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Chilmark, along with West Tisbury and Aquinnah, is often referred to as "up-island." This town is known for its rolling meadows, stone walls, and one of the Island's finest beaches, Lucy Vincent Beach.

29 Vacation Properties in Chilmark
Sleeps
A fee-based feature highlighting availability within the next 4 weeks.

Chilmark vacation rentals that sleep 16

Menemsha Pond
ID 34454
8 BR
5 baths
Sleeps 16
Beautiful Sunsets On Menemsha Pond
Beautiful Sunsets On Menemsha Pond
Distance to beach: 0.9 Menemsha Public Beach and 2.7 Lucy Vincent Beach
LAST MINUTE ALERT 8/27 - 9/3
OWNER SPECIAL:
SPECIAL DEAL Monday August 29th - Monday September 5th Price was $9500, now is $7500, save $ 2000!
Summer:
$8,000 - $10,000/wk
Off Season:
$7,000 - $9,000/wk
2

Chilmark vacation rentals that sleep 11

Chilmark
ID 30776
6 BR
1 ½ bath
Sleeps 11
Lucy Vincent House with Access to Private Beach
Lucy Vincent House with Access to Private Beach
Distance to beach: 1/2 mi to Lucy Vincent Beach-Private Section
1 review read review
OWNER SPECIAL:
2023 summer season now available and still time to book and enjoy a September vacation!
Summer:
$4,000 - $5,000/wk
Off Season:
$4,000/wk
4
Chilmark
ID 33079
6 BR
2 ½ baths
Sleeps 11
Farm House in Menemsha with North Shore Views!
Farm House in Menemsha with North Shore Views!
Distance to beach: 4.8 miles to Lucy Vincent Beach
Summer:
$14,000/wk
Off Season:
$14,000/wk

Chilmark vacation rentals that sleep 10

Chilmark
ID 34003
5 BR
3 baths
Sleeps 10
Summer cottage w/spectacular views & access to private beach
Summer cottage w/spectacular views & access to private beach
Distance to beach: 2/10 mile to private beach on Menemsha Pond
15 reviews read reviews
Summer:
$4,000 - $6,000/wk
$20,000 - $22,000/mo
Off Season:
$3,000 - $5,000/wk
$14,000 - $15,000/mo
3

Chilmark vacation rentals that sleep 9

Chilmark - Quansoo Beach
ID 34329
4 BR
7 ½ baths
Sleeps 9
Chilmark Estate with Pool, Tennis Court, Private Beach
Chilmark Estate with Pool, Tennis Court, Private Beach
Distance to beach: Quansoo Private Beach - Beach Key
Summer:
$20,000 - $30,000/wk
Off Season:
$18,000 - $25,000/wk
3

Chilmark vacation rentals that sleep 8

Chilmark
ID 32622
4 BR
3 ½ baths
Sleeps 8
Chilmark 4BR Near Beaches and Other Activities
Chilmark 4BR Near Beaches and Other Activities
Distance to beach: 1 mile to Menemsha Public Beach
2 reviews read reviews
Summer:
$6,000 - $7,000/wk
Off Season:
$600 - $900/night
$6,000/wk
4
Chilmark
ID 12106
3 BR
2 baths
Sleeps 8
Windfall...with vast water views of Lucy Vincent Beach
Windfall...with vast water views of Lucy Vincent Beach
Distance to beach: Brief walk & quick canoe ride to L. VIncent Beach
10 reviews read reviews
Summer:
$3,750 - $7,250/wk
Off Season:
$2,500 - $3,750/wk
Off Middle Road, Chilmark
ID 15956
3 BR
2 baths
Sleeps 8
Very Charming, Roomy Three Bedroom Home
Very Charming, Roomy Three Bedroom Home
Distance to beach: 2 miles by road/ 1 thru conservation land (walk). Lucy Vincent Beach and About 3 miles to public Menemsha beach.
12 reviews read reviews
Summer:
$4,000 - $4,500/wk
Off Season:
$3,000 - $4,500/wk
3
Chilmark
ID 36257
3 BR
2 ½ baths
Sleeps 8
Contemporary Chilmark with Blackpoint Beach Key
Contemporary Chilmark with Blackpoint Beach Key
Distance to beach: 4.6 mi to Lucy Vincent Beach and 1 mi Blackpoint Beach, 4.6 mi Lucy Vincent Beach
Summer:
$7,900/wk
Off Season:
$7,900/wk
Seven Gates
ID 35442
3 BR
3 ½ baths
Sleeps 8
Chilmark Estate with Private Beach and Water View
Chilmark Estate with Private Beach and Water View
Distance to beach: 5.2 mi to Lambert's Cove Beach and 0.5 miles to Seven Gates Association Beach
Summer:
$8,000/wk
Chilmark
ID 4383
2 BR
1 bath
Sleeps 8
Secluded Unique Natural Vacation House
Secluded Unique Natural Vacation House
Distance to beach: Three miles Lucy Vincent Beach and 5 miles Squibnocket Beach
2 reviews read reviews
LAST MINUTE ALERT 9/2 - 9/9
OWNER SPECIAL:
Best weeks of the summer: September 2-9 reduced to$1525 & September 9-16 reduced to $1375.
Summer:
$1,800/wk
Off Season:
$600 - $1,525/wk
2

Chilmark vacation rentals that sleep 6

Menemsha
ID 13297
3 BR
2 baths
Sleeps 6
Breathtaking Menemsha Views of Docks& Water Sunsets
Breathtaking Menemsha Views of Docks& Water Sunsets
Distance to beach: 2/10 mile to Menemsha Public Beach and 2.8 miles to Lucy Vincent Beach
12 reviews read reviews
Summer:
$3,500 - $6,000/wk
$28,000/mo
Off Season:
$2,500 - $4,000/wk
Menemsha (Chilmark)
ID 17311
3 BR
1 bath
Sleeps 6
Menemsha Village - Sunset House
Menemsha Village - Sunset House
Distance to beach: .2 Mile Menemsha Public Beach and 2.4 Miles Lucy Vincent Beach
2 reviews read reviews
Summer:
$2,800 - $3,400/wk
Off Season:
$2,000 - $3,000/wk
3
Chilmark
ID 22082
3 BR
2 baths
Sleeps 6
Contemporary Style w/Sunset Ocean Views
Contemporary Style w/Sunset Ocean Views
Distance to beach: 1 mile Menemsha Public Beach and 3 miles Lucy Vincent Beach
5 reviews read reviews
Summer:
$3,200 - $4,500/wk
Off Season:
$460/night
$3,200/wk
Chilmark
ID 33049
3 BR
2 baths
Sleeps 6
Secluded house in the woods with deck & streamside firepit
Secluded house in the woods with deck & streamside firepit
Distance to beach: 1 mile to Menemsha Public Beach and 2 miles to Lucy Vincent Beach
6 reviews read reviews
LAST MINUTE ALERT 9/10 - 9/17
OWNER SPECIAL:
September special! Rentals have been reduced $500 per week.
Summer:
$3,750 - $4,500/wk
Off Season:
$2,550 - $3,600/wk
Chilmark
ID 36339
3 BR
2 ½ baths
Sleeps 6
Charming Perfect Beachfront Cottage
Charming Perfect Beachfront Cottage
Distance to beach: On Private Beach; .8 mi to Squibnocket Beach
OWNER SPECIAL:
September available weeks only- $10,250 weekly. Two week minimum.
Summer:
$12,000/wk
Off Season:
$5,000 - $12,000/wk
Chilmark
ID 36425
3 BR
3 ½ baths
Sleeps 6
Wonderful Home!
Wonderful Home!
Distance to beach: 3.2 mi to Menemsha Public Beach and 5 mi to Lucy Vincent Beach
Summer:
$5,000 - $5,500/wk
Off Season:
$5,000/wk
Chilmark
ID 30704
3 BR
1 ½ bath
Sleeps 6
Molly's Cottage: Views of Menemsha Creek & Pond
Molly's Cottage: Views of Menemsha Creek & Pond
Distance to beach: 1/4 mile to Menemsha Beach
Summer:
$3,500 - $3,750/wk
Off Season:
$275 - $325/night
$1,100 - $1,950/wk
Guest Cottage
ID 36122
2 BR
1 bath
Sleeps 6
Dreamy Guest Cottage, Art Shack & Little Cottage; Sept 5-18
Dreamy Guest Cottage, Art Shack & Little Cottage; Sept 5-18
Distance to beach: 3.4 mi to Lucy Vincent Beach and 5 mi to Squibnocket Beach
2 reviews read reviews
Summer:
$2,000 - $3,000/wk
Off Season:
$2,000/wk
Chilmark
ID 33083
2 BR
2 baths
Sleeps 6
Sophisticated Country Charmer with Central Air
Sophisticated Country Charmer with Central Air
Distance to beach: 2.8 mi to Menemsha Public Beach
Summer:
$3,200 - $3,600/wk
Off Season:
$2,700 - $3,200/wk

Chilmark vacation rentals that sleep 5

Walk to private QBA beach
ID 10393
2 BR
2 baths
Sleeps 5
Hard to find locked gate beach 1 mile from ocean
Hard to find locked gate beach 1 mile from ocean
Distance to beach: Walk or drive to South Beach or Tisbury Great Pond
7 reviews read reviews
Summer:
$3,800 - $4,400/wk
Off Season:
$4,000/wk
Chilmark
ID 23618
2 BR
1 bath
Sleeps 5
Menemsha Gem with Vineyard Sound Waterview
Menemsha Gem with Vineyard Sound Waterview
Distance to beach: 2/10 mile Menemsha Beach
Summer:
$3,100 - $3,200/wk
Off Season:
$1,600 - $2,900/wk
2
Chilmark
ID 34169
2 BR
2 baths
Sleeps 5
Chilmark Casita - New Listing! Newly Renovated w/Central AC!
Chilmark Casita - New Listing! Newly Renovated w/Central AC!
Distance to beach: 4.6 mi to Lucy Vincent Beach and Squibnocket Beach
4 reviews read reviews
Summer:
$4,000 - $5,000/wk
$18,000 - $24,500/mo
Off Season:
$350 - $600/night
$300 - $3,000/wk
$6,300 - $13,000/mo
2

Chilmark vacation rentals that sleep 4

Chilmark, off South Rd. adjace
ID 13169
2 BR
1 bath
Sleeps 4
On Upper Chilmark Pond overlooking Lucy Vincent Beach
On Upper Chilmark Pond overlooking Lucy Vincent Beach
Distance to beach: See below. Lucy Vincent Beach and 100 yards to dock, 6 min. paddle to beach.
11 reviews read reviews
Summer:
$4,750 - $5,500/wk
Off Season:
$2,250 - $5,000/wk
3
Menemsha (Chilmark)
ID 17189
2 BR
1 bath
Sleeps 4
Menemsha Harbor Cottage: Tilton House
Menemsha Harbor Cottage: Tilton House
Distance to beach: .2 Mile Menemsha Public Beach and 2.4 Miles Lucy Vincent Beach
1 review read review
Summer:
$2,000 - $2,800/wk
Off Season:
$1,700 - $2,400/wk
2
Tisbury Great Pond
ID 32998
2 BR
2 baths
Sleeps 4
FERRY TIX, Quansoo Beach key, A/C,Tisbury Gt. Pond, boats
FERRY TIX, Quansoo Beach key, A/C,Tisbury Gt. Pond, boats
Distance to beach: 1/2 mile by boat (4 kayaks), 7/10 mile foot/drive
2 reviews read reviews
Summer:
$4,000 - $4,500/wk
Off Season:
$2,800 - $3,250/wk
2
Chilmark
ID 4029
1 BR
1 bath
Sleeps 4
Stonewall Beach Guest Cottage
Stonewall Beach Guest Cottage
Distance to beach: 1/2 mile to Stonewall Beach
Summer:
$2,200/wk
Off Season:
$1,100 - $1,800/wk
2

Chilmark vacation rentals that sleep 2

Menemsha (Chilmark)
ID 18146
1 BR
1 bath
Sleeps 2
Davis House off Menemsha Harbor
Davis House off Menemsha Harbor
Distance to beach: .2 Mile Menemsha Public Beach and 2.4 Miles Lucy Vincent Beach
5 reviews read reviews
LAST MINUTE ALERT 9/1 - 9/8
OWNER SPECIAL:
$1500 (down from $1900) for Sept. 1st - Sept. 8th. Thu-Thu.
Summer:
$1,700 - $2,100/wk
Off Season:
$1,400 - $1,900/wk
4
Chilmark
ID 31847
1 BR
1 bath
Sleeps 2
Storybook Cottage in Chilmark
Storybook Cottage in Chilmark
Distance to beach: Menemsha Beach 3.4 miles
Summer:
$2,625/wk
Off Season:
$2,625/wk