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

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Our top choices for Chilmark holiday homes

1. Vineyard Luxury "Yurt"

Vineyard Luxury "Yurt"
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"The yurt was clean and nice and served all of our needs."
United States
David C.
The price is HK$2,016
HK$3,777 total
includes taxes & fees
11 Nov - 12 Nov
Vineyard Luxury "Yurt"

2. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"This place was just what we needed! Would definitely stay again. Cozy and feels very homey! Thanks!"
United States
Chris S.
The price is HK$2,111
HK$5,320 total
includes taxes & fees
11 Nov - 12 Nov
Oak Bluffs 4BR • 5 Min Drive to Downtown

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

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is HK$1,220
HK$4,474 total
includes taxes & fees
3 Nov - 4 Nov
Backyard Retreat / 5 Min > Beach & Main St

4. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is HK$2,440
HK$6,441 total
includes taxes & fees
3 Nov - 4 Nov
Walk to Beach! Oak Bluffs Home & Studio

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

New 4 BR house near center and beaches with bikes
Katama
9.8 out of 10, Exceptional, (13 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is HK$4,691
HK$13,074 total
includes taxes & fees
15 Nov - 16 Nov
New 4 BR house near center and beaches with bikes

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

Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
Seconsett Island
10.0 out of 10, Exceptional, (45 reviews)
"Great place with kayaks and paddle boards, beach, close to Mashpee Commons. Host was great and place was clean and quaint."
United States
Michele M.
The price is HK$1,236
HK$3,344 total
includes taxes & fees
3 Nov - 4 Nov
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

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

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (227 reviews)
"Great location "
United States
Stephanie B.
The price is HK$1,412
HK$4,103 total
includes taxes & fees
3 Nov - 4 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

8. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is HK$2,329
HK$6,764 total
includes taxes & fees
3 Nov - 4 Nov
West Falmouth Family Retreat Near Chapoquoit Beach

9. 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, (40 reviews)
"Beautiful and relaxing location."
United States
Lauren F.
The price is HK$1,765
HK$3,759 total
includes taxes & fees
30 Nov - 1 Dec
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

10. 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, (3 reviews)
"Brenda and Derek were amazing hosts. They have a beautifully landscaped property with all the amenities needed for a relaxing family vacation. They are super responsive and take a lot of pride in giving their guests a top-notch experience. We will definitely consider staying at their properties again."
United States
Lamar A.
The price is HK$15,690
HK$23,773 total
includes taxes & fees
30 Nov - 1 Dec
Beautiful Estate with salt water pool & pond with kayaks

11. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (31 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is HK$5,648
HK$8,754 total
includes taxes & fees
3 Nov - 4 Nov
The Seashell Cove - Martha's Vineyard

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

Nice home near Mashpee Commons and all Falmouth has to offer
Falmouth
6.0 out of 10, (3 reviews)
"Quiet location"
United States
andrea m.
The price is HK$1,984
HK$7,256 total
includes taxes & fees
3 Nov - 4 Nov
Nice home near Mashpee Commons and all Falmouth has to offer

13. Stunning 4-bedroom Private Fresh Water Beach Front

Stunning 4-bedroom Private Fresh Water Beach Front
East Falmouth
10.0 out of 10, Exceptional, (45 reviews)
"Great trip and time on the lake. Highly recommend this property for families looking for ease and convenience."
United States
Kathryn C.
The price is HK$2,153
HK$5,356 total
includes taxes & fees
3 Nov - 4 Nov
Stunning 4-bedroom Private Fresh Water Beach Front

14. < 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
Oak Bluffs
7.4 out of 10, Good, (3 reviews)
"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...
United States
Kate K.
The price is HK$3,428
HK$7,001 total
includes taxes & fees
3 Nov - 4 Nov
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

15. 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, (19 reviews)
"Jessica was absolutely amazing and so was the house! We stayed here for our family vacation and it was perfect. 5 stars all around!"
United States
Kelsey B.
The price is HK$2,581
HK$6,455 total
includes taxes & fees
1 Dec - 2 Dec
Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

16. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
7.0 out of 10, Good, (12 reviews)
"Loved this spot. Perfect central island location. Fantastic owner with an incredible response time. Would recommend this property to all5 stars"
United States
Eli R.
The price is HK$2,063
HK$4,828 total
includes taxes & fees
3 Nov - 4 Nov
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

17. Beautiful Home in Falmouth Village

Beautiful Home in Falmouth Village
Falmouth
10.0 out of 10, Exceptional, (17 reviews)
"We had a family reunion and 75 Locust Street was the central hub of the four night stay. The house is beautiful, clean and we had family from all over stay there. We'd go back in a heartbeat. Easy access to downtown and the hosts were communicative and informative."
United States
Melissa L.
The price is HK$3,495
HK$8,705 total
includes taxes & fees
3 Nov - 4 Nov
Beautiful Home in Falmouth Village

18. Cape Cod Escape at Casa de Leo!

Cape Cod Escape at Casa de Leo!
Falmouth
8.0 out of 10, Very good, (1 review)
"The host was very accommodating. With that said, he definitely needs to change cleaning companies. There were various issues. The sheets were sandy; the master didn’t have a flat sheet, just a dirty mattress cover, the floors are not being cleaned-extremely dusty! The tubs had hair. There were cigarettes left on the outside table along with dried food from the last renters. This is the fault of lazy cleaners. Cameron sent the cleaners back out but they were rude to my family (because they were...
United States
Shellie K.
The price is HK$5,327
HK$11,770 total
includes taxes & fees
4 Nov - 5 Nov
Cape Cod Escape at Casa de Leo!

19. Coastal chic meets French Provençal in this newly renovated oceanfront home.

Coastal chic meets French Provençal in this newly renovated oceanfront home.
East Falmouth
10.0 out of 10, Exceptional, (101 reviews)
"Great views, beautiful setting . Scott was so attentive and easy to work with. We had a great time!"
United States
Ben L.
The price is HK$3,522
HK$8,619 total
includes taxes & fees
19 Nov - 20 Nov
Coastal chic meets French Provençal in this newly renovated oceanfront home.

20. 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, (54 reviews)
"We had the best week at 67 Tide Run! The property is gorgeous. We enjoyed kayaking and fishing from the dock. It was plenty big enough for our family of 10. We are going to miss the views. It’s perfect! You cannot go wrong booking Jamie’s home."
United States
cindy w.
The price is HK$4,315
HK$9,185 total
includes taxes & fees
6 Nov - 7 Nov
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
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
560
Accommodation
867 Vacation Homes
Lowest Price
HK$3,344
Highest Price
HK$23,773

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