Chilmark 2-bedroom Vacation Rentals, Homes & More - 15 Rentals Available.
15 Vacation rentals
Filters applied: 2+ Bedrooms
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
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
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
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 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
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
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
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
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
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
ENJOY OCEAN VIEWS FROM THIS CHILMARK HOME
Chilmark House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$786
from $786 / 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
WATERFRONT VINEYARD CONTEMPORARY HOME LOCATED ON TISBURY GREAT POND
Chilmark House
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- 7 nights min
- Ask about children
- Air conditioning
$2000
from $2000 / night
Amazing Water View Home (412)
Chilmark House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
$643
from $643 / night
Your search has been expanded 8.8 miles to include more rentals
Enjoy beautiful views of Vineyard Sound!
Menemsha House - 0.1 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 9 9
- Min stay varies
- Ask about children
$714
from $714 / night
BEAUTIFUL POST AND BEAM HOME WITH WATERVIEWS OF LOBSTERVILLE BEACH
Aquinnah House - 1.9 miles away
- 5 bedrooms 5
- 3 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
- Air conditioning
$643
from $643 / night
GUEST HOUSE WITH STATE OF THE ART KITCHEN & NICE WATERVIEWS.
Aquinnah House - 2.2 miles away
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Ask about children
- Air conditioning
$357
from $357 / night
ENJOY SUNSETS & WATERVIEWS FROM THIS BEAUTIFUL AQUINNAH HOUSE & GUEST HOUSE
Aquinnah House - 2.6 miles away
- 7 bedrooms 7
- 6 bathrooms
- Sleeps 14 14
- Min stay varies
- Ask about children
- Air conditioning
$786
from $786 / night
EXPERIENCE THE OLD WORLD CHARM OF MARTHA'S VINEYARD IN THIS SEA CAPTAINS HOME
West Tisbury House - 3.4 miles away
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Ask about children
$214
from $214 / night
Beautiful Home with Central Air Conditioning Located by Long Point Beach
West Tisbury House - 5.1 miles away
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Air conditioning
$300
from $300 / night
BEAUTIFUL POST & BEAM HOME SET ON 7 ACRES
West Tisbury House - 5.1 miles away
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Air conditioning
$357
from $357 / night
Water View Ice House Pond (411)
West Tisbury House - 5.1 miles away
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
$358
from $358 / night
Charming Guest House (408)
West Tisbury House - 5.1 miles away
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Ask about children
- Air conditioning
$243
from $243 / night
Idylic Vineyard Escape! (407)
West Tisbury House - 5.1 miles away
- 4 bedrooms 4
- 5 bathrooms
- Sleeps 14 14
- 7 nights min
- Ask about children
- Air conditioning
$800
from $800 / night
Beatiful, 5 Bedroom West Tisbury Home with Pool
West Tisbury House - 5.1 miles away
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 7 7
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1143
from $1143 / night
STROLL DOWN TO THE POND TO COOL OFF OR GO KAYAKING ON A WARM DAY
West Tisbury House - 5.2 miles away
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 10 10
- 7 nights min
- Ask about children
$429
from $429 / night
Mill Pond House is a beautifully restored farm house built in the 1880s.
West Tisbury House - 5.4 miles away
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Air conditioning
$514
from $514 / night
ENJOY BEAUTIFUL WATERVIEWS FROM THIS CHARMING VINEYARD HOME
West Tisbury House - 6.1 miles away
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Ask about children
$286
from $286 / night
Classic Vineyard Farm House Colonial
West Tisbury House - 7.4 miles away
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 10 10
- 7 nights min
- Child friendly
$558
from $558 / night
BEACH/POOL/TENNIS/WATERVIEWS-WOW!
West Tisbury House - 7.5 miles away
- 4 bedrooms 4
- 5 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Ask about children
$3143
from $3143 / night
Beautiful West Tisbury Home with Association Pool
West Tisbury House - 8.2 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$329
from $329 / night
CHARMING PRIVATE COTTAGE WITH A YARD THAT IS A SLICE OF HEAVEN ON EARTH
West Tisbury House - 8.3 miles away
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 5 5
- Min stay varies
- Ask about children
$193
from $193 / night
LOVELY COTTAGE CONVENIENTLY LOCATED TO LAMBERT'S COVE BEACH
West Tisbury House - 8.3 miles away
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Ask about children
$157
from $157 / night
PRIVATE BEACHFRONT HOUSE WITH PANORAMIC VIEWS OF VINEYARD SOUND
West Tisbury House - 8.4 miles away
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$858
from $858 / night
BEAUTIFUL EDGARTOWN COLONIAL WITH POOL
Edgartown House - 8.5 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
$1015
from $1015 / night
Oyster Watcha Meadow Guest House
Edgartown House - 8.7 miles away
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$607
from $607 / night
Oyster Watcha Meadow-Main House
Edgartown House - 8.7 miles away
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 9 9
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$858
from $858 / night
Situated in an open meadow, with summer breezes.
Edgartown House - 8.8 miles away
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$286
from $286 / night
IDYLLIC AWARD WINNING HOME SET ON THE OUTSKIRTS OF EDGARTOWN
Edgartown House - 8.8 miles away
- 3 bedrooms 3
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$571
from $571 / night
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