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!

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$2,470
HK$6,658 total
includes taxes & fees
17 Sept - 18 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

2. 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$1,584
HK$6,110 total
includes taxes & fees
22 Sept - 23 Sept
Cozy Cottage walk to Menauhant Beach

3. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is HK$2,816
HK$6,098 total
includes taxes & fees
27 Sept - 28 Sept
Charming Vacation Home in Oak Bluffs.

4. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is HK$3,051
HK$7,323 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$4,156
HK$11,458 total
includes taxes & fees
16 Sept - 17 Sept
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, (43 reviews)
"Great stay!"
United States
Kian S.
The price is HK$1,372
HK$3,572 total
includes taxes & fees
1 Oct - 2 Oct
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

7. < 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$3,427
HK$7,367 total
includes taxes & fees
24 Sept - 25 Sept
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

8. 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$3,121
HK$10,722 total
includes taxes & fees
1 Oct - 2 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

9. Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
East Falmouth
10.0 out of 10, Exceptional, (49 reviews)
"A perfect location and awesome for a family vacation"
United States
joyce b.
The price is HK$1,176
HK$7,674 total
includes taxes & fees
12 Oct - 13 Oct
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

10. 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$2,364
HK$5,408 total
includes taxes & fees
21 Sept - 22 Sept
Stunning 4-bedroom Private Fresh Water Beach Front

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$10,587
HK$17,511 total
includes taxes & fees
19 Sept - 20 Sept
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

12. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is HK$1,827
HK$6,560 total
includes taxes & fees
7 Oct - 8 Oct
West Falmouth Family Retreat Near Chapoquoit Beach

13. 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$3,960 total
includes taxes & fees
30 Sept - 1 Oct
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

14. 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, (221 reviews)
"Great location "
United States
Stephanie B.
The price is HK$1,804
HK$4,613 total
includes taxes & fees
14 Oct - 15 Oct
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

15. Haven in Hatchville - newly renovated home

Haven in Hatchville - newly renovated home
East Falmouth
The price is HK$2,064
HK$7,807 total
includes taxes & fees
22 Sept - 23 Sept
Haven in Hatchville - newly renovated home

16. 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 HK$2,753
HK$6,418 total
includes taxes & fees
14 Sept - 15 Sept
Spring Escape in Hatchville – Sleeps 6 + Dogs!

17. 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$1,524
HK$7,047 total
includes taxes & fees
24 Sept - 25 Sept
Nice home near Mashpee Commons and all Falmouth has to offer

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

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is HK$1,795
HK$5,053 total
includes taxes & fees
14 Sept - 15 Sept
Backyard Retreat / 5 Min > Beach & Main St

19. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.6 out of 10, (11 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$2,478
HK$5,606 total
includes taxes & fees
14 Sept - 15 Sept
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

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$3,150
HK$9,237 total
includes taxes & fees
20 Sept - 21 Sept
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
434
Accommodation
867 Vacation Homes
Lowest Price
HK$3,960
Highest Price
HK$17,511

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