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Martha's Vineyard Vacation Rentals

Chilmark Vacation Rentals

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.

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

Chilmark vacation rentals that sleep 11

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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:
September weeks still available! 2024 dates to open July 1st!
Summer:
 $4,500 - $5,000/wk
Off Season:
 $3,500 - $4,500/wk
4

Chilmark vacation rentals that sleep 10

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Abels Hill
ID 36815
7 BR
4 ½ baths
Sleeps 10
Historical Waterview Home in Abels Hill
Historical Waterview Home in Abels Hill
Distance to beach: 2.1 mi to Lucy Vincent Beach
Summer:
 $16,000/wk
Off Season:
 $16,000/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
Oceanview Farm
ID 36802
5 BR
4 baths
Sleeps 10
Oceanview Farm//Hilltop with South Shore Views
Oceanview Farm//Hilltop with South Shore Views
Distance to beach: 1.9 mi to Lucy Vincent Beach
Summer:
 $10,000 - $15,000/wk
Off Season:
 $10,000/wk
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:
 $12,000/wk
 $60,000 - $80,000/mo
Off Season:
 $12,000/wk
 $60,000 - $80,000/mo

Chilmark vacation rentals that sleep 9

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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
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
Off Season:
 $600 - $750/night
 $4,000 - $5,000/wk
 $18,000 - $20,000/mo

Chilmark vacation rentals that sleep 8

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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: 2/10 mi Abel's Hill Private Beach/free parking
LAST MINUTE ALERT 7/1 - 7/8 and 7/8 - 7/15
OWNER SPECIAL:
July recently freed up. Be in touch by June 15 for reduced rates.
Summer:
 $7,000 - $7,700/wk
 $26,000 - $36,000/mo
Off Season:
 $5,000 - $7,000/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:
 $6,000 - $7,000/wk
Off Season:
 $600 - $900/night
 $4,000 - $6,000/wk
4
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:
 $9,000 - $12,000/wk
Off Season:
 $4,500 - $11,000/wk
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
Summer:
 $10,850 - $11,830/wk
 $50,000 - $52,300/mo
Off Season:
 $600 - $950/night
 $4,000 - $7,000/wk
 $9,500 - $30,000/mo
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
OWNER SPECIAL:
Last minute cancellation.
Summer:
 $4,000 - $7,250/wk
Off Season:
 $3,000 - $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
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:
 $1,625 - $1,875/wk
Off Season:
 $650 - $1,675/wk
2

Chilmark vacation rentals that sleep 7

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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
OWNER SPECIAL:
JUST LISTED! Reduced rates for August 2023.
Summer:
 $1,000/night
 $5,000 - $8,000/wk
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 Squibnocket Beach 5.4 miles away
Summer:
 $2,940 - $3,675/wk
 $15,000/mo
Off Season:
 $2,500 - $3,150/wk
 $10,000/mo
1

Chilmark vacation rentals that sleep 6

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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 - $3,500/wk
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:
 $2,000 - $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
OWNER SPECIAL:
$500 off listed price on any week in June!
Summer:
 $3,500 - $4,750/wk
Off Season:
 $2,700 - $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
OWNER SPECIAL:
Last minute availability- Special $7000/week.
Summer:
 $10,500/wk
Off Season:
 $7,000 - $10,500/wk
Chilmark: Quansoo Bright and A
ID 37503
3 BR
2 ½ baths
Sleeps 6
Chilmark: Quansoo- Bright & Airy Post & Beam
Chilmark: Quansoo- Bright & Airy Post & Beam
Distance to beach: 10 minutes Lambert's Cove Beach and 10 minutes Lucy Vincent Beach
Summer:
 $5,000 - $6,500/wk
Off Season:
 $5,000/wk
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:
 $3,000 - $5,200/wk
Off Season:
 $2,000 - $3,800/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
Guest Cottage
ID 36122
2 BR
1 bath
Sleeps 6
Guest Cottage, Art Shack & Little Cottage; Sept 5-Oct 7
Guest Cottage, Art Shack & Little Cottage; Sept 5-Oct 7
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

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Walk to private QBA beach
ID 10393
2 BR
2 baths
Sleeps 5
Rustic cottage: locked gate
Rustic cottage: locked gate
Distance to beach: Walk or drive to South Beach or Tisbury Great Pond
7 reviews read reviews
Summer:
 $3,600 - $4,000/wk
Off Season:
 $3,000 - $3,500/wk
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
8 reviews read reviews
Summer:
 $2,500 - $5,000/wk
 $18,000 - $24,500/mo
Off Season:
 $250 - $428/night
 $1,500 - $4,000/wk
 $13,000/mo
3
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 vacation rentals that sleep 4

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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.
12 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
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:
 $3,600 - $4,500/wk
Off Season:
 $2,950 - $3,500/wk
2
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
Summer:
 $5,500/wk
4
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:
 $775/night
 $4,750 - $6,000/wk
 $20,000 - $26,000/mo
Off Season:
 $375 - $500/night
 $2,750 - $4,750/wk
 $20,000 - $23,000/mo
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
 $1,800 - $2,400/wk
2
South Side with Private Access
ID 36816
2 BR
1 bath
Sleeps 4
Small Beach Cottage with Grand Amenities
Small Beach Cottage with Grand Amenities
Distance to beach: 2.8 mi to Lucy Vincent Beach
Summer:
 $5,800 - $6,800/wk
Off Season:
 $5,600 - $6,000/wk
3
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:
 $1,200 - $1,800/wk
2

Chilmark vacation rentals that sleep 2

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Menemsha (Chilmark)
ID 18146
1 BR
1 bath
Sleeps 2
Menemsha Harbor - Davis House
Menemsha Harbor - Davis House
Distance to beach: .2 Mile Menemsha Public Beach and 2.4 Miles Lucy Vincent Beach
6 reviews read reviews
LAST MINUTE ALERT 6/8 - 6/15
OWNER SPECIAL:
Price reduction: $500 off for now - June 8th. $250 off for June 8th - 15th.
Summer:
 $1,700 - $2,100/wk
Off Season:
 $1,400 - $1,900/wk
4