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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.

25 Vacation Properties in Chilmark
Sleeps

Chilmark vacation rentals that sleep 8

Chilmark
ID 9224
4 BR
2 baths
Sleeps 8
Spacious, Conveniently Located Raised Cape in Chilmark
Spacious, Conveniently Located Raised Cape in Chilmark
Distance to beach: 5 mi to Lucy Vincent & Menemsha; 8 to Squibnocket
Off Season:
$200 - $300/night
$1,250 - $2,000/wk
Chilmark
ID 2903
4 BR
2 baths
Sleeps 8
Sweeping Ocean Views
Sweeping Ocean Views
Distance to beach: less than 3/10 mile to private association beach
Summer:
$4,000 - $4,700/wk
Off Season:
$2,500 - $3,500/wk
Chilmark
ID 4390
4 BR
2 ½ baths
Sleeps 8
4 Bedroom on 5 acres of Chilmark Woodlands
4 Bedroom on 5 acres of Chilmark Woodlands
Distance to beach: 3 miles to Lucy Vincent Beach, 5 to Sqibnocket
2 reviews read reviews
Summer:
$4,200/wk
Chilmark
ID 5312
4 BR
3 ½ baths
Sleeps 8
The Little Gem on Abel's Hill - Panoramic View - Chilmark
The Little Gem on Abel's Hill - Panoramic View - Chilmark
Distance to beach: Approx. 2/10 mile walk to Abel's Hill Beach
Chilmark
ID 19917
4 BR
3 baths
Sleeps 8
The ''New House'' @ Abels Hill - Private Beach + Tennis
The ''New House'' @ Abels Hill - Private Beach + Tennis
Distance to beach: 7 min walk, or 1 1/2 minute drive, private beach
3 reviews read reviews
Summer:
$800 - $900/night
$6,750 - $7,750/wk
Off Season:
$3,000 - $6,500/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
4 reviews read reviews
Summer:
$3,500 - $6,500/wk
Off Season:
$2,500 - $3,500/wk
Chilmark
ID 15956
3 BR
2 baths
Sleeps 8
Very Charming, Roomy Three Bedroom Home
Very Charming, Roomy Three Bedroom Home
Distance to beach: 2.5mi by road or 1mi walking through conservation
7 reviews read reviews
Summer:
$3,500 - $4,750/wk
Off Season:
$2,250 - $4,750/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
1 review read review
Summer:
$1,675 - $1,700/wk
Off Season:
$100 - $225/night
$550 - $1,700/wk

Chilmark vacation rentals that sleep 7

Chilmark
ID 26224
3 BR
2 baths
Sleeps 7
French Country Style Farmhouse Chilmark w/ HTub FERRY TIX
French Country Style Farmhouse Chilmark w/ HTub FERRY TIX
Distance to beach: 4 min drive Lucy Vincent or Squibnocket Beaches
7 reviews read reviews
Summer:
$550 - $575/night
$2,500 - $4,000/wk
Off Season:
$3,700/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: 5-minute walk on private hillside path
10 reviews read reviews
Summer:
$600 - $1,000/night
$4,000 - $6,000/wk
Off Season:
$350 - $500/night
$2,500 - $4,000/wk
Chilmark - off Meetinghouse Ro
ID 20412
3 BR
2 baths
Sleeps 6
Charming Chilmark Home/CENTRAL AIR w. ferry tickets
Charming Chilmark Home/CENTRAL AIR w. ferry tickets
Distance to beach: 3 miles to Lucy Vincent; 3.5 miles to Squibnocket
Summer:
$1,800 - $3,000/wk
Off Season:
$1,800 - $2,000/wk
Chilmark
ID 26542
3 BR
2 baths
Sleeps 6
Tisbury Great Pond, QBA Beach key, ferry tix, A/C, 4 boats
Tisbury Great Pond, QBA Beach key, ferry tix, A/C, 4 boats
Distance to beach: Quansoo Beach Association key included - 7/10 mile
Summer:
$17,500 - $25,000/wk
Off Season:
$12,000/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:
$3,250 - $3,500/wk
$12,000/mo
Off Season:
$250 - $325/night
$1,000 - $1,750/wk
$4,500 - $6,000/mo
Chilmark
ID 3473
3 BR
3 baths
Sleeps 6
Private 3 bedroom 3 bath Cedar Home on Hill in Chilmark
Private 3 bedroom 3 bath Cedar Home on Hill in Chilmark
Distance to beach: 10 minute drive to Lucy Vincent Beach
Summer:
$425 - $500/night
$2,500 - $3,000/wk
Off Season:
$425 - $500/night
$2,500 - $3,000/wk
Chilmark - Lucy Vincent Beach
ID 4172
3 BR
1 ½ bath
Sleeps 6
Lucy Vincent Beach Oceanfront Contemporary
Lucy Vincent Beach Oceanfront Contemporary
Distance to beach: New - path to the beach - or boat to Lucy Vincent
11 reviews read reviews
Summer:
$6,300 - $7,875/wk
Off Season:
$3,675 - $5,250/wk
Chilmark
ID 7701
3 BR
3 baths
Sleeps 6
Charming Chilmark Property
Charming Chilmark Property
Distance to beach: 3 miles to Lucy Vincent Beach
4 reviews read reviews
Summer:
$1,400 - $2,600/wk
Off Season:
$1,200 - $1,500/wk
$4,800/mo
Menemsha (Chilmark)
ID 17311
Summer:
$2,800 - $3,200/wk
Off Season:
$1,500 - $1,800/wk
Chilmark
ID 13169
2 BR
1 bath
Sleeps 6
On Upper Chilmark Pond overlooking Lucy Vincent Beach
On Upper Chilmark Pond overlooking Lucy Vincent Beach
Distance to beach: 100 yards to dock, 6 min. paddle to beach.
10 reviews read reviews
Summer:
$3,250 - $5,750/wk
Off Season:
$2,250 - $5,750/wk
ACROSS FROM QUANSOO FARM!
ID 10393
2 BR
2 baths
Sleeps 6
EXCLUSIVE PRIVATE Chilmark Quansoo LOCKED GATE BEACH!
EXCLUSIVE PRIVATE Chilmark Quansoo LOCKED GATE BEACH!
Distance to beach: Less than a mile to Quansoo Beach Association
3 reviews read reviews
Summer:
$3,000 - $3,600/wk
Off Season:
$2,000 - $3,500/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:
$2,400 - $3,000/wk
Off Season:
$1,300 - $2,700/wk

Chilmark vacation rentals that sleep 4

Menemsha (Chilmark)
ID 17189
2 BR
1 bath
Sleeps 4
Menemsha Harbor Cottage: Tilton House
Menemsha Harbor Cottage: Tilton House
Distance to beach: less than 2/10ths of a mile to Menemsha Beach
1 review read review
Off Season:
$1,200 - $1,500/wk
85 Tea Lane, Chilmark
ID 22294
2 BR
1 bath
Sleeps 4
Quiet, Secluded Chilmark Cottage
Quiet, Secluded Chilmark Cottage
Distance to beach: 3 Miles to Lucy Vincent Beach
13 reviews read reviews
Summer:
$1,800 - $2,000/wk
Off Season:
$1,800/wk
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:
$1,500 - $1,900/wk
Off Season:
$850 - $1,900/wk

Chilmark vacation rentals that sleep 2

Chilmark
ID 2470
1 BR
1 bath
Sleeps 2
Relax & Rejuvenate in Ideal Cottage Setting
Relax & Rejuvenate in Ideal Cottage Setting
Distance to beach: 5 miles to Lucy Vincent, the Island's best beach
37 reviews read reviews
Summer:
$1,700 - $2,000/wk
Off Season:
$125 - $200/night
$700 - $1,900/wk
Menemsha (Chilmark)
ID 18146
1 BR
1 bath
Sleeps 2
Davis House off Menemsha Harbor
Davis House off Menemsha Harbor
Distance to beach: less than 2/10ths of a mile to Menemsha Beach
3 reviews read reviews
Summer:
$1,200 - $1,800/wk
Off Season:
$1,200 - $1,800/wk