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

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Our top choices for Chilmark vacation 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 CA $436
CA $1,087 total
includes taxes & fees
Sep 12 - Sep 13
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 CA $436
CA $1,175 total
includes taxes & fees
Sep 11 - Sep 12
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 CA $539
CA $1,327 total
includes taxes & fees
Sep 25 - Sep 26
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 CA $552
CA $1,147 total
includes taxes & fees
Sep 27 - Sep 28
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 CA $266
CA $1,046 total
includes taxes & fees
Sep 8 - Sep 9
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 CA $734
CA $2,023 total
includes taxes & fees
Sep 9 - Sep 10
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 CA $1,869
CA $3,091 total
includes taxes & fees
Sep 9 - Sep 10
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 CA $454
CA $1,109 total
includes taxes & fees
Sep 9 - Sep 10
< 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 CA $311
CA $696 total
includes taxes & fees
Sep 30 - Oct 1
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 CA $551
CA $1,893 total
includes taxes & fees
Oct 1 - Oct 2
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 CA $938
CA $1,552 total
includes taxes & fees
Sep 6 - Sep 7
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 CA $386
CA $1,407 total
includes taxes & fees
Sep 16 - Sep 17
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 CA $437
CA $990 total
includes taxes & fees
Sep 9 - Sep 10
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 CA $349
CA $1,203 total
includes taxes & fees
Oct 1 - Oct 2
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 CA $570
CA $1,560 total
includes taxes & fees
Sep 16 - Sep 17
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 CA $464
CA $1,060 total
includes taxes & fees
Sep 23 - Sep 24
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 CA $3,404
CA $5,189 total
includes taxes & fees
Sep 13 - Sep 14
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 CA $396
CA $1,398 total
includes taxes & fees
Sep 8 - Sep 9
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 CA $572
CA $1,668 total
includes taxes & fees
Sep 16 - Sep 17
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 CA $667
CA $1,303 total
includes taxes & fees
Sep 8 - Sep 9
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.
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Chilmark Vacation Homes information

Number of reviews
218
Accommodation
897 Vacation Homes
Lowest Price
CA $696
Highest Price
CA $5,189

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