Chilmark 2-bedroom Vacation Rentals, Homes & More - 702 Rentals Available.
702 Vacation rentals
Filters applied: 2+ Bedrooms
Secluded Unique Natural Vacation House
Chilmark House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 8 8
- 7 nights min
- Child friendly
$240.00
from $240.00 / night
SPANM - Sweet Chilmark Cottage, Spacious Screened Porch and Deck Area, Private L
Chilmark House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
$329.00
from $329.00 / night
LEWID - Menemsha Waterfront, Magnificent Views and Private Location, WiFi
Chilmark House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
$572.00
from $572.00 / night
FERRN - Summer in Chilmark, Private Location, Large Deck w Outdoor Dining Area,
Chilmark House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$400.00
from $400.00 / night
SMITD - Top Side Cottage, set in the Iconic Village of Menemsha and Overlooking
Chilmark House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Ask about children
- Air conditioning
$215.00
from $215.00 / night
Spectacular Home with Waterviews of Vineyard Sound and Elizabeth Islands
Chilmark House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Air conditioning
$1,357.00
from $1,357.00 / night
TEELK - Menemsha Village Cottage, Walk to Menemsha Beach, A/C, WiFi
Chilmark House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$350.00
from $350.00 / night
ALDEN - Picturesque Stone Wall Pond Waterfront, Walk to Private Association Beac
Chilmark House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$429.00
from $429.00 / night
LORUJ - Spacious Ocean View Home, Private Association Beach - South Shore - Inq
Chilmark House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$700.00
from $700.00 / night
ALDEM - Gorgeous Waterfront Home, Magnificent Views of the Atlantic, Great Kaya
Chilmark House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$500.00
from $500.00 / night
NOBLM - Distinctive Luxury Summer Retreat, Private Tennis Courts, Private Associ
Chilmark House
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 9 9
- 7 nights min
- Ask about children
- Air conditioning
$1,265.00
from $1,265.00 / night
GIBBT - Large Deck, Wifi, A/C, Conveniently Located in One of The Most Beautifu
Chilmark House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$215.00
from $215.00 / night
ALDEB - Waterfront, Hi Speed Internet
Chilmark House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Ask about children
$358.00
from $358.00 / night
LEWDG - Waterfront, Waterview, Walk to Beach, Hi Speed Internet, WiFi
Chilmark House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
$429.00
from $429.00 / night
SAWYW - Designer Luxury with Oustanding Atlantic Ocean Views, Private Beaches,
Chilmark House
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- 7 nights min
- Ask about children
- Air conditioning
$1,567.00
from $1,567.00 / night
ENRIP - Privacy, Lovely Yard, Short Drive to Lucy Vincent Beach
Chilmark House
- 5 bedrooms 5
- 3 bathrooms
- Sleeps 12 12
- 7 nights min
- Ask about children
$500.00
from $500.00 / night
HORNP - Squibnocket Farm Waterfront, Private Beach,
Chilmark House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 9 9
- 7 nights min
- Ask about children
$1,715.00
from $1,715.00 / night
BRESP - Waterview, Association Beach
Chilmark House
- 6 bedrooms 6
- 4 bathrooms
- Sleeps 10 10
- 7 nights min
- Ask about children
$1,215.00
from $1,215.00 / night
JAFFP - Cottage by the Sea, Ocean and Beachfront Location, Private one of a Kin
Chilmark House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Ask about children
$258.00
from $258.00 / night
CHARMING WATERFRONT COTTAGE WITH WONDERFUL VIEWS OF THE ATLANTIC OCEAN
Chilmark House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Ask about children
$357.00
from $357.00 / night
BLASD - A Gem in Chilmark, Impeccably Maintained Home, Multiple Decks and Patio
Chilmark House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$500.00
from $500.00 / night
CHARMING HOME W/VIEWS OF VINEYARD SOUND & ELIZABETH ISLANDS
Chilmark House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$286.00
from $286.00 / night
MCAUM - Thoughtfull Architectual Design set Amidst an Estate Property, Bordered
Chilmark House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 7 7
- 7 nights min
- Ask about children
- Air conditioning
$929.00
from $929.00 / night
Gracious and Spacious Chilmark Home with a Pool
Chilmark House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$571.00
from $571.00 / night
KOGAB - Chilmark, South Road, 3 Miles to Lucy Vincent Beach, WiFi
Chilmark House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
$436.00
from $436.00 / night
MICHA - Chilmark Hilltop Luxury Home, A/C, Wifi Internet
Chilmark House
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$1,143.00
from $1,143.00 / night
PERRG - North Slope Hilltop House. Private yard, Screeen Porch and Patio, All
Chilmark House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$286.00
from $286.00 / night
ATLANTIC OCEAN BREEZES, GLORIOUS VIEWS!
Chilmark House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Air conditioning
$429.00
from $429.00 / night
WATERFRONT VINEYARD CONTEMPORARY HOME LOCATED ON TISBURY GREAT POND
Chilmark House
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
- Air conditioning
$1,786.00
from $1,786.00 / night
HERGT - Luxury Retreat Chilmark, Key to Quansoo Private Association Beach, Set o
Chilmark House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$929.00
from $929.00 / night
MEINT - Stately Historic Chilmark Home, All Newly updated to Luxury Standards, P
Chilmark House
- 5 bedrooms 5
- 3 bathrooms
- Sleeps 10 10
- 7 nights min
- Ask about children
- Air conditioning
$572.00
from $572.00 / night
Chilmark Vacation Home with Lovely Views and Pool
Chilmark House
- 6 bedrooms 6
- 4 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Ask about children
$858.00
from $858.00 / night
ROSSR - Chilmark, Waterview, Private Pool
Chilmark House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 14 nights min
- Swimming pool
- Ask about children
$1,179.00
from $1,179.00 / night
SPACIOUS AND COMFORTABLE CHILMARK CAPE WITH CENTRAL AIR CONDITIONING
Chilmark House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Air conditioning
$179.00
from $179.00 / night
CLASSIC VINEYARD FISHING VILLAGE VIEWS FROM THIS QUINTESSENTIAL COTTAGE
Chilmark House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Ask about children
$143.00
from $143.00 / night
ARCHITECTURAL AWARD WINNING HOME WITH PANORAMIC VIEWS OF THE VINEYARD SOUND
Chilmark House
- 6 bedrooms 6
- 4 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
$1,071.00
from $1,071.00 / night
JAFFJ - Ocean House, Private South Shore Beach, Sweeping Lawns and Gorgous Gar
Chilmark House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$429.00
from $429.00 / night
CHARMING COUNTRY HOME IN CHILMARK
Chilmark House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$314.00
from $314.00 / night
ENJOY OCEAN VIEWS FROM THIS CHILMARK HOME
Chilmark House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$643.00
from $643.00 / night
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