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Check prices for these dates

Next weekend
Apr 25 - Apr 27
In two weeks
May 2 - May 4
In one month
May 16 - May 18
In two months
Jun 13 - Jun 15

Compare 49 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
10.0 out of 10, Exceptional, (1)
"Perfect. Great."
Family-friendly Tisbury Escape - Walk to Town
Charming Cape Cod Home w/ Patio, 2 Mi to Beach!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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

3.0 star property
Charming Cape Cod Home w/ Patio, 2 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!
2 Mi to South Cape Beach State Park: Home w/ Yard!
Property grounds

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) | Interior

Family-friendly Falmouth Home < 1 Mi to Beach!

3.0 star property
Family-friendly Falmouth Home < 1 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
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
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!
Charming East Falmouth Home w/ Hot Tub!
Terrace/patio

Charming East Falmouth Home w/ Hot Tub!

3.0 star property
Charming East Falmouth Home w/ Hot Tub!
Charming MV Cottage: Walk to Dtwn Oak Bluffs!
Exterior

Charming MV Cottage: Walk to Dtwn Oak Bluffs!

3.0 star property
Charming MV Cottage: Walk to Dtwn Oak Bluffs!
Modern Mashpee Home w/ Porch: Beach & Lake Access!
Interior

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

3.0 star property
Modern Mashpee Home w/ Porch: Beach & Lake Access!
Martha's Vineyard Home: Walk to Oak Bluffs Beach!
Microwave, oven, stovetop, cookware/dishes/utensils

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

3.0 star property
Martha's Vineyard Home: Walk to Oak Bluffs Beach!
Remodeled East Falmouth Home - Close to Beaches!
House (3 Bedrooms) | Interior

Remodeled East Falmouth Home - Close to Beaches!

3.0 star property
Remodeled East Falmouth Home - Close to Beaches!
Oak Bluffs 3-Bed Cottage, Walk to Town
Family Cottage | Living area | Flat-screen TV, fireplace

Oak Bluffs 3-Bed Cottage, Walk to Town

3.5 star property
Oak Bluffs 3-Bed Cottage, Walk to Town
Cape Cod Cottage w/ Deck, Grill, & Games!
Exterior

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

3.0 star property
Cape Cod Cottage w/ Deck, Grill, & Games!
East Falmouth Home w/ Game Room - 2 Mi to Beach!
Interior

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

3.0 star property
East Falmouth Home w/ Game Room - 2 Mi to 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
Beautiful Mashpee Vacation Rental w/ Private Pool!
Interior

Beautiful Mashpee Vacation Rental w/ Private Pool!

3.0 star property
Beautiful Mashpee Vacation Rental w/ Private Pool!
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!
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

InnSeason Resorts Captain's Quarters
Seasonal outdoor pool

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (165)
"Beautiful property. Lots of amenities. Excellent appliances. Great location. View of the ocean & pool. Peaceful."
The price is NT$4,842
NT$5,541 total
includes taxes & fees
Apr 17 - Apr 18
InnSeason Resorts Captain's Quarters
The Club at New Seabury
Private beach nearby, beach bar

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (315)
"Excellent after hours check-in process. Clean and comfy townhouse. Wonderful amenities. "
The price is NT$6,132
NT$7,018 total
includes taxes & fees
Apr 21 - Apr 22
The Club at New Seabury
Sea Mist Resort
Indoor pool, outdoor pool, sun loungers

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (117)
"Cute and relaxing, just enough on property to do if you have little ones or want to relax with some options!"
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.