Chilmark 2-bedroom Vacation Rentals, Homes & More - 663 Rentals Available.
663 Vacation rentals
Filters applied: 2+ Bedrooms
Chilmark Farmhouse with access to Hancock Beach
Chilmark House
- 5 bedrooms 5
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Ask about children
- Air conditioning
$571.00
from $571.00 / 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
$701.00
from $701.00 / 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
MEINW - Wade's Cove Waterfront Luxury Residence, Key to Private Hancock Beach,
Chilmark House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$1,429.00
from $1,429.00 / 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
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
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
$572.00
from $572.00 / 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
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
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
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
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
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
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
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
$857.00
from $857.00 / 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
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
$179.00
from $179.00 / 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
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
$179.00
from $179.00 / 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
Luxury Expanded Cape on Wade's Cove & Key to Hancock Beach
Chilmark House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
$1,429.00
from $1,429.00 / night
BRESP - Waterview, Association Beach
Chilmark House
- 6 bedrooms 6
- 4 bathrooms
- sleeps 10 10
- 7 nights min
- Ask about children
$1,429.00
from $1,429.00 / 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
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
- Air conditioning
$436.00
from $436.00 / 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
SEFER - Pinkletink House! Custom New home on Prospect Hill , Chilmark, Gorgeous
Chilmark House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 9 9
- 7 nights min
- Ask about children
- Air conditioning
$1,715.00
from $1,715.00 / 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
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
$1,358.00
from $1,358.00 / night
PETEC - Post and Beam Charm, Sleeps 8, Short Drive to Lucy Vincent and Squibnock
Chilmark House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 1 night min
- Ask about children
- Air conditioning
$435.00
from $435.00 / night
BERNJ - Menemsha Sea Coast Cottage, Gorgeous Waterviews, Walk to Menemsha Beach,
Chilmark House
- 5 bedrooms 5
- 3 bathrooms
- sleeps 8 8
- 14 nights min
- Ask about children
$1,072.00
from $1,072.00 / night
Your search has been expanded 19.3 miles to include more rentals
Waterfront-Martha's Vineyard
Edgartown House - 10.8 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Child friendly
- Private garden
$328.00
from $328.00 / night
Minutes to Menauhant Beach - Newly Furnished
Falmouth House - 18.6 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 1 night min
- Ask about children
- Air conditioning
- Pet friendly
Responds fast! Avg. 3 hours 39 minutes
$430.00
from $430.00 / night
Classic Vineyard Farm House Colonial
West Tisbury House - 7.2 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- 7 nights min
- Child friendly
$638.00
from $638.00 / night
New Cape House Steps to the Beach in East Falmouth
Falmouth House - 18.7 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 2 nights min
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
Responds fast! Avg. 3 hours 39 minutes
$430.00
from $430.00 / night
Beach House on Seconsett Island
Mashpee Cottage - 19.3 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 8 8
- 2 nights min
- Nearest beach 3 mi
- Child friendly
- Air conditioning
$201.00
from $201.00 / night
66 Central Ave
Falmouth Farmhouse - 18.7 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Child friendly
- Air conditioning
- Pet friendly
$131.00
from $131.00 / night
Remodeled Stone Barn & panoramic salt marsh view
Falmouth House - 17.2 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Ask about children
- Private garden
$250.00
from $250.00 / night
Magnificent Contemporary on Exclusive Point
Falmouth House - 15.4 miles away
- 3 bedrooms 3
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
Responds fast! Avg. 2 hours 32 minutes
$459.00
from $459.00 / night
59 Menauhant Road
Falmouth House - 15.9 miles away
- 7 bedrooms 7
- 5 bathrooms
- sleeps 19 19
- 1 night min
- Ask about children
- Ask about pets
$1,428.00
from $1,428.00 / night
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