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

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

Oak Bluffs

Karen M.

HK$6,659 total

includes taxes & fees

17 Sept - 18 Sept

2. Charming Vacation Home in Oak Bluffs.

Oak Bluffs

HK$6,501 total

includes taxes & fees

4 Oct - 5 Oct

3. Cozy Cottage walk to Menauhant Beach

East Falmouth

Grace P.

HK$6,039 total

includes taxes & fees

28 Sept - 29 Sept

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

Katama

Susan M.

HK$10,944 total

includes taxes & fees

17 Sept - 18 Sept

5. Walk to Beach! Oak Bluffs Home & Studio

Oak Bluffs

HK$7,325 total

includes taxes & fees

25 Sept - 26 Sept

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

Seconsett Island

Kian S.

HK$3,466 total

includes taxes & fees

1 Oct - 2 Oct

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

Oak Bluffs

Sherri R.

HK$10,243 total

includes taxes & fees

1 Oct - 2 Oct

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

Falmouth

HK$8,116 total

includes taxes & fees

20 Sept - 21 Sept

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$7,369 total

includes taxes & fees

17 Sept - 18 Sept

10. Stunning 4-bedroom Private Fresh Water Beach Front

East Falmouth

Kathryn C.

HK$5,409 total

includes taxes & fees

21 Sept - 22 Sept

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

Falmouth

Stephanie B.

HK$5,081 total

includes taxes & fees

6 Oct - 7 Oct

12. The Seashell Cove - Martha's Vineyard

Katama

Eric C.

HK$10,007 total

includes taxes & fees

14 Oct - 15 Oct

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

Oak Bluffs

Priyanka D.

HK$16,798 total

includes taxes & fees

19 Sept - 20 Sept

5 bedrooms, iron/ironing board, WiFi, bed sheets

14. West Falmouth Family Retreat Near Chapoquoit Beach

Falmouth

HK$6,675 total

includes taxes & fees

14 Oct - 15 Oct

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

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

East Falmouth

HK$7,593 total

includes taxes & fees

29 Sept - 30 Sept

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

Falmouth

Lynn S.

HK$6,419 total

includes taxes & fees

17 Sept - 18 Sept

18. Haven in Hatchville - newly renovated home

East Falmouth

HK$7,755 total

includes taxes & fees

28 Sept - 29 Sept

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

Falmouth

andrea m.

HK$7,040 total

includes taxes & fees

24 Sept - 25 Sept

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

Mansion House Inn And Spa

10/10 Excellent

"Great location, very clean, excellent staff. Entering the property from the parking area was a bit challenging."

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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