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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.

41 properties

Chilmark Guide

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

Distance to beach: 4 miles - Lucy Vincent; 1 mile-Great Rock Bight

5.04 reviews

Summer:
$7,700 - $10,150/wk

Off Season:
$4,920 - $10,150/wk

Chilmark vacation rentals that sleep 11

Chilmark

ID 30776

6 BR

1 ½ bath

Sleeps 11

Lucy Vincent House with Access to Private Beach

Distance to beach: 1/2 mile Lucy Vincent Beach and 2 miles Menemsha Public Beach

5.05 reviews

Summer:
$4,500 - $5,500/wk

Off Season:
$4,000 - $4,800/wk

Chilmark vacation rentals that sleep 10

Chilmark

ID 34003

5 BR

3 baths

Sleeps 10

Summer cottage w/spectacular views & access to private beach

Distance to beach: 2/10 mile to private beach on Menemsha Pond

4.915 reviews

Summer:
$4,500 - $6,000/wk

Off Season:
$3,500 - $5,000/wk

Chilmark

ID 29790

5 BR

3 baths

Sleeps 10

Water view, PRIVATE BLACK POINT BEACH KEY in Chilmark

Distance to beach: 1/2 mi Lucy Vincent Beach and BLACK POINT BEACH , squibnocket, menemsha

OWNER SPECIAL:

PRIME SUMMER WEEKS AVAILABLE luxurious homes reduced prices.

Summer:
$12,500 - $14,000/wk

Menemsha

ID 38302

4 BR

3 baths

Sleeps 10

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

Summer:
$8,000/wk

Off Season:
$600 - $1,200/night
$4,000 - $8,000/wk

Chilmark vacation rentals that sleep 9

Chilmark

ID 8790

5 BR

2 ½ baths

Sleeps 9

Nocket Downs, located in Blacksmith Valley

Distance to beach: 10 min. walk/Squibnocket; 2 mi/pvt. Aquinnah Beach

Summer:
$11,000 - $12,000/wk

Off Season:
$900 - $1,500/night
$6,000 - $10,000/wk

Chilmark - Quansoo Beach

ID 34329

4 BR

7 ½ baths

Sleeps 9

Chilmark Estate with Pool, Tennis Court, Private Beach

Distance to beach: Quansoo Private Beach - Beach Key

Summer:
$30,000 - $35,000/wk

Off Season:
$20,000 - $25,000/wk

Chilmark vacation rentals that sleep 8

Chilmark

ID 32622

4 BR

3 ½ baths

Sleeps 8

Chilmark 4BR Near Beaches and Other Activities

Distance to beach: 1 mile to Menemsha Public Beach

5.02 reviews

Summer:
$4,000 - $7,000/wk

Off Season:
$700 - $800/night
$3,500 - $6,000/wk
$2,500 - $8,000/mo

Spring Point

ID 37993

4 BR

2 baths

Sleeps 8

Spectacular Chilmark Sunset Water Views,Private Beach/Tennis

Distance to beach: 5 Min Walk-Private Assoc Beach;5.8 mi Lucy Vincent

5.01 review

OWNER SPECIAL:

Sept Weekend Special: Stay Fri-Sun for just $1295 (including cleaning!). Parties of 5 or less.

Summer:
$5,500 - $9,500/wk

Off Season:
$5,000 - $5,500/wk

Chilmark

ID 37880

4 BR

2 ½ baths

Sleeps 8

Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket

Distance to beach: 2/10 mi to Squibnocket Beach

5.01 review

Summer:
$7,500 - $8,500/wk
$32,000 - $36,000/mo

Off Season:
$6,000 - $7,500/wk

Chilmark

ID 22789

4 BR

1 ½ bath

Sleeps 8

Windy Gates Barn

Distance to beach: "Windy Gates" private beach with 80' cliff-view

Summer:
$3,000 - $5,000/wk

Chilmark

ID 40559

4 BR

4 baths

Sleeps 8

Amazing Ocean Views!!! Elegant Home, Ferry Tickets Avail

Distance to beach: 2.0 mi to Lucy Vincent Beach and Private beach shared with one other home

Summer:
$12,000/wk

Off Season:
$12,000/wk

Chilmark

ID 12106

3 BR

1 ½ bath

Sleeps 8

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

4.913 reviews

Summer:
$4,500 - $8,000/wk

Off Season:
$3,000 - $7,500/wk

Off Middle Road, Chilmark

ID 15956

3 BR

2 baths

Sleeps 8

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.

4.812 reviews

Summer:
$3,500 - $5,000/wk

Off Season:
$3,000 - $5,000/wk

Chilmark

ID 32322

3 BR

2 ½ baths

Sleeps 8

Gorgeous Remodeled High End Chilmark Home

Distance to beach: 1.7 miles Lucy Vincent Beach

Summer:
$5,500 - $6,500/wk

Off Season:
$5,000 - $5,500/wk

Chilmark

ID 32594

3 BR

2 baths

Sleeps 8

Beautiful Chilmark Cottage Close to Beaches

Distance to beach: 3.4 mi To Lucy Vincent Beach

Summer:
$3,800 - $4,000/wk

Off Season:
$3,500 - $4,000/wk

Chilmark

ID 4383

2 BR

1 bath

Sleeps 8

Secluded Unique Natural Vacation House

Distance to beach: Three miles Lucy Vincent Beach and 5 miles Squibnocket Beach

4.84 reviews

Summer:
$1,700 - $1,975/wk

Off Season:
$725 - $1,875/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

Distance to beach: New - path to the beach - or boat to Lucy Vincent

5.012 reviews

OWNER SPECIAL:

Ferry tickets available for 8/24-8-31 for purchase.- price now $9,500.

Summer:
$9,500/wk

Off Season:
$5,000 - $7,500/wk

Menemsha

ID 13297

3 BR

2 baths

Sleeps 6

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

5.014 reviews

OWNER SPECIAL:

Last week in August 2025 just became available. Can include car ferry rez.

Summer:
$4,000 - $7,000/wk

Off Season:
$3,000 - $4,000/wk

off MeetingHouse Road

ID 36122

3 BR

1 bath

Sleeps 6

Guest Cottage, Art Shack & Sleeping Cottage Aug 22-30

Distance to beach: 3.4 mi to Lucy Vincent Beach and 5 mi to Squibnocket Beach

5.03 reviews

Summer:
$2,000 - $3,000/wk

Off Season:
$1,800 - $2,500/wk

Chilmark

ID 36339

3 BR

2 ½ baths

Sleeps 6

Charming Perfect-The Only Beachfront Cottage for Rent

Distance to beach: On Private Beach; .8 mi to Squibnocket Beach

5.02 reviews

OWNER SPECIAL:

New weekly rates for July and August! Get in touch today.

Summer:
$8,250 - $11,000/wk

Off Season:
$7,000 - $9,950/wk

Chilmark

ID 26542

3 BR

2 baths

Sleeps 6

FERRY TIX Waterfront,A/C,Quansoo key,4 kayaks,1 paddleboard

Distance to beach: Quansoo Beach 7/10 mile drive, 4/10 via boats

5.02 reviews

Summer:
$13,500 - $16,500/wk

Menemsha

ID 38714

3 BR

3 ½ baths

Sleeps 6

Fully Renovated w/ Amazing Waterviews of Vineyard Sound

Distance to beach: .4 mi by path or.7 by road to Menemsha Public Beach

12 reviews

Summer:
$875 - $1,000/night
$6,825/wk

Off Season:
$650 - $850/night
$4,550 - $6,825/wk

Chilmark

ID 40449

3 BR

2 baths

Sleeps 6

Enjoy Menemsha Sunsets at this Newly Renovated 3BR Cottage

Distance to beach: 0.4 mi to Menemsha Public Beach

Summer:
$2,000 - $2,500/night
$8,000 - $10,000/wk

Off Season:
$2,000 - $2,500/night
$7,000 - $8,000/wk

Menemsha (Chilmark)

ID 17311

3 BR

1 bath

Sleeps 6

Menemsha Village - Sunset House

Distance to beach: .2 Mile Menemsha Public Beach and 2.4 Miles Lucy Vincent Beach

5.02 reviews

Summer:
$3,700/wk

Off Season:
$2,400 - $2,600/wk

Chilmark

ID 22082

3 BR

2 baths

Sleeps 6

Contemporary Style w/Sunset Ocean Views

Distance to beach: 1 mile Menemsha Public Beach and 3 miles Lucy Vincent Beach

4.77 reviews

Summer:
$645 - $800/night
$4,500 - $5,600/wk

Off Season:
$510 - $715/night
$3,800 - $5,000/wk

Chilmark

ID 30704

3 BR

1 ½ bath

Sleeps 6

Molly's Cottage: Views of Menemsha Creek & Pond

Distance to beach: 1/4 mile to Menemsha Beach

Summer:
$4,250/wk

Off Season:
$400 - $500/night
$600 - $2,500/wk

Chilmark

ID 33049

3 BR

2 baths

Sleeps 6

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

4.912 reviews

Summer:
$3,250 - $4,750/wk
$18,200 - $23,500/mo

Off Season:
$2,200 - $4,500/wk
$11,400 - $11,600/mo

Menemsha

ID 37434

3 BR

2 baths

Sleeps 6

Menemsha Knoll Cottage

Distance to beach: .5 milies Menemsha Public Beach and Squibnocket Beach

Summer:
$7,200/wk

Off Season:
$5,225 - $7,200/wk

Chilmark

ID 40019

3 BR

3 baths

Sleeps 6

Charming Chilmark Rental Near West Tisbury Center!

Distance to beach: 3.9 mi to Lucy Vincent Beach

Summer:
$3,675 - $3,925/wk

Off Season:
$3,675 - $3,925/wk

Chilmark vacation rentals that sleep 5

Chilmark

ID 39825

3 BR

1 ½ bath

Sleeps 5

1840's farm house

Distance to beach: 0.5 mi to Lucy Vincent Beach

Summer:
$2,850 - $3,000/wk
$11,400 - $12,000/mo

Off Season:
$2,850 - $3,000/wk

Chilmark

ID 23618

2 BR

1 bath

Sleeps 5

Menemsha Gem with Vineyard Sound Waterview

Distance to beach: 2/10 mile Menemsha Beach

Summer:
$3,000 - $3,300/wk

Off Season:
$1,700 - $3,000/wk

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

Distance to beach: See below. Lucy Vincent Beach and 100 yards to dock, 6 min. paddle to beach.

5.014 reviews

Summer:
$4,500 - $6,000/wk

Off Season:
$2,750 - $6,000/wk

Walk to private QBA beach

ID 10393

2 BR

2 baths

Sleeps 4

I mile to locked gate beach & Great Tisbury Pond.

Distance to beach: Walk or drive to South Beach or Tisbury Great Pond

4.17 reviews

Summer:
$3,300 - $3,900/wk

Off Season:
$3,000 - $3,800/wk

Tisbury Great Pond

ID 32998

2 BR

2 baths

Sleeps 4

Quansoo Beach key, A/C, 4 kayaks,1 paddleboard

Distance to beach: 1/2 mile by boat (4 kayaks), 7/10 mile foot/drive

5.04 reviews

OWNER SPECIAL:

Unexpected Availability – Two August Weeks Now Open! Flexible Start Dates Available – Inquire Today!

Summer:
$3,500 - $4,750/wk

Off Season:
$2,900 - $3,250/wk

Chilmark

ID 34169

2 BR

2 baths

Sleeps 4

Chilmark Casita - New Listing! Newly Renovated w/Central AC!

Distance to beach: 4.6 mi to Lucy Vincent Beach and Squibnocket Beach

4.914 reviews

Summer:
$300 - $450/night
$3,000 - $4,500/wk
$12,000 - $16,000/mo

Off Season:
$350 - $500/night
$1,500 - $4,500/wk
$4,000 - $8,000/mo

Chilmark

ID 39284

2 BR

1 bath

Sleeps 4

Contemporary Cottage in Chilmark

Distance to beach: 4.6 mi to Lucy Vincent Beach

Summer:
$3,000 - $3,600/wk

Off Season:
$400 - $495/night
$2,600 - $3,000/wk

Menemsha (Chilmark)

ID 17189

2 BR

1 bath

Sleeps 4

Menemsha - Tilton House August 28th - Sept. 4th available.

Distance to beach: .2 Mile Menemsha Public Beach and 2.4 Miles Lucy Vincent Beach

5.01 review

Summer:
$2,500 - $3,300/wk

Off Season:
$2,200 - $3,300/wk

Chilmark

ID 40083

2 BR

1 bath

Sleeps 4

Beetlebung Guest House/Access to Tennis Courts & Hiking

Distance to beach: 1.4 mi to Menemsha Public Beach and Lucy Vincent beach and Squibnocket beach close

Summer:
$2,000 - $2,500/wk

Off Season:
$200 - $285/night
$1,200 - $2,000/wk

Chilmark

ID 4029

1 BR

1 bath

Sleeps 4

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

Chilmark vacation rentals that sleep 2

Menemsha (Chilmark)

ID 18146

1 BR

1 bath

Sleeps 2

Menemsha -Davis House. 8/14-8/21 available w/ boat reserv.

Distance to beach: .2 Mile Menemsha Public Beach and 2.4 Miles Lucy Vincent Beach

5.06 reviews

Summer:
$2,100 - $2,300/wk

Off Season:
$1,600 - $2,300/wk