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

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Our top choices for Chilmark vacation 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, (10 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is CA $704
CA $1,533 total
includes taxes & fees
Oct 15 - Oct 16
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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 CA $512
CA $1,199 total
includes taxes & fees
Oct 14 - Oct 15
Oak Bluffs 4BR • 5 Min Drive to Downtown

3. 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, (12 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is CA $754
CA $2,366 total
includes taxes & fees
Oct 15 - Oct 16
New 4 BR house near center and beaches with bikes

4. 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, (10 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is CA $567
CA $1,944 total
includes taxes & fees
Oct 11 - Oct 12
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

5. Delightful 3-bedroom house with AC in Oak Bluffs

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
The price is CA $639
CA $1,639 total
includes taxes & fees
Oct 30 - Oct 31
Delightful 3-bedroom house with AC in Oak Bluffs

6. 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 CA $1,920
CA $3,170 total
includes taxes & fees
Oct 11 - Oct 12
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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, (224 reviews)
"Great location "
United States
Stephanie B.
The price is CA $257
CA $738 total
includes taxes & fees
Nov 1 - Nov 2
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

8. 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 CA $451
CA $1,005 total
includes taxes & fees
Oct 12 - Oct 13
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

9. 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 CA $3,564
CA $5,301 total
includes taxes & fees
Oct 12 - Oct 13
Beautiful Estate with salt water pool & pond with kayaks

10. 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 CA $1,027
CA $1,674 total
includes taxes & fees
Oct 14 - Oct 15
The Seashell Cove - Martha's Vineyard

11. Stunning 4-bedroom Private Fresh Water Beach Front

Stunning 4-bedroom Private Fresh Water Beach Front
East Falmouth
10.0 out of 10, Exceptional, (44 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 CA $403
CA $992 total
includes taxes & fees
Oct 11 - Oct 12
Stunning 4-bedroom Private Fresh Water Beach Front

12. Cozy Cottage walk to Menauhant Beach

Cozy Cottage walk to Menauhant Beach
East Falmouth
8.8 out of 10, Excellent, (9 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 CA $372
CA $1,203 total
includes taxes & fees
Oct 12 - Oct 13
Cozy Cottage walk to Menauhant Beach

13. 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, (44 reviews)
"Great stay!"
United States
Kian S.
The price is CA $249
CA $654 total
includes taxes & fees
Oct 20 - Oct 21
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

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 CA $623
CA $1,339 total
includes taxes & fees
Oct 11 - Oct 12
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

15. 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 CA $624
CA $1,655 total
includes taxes & fees
Oct 11 - Oct 12
Beautiful Home in Falmouth Village

16. 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 CA $406
CA $820 total
includes taxes & fees
Oct 31 - Nov 1
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

17. Recently renovated 3 bedroom

Recently renovated 3 bedroom
Falmouth
10.0 out of 10, Exceptional, (4 reviews)
"The home worked out well for our needs. They have a very nice fully fenced in yard which was very beneficial."
United States
Rosemary P.
The price is CA $624
CA $1,755 total
includes taxes & fees
Oct 14 - Oct 15
Recently renovated 3 bedroom

18. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is CA $302
CA $1,092 total
includes taxes & fees
Oct 12 - Oct 13
West Falmouth Family Retreat Near Chapoquoit Beach

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 CA $349
CA $1,353 total
includes taxes & fees
Oct 12 - Oct 13
Nice home near Mashpee Commons and all Falmouth has to offer

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

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is CA $296
CA $912 total
includes taxes & fees
Oct 12 - Oct 13
Backyard Retreat / 5 Min > Beach & Main St
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 Vacation Homes information

Number of reviews
470
Accommodation
863 Vacation Homes
Lowest Price
CA $654
Highest Price
CA $5,301

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