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

Holiday Homes in Chilmark

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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 €728
includes taxes & fees
17 Sept - 18 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

2. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is €723
includes taxes & fees
4 Oct - 5 Oct
Charming Vacation Home in Oak Bluffs.

3. 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 €672
includes taxes & fees
28 Sept - 29 Sept
Cozy Cottage walk to Menauhant Beach

4. 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 €1,202
includes taxes & fees
17 Sept - 18 Sept
New 4 BR house near center and beaches with bikes

5. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is €792
includes taxes & fees
25 Sept - 26 Sept
Walk to Beach! Oak Bluffs Home & Studio

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 €380
includes taxes & fees
1 Oct - 2 Oct
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

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, (9 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is €1,124
includes taxes & fees
1 Oct - 2 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

8. 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 €900
includes taxes & fees
20 Sept - 21 Sept
Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow

9. < 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 €807
includes taxes & fees
17 Sept - 18 Sept
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

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 €632
includes taxes & fees
24 Sept - 25 Sept
Stunning 4-bedroom Private Fresh Water Beach Front

11. 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.
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

12. 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 €1,094
includes taxes & fees
14 Oct - 15 Oct
The Seashell Cove - Martha's Vineyard

13. 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 €1,900
includes taxes & fees
19 Sept - 20 Sept
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

14. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is €746
includes taxes & fees
7 Oct - 8 Oct
West Falmouth Family Retreat Near Chapoquoit Beach

15. 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 €438
includes taxes & fees
30 Sept - 1 Oct
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

16. Welcome to your Cape Cod getaway! ONLY 1.5 miles to Menauhant Beach, this charmi

Welcome to your Cape Cod getaway! ONLY 1.5 miles to Menauhant Beach, this charmi
East Falmouth
The price is €828
includes taxes & fees
28 Sept - 29 Sept
Welcome to your Cape Cod getaway! ONLY 1.5 miles to Menauhant Beach, this charmi

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

Spring Escape in Hatchville – Sleeps 6 + Dogs!
Falmouth
10.0 out of 10, Exceptional, (14 reviews)
"Enjoyed our stay. Everything was clean and well kept. "
United States
Lynn S.
The price is €703
includes taxes & fees
17 Sept - 18 Sept
Spring Escape in Hatchville – Sleeps 6 + Dogs!

18. Haven in Hatchville - newly renovated home

Haven in Hatchville - newly renovated home
East Falmouth
The price is €875
includes taxes & fees
28 Sept - 29 Sept
Haven in Hatchville - newly renovated home

19. 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 €794
includes taxes & fees
24 Sept - 25 Sept
Nice home near Mashpee Commons and all Falmouth has to offer

20. 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 €615
includes taxes & fees
17 Sept - 18 Sept
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
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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Chilmark Holiday Homes information

Number of reviews
7,409
Accommodation
878 Holiday Homes
Lowest Price
€102
Highest Price
€330