Chilmark 2-bedroom Vacation Rentals, Homes & More - 44 Rentals Available.
44 Vacation rentals
Filters applied: 2+ Bedrooms
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
$150
from $150 / 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
from $357 / night
ITALA - North Slope Custom Home, Large Wrap Around Deck, WiFi
Chilmark House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
$383
from $383 / 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
from $571 / night
HERGT - Luxury Retreat Chilmark, Key to Quansoo Private Association Beach, Set
Chilmark House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$772
from $772 / night
Spacious Menemsha Waterview Rental (69)
Chilmark House
- 5 bedrooms 5
- 2 bathrooms
- Sleeps 9 9
- 7 nights min
- Ask about children
$429
from $429 / night
CLASSIC VINEYARD FISHING VILLAGE VIEWS FROM THIS QUINTESSENTIAL COTTAGE
Chilmark House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 6 6
- Min stay varies
- Ask about children
$143
from $143 / 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
$454
from $454 / night
ALDEM - Gorgeous Waterfront Home, Magnificent Views of the Atlantic, Great
Chilmark House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$500
from $500 / 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
$258
from $258 / night
SAWYW - Designer Luxury with Oustanding Atlantic Ocean Views, Private
Chilmark House
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- 7 nights min
- Ask about children
- Air conditioning
$1536
from $1536 / night
LORUJ - Spacious Ocean View Home, Private Association Beach - South Shore
Chilmark House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$679
from $679 / night
ALDEN - Picturesque Stone Wall Pond Waterfront, Walk to Private Association
Chilmark House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$429
from $429 / 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
from $286 / 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
$604
from $604 / night
HORNP - Squibnocket Farm Waterfront, Private Beach,
Chilmark House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 9 9
- 7 nights min
- Ask about children
$1715
from $1715 / 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
$1357
from $1357 / night
JAFFP - Waterfront Guest House, Private Beach
Chilmark House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Ask about children
$429
from $429 / night
MEINT - Stately Historic Chilmark Home, All Newly updated to Luxury Standards
Chilmark House
- 5 bedrooms 5
- 3 bathrooms
- Sleeps 1 1
- 14 nights min
- Ask about children
- Air conditioning
$715
from $715 / night
ARCHITECTURAL AWARD WINNING HOME WITH PANORAMIC VIEWS OF THE VINEYARD SOUND
Chilmark House
- 6 bedrooms 6
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
$1071
from $1071 / 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
from $350 / night
SPANM - Sweet Chilmark Cottage, Spacious Screened Porch and Deck Area, Private
Chilmark House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
$358
from $358 / 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
from $858 / night
ATLANTIC OCEAN BREEZES, GLORIOUS VIEWS!
Chilmark House
- 4 bedrooms 4
- 5 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$429
from $429 / 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
$779
from $779 / night
ALDEB - Waterfront, Hi Speed Internet
Chilmark House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Ask about children
$358
from $358 / night
GIBBT - Large Deck, Wifi, A/C, Conveniently Located in One of The Most
Chilmark House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$150
from $150 / night
WHITP - 2 week minimum stay, Pristine Hilltop Ocean View, 1.2 Miles to Lucy
Chilmark House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 14 nights min
- Ask about children
$343
from $343 / night
BRESP - Waterview, Association Beach
Chilmark House
- 6 bedrooms 6
- 4 bathrooms
- Sleeps 10 10
- 7 nights min
- Ask about children
$1229
from $1229 / night
BERWD - Waterview, Walk to Menemsha Beach
Chilmark House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 10 10
- 7 nights min
- Ask about children
$743
from $743 / 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
from $500 / night
DIETR - Menemsha Pond Waterfront, Wifi, Central A/C
Chilmark House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$572
from $572 / night
SMITD - Top Side Cottage, set in the Iconic Village of Menemsha and
Chilmark House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Ask about children
- Air conditioning
$215
from $215 / 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
$486
from $486 / night
CHARMING COUNTRY HOME IN CHILMARK
Chilmark House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$314
from $314 / night
TRANQUIL HOME OVERLOOKNG THE OCEAN. ADD A BEACH AND WHAT COULD BE BETTER
Chilmark House
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$2215
from $2215 / night
ROSSR - Chilmark, Waterview, Private Pool
Chilmark House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 14 nights min
- Swimming pool
- Ask about children
$893
from $893 / night
BERNJ - Menemsha Sea Coast Cottage, Gorgeous Waterviews, Walk to Menemsha
Chilmark House
- 5 bedrooms 5
- 3 bathrooms
- Sleeps 8 8
- 14 nights min
- Ask about children
$929
from $929 / night
JAFFJ - Ocean House, Private South Shore Beach, Sweeping Lawns and Gorgous
Chilmark House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
$429
from $429 / night
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