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

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Chilmark holiday homes

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

1. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is £689
includes taxes & fees
31 Aug - 1 Sept
Walk to Beach! Oak Bluffs Home & Studio
A two-story house with a brick chimney, a wooden deck, and a wooden fence.

2. serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
West Tisbury
The price is £566
includes taxes & fees
21 Sept - 22 Sept
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
A spacious living area with a high ceiling, a dining table, and a kitchen area.

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

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (9 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is £617
includes taxes & fees
11 Sept - 12 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A circular stone patio with Adirondack chairs and a small table in a forested area.

4. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.8 out of 10, (9 reviews)
"We had a perfect pre-/off-season stay with plenty of sleeping space. The location is fantastic—right between Vineyard Haven and Edgartown—making it easy to bike to both, plus there’s a beach across the street. The WiFi wasn’t working when we first arrived, but the owner was incredibly responsive and went above and beyond to fix it quickly. We’ll definitely be back!"
United States
Bethann N.
The price is £514
includes taxes & fees
31 Aug - 1 Sept
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

5. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is £704
includes taxes & fees
9 Sept - 10 Sept
Charming Vacation Home in Oak Bluffs.
A residential area with a well-maintained lawn, a stone retaining wall, and a two-story house with a blue door.

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

New 4 BR house near center and beaches with bikes
Katama
10.0 out of 10, Exceptional, (8 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is £1,050
includes taxes & fees
17 Sept - 18 Sept
New 4 BR house near center and beaches with bikes
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

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (8 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is £1,035
includes taxes & fees
7 Sept - 8 Sept
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A modern kitchen with white cabinets, a wooden dining table, and black chairs.

8. Walk to Town/Golf Club - Renovated Edgartown Home

Walk to Town/Golf Club - Renovated Edgartown Home
Edgartown
10.0 out of 10, Exceptional, (47 reviews)
"Great house in a great location—just a short, easy walk to downtown Edgartown"
United States
Steven M.
The price is £763
includes taxes & fees
2 Sept - 3 Sept
Walk to Town/Golf Club - Renovated Edgartown Home
A modern interior with a wooden staircase, a kitchen area, and a living space with a sofa and coffee table.

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

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.8 out of 10, Exceptional, (12 reviews)
"TLDR: House is nice,"
United States
Rachel
The price is £1,617
includes taxes & fees
8 Sept - 9 Sept
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
A wooden boardwalk leading to a beach with a lighthouse in the distance.

10. Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Falmouth
10.0 out of 10, Exceptional, (18 reviews)
"This is a beautiful and unique home with plenty of space and activities for the family. The photos were accurate and there was so much space for everyone to relax. We enjoyed our stay so much. "
United States
Lisa F.
The price is £572
includes taxes & fees
1 Sept - 2 Sept
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
A dining area with a view of the sea, a wooden table set with plates and glasses, and a coffee maker on the counter.

11. A View Fit for Royalty! Top Compliments: so clean! fab hot tub! best view!

A View Fit for Royalty! Top Compliments: so clean! fab hot tub! best view!
Tisbury
10.0 out of 10, Exceptional, (31 reviews)
"Host was very informative before the arrival, house was spotless and everything was easy to find "
United States
Anonymous traveller
The price is £1,082
includes taxes & fees
24 Aug - 25 Aug
A View Fit for Royalty! Top Compliments: so clean! fab hot tub! best view!
A spacious living area with wooden beams, a dining table, and a sofa.

12. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (29 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is £884
includes taxes & fees
6 Sept - 7 Sept
The Seashell Cove - Martha's Vineyard
A spacious kitchen with a large island, wooden flooring, and a dining area with chairs and a table.

13. Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops
Falmouth
10.0 out of 10, Exceptional, (17 reviews)
"Super neat and clean rental with plenty of space for our large group. We were only there one night but would definitely stay again if in the area!"
United States
Laura K.
The price is £678
includes taxes & fees
27 Aug - 28 Aug
Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops
A waterfront marina with boats docked, buildings with gabled roofs, and a clear blue sky.

14. Walk to downtown Edgartown in quiet neighborhood - Perfect Location!

Walk to downtown Edgartown in quiet neighborhood - Perfect Location!
Edgartown
10.0 out of 10, Exceptional, (5 reviews)
"One of the most well equipped vacation rentals I’ve stayed in. A simple, but well curated place. Thank you to our hosts!"
United States
Anonymous traveller
Walk to downtown Edgartown in quiet neighborhood - Perfect Location!
A two-story house with a stone facade, a covered patio, and a well-maintained garden.

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

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"I can’t say enough about this beautiful property. pictures don’t do any justice for this piece of heaven. The flowers were everywhere , it’s so apparent that the property owners take such pride in this beautiful property. The place was spotless when we walked in the door. We met the owners on arrival , they surprised us with a beautiful ballon to celebrate my 50th birthday. My family enjoyed the pool and the fun Tiki. The outdoor fireplace was inviting after the sun went down. I was a little...
United States
Miriam D.
The price is £2,757
includes taxes & fees
21 Sept - 22 Sept
Beautiful Estate with salt water pool & pond with kayaks
A modern kitchen with white cabinetry, a central island, skylights, and a view of the outdoors.

16. Recently renovated 3 bedroom

Recently renovated 3 bedroom
Falmouth
10.0 out of 10, Exceptional, (3 reviews)
"Stay was awesome! Perfect house for family gatherings "
United States
Diana P.
The price is £1,203
includes taxes & fees
23 Aug - 24 Aug
Recently renovated 3 bedroom
A spacious kitchen with a large island, wooden ceiling beams, and large windows.

17. Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!

Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!
East Falmouth
9.8 out of 10, Exceptional, (76 reviews)
"This property is 100% portrayed as in the photos. The view is exactly as beautiful as in the photos. My family and I enjoyed are stay in this gorgeous home. "
United States
Erin S.
The price is £764
includes taxes & fees
7 Sept - 8 Sept
Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!
A beach with clear water and a sandy shore.

18. New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
Little Neck Bay
9.8 out of 10, Exceptional, (51 reviews)
"A wonderful home in a fabulous setting. The home has spacious & well laid out with a variety of beautiful outdoor spaces. Comfortable, with sufficient spaces inside and out; everyone had space to enjoy the property. We stayed for a week and never tired of the outdoor views. Convenient to great shopping and excellent beaches."
United States
Eric S.
The price is £1,038
includes taxes & fees
29 Aug - 30 Aug
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
A beach with a clear sky and a crescent moon.

19. Adorable beach house! 3 min walk to beach!

Adorable beach house! 3 min walk to beach!
Popponesset
9.8 out of 10, Exceptional, (30 reviews)
"We had a great stay! The place was clean, well decorated, and close to the beach! The property managers were also very nice and easy to reach out to!"
United States
Allison W.
The price is £818
includes taxes & fees
21 Sept - 22 Sept
Adorable beach house! 3 min walk to beach!
A two-story house with a dark roof, a front porch with outdoor seating, and a fire pit.

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

Spring Escape in Hatchville – Sleeps 6 + Dogs!
Falmouth
10.0 out of 10, Exceptional, (13 reviews)
"Enjoyed our stay. Everything was clean and well kept. "
United States
Lynn S.
The price is £861
includes taxes & fees
23 Aug - 24 Aug
Spring Escape in Hatchville – Sleeps 6 + Dogs!
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.
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Top Chilmark Hotel Reviews

Red Horse Inn

Red Horse Inn

10/10 Excellent
"We had a great time!"
Jack 1-night trip
Posted 2 hours ago
Red Horse Inn

Find out more about Chilmark

Chilmark Holiday Homes information

Number of reviews
5,853
Accommodation
914 Holiday Homes
Lowest Price
£105
Highest Price
£323