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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.

32 Vacation Properties in Chilmark

Chilmark vacation rentals that sleep 16

Menemsha Pond
ID 34454
8 BR
5 ½ 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:
$1,800 - $2,500/night
$10,000/wk
Off Season:
$800 - $1,200/night
$6,000 - $9,000/wk
$4,000 - $7,000/mo
2

Chilmark vacation rentals that sleep 14

South Shore Bluff
ID 36783
7 BR
7 ½ baths
Sleeps 14
Island Escape: Atlantic Bluff, South Shore Compound
Island Escape: Atlantic Bluff, South Shore Compound
Distance to beach: 2.2 mi to Lucy Vincent Beach and Cliff carved stairs to your own private beach
Summer:
$80,000/wk
Off Season:
$80,000/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
2 reviews read reviews
OWNER SPECIAL:
2023 summer season now available!
Summer:
$4,500 - $5,000/wk
Off Season:
$3,500 - $4,500/wk
4

Chilmark vacation rentals that sleep 10

Chilmark
ID 17283
5 BR
3 baths
Sleeps 10
Lovely 5 Bedroom 3 Bath Vacation Home in Chilmark
Lovely 5 Bedroom 3 Bath Vacation Home in Chilmark
Distance to beach: 4 miles - Lucy Vincent; 1 mile-Great Rock Bight
3 reviews read reviews
Summer:
$9,500/wk
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:
$5,000 - $6,000/wk
Off Season:
$3,500 - $5,000/wk
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 - $32,000/wk
Off Season:
$18,000 - $25,000/wk
3

Chilmark vacation rentals that sleep 8

Chilmark
ID 33082
4 BR
3 baths
Sleeps 8
Idyllic Chilmark Home With Pool
Idyllic Chilmark Home With Pool
Distance to beach: 1.8 mi to Lucy Vincent Beach
Summer:
$12,400 - $13,500/wk
Off Season:
$7,350 - $8,300/wk
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:
$24,000 - $42,000/wk
Off Season:
$24,000/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
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
11 reviews read reviews
Summer:
$4,000 - $7,250/wk
Off Season:
$3,250 - $4,000/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:
$3,750 - $5,000/wk
Off Season:
$2,000 - $5,000/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:
$10,000/wk
Off Season:
$10,000/wk
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:
$8,500/wk
Off Season:
$7,500/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
3 reviews read reviews
Off Season:
$575 - $1,325/wk
2

Chilmark vacation rentals that sleep 7

The Camp // Gadget
ID 35763
3 BR
1 bath
Sleeps 7
Summer Camp
Summer Camp
Distance to beach: 2.8 mi to Lucy Vincent Beach and Access to the private Hancock Beach
Summer:
$3,000 - $3,500/wk
$15,000/mo
Off Season:
$2,500 - $3,000/wk
$10,000/mo
1

Chilmark vacation rentals that sleep 6

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:
$3,360 - $4,750/wk
Off Season:
$460 - $480/night
$3,360/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 - $4,000/wk
Off Season:
$1,800 - $3,500/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
11 reviews read reviews
Summer:
$3,500 - $4,750/wk
Off Season:
$2,550 - $3,350/wk
Chilmark
ID 36339
3 BR
2 ½ baths
Sleeps 6
Charming Perfect-The Only Beachfront Cottage for Rent
Charming Perfect-The Only Beachfront Cottage for Rent
Distance to beach: On Private Beach; .8 mi to Squibnocket Beach
Summer:
$12,000/wk
Off Season:
$8,500 - $12,000/wk
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
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:
$3,000 - $3,400/wk
Off Season:
$1,500 - $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:
$3,300 - $3,700/wk
Off Season:
$2,800 - $3,300/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 - $2,500/wk

Chilmark vacation rentals that sleep 5

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 - $3,300/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
7 reviews read reviews
Summer:
$3,000 - $6,000/wk
$18,000 - $24,500/mo
Off Season:
$350 - $600/night
$900 - $4,000/wk
$6,300 - $13,000/mo
2
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
Off Season:
$4,000/wk

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:
$4,000 - $6,000/wk
Off Season:
$2,250 - $5,500/wk
3
Tisbury Great Pond
ID 32998
2 BR
2 baths
Sleeps 4
Quansoo Beach key, A/C,4 kayaks,1 paddleboard, FERRY TIX!
Quansoo Beach key, A/C,4 kayaks,1 paddleboard, FERRY TIX!
Distance to beach: 1/2 mile by boat (4 kayaks), 7/10 mile foot/drive
2 reviews read reviews
Summer:
$3,600 - $4,500/wk
Off Season:
$2,950 - $3,500/wk
2
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:
$257 - $343/night
$1,700 - $2,400/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:
$1,100 - $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
6 reviews read reviews
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