Your browser's security settings have disabled Javascript, which is required to use this web site effectively.
Please alter your security settings. Click here to see how.
   

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.

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

Chilmark vacation rentals that sleep 14

Abel's Hill
ID 38960
7 BR
3 ½ baths
Sleeps 14
Private Family Compound, Seconds from the Beach
Private Family Compound, Seconds from the Beach
Distance to beach: .1 miles to South Beach, Chilmark
Summer:
$10,000 - $13,000/wk
Off Season:
$8,000 - $13,000/wk
6

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
OWNER SPECIAL:
Round trip Saturday to Saturday transferable ferry tickets available.
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 mile Lucy Vincent Beach and 2 miles Menemsha Public Beach
5 reviews read reviews
OWNER SPECIAL:
2025 bookings now available!
Summer:
$4,500 - $5,500/wk
Off Season:
$4,000 - $4,500/wk
6

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
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:
$7,000 - $85,000/wk
Off Season:
$800 - $1,200/night
$4,000 - $8,500/wk
$22,000 - $24,000/mo
10
Allen Farm Hilltop Farmhouse
ID 37535
3 BR
3 baths
Sleeps 10
Allen Farm Hilltop Farmhouse/Sweeping Ocean Views
Allen Farm Hilltop Farmhouse/Sweeping Ocean Views
Distance to beach: .25 mi to Lucy Vincent Beach
Summer:
$12,500/wk
$12,500/mo
Off Season:
$12,500/wk
6

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 vacation rentals that sleep 8

off Tea Lane
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:
Last-minute availability with price drop! June 22-July 5, min. 4 nights, sleeps 8, $500 per night!
Summer:
$500 - $850/night
$3,000 - $6,000/wk
$19,000/mo
Off Season:
$3,500 - $4,750/wk
5
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:
$4,000 - $6,000/wk
Off Season:
$4,000 - $6,000/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:
$4,875 - $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:
$7,500 - $12,000/wk
Off Season:
$4,500 - $11,000/wk
Chilmark
ID 37880
Summer:
$6,000 - $8,500/wk
Off Season:
$5,915 - $6,500/wk
Chilmark
ID 38979
4 BR
3 ½ baths
Sleeps 8
Contemporary Vacation Rental in Chilmark with a Pool 2017
Contemporary Vacation Rental in Chilmark with a Pool 2017
Distance to beach: 3.9 mi to Lucy Vincent Beach and Quansoo Association Beach about 2 Miles
Summer:
$9,000 - $11,000/wk
Off Season:
$5,500 - $10,000/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:
$5,000 - $7,000/wk
Off Season:
$700 - $800/night
$4,000 - $5,000/wk
4
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
1 review read review
OWNER SPECIAL:
7/19 - 7/26 and 8/23 - 8/30: Free Ferry Reservation with confirmed booking!
Summer:
$5,500 - $9,500/wk
Off Season:
$5,000 - $5,500/wk
5
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:
$6,000 - $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
LAST MINUTE ALERT 7/14 - 7/21
OWNER SPECIAL:
Prime July weeks available! Short drive to Lucy Vincent Beach- wkly rates have been discounted!
Summer:
$1,250 - $1,950/wk
Off Season:
$700 - $1,850/wk
2

Chilmark vacation rentals that sleep 7

Menemsha
ID 39135
4 BR
2 ½ baths
Sleeps 7
Private Menemsha Rental Close To Harbor, Town And Beach!
Private Menemsha Rental Close To Harbor, Town And Beach!
Distance to beach: 1.0 mi to Menemsha Public Beach
Summer:
$3,000 - $4,500/wk
Off Season:
$3,000/wk
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
9

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
14 reviews read reviews
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:
$4,000/wk
Off Season:
$2,200 - $4,000/wk
3
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
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 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:
$4,364 - $12,000/wk
Off Season:
$8,500 - $11,500/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
12 reviews read reviews
Summer:
$13,000/wk
Off Season:
$5,000 - $6,000/wk
4
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
Guest Cottage
ID 36122
2 BR
1 bath
Sleeps 6
Guest Cottage, Art Shack & Cottage/ Avail Sept 22 - October
Guest Cottage, Art Shack & Cottage/ Avail Sept 22 - October
Distance to beach: 3.4 mi to Lucy Vincent Beach and 5 mi to Squibnocket Beach
3 reviews read reviews
Summer:
$2,000 - $3,000/wk
Off Season:
$1,800 - $2,500/wk
6
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 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.
14 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 Harborside Cottage. $500 off week of July 18-25.
Menemsha Harborside Cottage. $500 off week of July 18-25.
Distance to beach: .2 Mile Menemsha Public Beach and 2.4 Miles Lucy Vincent Beach
1 review read review
OWNER SPECIAL:
Price reduction by $500: One week from July 18th - 25th. Price as listed.
Summer:
$2,800 - $3,300/wk
Off Season:
$2,200 - $3,300/wk
3
Walk to private QBA beach
ID 10393
2 BR
2 baths
Sleeps 4
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
Summer:
$3,850 - $4,000/wk
Off Season:
$4,000/wk
6
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:
$3,200 - $3,500/wk
2
Chilmark
ID 34169
2 BR
2 baths
Sleeps 4
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
11 reviews read reviews
Summer:
$571 - $642/night
$3,000 - $4,500/wk
$14,000 - $19,000/mo
Off Season:
$225 - $300/night
$1,500 - $3,000/wk
$6,000 - $10,000/mo
3
South Side with Private Access
ID 36816
2 BR
1 bath
Sleeps 4
Small Beach Cottage With Water View and Grand Amenities
Small Beach Cottage With Water View and Grand Amenities
Distance to beach: 2.8 mi to Lucy Vincent Beach
OWNER SPECIAL:
Fair and Illumination week still available at this nice little beach house.
Summer:
$4,000 - $6,800/wk
Off Season:
$3,000 - $4,500/wk
3
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
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:
$350 - $750/night
$3,000 - $5,200/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:
$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:
$214/night
$1,300 - $2,300/wk
5