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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.

42 properties

Chilmark Guide

A fee-based feature highlighting availability within the next 4 weeks.

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

ID 40589

5 BR

1 ½ bath

Sleeps 12

Private Waterfront Retreat w/ Panoramic Views on 11.4 Acres

Distance to beach: On Private Beach

Summer:
$6,900/wk

Off Season:
$4,200 - $6,000/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:
$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:

Drastic discounts (shown in pricing).

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

ID 36536

4 BR

3 ½ baths

Sleeps 10

Chilmark Retreat, Two August Weeks Left!

Distance to beach: 1 1/2 miles Lucy Vincent Beach and 2.2 miles

OWNER SPECIAL:

Ferry Tickets available for August 23rd Week! Only two weeks Left!

Summer:
$7,000/wk
$7,000/mo

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:
$25,000 - $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 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 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 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

LAST MINUTE ALERT 7/20 - 7/27

OWNER SPECIAL:

July 13-20 available, rate reduced from $1950 to $1550, andtlu.

Summer:
$1,550 - $1,975/wk

Off Season:
$725 - $1,875/wk

Chilmark vacation rentals that sleep 6

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

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

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

Menemsha (Chilmark)

ID 17311

3 BR

1 bath

Sleeps 6

Menemsha Village - Sunset House. Recent opening: 7/24-7/31

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

5.02 reviews

OWNER SPECIAL:

Last minute opening due to cancelation. 7/24-7/31. Price reduced to $2500.00 plus fees and taxes.

Summer:
$2,500 - $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
$5,000/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:
$3,500 - $4,750/wk
$18,200 - $23,500/mo

Off Season:
$2,450 - $4,500/wk
$11,600/mo

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:
$2,500 - $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

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
$5,600 - $6,825/wk

Off Season:
$650 - $850/night
$5,250 - $6,825/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:
$3,775 - $3,925/wk

Off Season:
$3,775 - $3,925/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

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

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 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

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

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:
$2,300/wk

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