Photo by Wen C.

Search Cottages in Chilmark

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Compare 43 Cottages in Chilmark with updated reviews, rates, and availability.

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!
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
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!
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!
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!
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
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!
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!
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!
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!
Beautiful Mashpee Vacation Rental w/ Private Pool!
Miscellaneous

Beautiful Mashpee Vacation Rental w/ Private Pool!

3.0 star property
Beautiful Mashpee Vacation Rental w/ Private Pool!
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
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
Oak Bluffs 3-Bed Cottage, Walk to Town
Family Cottage | Private kitchen | Fridge, microwave, oven, stovetop

Oak Bluffs 3-Bed Cottage, Walk to Town

3.5 star property
Oak Bluffs 3-Bed Cottage, Walk to Town
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
Sunny Beach House Getaway - Steps From Water!
Property grounds

Sunny Beach House Getaway - Steps From Water!

3.0 star property
Sunny Beach House Getaway - Steps From Water!
Updated Falmouth Family Home ~ 2 Mi to Beach!
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Updated Falmouth Family Home ~ 2 Mi to Beach!

3.0 star property
Updated Falmouth Family Home ~ 2 Mi to 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

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, (307)
"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$4,361
NT$4,991 total
includes taxes & fees
Dec 29 - Dec 30
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, (154)
"Very clean property. Beach just across street. Great views."
The price is NT$4,679
NT$5,355 total
includes taxes & fees
Jan 22 - 2025/1/23
InnSeason Resorts Captain's Quarters
Sea Mist Resort by VRI Americas
Exterior

Sea Mist Resort by VRI Americas

3.0 star property
8.8 out of 10, Excellent, (113)
"I liked having 2 floors as it was a townhouse. Having an equipped kitchen and 2 baths was really a nice convenience for a family of 4. Plenty of closet space and a slider out to the back area where you can sit outside and also use their grills. The place does need updating. It is clearly showing wear. The furnishings and amenities like the TV's are out of date. Regardless, we enjoyed our stay and would stay again. "
Sea Mist Resort by VRI Americas
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?
Prices for cottages in Chilmark range between and per night. No matter your budget, you’ll find the perfect place to soak up nature’s beauty. 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 a getaway should be simple, so if you’re searching for cottages in Chilmark at the perfect price, Expedia can help. Keep the budget in check and pick a thrifty option far away from the downtown buzz, or splurge on an upmarket cottage to spoil the ones you love most.
How can I find cheap cottages in Chilmark?
Expedia is here to help you track down cheap cottages in Chilmark. To find your dream stay in a matter of clicks, use the filter tool to refine your search by amenities, budget and star rating.
What is there to do in Chilmark near my cottage?
There are tons of wonderful things to see and do in Chilmark. Drop by renowned attractions like Menemsha Beach, Lucy Vincent Beach and The Yard. Waskosim’s Rock Reservation, Fulling Mill Brook Preserve and Chilmark Chocolates are other must-see’s.