
"A Vacasa managed property that has everything you could want. We stayed 4 nights with our whole family and our small dog. It had everything we could want and we enjoyed ourselves. Recently redone, with good fit and finish and places to hang cook and relax off a dirt road that is well situated. Our only comments would be that there were some things needing fixing like the grill handle, lights not in sockets, and general disarray of bedding and supplies in the closets. While clean and fresh...
Beautiful dog-friendly home with water view, balcony & washer/dryer
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
Outdoor dining

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.

10.0 out of 10, Exceptional, (45)
"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 + Lvl 2 EV charger.
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.

Frequently asked questions

What is Chilmark like for a resort vacation?
You deserve some time off, and a resort is just the place to find all the amenities and services you need for a relaxing stay in Chilmark. One of the comfortable resort hotels in the area might be just what you’re looking for, whether you’re hoping for great restaurants on site, shopping possibilities, or fun activities to try.
What's a favorite resort for my stay in Chilmark?
Our top-rated resorts near Chilmark: Captain’s Quarters Resort Oceanfront suite, beautiful ocean view, swimming pool - Beach resort. 16 mi (25.8 km) from Chilmark. Features a garden, concierge services, and an outdoor pool. Deluxe suite at the oceanfront Surfside Resort - Beach resort. 16.3 mi (26.3 km) from Chilmark. Has a garden, concierge services, and an indoor pool. Cozy History Resort Located in the center of the city - 10.6 mi (17.1 km) from Chilmark. Martha’s Vineyard Waterfront 1 Bedroom King Bed - Available October 9-16 - 12.4 mi (20 km) from Chilmark. Amenities include an outdoor pool. Studio Villa directly across from beach. Sleeps 4 - 15.3 mi (24.6 km) from Chilmark.
What can I do in Chilmark?
For some time by the water, you can head to Menemsha Beach and Lucy Vincent Beach. For more to see in the area, you can spend time at Chilmark Town Hall or Chilmark Public Library.
What's the weather like in Chilmark?
The hottest months are usually August and July with an average temp of 68°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Chilmark is 50 inches.
What's the best way to get to and around Chilmark?
Fly into Vineyard Haven, MA (MVY-Martha’s Vineyard), which is located 7.6 mi (12.2 km) from the city center. Otherwise, you can search for flights to New Bedford, MA (EWB-New Bedford Regional), which is 25.4 mi (40.8 km) away. If you’d like to explore around the area, consider renting a car to take in more sights.