Search results; Over 1,000 places in Chilmark

Guest favorite
Guesthouse in Chilmark
Beautifully Renovated 1800s Chilmark Barn
3 beds
Jul 7 – 12
R35,313 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 91 reviews
Top guest favorite
Home in Chilmark
The Blueberry House on Martha’s Vineyard
2 beds
Jul 5 – 10
R46,774 ZAR for 5 nights, originally R62,979 ZAR
for 5 nights
5.0 out of 5 average rating, 16 reviews
Guest favorite
Guest suite in West Tisbury
Studio Guest Suite in Modern Barn House
Free cancellation
Sep 7 – 12
R16,587 ZAR for 5 nights
for 5 nights
4.91 out of 5 average rating, 128 reviews
Home in Chilmark
Quiet, Bright & Open MV home
6 beds
Jul 1 – 6
R80,899 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Guest favorite
Place to stay in Aquinnah
Water View "Tower" Room on Martha's Vineyard
1 bed
Jul 15 – 20
R21,081 ZAR for 5 nights
for 5 nights
4.83 out of 5 average rating, 224 reviews
Home in Aquinnah
Secluded Aquinnah Cottage
1 queen bed
Sep 1 – 6
R43,339 ZAR for 5 nights
for 5 nights
4.7 out of 5 average rating, 10 reviews
Guest favorite
Cottage in Chilmark
Walk to the beach: Charming Menemsha Cottage
4 beds
Aug 31 – Sep 7
R107,009 ZAR for 7 nights
for 7 nights
5.0 out of 5 average rating, 49 reviews
Guest favorite
Home in Chilmark
Charming Chilmark Cottage
2 beds
Jul 6 – 13
R59,390 ZAR for 7 nights
for 7 nights
4.97 out of 5 average rating, 39 reviews
Top guest favorite
Guesthouse in Chilmark
4-Season Guest House on Historic Chilmark Estate
1 queen bed
Oct 10 – 15
R35,313 ZAR for 5 nights
for 5 nights
4.99 out of 5 average rating, 96 reviews
Guest favorite
Home in Chilmark
The Gem on Abel’s Hill, Chilmark
5 beds
Jul 14 – 19
R108,079 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 6 reviews
Guest favorite
Home in Chilmark
Beautiful Middle Road, Chilmark
2 beds
Jul 1 – 6
R77,046 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 11 reviews
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More stays available for your dates

Guest favorite
Home in Chilmark
Cozy Waterfront Cottage, Newly Remodeled!
4 beds
Sep 7 – 12
R72,659 ZAR for 5 nights
for 5 nights
4.86 out of 5 average rating, 51 reviews
Guest favorite
Home in Chilmark
2 BR-Private guest house with Hot Tub and Fire Pit
2 queen beds
Aug 31 – Sep 5
R42,590 ZAR for 5 nights, originally R55,554 ZAR
for 5 nights
4.99 out of 5 average rating, 70 reviews
Guest favorite
Home in Chilmark
Fun, Authentic, Waterfront Cottage/air conditioned
Free cancellation
Aug 24 – 29
R112,145 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 29 reviews
Cottage in Chilmark
Charming 1 BR Ocean View Cottage, Path to Beach
Free cancellation
Sep 1 – 6
R52,863 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 12 reviews
Guest favorite
Apartment in West Tisbury
Butterfly Farm Sanctuary Bright Sunny Studio Apt
1 queen bed
Aug 17 – 22
R41,413 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 56 reviews
Home in Chilmark
Come relax on our Water View Farm with Ocean Views
Free cancellation
Sep 1 – 6
R49,545 ZAR for 5 nights
for 5 nights
4.84 out of 5 average rating, 19 reviews
Home in Chilmark
Tranquil Chilmark retreat
4 beds
Jul 6 – 13
R92,991 ZAR for 7 nights
for 7 nights