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Aug 22 - Aug 24
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Cottages in Chilmark

Beach & Lake Access: Home w/ Porch in Mashpee!
House (4 Bedrooms) | Interior

Beach & Lake Access: Home w/ Porch in Mashpee!

3.0 star property
Beach & Lake Access: Home w/ Porch in Mashpee!
Cozy Vineyard Haven Cottage < 1 Mi to Beach!
Cottage (1 Bedroom) | Interior

Cozy Vineyard Haven Cottage < 1 Mi to Beach!

3.0 star property
Cozy Vineyard Haven Cottage < 1 Mi to Beach!
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!
Easy Access to Beaches: Vineyard Haven House
House (3 Bedrooms) | Front of property

Easy Access to Beaches: Vineyard Haven House

3.0 star property
Easy Access to Beaches: Vineyard Haven House
Charming Cape Cod Home w/ Patio, 2 Mi to Beach!
House (3 Bedrooms) | Interior

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
House (5 Bedrooms) | Interior

Family-friendly Tisbury Escape - Walk to Town

3.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect. Great."
Family-friendly Tisbury Escape - Walk to Town
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!
< 1 Mi to Beach: Family-friendly Falmouth Home!
House (4 Bedrooms) | Interior

< 1 Mi to Beach: Family-friendly Falmouth Home!

3.0 star property
< 1 Mi to Beach: Family-friendly Falmouth Home!
Ping-pong Table, Beach Access: North Falmouth Home
House (4 Bedrooms) | 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!
Mattapoisett Home on 7 Acres w/ Private Beach!
Interior

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!
Cozy Edgartown Vacation Rental Near Beach!
Interior

Cozy Edgartown Vacation Rental Near Beach!

3.0 star property
Cozy Edgartown Vacation Rental Near Beach!
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
Steps to Inkwell Beach: Victorian Home!
House (6 Bedrooms) | Interior

Steps to Inkwell Beach: Victorian Home!

3.0 star property
Steps to Inkwell Beach: Victorian Home!
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
Near Beaches & Trails: Home in East Falmouth
House (4 Bedrooms) | Interior

Near Beaches & Trails: Home in East Falmouth

3.0 star property
Near Beaches & Trails: Home in East Falmouth
1/2 Mi to Beach: Stunning Home w/ Deck in Falmouth
Interior

1/2 Mi to Beach: Stunning Home w/ Deck in Falmouth

3.0 star property
1/2 Mi to Beach: Stunning Home w/ Deck in Falmouth
Bike to Private Beach: Cape Cod Escape w/ Sunroom
House (4 Bedrooms) | Interior

Bike to Private Beach: Cape Cod Escape w/ Sunroom

3.0 star property
Bike to Private Beach: Cape Cod Escape w/ Sunroom
Martha's Vineyard Home: Walk to Oak Bluffs Beach!
House (2 Bedrooms) | Interior

Martha's Vineyard Home: Walk to Oak Bluffs Beach!

3.0 star property
Martha's Vineyard Home: Walk to Oak Bluffs Beach!
Traditional Martha's Vineyard Home w/ Porch & Yard
Terrace/patio

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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Top Chilmark Hotel Reviews

Falmouth Tides

Falmouth Tides

10/10 Excellent
"So beautiful - what a place to stay with the beach directly on the doorstep! The room was lovely and clean and my children loved the record player and toasting marshmallows on the night time fire pits."
Hannah 2-night trip
Posted 2 days ago
Falmouth Tides

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.