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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.

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

Chilmark vacation rentals that sleep 15

Chilmark
ID 32305
6 BR
4 ½ baths
Sleeps 15
Renovated Antique on Tisbury Great Pond w/AC & Separate Apt.
Renovated Antique on Tisbury Great Pond w/AC & Separate Apt.
Distance to beach: Squibnocket Beach - 7.9 miles (19 minutes) Squibnocket Beach and South Beach by motorboat is 9/10 mile
LAST MINUTE ALERT 8/2 - 8/9
OWNER SPECIAL:
Price for Fri., Aug. 2-9 reduced from $12,000 to $9500.
Summer:
$9,500 - $13,000/wk
$48,000 - $50,000/mo
Off Season:
$9,000/wk

Chilmark vacation rentals that sleep 10

Chilmark
ID 29790
5 BR
3 baths
Sleeps 10
Water view, private beach key access in Chilmark
Water view, private beach key access in Chilmark
Distance to beach: 1/2 mile to Lucy Vincent beach
Summer:
$8,000 - $8,500/wk
Off Season:
$7,500/wk
Chilmark
ID 31702
3 BR
3 ½ baths
Sleeps 10
Celeb Owned Hilltop Home w/ Hot Tub SOME JULY FERRY TIX !
Celeb Owned Hilltop Home w/ Hot Tub SOME JULY FERRY TIX !
Distance to beach: 4.8 miles to Lucy Vincent Beach
Summer:
$3,700 - $4,200/wk
Off Season:
$685/night
$3,600/wk

Chilmark vacation rentals that sleep 8

Chilmark
ID 2903
4 BR
2 baths
Sleeps 8
Sweeping Ocean Views
Sweeping Ocean Views
Distance to beach: 3 miles Menemsha Public Beach and 3.5 miles Lucy Vincent Beach
5 reviews read reviews
OWNER SPECIAL:
Due to last minute cancellation from long term summer tenant, July & August can be yours.
Summer:
$4,000 - $5,200/wk
$20,000/mo
Off Season:
$3,000 - $4,700/wk
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
Summer:
$3,300 - $3,500/wk
$12,000 - $15,000/mo
Off Season:
$425 - $180/night
$1,250 - $3,000/wk
Chilmark
ID 31816
4 BR
2 baths
Sleeps 8
Perfect Summer Retreat!
Perfect Summer Retreat!
Distance to beach: Lucy Vincent Beach 2.5 miles
Summer:
$4,500 - $5,500/wk
Off Season:
$4,500 - $5,000/wk
Chilmark
ID 31852
4 BR
2 baths
Sleeps 8
Over South: Authentic Chilmark Farmhouse
Over South: Authentic Chilmark Farmhouse
Distance to beach: 2 Miles/3 minute drive Squibnocket Beach and 2 Miles/3 Min drive to Lucy Vincent Beach
Summer:
$2,800/wk
Off Season:
$300 - $400/night
$2,100/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:
$4,500 - $6,000/wk
Off Season:
$4,000 - $6,000/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:
$3,750 - $4,200/wk
$16,000/mo
Off Season:
$400 - $500/night
$3,750 - $4,200/wk
$15,000/mo
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:
$30,000/mo
Off Season:
$500 - $650/night
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:
$3,250 - $6,500/wk
Off Season:
$2,500 - $4,000/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 - $5,000/wk
Off Season:
$2,000 - $4,750/wk
Chilmark
ID 26224
3 BR
2 baths
Sleeps 8
Fr Country Style Farmhouse Chilmark w/ HTub FERRY TIX AUGUST
Fr Country Style Farmhouse Chilmark w/ HTub FERRY TIX AUGUST
Distance to beach: 4 min drive Lucy Vincent or Squibnocket Beaches
7 reviews read reviews
Summer:
$3,500 - $3,997/wk
Off Season:
$520/night
$3,500 - $3,640/wk
Chilmark
ID 32322
3 BR
2 ½ baths
Sleeps 8
Gorgeous Remodeled High End Chilmark Home
Gorgeous Remodeled High End Chilmark Home
Distance to beach: 1.7 miles Lucy Vincent Beach
Summer:
$4,500 - $5,000/wk
Off Season:
$3,800 - $5,000/wk
Chilmark
ID 32489
3 BR
3 baths
Sleeps 8
Everybody's Favorite View in Chilmark
Everybody's Favorite View in Chilmark
Distance to beach: 1/2 mile Lucy Vincent Beach and 2 miles Squibnocket Beach
Summer:
$5,000/wk
$25,000/mo
Chilmark
ID 32594
3 BR
2 baths
Sleeps 8
Beauiful Chilmark Cottage Close to Beaches
Beauiful Chilmark Cottage Close to Beaches
Distance to beach: 3.4 mi To Lucy Vincent Beach
Summer:
$3,500/wk
Off Season:
$3,500/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 to Lucy Vincent Beach - 10 min drive
1 review read review
Summer:
$1,475 - $1,725/wk
Off Season:
$600 - $1,725/wk

Chilmark vacation rentals that sleep 6

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:
$1,500 - $2,800/wk
$8,000/mo
Off Season:
$1,200 - $2,500/wk
$5,000 - $5,500/mo
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
11 reviews read reviews
Summer:
$600 - $1,000/night
$3,500 - $6,000/wk
$20,000 - $24,000/mo
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
Charming Chilmark Home/CENTRAL AIR
Distance to beach: 3 miles to Lucy Vincent; 3.5 miles to Squibnocket
1 review read review
Summer:
$1,800 - $3,000/wk
Off Season:
$1,800 - $2,000/wk
$5,000/mo
Chilmark
ID 26542
3 BR
2 baths
Sleeps 6
NEW RATES! A/C, QUANSOO Beach key,4 boats, waterfront
NEW RATES! A/C, QUANSOO Beach key,4 boats, waterfront
Distance to beach: Quansoo Beach w/key 7/10 mile drive, 4/10 by water
2 reviews read reviews
OWNER SPECIAL:
NEWLY REDUCED rental RATES w/ confirmed reservation 8/11-18 FERRY TIX available.
Summer:
$7,000 - $10,000/wk
Off Season:
$5,500/wk
Menemsha (Chilmark)
ID 17311
Summer:
$2,000 - $3,200/wk
Off Season:
$1,200 - $2,100/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 - $5,000/mo
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 - $6,000/wk
Off Season:
$2,250 - $5,750/wk
Quansoo Road across from Quans
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: Walk or drive to South Beach or Tisbury Great Pond
4 reviews read reviews
Summer:
$2,700 - $3,600/wk
Off Season:
$2,500 - $3,300/wk

Chilmark vacation rentals that sleep 5

Chilmark
ID 32649
3 BR
2 baths
Sleeps 5
Hilltop 3BR. Perfect for Small Family or Couples!
Hilltop 3BR. Perfect for Small Family or Couples!
Distance to beach: 10 minute drive Lucy Vincent Beach and 15 minute drive Squibnocket Beach
Summer:
$2,000/wk
$7,500/mo
Off Season:
$2,000/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:
$2,400 - $3,000/wk
Off Season:
$1,400 - $2,700/wk

Chilmark vacation rentals that sleep 4

Menemsha (Chilmark)
ID 17189
2 BR
1 bath
Sleeps 4
Menemsha Harbor Cottage: Tilton House - discounted week
Menemsha Harbor Cottage: Tilton House - discounted week
Distance to beach: less than 2/10ths of a mile to Menemsha Beach
1 review read review
Summer:
$1,700 - $2,400/wk
Off Season:
$1,200 - $1,800/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
15 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:
$900 - $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
39 reviews read reviews
Summer:
$1,800 - $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:
$1,000 - $1,500/wk