Photo by Wen C.

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Check prices for these dates

Next weekend
Mar 14 - Mar 16
In two weeks
Mar 21 - Mar 23
In one month
Apr 4 - Apr 6
In two months
May 2 - May 4

Compare 42 Cottages in Chilmark with updated reviews, rates, and availability.

Family-friendly Tisbury Escape - Walk to Town
Interior

Family-friendly Tisbury Escape - Walk to Town

3.0 star property
Family-friendly Tisbury Escape - Walk to Town
Charming Cape Cod Home w/ Patio, 2 Mi to Beach!
House (3 Bedrooms) | Living area | TV, fireplace, books

Charming Cape Cod Home w/ Patio, 2 Mi to Beach!

3.0 star property
Charming Cape Cod Home w/ Patio, 2 Mi to Beach!
Ping-pong Table, Beach Access: North Falmouth Home
Interior

Ping-pong Table, Beach Access: North Falmouth Home

3.0 star property
Ping-pong Table, Beach Access: North Falmouth Home
2 Mi to South Cape Beach State Park: Home w/ Yard!
House (2 Bedrooms) | Interior

2 Mi to South Cape Beach State Park: Home w/ Yard!

3.0 star property
2 Mi to South Cape Beach State Park: Home w/ Yard!
Family-friendly Falmouth Home < 1 Mi to Beach!
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Family-friendly Falmouth Home < 1 Mi to Beach!

3.0 star property
Family-friendly Falmouth Home < 1 Mi to Beach!
Cozy Vineyard Haven Cottage < 1 Mi to Beach!
Microwave, oven, stovetop, cookware/dishes/utensils

Cozy Vineyard Haven Cottage < 1 Mi to Beach!

3.0 star property
Cozy Vineyard Haven Cottage < 1 Mi to Beach!
Vineyard Haven House - Easy Access to Beaches
TV

Vineyard Haven House - Easy Access to Beaches

3.0 star property
Vineyard Haven House - Easy Access to Beaches
Charming MV Cottage: Walk to Dtwn Oak Bluffs!
Outdoor dining

Charming MV Cottage: Walk to Dtwn Oak Bluffs!

3.0 star property
Charming MV Cottage: Walk to Dtwn Oak Bluffs!
Charming East Falmouth Home w/ Hot Tub!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, coffee/tea maker

Charming East Falmouth Home w/ Hot Tub!

3.0 star property
Charming East Falmouth Home w/ Hot Tub!
Mattapoisett Home on 7 Acres w/ Private Beach!
TV, books

Mattapoisett Home on 7 Acres w/ Private Beach!

3.0 star property
4.0 out of 10, (1)
"One bathroom was updated, only 3 of the bedrooms had a/c. Sunken living room and 1st floor br had ants and bugs crawling around. All the prongs I saw (other than the bathroom) were 2 prong outlets, no light switches in bedrooms. The whole house smelled like mold and mildew. I had to get 2 air purifiers due to smell. We left 2 days early. Just wasn’t enjoyable. Good news - great private property and very close to beach. Owner did respond quickly to initial queries."
Mattapoisett Home on 7 Acres w/ Private Beach!
3 Mi to Beach & Town: Martha's Vineyard Home
Terrace/patio

3 Mi to Beach & Town: Martha's Vineyard Home

3.0 star property
3 Mi to Beach & Town: Martha's Vineyard Home
East Falmouth Home w/ Game Room - 2 Mi to Beach!
TV

East Falmouth Home w/ Game Room - 2 Mi to Beach!

3.0 star property
East Falmouth Home w/ Game Room - 2 Mi to Beach!
Remodeled East Falmouth Home - Close to Beaches!
TV, table tennis, books

Remodeled East Falmouth Home - Close to Beaches!

3.0 star property
Remodeled East Falmouth Home - Close to Beaches!
Cape Cod Cottage w/ Deck, Grill, & Games!
Interior

Cape Cod Cottage w/ Deck, Grill, & Games!

3.0 star property
Cape Cod Cottage w/ Deck, Grill, & Games!
Falmouth Retreat w/ Sunroom - Walk to Beaches
Interior

Falmouth Retreat w/ Sunroom - Walk to Beaches

3.0 star property
Falmouth Retreat w/ Sunroom - Walk to Beaches
Spacious East Falmouth House - Walk to Great Pond!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Spacious East Falmouth House - Walk to Great Pond!

3.0 star property
Spacious East Falmouth House - Walk to Great Pond!
Spacious Waterfront Falmouth Home on Jenkins Pond!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Spacious Waterfront Falmouth Home on Jenkins Pond!

3.0 star property
Spacious Waterfront Falmouth Home on Jenkins Pond!
Peaceful Chilmark Farmhouse by Menemsha Beach
Snorkeling

Peaceful Chilmark Farmhouse by Menemsha Beach

3.0 star property
Peaceful Chilmark Farmhouse by Menemsha Beach
Mashpee Home w/ Beach Gear & Bbq: 2 Mi to Shore
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Mashpee Home w/ Beach Gear & Bbq: 2 Mi to Shore

3.0 star property
Mashpee Home w/ Beach Gear & Bbq: 2 Mi to Shore
Traditional Martha's Vineyard Home w/ Porch & Yard
Exterior

Traditional Martha's Vineyard Home w/ Porch & Yard

3.0 star property
Traditional Martha's Vineyard Home w/ Porch & Yard
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

The Club at New Seabury
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (313)
"accommodation was good but cleanliness could have been better. Not bad but some areas needed more attention. Good restaurant and bar service on Thursday. No restaurant available on Saturday."
The price is NT$5,287
NT$6,050 total
includes taxes & fees
Mar 12 - Mar 13
The Club at New Seabury
InnSeason Resorts Captain's Quarters
On the beach, white sand

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (160)
"The rooms where very clean and well taken care of."
The price is NT$3,865
NT$4,423 total
includes taxes & fees
Mar 5 - Mar 6
InnSeason Resorts Captain's Quarters
Sea Mist Resort
Exterior

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (115)
"we had a great stay with our grandchildren"
Sea Mist Resort
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

How much do cottages in Chilmark cost?
You can expect to pay between and per night for cottages in Chilmark. No matter your budget, a fantastic stay is just a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Chilmark with Expedia?
We think that vacations should be a walk in the park, so if you’re searching for cottages in Chilmark at an affordable price, Expedia can help. Keep the budget under control and pick a low-cost option far away from the city rush, or book a 5-star cottage to treat your loved ones.
How can I find cheap cottages in Chilmark?
With Expedia’s filter tool, sourcing cheap cottages in Chilmark is a snap. To find properties that’ll make your wallet smile, narrow down your search by star rating, budget and amenities.
What is there to do in Chilmark near my cottage?
Whatever you’re interested in, Chilmark has lots of things to keep you entertained. Menemsha Beach, Lucy Vincent Beach and The Yard are on many visitors’ trip plans. Don’t forget about Chilmark Chocolates, Waskosim’s Rock Reservation and Fulling Mill Brook Preserve either. With Expedia’s hotel deals in Chilmark, you’ll be able to discover more neat attractions like these with the money you save.