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

Holiday Homes in Chilmark

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Our top choices for Chilmark holiday homes

1. serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
West Tisbury
The price is AU$1,069
includes taxes & fees
14 Sept - 15 Sept
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

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 AU$1,158
includes taxes & fees
11 Sept - 12 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

3. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is AU$1,298
includes taxes & fees
13 Sept - 14 Sept
Walk to Beach! Oak Bluffs Home & Studio

4. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is AU$1,117
includes taxes & fees
27 Sept - 28 Sept
Charming Vacation Home in Oak Bluffs.

5. 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 AU$1,051
includes taxes & fees
8 Sept - 9 Sept
Cozy Cottage walk to Menauhant Beach

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

New 4 BR house near center and beaches with bikes
Katama
9.6 out of 10, Exceptional, (10 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is AU$1,981
includes taxes & fees
7 Sept - 8 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
9.8 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 AU$3,056
includes taxes & fees
8 Sept - 9 Sept
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

8. < 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 AU$1,087
includes taxes & fees
10 Sept - 11 Sept
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

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)
"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 AU$678
includes taxes & fees
30 Sept - 1 Oct
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

10. 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, (8 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is AU$1,822
includes taxes & fees
1 Oct - 2 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

11. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.6 out of 10, Exceptional, (30 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is AU$1,571
includes taxes & fees
7 Sept - 8 Sept
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 AU$1,380
includes taxes & fees
15 Sept - 16 Sept
Nice home near Mashpee Commons and all Falmouth has to offer

13. 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 AU$1,001
includes taxes & fees
7 Sept - 8 Sept
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

14. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is AU$1,182
includes taxes & fees
1 Oct - 2 Oct
West Falmouth Family Retreat Near Chapoquoit Beach

15. Beautiful Home in Falmouth Village

Beautiful Home in Falmouth Village
Falmouth
10.0 out of 10, Exceptional, (15 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 AU$1,532
includes taxes & fees
16 Sept - 17 Sept
Beautiful Home in Falmouth Village

16. 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 AU$1,037
includes taxes & fees
30 Sept - 1 Oct
Stunning 4-bedroom Private Fresh Water Beach Front

17. 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 AU$5,067
includes taxes & fees
13 Sept - 14 Sept
Beautiful Estate with salt water pool & pond with kayaks

18. Haven in Hatchville - newly renovated home

Haven in Hatchville - newly renovated home
East Falmouth
The price is AU$1,407
includes taxes & fees
8 Sept - 9 Sept
Haven in Hatchville - newly renovated home

19. 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 AU$1,621
includes taxes & fees
15 Sept - 16 Sept
Recently renovated 3 bedroom

20. Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!

Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!
East Falmouth
9.8 out of 10, Exceptional, (76 reviews)
"We had a great stay. Host was very friendly and the house was clean and perfect location for our trip. Very quiet area and beautiful lake view."
United States
Devin R.
The price is AU$1,316
includes taxes & fees
7 Sept - 8 Sept
Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chilmark Hotel Reviews

Find out more about Chilmark

Chilmark Holiday Homes information

Number of reviews
218
Accommodation
878 Holiday Homes
Lowest Price
AU$678
Highest Price
AU$5,067

Explore a world of travel with Expedia