Bedrooms

Clear

Done

Price

WAny

per nightAny

Weeks to Search

Sep 17

Sep 24

Oct 1

Oct 8

Sleeps

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.

Chilmark Travel Guide

36 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

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

4 reviews read reviews

Summer:
$7,350 - $10,150/wk

Off Season:
$4,200 - $7,350/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 reviews read reviews

OWNER SPECIAL:

10% off of 2025 weeks if booked between now and December 31st!

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

15 reviews read reviews

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

Off Season:
$3,500 - $5,000/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 read reviews

Off Season:
$850 - $1,200/night
$4,000 - $8,500/wk
$22,000 - $24,000/mo

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

Distance to beach: Quansoo Private Beach - Beach Key

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

Off Season:
$28,000/wk

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

Distance to beach: 3.4 miles to Lucy Vincent Beach, 6 to Squibnocket

8 reviews read reviews

Summer:
$4,000 - $5,500/wk

Off Season:
$300 - $500/night
$2,000 - $4,500/wk

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

2 reviews read reviews

Summer:
$5,500 - $7,000/wk

Off Season:
$700 - $800/night
$5,000 - $6,000/wk

Chilmark

ID 33082

4 BR

3 baths

Sleeps 8

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

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

1 review read review

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

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

Chilmark

ID 38979

4 BR

3 ½ baths

Sleeps 8

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:
$20,500 - $25,000/wk

Off Season:
$12,000 - $20,500/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

1 review read review

Off Season:
$5,915 - $6,500/wk

Chilmark

ID 12106

3 BR

2 baths

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

13 reviews read reviews

Summer:
$4,500 - $8,250/wk

Off Season:
$3,000 - $7,750/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.

12 reviews read reviews

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

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

3 reviews read reviews

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

Off Season:
$700 - $1,875/wk

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!

Distance to beach: 1.0 mi to Menemsha Public Beach

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

Off Season:
$3,000/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

12 reviews read reviews

Summer:
$14,000/wk

Off Season:
$5,500/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

14 reviews read reviews

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

Off Season:
$2,500 - $4,000/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

2 reviews read reviews

Summer:
$3,700/wk

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

12 reviews read reviews

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

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

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

2 reviews read reviews

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

Off Season:
$7,500 - $12,000/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

2 reviews read reviews

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

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

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 read reviews

Summer:
$6,825/wk

Off Season:
$650 - $850/night
$3,500 - $6,825/wk
$26,000 - $26,350/mo

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

7 reviews read reviews

OWNER SPECIAL:

Sign lease by Dec. 20 and we'll submit your ferry reservation in the SSA early headstart program.

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

Off Season:
$510 - $715/night
$3,550 - $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

Off Season:
$500/night
$2,750 - $3,000/wk

Guest Cottage

ID 36122

2 BR

1 bath

Sleeps 6

Guest Cottage, Art Shack & Sleeping Cottage

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

Chilmark

ID 38587

2 BR

1 bath

Sleeps 6

Chilmark Cottage Escape

Distance to beach: 4.3 mi to Lucy Vincent Beach

1 review read review

Summer:
$2,600/wk

Off Season:
$2,100/wk

Chilmark vacation rentals that sleep 5

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.

14 reviews read reviews

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

Off Season:
$2,500 - $6,000/wk

Menemsha (Chilmark)

ID 17189

2 BR

1 bath

Sleeps 4

Menemsha Harborside Cottage, Tilton House

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

1 review read review

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

Off Season:
$2,200 - $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

7 reviews read reviews

Summer:
$3,400 - $3,900/wk

Off Season:
$3,300 - $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

2 reviews read reviews

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

Off Season:
$2,950 - $3,750/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

14 reviews read reviews

Summer:
$2,500 - $3,500/wk
$14,000 - $15,800/mo

Off Season:
$350 - $500/night
$1,500 - $3,000/wk
$8,000 - $10,000/mo

Chilmark

ID 38624

2 BR

1 bath

Sleeps 4

Boat House on the Water in Chilmark

Distance to beach: Chockers Beach is just a few feet down the path

Off Season:
$500 - $750/night
$4,500 - $5,200/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 Harbor - Davis House

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

6 reviews read reviews

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

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