Chilmark Vacation Homes

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

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Our top choices for Chilmark holiday homes

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

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

Oak Bluffs

Karen M.

HK$6,658 total

includes taxes & fees

17 Sept - 18 Sept

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

2. Cozy Cottage walk to Menauhant Beach

East Falmouth

Grace P.

HK$6,110 total

includes taxes & fees

22 Sept - 23 Sept

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

3. Charming Vacation Home in Oak Bluffs.

Oak Bluffs

HK$6,098 total

includes taxes & fees

27 Sept - 28 Sept

An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

4. Walk to Beach! Oak Bluffs Home & Studio

Oak Bluffs

HK$7,323 total

includes taxes & fees

25 Sept - 26 Sept

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

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

Katama

Susan M.

HK$11,458 total

includes taxes & fees

16 Sept - 17 Sept

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

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

Seconsett Island

Kian S.

HK$3,572 total

includes taxes & fees

1 Oct - 2 Oct

A cozy living room with a wooden ceiling, a stone fireplace, a leather sofa, and a dining area with a table and chairs.

7. < 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.

HK$7,367 total

includes taxes & fees

24 Sept - 25 Sept

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

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

Oak Bluffs

Sherri R.

HK$10,722 total

includes taxes & fees

1 Oct - 2 Oct

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Top Chilmark Hotel Reviews

Vineyard Harbor Motel - Private Beach

10/10 Excellent

"Excellent customer service."

Falmouth Tides

8/10 Good

"The hotel was adorable and clean, the retro feel and free bikes were awesome just didn’t like my room on the end by the public pier it was noisy and the coffee truck (which had great coffee) was right outside my room so very little privacy in the morning. Absolutely stay here but just ask for rooms facing ocean!"

Harbor View Hotel

10/10 Excellent

"We had a fantastic week at the Harbor View. Staff were all excellent and helpful! Loved sitting on the veranda having coffee. Beds and room amenities were great. The only thing I would have been happier with is if there had been a separate baby pool for the youngest kids. I really enjoyed the pool but once lots of kids and babies started using it I was not interested and felt I was unable to enjoy it."

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