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$6,659 total

includes taxes & fees

17 Sept - 18 Sept

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

2. Charming Vacation Home in Oak Bluffs.

Oak Bluffs

HK$6,501 total

includes taxes & fees

4 Oct - 5 Oct

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

3. Cozy Cottage walk to Menauhant Beach

East Falmouth

Grace P.

HK$6,038 total

includes taxes & fees

28 Sept - 29 Sept

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

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

Katama

Susan M.

HK$10,943 total

includes taxes & fees

17 Sept - 18 Sept

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

5. Walk to Beach! Oak Bluffs Home & Studio

Oak Bluffs

HK$7,324 total

includes taxes & fees

25 Sept - 26 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$3,573 total

includes taxes & fees

6 Oct - 7 Oct

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

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

Oak Bluffs

Sherri R.

HK$10,242 total

includes taxes & fees

1 Oct - 2 Oct

A dining area with a table set for six, a chandelier, and large windows offering a view of the outdoors.

8. Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow

Falmouth

HK$8,115 total

includes taxes & fees

20 Sept - 21 Sept

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

9. < 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$7,368 total

includes taxes & fees

17 Sept - 18 Sept

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

10. Stunning 4-bedroom Private Fresh Water Beach Front

East Falmouth

Kathryn C.

HK$5,409 total

includes taxes & fees

21 Sept - 22 Sept

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

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

Falmouth

Stephanie B.

HK$5,081 total

includes taxes & fees

5 Oct - 6 Oct

A spacious living area with wooden beams, a dining table, and a sofa.

12. The Seashell Cove - Martha's Vineyard

Katama

Eric C.

HK$10,005 total

includes taxes & fees

14 Oct - 15 Oct

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

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

Oak Bluffs

Priyanka D.

HK$16,795 total

includes taxes & fees

19 Sept - 20 Sept

A bedroom with a bed, a wooden wardrobe, a fireplace, and a painting on the wall.

14. West Falmouth Family Retreat Near Chapoquoit Beach

Falmouth

HK$6,554 total

includes taxes & fees

14 Oct - 15 Oct

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

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

Fairhaven

Jainessa

HK$3,961 total

includes taxes & fees

30 Sept - 1 Oct

A spacious living room with a fireplace, two white sofas, a round coffee table, and a ceiling fan.

16. Welcome to your Cape Cod getaway! ONLY 1.5 miles to Menauhant Beach, this charmi

East Falmouth

HK$7,566 total

includes taxes & fees

28 Sept - 29 Sept

A two-story house with a dark roof, a front porch with outdoor seating, and a fire pit.

17. Spring Escape in Hatchville – Sleeps 6 + Dogs!

Falmouth

Lynn S.

HK$6,418 total

includes taxes & fees

17 Sept - 18 Sept

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

18. Haven in Hatchville - newly renovated home

East Falmouth

HK$7,981 total

includes taxes & fees

26 Sept - 27 Sept

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

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

Falmouth

andrea m.

HK$7,385 total

includes taxes & fees

19 Sept - 20 Sept

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

20. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

Oak Bluffs

Bethann N.

HK$5,607 total

includes taxes & fees

17 Sept - 18 Sept

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Top Chilmark Hotel Reviews

The Coonamessett

8/10 Good

"We really enjoyed our stay at the Coonamessett. We chose it because we were planning to visit Martha’s Vineyard, and its location was very convenient for getting to Woods Hole, where we caught our ferry. It was also a convenient distance from the ferry parking lot. Tish at the front desk was patient, welcoming, and extremely helpful throughout our stay. The property itself is charming, with beautiful grounds and a lovely, quaint feel. Our room had a cozy cottage feel and was quite spacious. The shower was clean and well stocked, and the two AC units worked very efficiently. We also appreciated having two TVs—one in the sitting area and one in the bedroom. There was plenty of closet space, which conveniently also housed the refrigerator and a collapsible luggage bench. A few things to note: there is no tea/coffee service or microwave in the room. We stayed in Room 8, which did not really have a water view, despite the property being advertised as having water views. Rooms 30 and possibly Room 1 appear to have better water views. Breakfast was fresh and delicious, although the offerings were the same throughout our stay. That’s fairly typical of hotels, but given that the Coonamessett is on the higher end, a little more variety would have been a nice touch. Overall, we had a very enjoyable stay. The charming setting, comfortable accommodations, convenient location, and wonderful hospitality made it a pleasant experience."

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!"

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