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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.

43 Vacation Properties in Chilmark
Sleeps

Chilmark vacation rentals that sleep 12

Chilmark
ID 17283
5 BR
3 baths
Sleeps 12
5 Acre Estate with 5 Bedroom 3 Bath Home in Chilmark
5 Acre Estate with 5 Bedroom 3 Bath Home in Chilmark
Distance to beach: 4 miles - Lucy Vincent; 1 mile-Great Rock Bight
4 reviews read reviews
Summer:
$7,000 - $9,800/wk
Off Season:
$4,200 - $7,000/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
4 reviews read reviews
OWNER SPECIAL:
Enjoy 10% off of rental rate for remaining August weeks--only for a limited time!
Summer:
$4,500 - $5,500/wk
Off Season:
$4,000 - $4,500/wk
5

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:
$4,500 - $6,000/wk
Off Season:
$3,000 - $35,000/wk
3
Chilmark
ID 38567
5 BR
2 baths
Sleeps 10
The Field House/Walk to Pond
The Field House/Walk to Pond
Distance to beach: Walk to Chilmark Pond; 2.3mi Lucy Vincent Beach
Summer:
$6,000 - $7,500/wk
$30,000/mo
Off Season:
$450 - $860/night
$3,150 - $6,000/wk
$15,450 - $24,000/mo
3
Menemsha
ID 38302
4 BR
3 baths
Sleeps 10
The Barn w/ Views of Menemsha and Aquinnah/Walk to Beach
The Barn w/ Views of Menemsha and Aquinnah/Walk to Beach
Distance to beach: 4/10ths of a mile Menemsha Public Beach and 2 miles Lucy Vincent Beach
4 reviews read reviews
Summer:
$8,000 - $8,500/wk
Off Season:
$800 - $1,200/night
$5,000 - $8,500/wk
$20,000 - $24,000/mo
11

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:
$30,000 - $35,000/wk
Off Season:
$25,000 - $28,000/wk
3
Chilmark
ID 37187
4 BR
3 ½ baths
Sleeps 9
Secluded Family Home in the Hills of Chilmark/8+ acres
Secluded Family Home in the Hills of Chilmark/8+ acres
Distance to beach: 4 mi to Lucy Vincent Beach and 5 mi to Squibnocket Beach
2 reviews read reviews
Summer:
$5,000 - $7,000/wk
$20,000/mo
Off Season:
$600 - $1,000/night
$4,000 - $5,000/wk
$10,000 - $20,000/mo
6

Chilmark vacation rentals that sleep 8

Chilmark
ID 7128
4 BR
2 baths
Sleeps 8
Deck House w/Windows Galore + Tennis & Chilmark Beach Access
Deck House w/Windows Galore + Tennis & Chilmark Beach Access
Distance to beach: 3.4 miles to Lucy Vincent Beach, 6 to Squibnocket
7 reviews read reviews
OWNER SPECIAL:
No-worries ten-day stay WITH FERRY RESERVATIONS! August 13-23. Write for info.
Summer:
$500 - $850/night
$5,000 - $6,000/wk
$19,000/mo
Off Season:
$400 - $500/night
$2,800 - $5,000/wk
6
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:
$5,000 - $6,000/wk
4
Chilmark, Marthas Vineyard
ID 13075
4 BR
2 baths
Sleeps 8
Middle Road , Chilmark , Marthas Vineyard.
Middle Road , Chilmark , Marthas Vineyard.
Distance to beach: Apx. 3- 5 miles. Lucy Vincent & Squibnocket bea
Summer:
$3,500 - $5,600/wk
Off Season:
$3,500 - $4,700/wk
Chilmark
ID 33082
4 BR
3 baths
Sleeps 8
Idyllic Chilmark Home With Spa Pool
Idyllic Chilmark Home With Spa Pool
Distance to beach: 1.8 mi to Lucy Vincent Beach
Summer:
$12,400 - $13,500/wk
Off Season:
$4,800 - $8,300/wk
Abel's Hill
ID 37384
4 BR
2 ½ baths
Sleeps 8
Lovely Chilmark Home on Abel's Hill - Private Beach, Tennis
Lovely Chilmark Home on Abel's Hill - Private Beach, Tennis
Distance to beach: 2.4 mi to Lucy Vincent Beach and key access to Abels Hill Beach (Private)
2 reviews read reviews
Summer:
$8,000 - $12,000/wk
Off Season:
$4,000 - $11,000/wk
Spring Point
ID 37993
4 BR
2 baths
Sleeps 8
Spectacular Chilmark Sunset Water Views,Private Beach/Tennis
Spectacular Chilmark Sunset Water Views,Private Beach/Tennis
Distance to beach: 5 Min Walk-Private Assoc Beach;5.8 mi Lucy Vincent
Summer:
$5,500 - $9,500/wk
Off Season:
$5,000 - $5,500/wk
6
Chilmark
ID 37880
Summer:
$8,500/wk
Off Season:
$6,000 - $8,250/wk
Chilmark
ID 38448
4 BR
2 baths
Sleeps 8
Up-island Historic Chilmark Farm House
Up-island Historic Chilmark Farm House
Distance to beach: 3.3 mi to Lucy Vincent Beach
Summer:
$9,000/wk
6
Chilmark
ID 36142
4 BR
3 baths
Sleeps 8
Mid Century - Lots of Light - Lucy Vincent Beach!
Mid Century - Lots of Light - Lucy Vincent Beach!
Distance to beach: 1 mi to Lucy Vincent Beach and 3 mi to Menemsha Public Beach
1 review read review
Off Season:
$600 - $950/night
$4,200 - $7,000/wk
$9,500 - $23,500/mo
6
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: 1/4 mile to beach Lucy Vincent Beach and Brief walk & quick canoe ride to L. VIncent Beach
12 reviews read reviews
Summer:
$4,500 - $7,750/wk
Off Season:
$3,250 - $6,000/wk
5
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
Summer:
$1,675 - $1,950/wk
Off Season:
$700 - $1,850/wk
2

Chilmark vacation rentals that sleep 7

Chilmark
ID 37658
4 BR
2 baths
Sleeps 7
Quiet, Bright and Open - Spacious/Central A/C
Quiet, Bright and Open - Spacious/Central A/C
Distance to beach: 3.2 mi to Lucy Vincent Beach and 5.8 mi to Squibnocket Beach
Summer:
$6,000 - $7,000/wk
10

Chilmark vacation rentals that sleep 6

Menemsha
ID 38714
4 BR
3 ½ baths
Sleeps 6
Private Menemsha Home with Water View
Private Menemsha Home with Water View
Distance to beach: .4 mi by path or.7 by road to Menemsha Public Beach
7 reviews read reviews
Summer:
$950 - $1,000/night
$6,650/wk
$2,900 - $29,450/mo
Off Season:
$650 - $850/night
$4,550 - $6,650/wk
$20,000 - $28,500/mo
3
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
14 reviews read reviews
OWNER SPECIAL:
Ferry car reservation includ. Sun 6/30/24 - Sun 7/7/24.
Summer:
$4,000 - $7,000/wk
Off Season:
$2,500 - $5,000/wk
8
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:
$3,500 - $4,000/wk
Off Season:
$2,200 - $4,000/wk
4
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
6 reviews read reviews
OWNER SPECIAL:
July 15-21 (Mon-Sun) in peak season with ferry reservation included!
Summer:
$720/night
$3,550 - $5,000/wk
Off Season:
$480 - $510/night
$3,550/wk
7
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
12 reviews read reviews
Summer:
$3,500 - $4,750/wk
Off Season:
$2,200 - $3,350/wk
6
Chilmark
ID 37690
3 BR
2 baths
Sleeps 6
Charming 3 BR in the Heart of Chilmark
Charming 3 BR in the Heart of Chilmark
Distance to beach: 2.4 mi to Lucy Vincent Beach
Summer:
$3,200 - $5,400/wk
Off Season:
$3,000 - $4,000/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:
$3,750 - $4,250/wk
Off Season:
$450 - $500/night
$2,000 - $3,500/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
1 review read review
Summer:
$11,000 - $12,000/wk
Off Season:
$7,500 - $11,500/wk
Chilmark
ID 38233
3 BR
2 baths
Sleeps 6
In the Woods, Next to trails, Minutes to Chilmark Beaches
In the Woods, Next to trails, Minutes to Chilmark Beaches
Distance to beach: 2.5 mi to Lucy Vincent Beach and 2.5 mi to Squibnocket Beach
Summer:
$3,500/wk
$12,000/mo
7
Guest Cottage
ID 36122
2 BR
1 bath
Sleeps 6
Guest Cottage, Art Shack & Little Cottage; june 29-july 18
Guest Cottage, Art Shack & Little Cottage; june 29-july 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:
$1,800 - $2,500/wk
6
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
Chilmark
ID 38587
2 BR
1 bath
Sleeps 6
Chilmark Cottage Escape
Chilmark Cottage Escape
Distance to beach: 4.3 mi to Lucy Vincent Beach
Summer:
$2,600/wk
Off Season:
$2,100/wk
6

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:
$1,700 - $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
10 reviews read reviews
Summer:
$571 - $642/night
$3,000 - $4,500/wk
$17,000 - $19,000/mo
Off Season:
$225 - $425/night
$1,500 - $3,000/wk
$6,000 - $6,500/mo
3
Walk to private QBA beach
ID 10393
2 BR
2 baths
Sleeps 5
QBA keys & 1 m. to beach
QBA keys & 1 m. to beach
Distance to beach: Walk or drive to South Beach or Tisbury Great Pond
7 reviews read reviews
6

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.
13 reviews read reviews
Summer:
$4,500 - $6,000/wk
Off Season:
$2,500 - $5,500/wk
3
Menemsha (Chilmark)
ID 17189
2 BR
1 bath
Sleeps 4
Menemsha Harbor: Tilton House -Some Boat Reservations avail
Menemsha Harbor: Tilton House -Some Boat Reservations avail
Distance to beach: .2 Mile Menemsha Public Beach and 2.4 Miles Lucy Vincent Beach
1 review read review
Summer:
$2,800 - $3,300/wk
Off Season:
$2,200 - $3,300/wk
4
Tisbury Great Pond
ID 32998
2 BR
2 baths
Sleeps 4
Ferry Tix, Quansoo Beach Key, A/C, 4 kayaks, 1 paddleboard
Ferry Tix, Quansoo Beach Key, A/C, 4 kayaks, 1 paddleboard
Distance to beach: 1/2 mile by boat (4 kayaks), 7/10 mile foot/drive
2 reviews read reviews
Summer:
$3,500 - $4,750/wk
Off Season:
$2,950 - $3,750/wk
2
Chilmark
ID 37741
2 BR
2 baths
Sleeps 4
'Blueberry House' in Beautiful Up-Island Martha's Vineyard
'Blueberry House' in Beautiful Up-Island Martha's Vineyard
Distance to beach: 2 mi to Menemsha Public Beach and 2 mi to Lucy Vincent Beach
Summer:
$4,250 - $5,500/wk
Off Season:
$350 - $500/night
$2,450 - $4,750/wk
Menemsha
ID 37873
2 BR
2 baths
Sleeps 4
Comfortable House Overlooking Menemsha: Waterviews + Sunsets
Comfortable House Overlooking Menemsha: Waterviews + Sunsets
Distance to beach: 5/10 mile walk on a path to Menemsha Public Beach and 2 1/2 miles to Lucy Vincent Beach
5 reviews read reviews
Summer:
$3,500/wk
$14,000/mo
2
Chilmark
ID 38624
2 BR
1 bath
Sleeps 4
Boat House on the Water in Chilmark
Boat House on the Water in Chilmark
Distance to beach: Chockers Beach is just a few feet down the path
Summer:
$5,000 - $5,200/wk
Off Season:
$3,000 - $5,200/wk
Chilmark
ID 34547
2 BR
2 baths
Sleeps 4
Charming New Construction w/Central AC in Chilmark
Charming New Construction w/Central AC in Chilmark
Distance to beach: 4 mi to Lucy Vincent Beach
4
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:
$2,000 - $2,300/wk
Off Season:
$1,300 - $2,000/wk
2

Chilmark vacation rentals that sleep 2

Menemsha (Chilmark)
ID 18146
1 BR
1 bath
Sleeps 2
Menemsha Harbor - Davis House -Some boat reservations avail.
Menemsha Harbor - Davis House -Some boat reservations avail.
Distance to beach: .2 Mile Menemsha Public Beach and 2.4 Miles Lucy Vincent Beach
6 reviews read reviews
Summer:
$1,900 - $2,300/wk
Off Season:
$1,300 - $2,300/wk
6