Chilmark Vacation Rentals

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Vacation Rentals in Chilmark

Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

Mashpee MA

With a stay at this vacation home in Mashpee (New Seabury), you'll be a 2-minute drive from South Cape Beach and 6 minutes from Popponesset Beach.

.5 mile Walk to Edgartown Center. Inside the triangle. 3 mi to South Beach.

Edgartown MA

With a stay at this vacation home, you'll be centrally located in Edgartown, within a 10-minute drive of Inkwell Beach and Oak Bluffs Harbor.

Coastal chic meets French Provençal in this newly renovated oceanfront home.

East Falmouth MA

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

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.

Washer

Dryer

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.

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

Oak Bluffs MA

When you stay at this vacation home in Oak Bluffs, you'll be by the sea, within a 10-minute drive of Oak Bluffs Harbor and Inkwell Beach.

Beautiful 3 bedroom house by the ocean

Fairhaven MA

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

Quaint, ranch style home in Oak Bluffs with central air

Oak Bluffs MA

When you stay at this vacation home in Oak Bluffs, you'll be by the sea, a 3-minute drive from Oak Bluffs Harbor and 8 minutes from Inkwell Beach.

Your Summer Home - Close to Beach, Shops, Cafes, & Ferry! 50+ ⭐️⭐️⭐️⭐️⭐️ Reviews

Vineyard Haven MA

With a stay at this vacation home, you'll be centrally located in Vineyard Haven, within a 15-minute drive of Oak Bluffs Harbor and Inkwell Beach.

Charming 2-bedroom house on Chappy with pool, Tennis, pickleball, WiFi and AC

Edgartown MA

With a stay at this vacation home in Edgartown, you'll be within a 10-minute drive of Mytoi Garden and Chappaquidick Dike Bridge.

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 Oak Bluffs Harbor.

Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts

Oak Bluffs MA

With a stay at this vacation home in Oak Bluffs, you'll be within a 10-minute drive of Oak Bluffs Harbor and Inkwell Beach.

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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.