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 Cottage Charm, Walk to Beach, On Bike Path, Near Town

Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
Oak Bluffs
8.8 out of 10, Excellent, (9 reviews)
"Loved our little cottage"
United States
Linda T.
The price is HK$3,099
HK$6,958 total
includes taxes & fees
28 Sept - 29 Sept
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

2. 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 HK$3,883
HK$8,263 total
includes taxes & fees
5 Oct - 6 Oct
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
The price is HK$2,817
HK$6,599 total
includes taxes & fees
27 Sept - 28 Sept
Oak Bluffs 4BR • 5 Min Drive to Downtown

4. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is HK$3,052
HK$7,326 total
includes taxes & fees
25 Sept - 26 Sept
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, (11 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is HK$4,158
HK$11,462 total
includes taxes & fees
23 Sept - 24 Sept
New 4 BR house near center and beaches with bikes

6. Cozy Cottage walk to Menauhant Beach

Cozy Cottage walk to Menauhant Beach
East Falmouth
8.8 out of 10, Excellent, (8 reviews)
"It was a great weekend spot. Had everything we needed, nicely decorated, and in a great and private location"
United States
Grace P.
The price is HK$1,502
HK$5,984 total
includes taxes & fees
30 Sept - 1 Oct
Cozy Cottage walk to Menauhant Beach

7. 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)
"The most perfect spot! Our host and the neighbors were so nice and gave us great tips! Would definitely stay again"
United States
Jainessa
The price is HK$1,765
HK$3,935 total
includes taxes & fees
30 Sept - 1 Oct
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

8. 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, (43 reviews)
"Great stay!"
United States
Kian S.
The price is HK$1,373
HK$3,574 total
includes taxes & fees
1 Oct - 2 Oct
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

9. 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, (9 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is HK$3,122
HK$10,305 total
includes taxes & fees
1 Oct - 2 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

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

Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow
Falmouth
The price is HK$2,212
HK$8,116 total
includes taxes & fees
28 Sept - 29 Sept
Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow

11. 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)
"This was an excellent stay at a beautiful property in Oak Bluffs! Rebecca was a great host who provided clear instructions and helped answer questions in a timely manner. Rooms were spacious, most tastefully decorated and we had everything that we needed. I definitely recommend staying here to have an unparalleled experience of the Vineyard."
United States
Priyanka D.
The price is HK$10,591
HK$16,798 total
includes taxes & fees
23 Sept - 24 Sept
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

12. Stunning 4-bedroom Private Fresh Water Beach Front

Stunning 4-bedroom Private Fresh Water Beach Front
East Falmouth
10.0 out of 10, Exceptional, (42 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$2,365
HK$5,661 total
includes taxes & fees
23 Sept - 24 Sept
Stunning 4-bedroom Private Fresh Water Beach Front

13. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is HK$1,663
HK$6,322 total
includes taxes & fees
5 Oct - 6 Oct
West Falmouth Family Retreat Near Chapoquoit Beach

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$7,370 total
includes taxes & fees
25 Sept - 26 Sept
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

15. 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, (223 reviews)
"Great location "
United States
Stephanie B.
The price is HK$1,804
HK$4,588 total
includes taxes & fees
19 Oct - 20 Oct
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

16. 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$1,517
HK$7,022 total
includes taxes & fees
24 Sept - 25 Sept
Nice home near Mashpee Commons and all Falmouth has to offer

17. 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$5,884
HK$9,411 total
includes taxes & fees
18 Oct - 19 Oct
The Seashell Cove - Martha's Vineyard

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

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is HK$3,013
HK$6,757 total
includes taxes & fees
25 Sept - 26 Sept
Backyard Retreat / 5 Min > Beach & Main St

19. Haven in Hatchville - newly renovated home

Haven in Hatchville - newly renovated home
East Falmouth
The price is HK$2,005
HK$7,700 total
includes taxes & fees
30 Sept - 1 Oct
Haven in Hatchville - newly renovated home

20. 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$2,829
HK$8,567 total
includes taxes & fees
4 Oct - 5 Oct
Recently renovated 3 bedroom
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
403
Accommodation
867 Vacation Homes
Lowest Price
HK$3,935
Highest Price
HK$16,798

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