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

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Our top choices for Chilmark holiday homes

1. NEW Construction: a Love Letter to Martha's Vineyard

NEW Construction: a Love Letter to Martha's Vineyard
West Tisbury
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay at this home in West Tisbury. The house was exactly as described - comfortable, clean, well-appointed, and thoughtfully stocked with everything we needed. The location was perfect for exploring the island while still feeling peaceful and relaxing. Jack was incredibly responsive, helpful, and easy to communicate with throughout our stay. We truly felt at home and would gladly stay here again. Highly recommend!"
United States
Nini D.
The price is HK$9,882
HK$16,970 total
includes taxes & fees
3 Aug - 4 Aug
NEW Construction: a Love Letter to Martha's Vineyard

2. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is HK$3,019
HK$7,437 total
includes taxes & fees
31 Aug - 1 Sept
Walk to Beach! Oak Bluffs Home & Studio

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

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
9.6 out of 10, Exceptional, (35 reviews)
"We were looking for a weekend away from home, and we're lucky to find this place available. We got great recommendations for places to eat nearby, and were able to enjoy the area. We'd stay here again!"
United States
Zachary S.
The price is HK$1,843
HK$4,056 total
includes taxes & fees
3 Aug - 4 Aug
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

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 HK$1,608
HK$4,494 total
includes taxes & fees
2 Aug - 3 Aug
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

5. NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Tisbury
10.0 out of 10, Exceptional, (16 reviews)
"We had an amazing time at this beautiful home. Great, clean space to spend an evening visit with friends and family. Great location with easy access around the island. Would highly recommend! "
United States
Jennifer T.
The price is HK$6,235
HK$11,423 total
includes taxes & fees
17 Aug - 18 Aug
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

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, (7 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is HK$8,626
HK$17,160 total
includes taxes & fees
31 Aug - 1 Sept
New 4 BR house near center and beaches with bikes

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

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (10 reviews)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
United States
Swathanthra M.
The price is HK$21,176
HK$30,759 total
includes taxes & fees
3 Aug - 4 Aug
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (7 reviews)
"This house was perfect for our getaway. Rebecca, the host, was extremely responsive and helpful during our trip. The house was as advertised. It was clean, well equipped, and the location was perfect as well "
United States
Louis R.
The price is HK$12,353
HK$19,265 total
includes taxes & fees
2 Aug - 3 Aug
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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

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

10. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is HK$11,757
HK$17,294 total
includes taxes & fees
23 Aug - 24 Aug
Charming Vacation Home in Oak Bluffs.

11. Newly remodeled 4BR Cape Cod home | Minutes to Chapoquoit and Old Silver beaches & Shining Sea Bike Pathway | Sleeps 8

Newly remodeled 4BR Cape Cod home | Minutes to Chapoquoit and Old Silver beaches & Shining Sea Bike Pathway | Sleeps 8
Falmouth
10.0 out of 10, Exceptional, (2 reviews)
"Great host and property. Terrific location close to everything. Host really wanted to ensure things went well and communicated great. Thanks for a great stay!"
United States
Matthew B.
Newly remodeled 4BR Cape Cod home | Minutes to Chapoquoit and Old Silver beaches & Shining Sea Bike Pathway | Sleeps 8

12. Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
Falmouth
9.6 out of 10, Exceptional, (18 reviews)
"Really beautiful place with a lot of space and a very helpful host"
United States
Gokul K.
The price is HK$4,510
HK$9,488 total
includes taxes & fees
4 Aug - 5 Aug
Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

13. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (28 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is HK$7,842
HK$12,010 total
includes taxes & fees
21 Aug - 22 Aug
The Seashell Cove - Martha's Vineyard

14. 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, (6 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is HK$3,921
HK$11,738 total
includes taxes & fees
1 Sept - 2 Sept
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

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 HK$22,350
HK$32,026 total
includes taxes & fees
31 Aug - 1 Sept
Beautiful Estate with salt water pool & pond with kayaks

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

Spring Escape in Hatchville – Sleeps 6 + Dogs!
Falmouth
10.0 out of 10, Exceptional, (12 reviews)
"Enjoyed our stay. Everything was clean and well kept. "
United States
Lynn S.
Spring Escape in Hatchville – Sleeps 6 + Dogs!

17. 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
9.6 out of 10, Exceptional, (50 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 HK$5,882
HK$11,283 total
includes taxes & fees
29 Aug - 30 Aug
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

18. 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 HK$4,687
HK$11,471 total
includes taxes & fees
23 Aug - 24 Aug
Recently renovated 3 bedroom

19. World Cup Ocean retreat 40 minute drive from Boston Stadium - Gillette

World Cup Ocean retreat 40 minute drive from Boston Stadium - Gillette
Fairhaven
8.4 out of 10, Very good, (5 reviews)
"The home was beautiful and well equipped. Perfect location in a quiet new england neighborhood. My family enjoyed our stay!"
United States
lea m.
World Cup Ocean retreat 40 minute drive from Boston Stadium - Gillette

20. Haven in Hatchville - newly renovated home

Haven in Hatchville - newly renovated home
East Falmouth
The price is HK$3,735
HK$9,964 total
includes taxes & fees
2 Aug - 3 Aug
Haven in Hatchville - newly renovated home
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

Find out more about Chilmark

Chilmark Vacation Homes information

Number of reviews
165
Accommodation
930 Vacation Homes
Lowest Price
HK$4,056
Highest Price
HK$32,026

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