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

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Our top choices for Chilmark vacation homes

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

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
The price is CA $637
CA $1,635 total
includes taxes & fees
Oct 30 - Oct 31
Delightful 3-bedroom house with AC in Oak Bluffs

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, (10 reviews)
"A clean accommodating space with an accommodating host - I recommended!"
United States
Collins E.
The price is CA $704
CA $1,533 total
includes taxes & fees
Oct 16 - Oct 17
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
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 $425
CA $1,076 total
includes taxes & fees
Nov 11 - Nov 12
Oak Bluffs 4BR • 5 Min Drive to Downtown

4. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is CA $337
CA $1,060 total
includes taxes & fees
Oct 19 - Oct 20
West Falmouth Family Retreat Near Chapoquoit Beach

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

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is CA $326
CA $948 total
includes taxes & fees
Oct 19 - Oct 20
Backyard Retreat / 5 Min > Beach & Main St

6. 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 $566
CA $1,939 total
includes taxes & fees
Oct 16 - Oct 17
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

7. 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 $449
CA $1,016 total
includes taxes & fees
Oct 19 - Oct 20
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

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, (45 reviews)
"Great place with kayaks and paddle boards, beach, close to Mashpee Commons. Host was great and place was clean and quaint."
United States
Michele M.
The price is CA $224
CA $624 total
includes taxes & fees
Oct 18 - Oct 19
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

9. 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 $256
CA $736 total
includes taxes & fees
Nov 1 - Nov 2
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

10. 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, (13 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is CA $754
CA $2,365 total
includes taxes & fees
Oct 19 - Oct 20
New 4 BR house near center and beaches with bikes

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 CA $1,920
CA $3,169 total
includes taxes & fees
Oct 16 - Oct 17
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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.
Cozy Cottage walk to Menauhant Beach

13. 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 $3,555
CA $5,413 total
includes taxes & fees
Oct 18 - Oct 19
Beautiful Estate with salt water pool & pond with kayaks

14. Stunning 4-bedroom Private Fresh Water Beach Front

Stunning 4-bedroom Private Fresh Water Beach Front
East Falmouth
10.0 out of 10, Exceptional, (45 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 19 - Oct 20
Stunning 4-bedroom Private Fresh Water Beach Front

15. Haven in Hatchville - newly renovated home

Haven in Hatchville - newly renovated home
East Falmouth
Haven in Hatchville - newly renovated home

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 CA $364
CA $1,394 total
includes taxes & fees
Oct 17 - Oct 18
Nice home near Mashpee Commons and all Falmouth has to offer

17. 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 $405
CA $826 total
includes taxes & fees
Oct 31 - Nov 1
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

18. < 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 $621
CA $1,336 total
includes taxes & fees
Oct 16 - Oct 17
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

19. 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 $960
CA $1,588 total
includes taxes & fees
Oct 18 - Oct 19
The Seashell Cove - Martha's Vineyard

20. 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.
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

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Chilmark Vacation Homes information

Number of reviews
456
Accommodation
863 Vacation Homes
Lowest Price
CA $624
Highest Price
CA $5,413

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