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)
"A clean accommodating space with an accommodating host - I recommended!"
United States
Collins E.
The price is CA $700
CA $1,524 total
includes taxes & fees
Oct 21 - Oct 22
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
The price is CA $634
CA $1,626 total
includes taxes & fees
Oct 30 - Oct 31
Delightful 3-bedroom house with AC in Oak Bluffs

3. 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 $563
CA $1,892 total
includes taxes & fees
Oct 21 - Oct 22
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

4. 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 $423
CA $1,080 total
includes taxes & fees
Nov 16 - Nov 17
Oak Bluffs 4BR • 5 Min Drive to Downtown

5. 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 $447
CA $997 total
includes taxes & fees
Oct 21 - Oct 22
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

6. 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 $255
CA $740 total
includes taxes & fees
Nov 17 - Nov 18
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

7. 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 $223
CA $621 total
includes taxes & fees
Oct 21 - Oct 22
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

8. 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 $749
CA $2,352 total
includes taxes & fees
Oct 21 - Oct 22
New 4 BR house near center and beaches with bikes

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 CA $618
CA $1,308 total
includes taxes & fees
Oct 21 - Oct 22
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

10. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is CA $335
CA $1,054 total
includes taxes & fees
Oct 21 - Oct 22
West Falmouth Family Retreat Near Chapoquoit Beach

11. 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 $404
CA $824 total
includes taxes & fees
Oct 31 - Nov 1
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

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

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is CA $283
CA $904 total
includes taxes & fees
Oct 21 - Oct 22
Backyard Retreat / 5 Min > Beach & Main St

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 CA $1,909
CA $3,158 total
includes taxes & fees
Oct 19 - Oct 20
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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 $401
CA $986 total
includes taxes & fees
Oct 21 - Oct 22
Stunning 4-bedroom Private Fresh Water Beach Front

15. 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 $958
CA $1,585 total
includes taxes & fees
Oct 18 - Oct 19
The Seashell Cove - Martha's Vineyard

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.
Nice home near Mashpee Commons and all Falmouth has to offer

17. New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
Little Neck Bay
9.8 out of 10, Exceptional, (54 reviews)
"We had the best week at 67 Tide Run! The property is gorgeous. We enjoyed kayaking and fishing from the dock. It was plenty big enough for our family of 10. We are going to miss the views. It’s perfect! You cannot go wrong booking Jamie’s home."
United States
cindy w.
The price is CA $631
CA $1,473 total
includes taxes & fees
Oct 30 - Oct 31
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

18. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is CA $550
CA $1,308 total
includes taxes & fees
Oct 21 - Oct 22
Walk to Beach! Oak Bluffs Home & Studio

19. Pool Escape in East Falmouth

Pool Escape in East Falmouth
East Falmouth
8.0 out of 10, Very good, (2 reviews)
"Great location! Close to everything and wonderful neighborhood. The fenced in back yard with the pool is amazing. Hosts are great to work with. Very responsive to any questions or needs."
United States
Gloria C.
The price is CA $673
CA $1,866 total
includes taxes & fees
Oct 21 - Oct 22
Pool Escape in East Falmouth

20. 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 $3,548
CA $5,403 total
includes taxes & fees
Oct 18 - Oct 19
Beautiful Estate with salt water pool & pond with kayaks
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
452
Accommodation
863 Vacation Homes
Lowest Price
CA $621
Highest Price
CA $5,403

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