Chilmark Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Chilmark

Luxury Loft Historic Center Oak Bluffs

Oak Bluffs MA

A stay at this vacation home places you in the heart of Oak Bluffs, within a 10-minute walk of Inkwell Beach and Circuit Avenue.

Kitchen

Washer

Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

Falmouth MA

A stay at this vacation home places you in the heart of Falmouth, within a 15-minute walk of Cape Cod Beaches and Main Street.

Kitchen

Washer

2-bedroom ocean-front Fairhaven home overlooking Buzzards Bay

Fairhaven MA

Located in Fairhaven, this vacation home is by the ocean, within a 15-minute drive of West Island and Unitarian Memorial Church.

Kitchen

Washer

Cozy getaway in a central location w/ a full kitchen & furnished deck

Oak Bluffs MA

With a stay at this vacation home in Oak Bluffs, you'll be by the sea, within a 10-minute drive of Inkwell Beach and Featherstone Center for the Arts.

Kitchen

Outdoor Space

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Falmouth MA

With a stay at this vacation home in East Falmouth, you'll be within a 5-minute drive of Cape Cod Beaches and Waquoit Bay National Estuarine Research Reserve.

Kitchen

Washer

Stunning Ocean & Martha’s Vineyard Views from this Falmouth Heights Gem

Falmouth MA

With a stay at this vacation home in Falmouth (Falmouth Heights), you'll be a 5-minute walk from Cape Cod Beaches and 8 minutes by foot from Falmouth Heights Beach.

Kitchen

Washer

Quaint home across from bike paths with large furnished deck, grill, & W/D

West Tisbury MA

When you stay at this vacation home in Vineyard Haven, you'll be by the sea, within a 5-minute drive of The Grey Barn and Farm and Polly Hill Arboretum.

Kitchen

Washer

Beach front! fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

East Falmouth MA

With a stay at this vacation home in East Falmouth, you'll be on the beach, within a 15-minute drive of Cape Cod Beaches and Cape Cod Winery.

Hot Tub

Kitchen

4-bedroom house in lovely Edgartown..Centrally located

Edgartown MA

With a stay at this vacation home in Edgartown, you'll be within a 10-minute drive of Inkwell Beach and Gus Ben David's World of Reptiles and Birds Park.

Kitchen

Washer

New Seabury FULLY RENOVATED beach house. Great location, pet friendly!

Mashpee MA

With a stay at this vacation home in Mashpee (New Seabury), you'll be within a 10-minute drive of Cape Cod Children's Museum and South Cape Beach State Park.

Kitchen

Washer

Salt Pond Cottage - Private Beach Access

Falmouth MA

With a stay at this vacation home in East Falmouth, you'll be within a 10-minute drive of Cape Cod Beaches and Cape Cod Winery.

Kitchen

Washer

Large New Seabury Home with Heated Pool and Hot Tub

Mashpee MA

With a stay at this vacation home in Mashpee (New Seabury), you'll be within a 15-minute drive of Cape Cod Beaches and South Cape Beach State Park.

Pool

Hot Tub

Don't see what you're looking for?

See all available properties in Chilmark

View all properties

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.