Photo by Wen C.

Search Cottages in Chilmark

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

Cape Cod Holiday Estates, a VRI resort
Indoor pool

Cape Cod Holiday Estates, a VRI resort

3.0 star property
9.6 out of 10, Exceptional, (120)
"Nice & clean. The only complaint Would be that the pool closed at 6 PM because they were low on staff so by the time we got back from sightseeing, we weren’t able to get in the pool"
Cape Cod Holiday Estates, a VRI resort
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!
Mashpee Home w/ Pool: 2 Mi to South Cape Beach!
House (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Mashpee Home w/ Pool: 2 Mi to South Cape Beach!

3.0 star property
Mashpee Home w/ Pool: 2 Mi to South Cape Beach!
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!
North Falmouth Home w/ Deck & Grill, Walk to Beach
Interior

North Falmouth Home w/ Deck & Grill, Walk to Beach

3.0 star property
North Falmouth Home w/ Deck & Grill, Walk to Beach
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/ Furnished Deck: Walk to Beach!
Beach towels

Cape Cod Cottage w/ Furnished Deck: Walk to Beach!

3.0 star property
Cape Cod Cottage w/ Furnished Deck: Walk 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!
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!
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, (304)
"will definitely go back again .. awesome place! "
The price is NT$4,804
NT$5,498 total
includes taxes & fees
Nov 24 - Nov 25
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."
InnSeason Resorts Captain's Quarters
Beachside Village Resort by VRI Americas
Beach nearby

Beachside Village Resort by VRI Americas

3.0 star property
9.2 out of 10, Wonderful, (86)
"A very nice place and wonderful location. You can see sunrise from this property. Staff are nice and friendly. A great experience!"
Beachside Village 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.