Chilmark Vacation Home Rentals from CA $656: Search Top Private Vacation Homes for Rent

A dock with boats, a small wooden structure, and a forested shoreline.

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Our top choices for Chilmark vacation homes

A backyard with a seating area, a white fence, and a variety of plants.

1. Delightful 3-bedroom house with AC in Oak Bluffs

Oak Bluffs

CA $1,639 total

includes taxes & fees

Oct 30 - Oct 31

A spacious living area with a high ceiling, a dining table, and a kitchen area.

2. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Oak Bluffs

Karen M.

CA $1,537 total

includes taxes & fees

Oct 14 - Oct 15

A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

3. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs

Chris S.

CA $1,089 total

includes taxes & fees

Nov 11 - Nov 12

A bedroom with a bed, two windows with curtains, a door, a bedside table with a lamp, and a picture on the wall.

4. West Falmouth Family Retreat Near Chapoquoit Beach

Falmouth

CA $1,103 total

includes taxes & fees

Oct 13 - Oct 14

A room with a white dresser, a lamp, a window with blinds, and a view of a deck and houses outside.

5. Backyard Retreat / 5 Min > Beach & Main St

Fairhaven

CA $867 total

includes taxes & fees

Oct 13 - Oct 14

A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

6. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Oak Bluffs

Sherri R.

CA $1,944 total

includes taxes & fees

Oct 13 - Oct 14

A circular stone patio with Adirondack chairs and a small table in a forested area.

7. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

Oak Bluffs

Eli R.

CA $1,019 total

includes taxes & fees

Oct 13 - Oct 14

A boat docked at a concrete pier with a sandy shore in the background.

8. Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

Seconsett Island

Kian S.

CA $656 total

includes taxes & fees

Oct 18 - Oct 19

A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

9. Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Falmouth

Stephanie B.

CA $738 total

includes taxes & fees

Nov 1 - Nov 2

A residential area with a well-maintained lawn, a stone retaining wall, and a two-story house with a blue door.

10. New 4 BR house near center and beaches with bikes

Katama

Susan M.

CA $2,371 total

includes taxes & fees

Oct 13 - Oct 14

A modern interior with a wooden staircase, a kitchen area, and a living space with a sofa and coffee table.

11. MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Oak Bluffs

CA $3,183 total

includes taxes & fees

Oct 13 - Oct 14

A deck with a fire pit, outdoor seating, and a blue umbrella.

12. Cozy Cottage walk to Menauhant Beach

East Falmouth

Grace P.

A two-story house with a stone facade, a covered patio, and a well-maintained garden.

13. Beautiful Estate with salt water pool & pond with kayaks

Oak Bluffs

Lamar A.

CA $5,427 total

includes taxes & fees

Oct 13 - Oct 14

A wooden deck overlooking a calm lake with trees and houses in the background.

14. Stunning 4-bedroom Private Fresh Water Beach Front

East Falmouth

Kathryn C.

CA $995 total

includes taxes & fees

Oct 13 - Oct 14

A modern kitchen with white cabinets, stainless steel appliances, and a wooden dining table.

15. Haven in Hatchville - newly renovated home

East Falmouth

CA $1,529 total

includes taxes & fees

Oct 13 - Oct 14

A living room with a sectional sofa, a coffee table, a TV, and a fireplace.

16. Nice home near Mashpee Commons and all Falmouth has to offer

Falmouth

andrea m.

CA $1,374 total

includes taxes & fees

Oct 13 - Oct 14

A water park with a large central pool, multiple slides, and a variety of play structures.

17. Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Fairhaven

Jainessa

CA $825 total

includes taxes & fees

Oct 31 - Nov 1

A spacious living room with a wooden staircase, a fireplace, and a leather sofa.

18. < 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

Oak Bluffs

"House was neat architectural wise and family history of home ownership was very cool. However, listing noted there was a washer/dryer and there was not. House also noted that there was a fire pit and it was rusted through. Screen door handles were broken, windows need repair, and house has animals living in the downstairs bathroom wall. House needs updates to charge what was being charged a night. In addition, there was a Nor’easter that hit the island and we attempted to contact the host to let...

Kate K.

CA $1,339 total

includes taxes & fees

Oct 13 - Oct 14