Chilmark 2-bedroom Vacation Rentals, Homes & More - 516 Rentals Available.
516 Vacation rentals
Filters applied: 2+ Bedrooms

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

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

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

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
$1,215.00
from $1,215.00 / 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
$214.00
from $214.00 / 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
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
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
$180.00
from $180.00 / 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
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
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
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
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
$1,822.00
from $1,822.00 / 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
PERRG - North Slope Hilltop House. Private yard, Screeened Porch and Patio, 8
Chilmark House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$429.00
from $429.00 / night
WINGR - 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
$1,858.00
from $1,858.00 / night
WATTL - Cottage with Screened Porch, Close to Menemsha Village Area and just a S
Chilmark House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Ask about children
- Air conditioning
$143.00
from $143.00 / night
$429.00
from $429.00 / night
SUDRL - Ocean View House! Luxury Main and Guest, Waterfront on the Vineyard Soun
Chilmark House
- 7 bedrooms 7
- 3 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$1,715.00
from $1,715.00 / night
Your search has been expanded 18.7 miles to include more rentals
86 Falmouth Heights Road
Falmouth House - 15.7 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 14 14
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$928.00
from $928.00 / night
85-89 Snug Harbor Lane
Falmouth House - 18.2 miles away
- 5 bedrooms 5
- 4 bathrooms
- sleeps 12 12
- 1 night min
- Ask about children
- Ask about pets
$1,285.00
from $1,285.00 / night
151 Nursery Road
Falmouth House - 16 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 1 night min
- Ask about children
- Ask about pets
$400.00
from $400.00 / night
33 Morris Street
Falmouth House - 17 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 1 night min
- Ask about children
- Ask about pets
$400.00
from $400.00 / night
219 Grand Avenue
Falmouth House - 15.7 miles away
- 13 bedrooms 13
- 8 bathrooms
- sleeps 23 23
- 1 night min
- Ask about children
- Ask about pets
$1,142.00
from $1,142.00 / night
22 Meadow Lane
Falmouth House - 15.2 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 5 5
- 1 night min
- Ask about children
- Ask about pets
$428.00
from $428.00 / 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
$1,857.00
from $1,857.00 / night
5 Onawa Lane
Falmouth House - 14.3 miles away
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- 1 night min
- Ask about children
- Ask about pets
$685.00
from $685.00 / night
368 Walker Street
Falmouth House - 14.8 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- 1 night min
- Ask about children
- Ask about pets
$714.00
from $714.00 / night
22 Worcester Court
Falmouth House - 15.8 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 1 night min
- Ask about children
- Ask about pets
$542.00
from $542.00 / night
286 Grand Avenue
Falmouth House - 15.5 miles away
- 2 bedrooms 2
- 3 bathrooms
- sleeps 4 4
- 1 night min
- Ask about children
- Pet friendly
$928.00
from $928.00 / night
856 Palmer Ave
Falmouth House - 16.8 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 1 night min
- Ask about children
- Ask about pets
$364.00
from $364.00 / night
20 Montgomery Avenue
Falmouth House - 15.7 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 12 12
- 1 night min
- Ask about children
- Ask about pets
$714.00
from $714.00 / night
185 Associates Road
Falmouth House - 17.9 miles away
- 9 bedrooms 9
- 6 bathrooms
- sleeps 14 14
- 1 night min
- Swimming pool
- Ask about children
- Ask about pets
$1,714.00
from $1,714.00 / night
Waterfront-Martha's Vineyard
Oak Bluffs 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
New Cape House Steps to the Beach in East Falmouth
Falmouth House - 18.7 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$430.00
from $430.00 / 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 34 minutes
$459.00
from $459.00 / 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
Ocean, lake, harbor and parkview Vineyard cottage
Oak Bluffs Cottage - 12.5 miles away
- 6 bedrooms 6
- 2 bathrooms
- sleeps 10 10
- min stay varies
- Nearest beach 0.2 mi
- Child friendly
- Car not necessary
Responds fast! Avg. 17 minutes
$573.00
from $573.00 / 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
$115.00
from $115.00 / night
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