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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
4 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
Summer:
$8,000 - $10,000/wk
Off Season:
$630/night
$4,000 - $9,500/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
OWNER SPECIAL:
Week of August 14th just became available!!
Summer:
$4,500 - $5,000/wk
Off Season:
$4,000 - $4,500/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:
$6,000 - $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 - $5,000/wk
$20,000 - $22,000/mo
Off Season:
$3,000 - $4,000/wk
$8,000 - $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:
$25,000 - $30,000/wk
Off Season:
$18,000 - $25,000/wk
3

Chilmark vacation rentals that sleep 8

Chilmark
ID 36142
4 BR
3 baths
Sleeps 8
Lots of Light!!
Lots of Light!!
Distance to beach: 1 mi to Lucy Vincent Beach and 3 mi to Menemsha Public Beach
Summer:
$9,000 - $11,000/wk
Off Season:
$2,000 - $8,000/wk
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
$5,000 - $6,000/wk
4
Chilmark
ID 35678
4 BR
2 ½ baths
Sleeps 8
Hilltop Estate-Private Tennis Court & Hot Tub
Hilltop Estate-Private Tennis Court & Hot Tub
Distance to beach: 3.5 mi to Lucy Vincent Beach and 5.6 mi to Squibnocket Beach
Summer:
$19,735 - $26,025/wk
Off Season:
$12,847 - $19,735/wk
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
8 reviews read reviews
Summer:
$4,250 - $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:
$3,500 - $4,500/wk
Off Season:
$3,250 - $4,500/wk
3
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 to Lucy Vincent Beach - 10 min drive
2 reviews read reviews
Summer:
$1,575 - $1,800/wk
Off Season:
$600 - $1,625/wk

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:
$4,000 - $6,000/wk
$20,000 - $28,000/mo
Off Season:
$2,500 - $4,000/wk
$10,000 - $12,000/mo
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 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 - $2,250/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 6/4 - 6/11
OWNER SPECIAL:
Price Drop! Save $250/wk ~ Now $2950 for June 4-11 & Now $3500 for June18-25 -See calendar for price
Summer:
$3,750 - $4,500/wk
Off Season:
$2,200 - $3,600/wk
Chilmark
ID 35959
3 BR
3 baths
Sleeps 6
Gorgeous Chilmark Home
Gorgeous Chilmark Home
Distance to beach: 3.2 mi to Menemsha Public Beach and Lucy Vincent beach 4.7 miles
Summer:
$6,000 - $7,000/wk
Off Season:
$6,000/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:
$1,800 - $3,000/wk
3
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
Exclusive Quansoo Beach, privacy, nature
Exclusive Quansoo Beach, privacy, nature
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:
$3,800 - $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:
$3,000 - $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
3 reviews read reviews
Summer:
$4,500 - $5,000/wk
Off Season:
$400 - $600/night
$1,500 - $4,500/wk
$8,000 - $12,000/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:
$2,000 - $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
LAST MINUTE ALERT 5/26 - 6/2 and 6/2 - 6/9
OWNER SPECIAL:
30% off weekly price. 1 or 2 weeks available: May 26th - June 9th.
Summer:
$2,000 - $2,800/wk
Off Season:
$180 - $225/night
$1,600 - $2,400/wk
2
85 Tea Lane, Chilmark
ID 22294
2 BR
1 bath
Sleeps 4
Quiet, Secluded Chilmark Cottage
Quiet, Secluded Chilmark Cottage
Distance to beach: 4 miles Lucy Vincent Beach and 5 miles Squibnocket Beach
27 reviews read reviews
Summer:
$2,100 - $2,200/wk
Off Season:
$2,100/wk
4
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 boats (several provided), 7/10 mile fo
2 reviews read reviews
Summer:
$3,100 - $4,500/wk
Off Season:
$2,250 - $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:
$1,800 - $2,200/wk
Off Season:
$1,000 - $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
3 reviews read reviews
Summer:
$1,900 - $2,100/wk
Off Season:
$1,300 - $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