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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.

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

Chilmark vacation rentals that sleep 11

Chilmark
ID 5258
4 BR
2 baths
Sleeps 11
Spectacular 6 acres on pond, ocean view, private beach
Distance to beach: Hancock Beach 1/2 mile along pond
Description
This summer house on Chilmark Pond offers the best of the Vineyard-- a spectacular location on the pond with sweeping views of South Beach situated in the midst of hundreds of acres of protected conse... read more
Key amenities
on salt water, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet, pet-friendly
Time active on this website
12 years, 10 months
Property ID 5258 listed by: Joshua
Summer:
$4,500 - $6,500/wk
Off Season:
$4,500 - $5,000/wk

Chilmark vacation rentals that sleep 10

Chilmark
ID 18228
5 BR
2 baths
Sleeps 10
Chilmark Contemporary Cape - Stunning Views - Great Escape
Distance to beach: Less than a mile to Menemsha Beach
17 reviews read reviews
Description
From its hilltop site in a private association, easy living is yours in this spacious and gracious home. The open concept, modern kitchen, with granite counters and stainless steel appliances adjoini... read more
Key amenities
view of salt water, deck/porch/patio, outdoor shower, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet, pet-friendly
Time active on this website
6 years, 6 months
Property ID 18228 listed by: Douglas Cochrane
Summer:
$4,500 - $6,000/wk
Off Season:
$2,000 - $6,000/wk
Chilmark
ID 25086
4 BR
4 baths
Sleeps 10
Four Bedroom Chilmark Gem
Distance to beach: Bike to Lucy Vincent
Description
A four plus bedroom Chilmark home located at beautiful Old Farm Rd. Just minutes from Lucy Vincent and Squibnocket Beaches and the Chilmark Community Center. Walk to tennis. There are two master suit... read more
Key amenities
deck/porch/patio, outdoor shower, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet
Time active on this website
1 year, 5 months
Property ID 25086 listed by: Metes & Bounds Realty
Summer:
$6,500 - $7,000/wk
Off Season:
$4,000 - $6,000/wk

Chilmark vacation rentals that sleep 9

Chilmark
ID 26224
3 BR
2 baths
Sleeps 9
Fr. Cntry Style Farmhouse Chilmark w/ HTub- 4 Day stay 7/4
Distance to beach: 4 min drive Lucy Vincent or Squibnocket Beaches
6 reviews read reviews
Description
Rustic and cozy, yet spacious, carved post and beam home on the edge of woods with deer and other wildlife, very close to both coveted Chilmark beaches, Gay Head Light and the Center of Chilmark which... read more
Key amenities
hot tub, outdoor shower, jacuzzi, washer&dryer, dishwasher, linens included, cable TV, wireless or wired internet, pet-friendly
Time active on this website
5 months
Property ID 26224 listed by: Betty Martin
Summer:
$3,400 - $4,000/wk
Off Season:
$500 - $600/night
$3,200 - $3,500/wk

Chilmark vacation rentals that sleep 8

Chilmark
ID 2903
4 BR
2 baths
Sleeps 8
Sweeping Ocean Views
Distance to beach: less than 3/10 mile to private association beach
Description
Sit on the deck among the treetops and view the Vineyard Sound and Elizabeth Islands from the North Shore of Martha's Vineyard. Take sunset walks along bluffs of private beach with spectacular ocean... read more
Key amenities
view of salt water, walk to a salt water beach, screened porch, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, cable TV, DVD or VCR
Time active on this website
16 years, 3 months
Property ID 2903 listed by: Bob
Summer:
$3,200 - $4,600/wk
Off Season:
$2,500 - $3,200/wk
Chilmark
ID 4390
4 BR
2 ½ baths
Sleeps 8
4 Bedroom on 5 acres of Chilmark Woodlands
Distance to beach: 3 miles to Lucy Vincent Beach, 5 to Sqibnocket
2 reviews read reviews
Description
Set on 5 acres of woods and meadow. A small farm setting with chickens and pigs and a garden for you to enjoy. Be a farmer for a week, without the work! Our hens lay eggs that you can collect every m... read more
Key amenities
screened porch, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet, pet-friendly
Time active on this website
14 years, 1 month
Property ID 4390 listed by: Jan or Rich
Summer:
$425/night
$4,000 - $4,200/wk
$15,200 - $16,000/mo
Off Season:
$575/night
$4,000/wk
Chilmark
ID 19917
4 BR
3 baths
Sleeps 8
The ''New House'' @ Abels Hill - Private Beach + Tennis
Distance to beach: 7 min walk, or 1 1/2 minute drive, private beach
3 reviews read reviews
Description
Eco-friendly home on exclusive Abel's Hill. Pristine, sun-filled, and fully equipped! Casa Nueva (The New House, built 2010) has four bedrooms, 3 baths, easy access for people with walkers and wheelc... read more
Key amenities
walk to a fresh water beach, screened porch, deck/porch/patio, outdoor shower, central A/C, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet, handicap accessibility
Time active on this website
5 years, 4 months
Property ID 19917 listed by: New Casa Alta on Abel's Hill South Beach Chilmark
Summer:
$750 - $1,000/night
$5,500 - $7,200/wk
Off Season:
$400 - $800/night
$300 - $6,500/wk
Chilmark
ID 26589
4 BR
2 ½ baths
Sleeps 8
Chilmark Private Atlantic Beach. One week left 7/2 has FT'S
Distance to beach: 1/2 mile to Black Point Atlantic Ocean beach
Description
Sand Sun Surf and an immaculate house and guest quarters, too................ WOW! This is not a fancy, posh beach house. It is a wonderful, relaxing, immaculate vacation destination for you and yo... read more
Key amenities
walk to a salt water beach, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, wireless or wired internet
Time active on this website
3 months
Property ID 26589 listed by: Susie Wallo, LAER Realty Partners
Summer:
$4,000/wk
Chilmark
ID 5312
4 BR
3 ½ baths
Sleeps 8
The Little Gem on Abel's Hill - Panoramic View - Chilmark
Distance to beach: Approx. 2/10 mile walk to Abel's Hill Beach
Description
Enjoy the quiet of up-Island Martha’s Vineyard. Sunny, Cape-style house with pool set on rise overlooking the Atlantic Ocean has cozy wood paneled living room and large eat-in kitchen, both with firep... read more
Key amenities
view of salt water, walk to a salt water beach, pool, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet, pet-friendly, handicap accessibility
Time active on this website
13 years, 3 months
Property ID 5312 listed by: Alicia
Summer:
$5,850 - $7,100/wk
Chilmark
ID 12106
3 BR
2 baths
Sleeps 8
Windfall
Distance to beach: Brief walk & quick canoe ride to L. VIncent Beach
2 reviews read reviews
Description
This Chilmark property is truly a sight to see, stay, and come back to again and again. Nestled atop 4 ½ acres with panoramic Atlantic Ocean views, the home is only a short canoe or kayak ride a... read more
Key amenities
view of fresh water, walk to a salt water beach, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet
Time active on this website
10 years, 2 months
Property ID 12106 listed by: Kris Trauernicht
Summer:
$3,250 - $6,500/wk
Off Season:
$2,500 - $3,250/wk
Chilmark
ID 15956
3 BR
2 baths
Sleeps 8
Very Charming, Roomy Three Bedroom Home
Distance to beach: 2.5mi by road or 1mi walking through conservation
5 reviews read reviews
Description
Fully equipped, open floor plan, contemporary three bedroom, two bath house on three acres surrounded on three sides by the Fulling Mill Conservation land. Immediate access to wonderful walking trails... read more
Key amenities
deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet, pet-friendly
Time active on this website
6 years, 1 month
Property ID 15956 listed by: John and Caroline Moore.
Summer:
$2,750 - $4,250/wk
$9,000 - $15,000/mo
Off Season:
$2,250 - $3,750/wk
Chilmark
ID 26404
3 BR
3 baths
Sleeps 8
Chilmark Private and Well-Situated: Boston Hill Getaway
Distance to beach: 1.4 mi to Lucy Vincent; 1.5 mi to Squibnocket
7 reviews read reviews
Description
Welcome to this wonderful home! With 3+ bedrooms, three full bathrooms, a jacuzzi and sauna, WIFI, comfortable office/study area, central air conditioning, and more, this house will make your vacation... read more
Key amenities
view of salt water, deck/porch/patio, outdoor shower, jacuzzi, central A/C, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet
Time active on this website
4 months
Property ID 26404 listed by: Stephen Seckler
Summer:
$3,100 - $4,600/wk
Off Season:
$300 - $442/night
$2,100 - $3,100/wk
Chilmark
ID 4383
2 BR
1 bath
Sleeps 8
Secluded Unique Natural Vacation House
Distance to beach: Three miles to Lucy Vincent Beach - 10 min drive
1 review read review
Description
Located at end of a dead end dirt rd on 1.5 acres with tall pines and oaks. Modified saltbox, owner designed & built in 1978 for potential active solar. First floor has a large country kitchen, livin... read more
Key amenities
deck/porch/patio, outdoor shower, washer&dryer
Time active on this website
13 years, 8 months
Property ID 4383 listed by: Don and Jean Murray
Summer:
$1,400 - $1,675/wk
Off Season:
$100 - $235/night
$500 - $1,500/wk

Chilmark vacation rentals that sleep 7

ACROSS FROM QUANSOO FARM!
ID 10393
2 BR
2 baths
Sleeps 7
Where the real people are vacationing! LOCKED GATE BEACH!
Distance to beach: Less than a mile to Quansoo Beach Association
1 review read review
Description
If you've ever wondered why people are so keen to go to Martha's Vineyard but wonder why they travel by ferry to just another ''version of Cape Cod'' this is the home for you! Go to Facebook page 90 Q... read more
Key amenities
deck/porch/patio, outdoor shower, jacuzzi, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet, pet-friendly, handicap accessibility
Time active on this website
2 years, 9 months
Property ID 10393 listed by: Claire DeVore
Summer:
$2,500 - $3,300/wk
$11,000 - $12,000/mo
Off Season:
$1,500 - $2,900/wk
$8,000/mo

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
10 reviews read reviews
Description
From the moment you drive down the long, semi-private driveway to the house, you sense the solitude and beauty of the surroundings. The house is located on its own eight secluded acres on Upper Chilma... read more
Key amenities
on a salt water beach, boat dock, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet
Time active on this website
14 years, 3 months
Property ID 4172 listed by: Candace or Dennis Guittarr
Summer:
$6,000 - $7,500/wk
Off Season:
$3,500 - $5,000/wk
Menemsha
ID 13297
3 BR
2 baths
Sleeps 6
Breathtaking Menemsha Views of Docks& Water Sunsets
Distance to beach: 5-minute walk on private hillside path
5 reviews read reviews
Description
Quintessential up-island 1920s house with walk to Menemsha beach & spectacular, panoramic water views & water sunsets looking west over Menemsha Harbor & Sound, Elizabeth Islands & Aquinnah Lighthouse... read more
Key amenities
view of fresh water, walk to a salt water beach, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet, pet-friendly
Time active on this website
9 years, 5 months
Property ID 13297 listed by: Nathaniel
Summer:
$600 - $1,000/night
$4,000 - $6,000/wk
$16,000 - $40,000/mo
Off Season:
$350 - $500/night
$2,500 - $3,500/wk
$10,000 - $15,000/mo
Menemsha (Chilmark)
ID 17311
3 BR
1 bath
Sleeps 6
Sunset House in Historic Fishing Village of Menemsha
Distance to beach: 2/10ths of a mile to Menemsha Beach
1 review read review
Description
You can enjoy the Menemsha Sunsets from your own private deck. This summer cottage was converted from an early fishing shack in the 1900s. It is a lovely, classic island cottage. It has views of M... read more
Key amenities
view of salt water, walk to a salt water beach, deck/porch/patio, outdoor shower, washer&dryer, cable TV, DVD or VCR, fireplace, wireless or wired internet
Time active on this website
7 years, 3 months
Property ID 17311 listed by: Barbara
Summer:
$2,800 - $3,200/wk
Off Season:
$1,500 - $1,800/wk
Chilmark
ID 3473
3 BR
3 baths
Sleeps 6
Private 3 bedroom 3 bath Cedar Home on Hill in Chilmark
Distance to beach: 10 minute drive to Lucy Vincent Beach
Description
Very private splendid 3 bedroom, 3 bath hilltop home with two master suites that have private baths, two fireplaces, and a large wraparound deck with hot tub that has a distant water view. Lucy Vince... read more
Key amenities
view of salt water, deck/porch/patio, outdoor shower, jacuzzi, washer&dryer, dishwasher, cable TV, DVD or VCR, fireplace, pet-friendly
Time active on this website
15 years, 3 months
Property ID 3473 listed by: Marcia and Ken
Summer:
$2,500 - $3,000/wk
Off Season:
$2,500/wk
Chilmark
ID 7701
3 BR
3 baths
Sleeps 6
Charming Chilmark Property
Distance to beach: 3 miles to Lucy Vincent Beach
2 reviews read reviews
Description
Located in Chilmark on Martha's Vineyard, this 3 bedroom, 3 bathroom property is a perfect spring, summer or fall getaway. Cathedral ceilings create bright, airy spaces. Amenities include air conditi... read more
Key amenities
screened porch, deck/porch/patio, outdoor shower, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet, handicap accessibility
Time active on this website
11 years, 7 months
Property ID 7701 listed by: Steven Shapse
Summer:
$1,200 - $2,500/wk
$9,000 - $10,000/mo
Off Season:
$1,000 - $1,400/wk
$3,000/mo
Chilmark
ID 13169
2 BR
1 bath
Sleeps 6
On Upper Chilmark Pond overlooking Lucy Vincent Beach
Distance to beach: 100 yards to dock, 6 min. paddle to beach.
9 reviews read reviews
LAST MINUTE ALERT 9/3 - 9/10
OWNER SPECIAL:
September is the very best time to visit the Vineyard and Lucy Vincent Beach is not crowded!
Description
Premier location if you desire privacy, views and easy access to a beautiful beach. Inviting cottage with spacious deck and a lawn for croquet, etc. One hundred yard walk to our dock where a canoe and... read more
Key amenities
on fresh water, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, fireplace, wireless or wired internet, pet-friendly
Time active on this website
9 years, 5 months
Property ID 13169 listed by: John and Caroline Moore.
Summer:
$3,250 - $5,250/wk
$19,000/mo
Off Season:
$2,000 - $4,250/wk
$5,000 - $13,000/mo

Chilmark vacation rentals that sleep 5

Chilmark
ID 16935
3 BR
1 bath
Sleeps 5
PortersPort
Distance to beach: 1 mile to Menemsha Beach, 2 miles to Lucy Vincent
Description
Located on the Crossroads between Menemsha and Chilmark, this home has two bedrooms upstairs, one bedroom downstairs, a large family room, a recently updated kitchen with a new floor and a screened-in... read more
Key amenities
walk to a salt water beach, screened porch, outdoor shower, A/C unit(s), washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet, pet-friendly
Time active on this website
1 year, 6 months
Property ID 16935 listed by: Tom
Summer:
$1,750 - $2,500/wk
Off Season:
$1,500/wk
Chilmark
ID 23618
2 BR
1 bath
Sleeps 5
Menemsha Gem with Vineyard Sound Waterview
Distance to beach: 2/10 mile Menemsha Beach
OWNER SPECIAL:
August 2017 now available!
Description
This Vineyard style cottage is located just steps from Menemsha Beach, the docks, fish markets, and restaurants. Enjoy fishing from the docks and sunset at the beach. Situated on a small hill above co... read more
Key amenities
view of salt water, walk to a salt water beach, deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet
Time active on this website
2 years, 9 months
Property ID 23618 listed by: Bob
Summer:
$2,300 - $3,100/wk
Off Season:
$1,300 - $2,600/wk

Chilmark vacation rentals that sleep 4

Menemsha (Chilmark)
ID 17189
2 BR
1 bath
Sleeps 4
Menemsha Harbor Cottage: Tilton House
Distance to beach: less than 2/10ths of a mile to Menemsha Beach
Description
Historic Menemsha Harbor Cottage available for four people. 100 feet to Menemsha Harbor and a two minute walk to the beach. Also, access to two exclusive town beaches (for a town fee): Squibnocke... read more
Key amenities
view of salt water, walk to a salt water beach, deck/porch/patio, outdoor shower, A/C unit(s), washer&dryer, cable TV, DVD or VCR, wireless or wired internet
Time active on this website
7 years, 1 month
Property ID 17189 listed by: Barbara
Summer:
$1,800 - $2,500/wk
Off Season:
$1,200 - $1,800/wk
85 Tea Lane, Chilmark
ID 22294
2 BR
1 bath
Sleeps 4
Quiet, Secluded Chilmark Cottage
Distance to beach: 3 Miles to Lucy Vincent Beach
3 reviews read reviews
Description
An ideal cottage for two couples or a small family. This is a two bedroom, one bath Cape with an alternate sleeping loft. The cottage is situated on two quiet, secluded acres in the up-island town of ... read more
Key amenities
deck/porch/patio, outdoor shower, washer&dryer, dishwasher, cable TV, DVD or VCR, fireplace, wireless or wired internet
Time active on this website
3 years, 7 months
Property ID 22294 listed by: Brian & Caroline Giles
Summer:
$1,800 - $2,000/wk
Off Season:
$1,700 - $1,800/wk
Chilmark
ID 4029
1 BR
1 bath
Sleeps 4
Stonewall Beach Guest Cottage
Distance to beach: 1/2 mile to Stonewall Beach
Description
The updated cottage features a waterview of Menemsha Pond/Vineyard Sound and private beach access to Stonewall Beach a 10 minute walk away. It is ideally suited for a couple, but does have a queen siz... read more
Key amenities
view of salt water, walk to a salt water beach, screened porch, deck/porch/patio, washer&dryer, linens included, cable TV, DVD or VCR, wireless or wired internet
Time active on this website
14 years, 5 months
Property ID 4029 listed by: Bob
Summer:
$1,500 - $1,850/wk
Off Season:
$850 - $1,700/wk

Chilmark vacation rentals that sleep 2

Chilmark
ID 2470
1 BR
1 bath
Sleeps 2
Relax & Rejuvenate in Ideal Cottage Setting
Distance to beach: 5 miles to Lucy Vincent, the Island's best beach
24 reviews read reviews
Description
This is a delightful escape, offering privacy, convenience and all the creature comforts. Nestled in a six-acre private estate in exclusive Chilmark, this 700 SF, one-bedroom cottage has many special ... read more
Key amenities
deck/porch/patio, outdoor shower, washer&dryer, dishwasher, linens included, cable TV, DVD or VCR, wireless or wired internet, pet-friendly
Time active on this website
16 years, 8 months
Property ID 2470 listed by: Mary
Summer:
$1,700 - $1,800/wk
Off Season:
$800 - $1,700/wk
Menemsha (Chilmark)
ID 18146
1 BR
1 bath
Sleeps 2
Davis House off Menemsha Harbor
Distance to beach: less than 2/10ths of a mile to Menemsha Beach
2 reviews read reviews
Description
Stay in the charming and historic fishing village of Menemsha. This quaint cottage is located a stones throw from the Menemsha Harbor. It is the smallest and most affordable of the three houses we re... read more
Key amenities
view of salt water, walk to a salt water beach, deck/porch/patio, cable TV, DVD or VCR, wireless or wired internet
Time active on this website
5 years, 6 months
Property ID 18146 listed by: Barbara
Summer:
$1,000 - $1,800/wk
Off Season:
$200/night
$1,000/wk