Chilmark 3-bedroom Vacation Rentals, Homes & More - 38 Rentals Available.
38 Vacation rentals
Filters applied: 3+ 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
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
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
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
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
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
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
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
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
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
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
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
BRESP - Waterview, Association Beach
Chilmark House
- 6 bedrooms 6
- 4 bathrooms
- Sleeps 10 10
- 7 nights min
- Ask about children
$1229
from $1229 / 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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
FERRN - Summer in Chilmark, Private Location, Large Deck w Outdoor Dining
Chilmark House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$400
from $400 / night
Amazing Water View Home (412)
Chilmark House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
$715
from $715 / night
Your search has been expanded 8.3 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
MCCAL - Waterview, A/C, WiFi, Menemsha Pond Access
Menemsha House - 1 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$743
from $743 / night
WEINS - Pristine Hilltop Restored Farm House with Distant Waterviews. Set on
Aquinnah House - 1.9 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 5 5
- 7 nights min
- Ask about children
$686
from $686 / 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
LORUA - Waterfront, Central A/C
Aquinnah House - 1.9 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$683
from $683 / night
KINNE - Easy Breezy Vacation Home with Distant Waterview, Tri-Level Living
Aquinnah House - 2 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
$286
from $286 / night
WEINP - Hilltop in Aquinah, Heated Pool, Spectacular Views, Expansive Decks
Aquinnah House - 2.3 miles away
- 5 bedrooms 5
- 3 bathrooms
- Sleeps 9 9
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1429
from $1429 / night
TIERD - Light House Rd Contemporary Retreat with Spectacular Unobstructed
Aquinnah House - 2.4 miles away
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$672
from $672 / 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
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
$429
from $429 / 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
DREIJ - Seven Gates Farm, Waterfront, Private Beach, WiFi
West Tisbury House - 5.2 miles away
- 3 bedrooms 3
- 1 bathroom
- Sleeps 6 6
- 7 nights min
- Ask about children
$636
from $636 / 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
FIELC - Spectacular Sunsets, Ocean View Main and Guest House, Private
West Tisbury House - 5.5 miles away
- 10 bedrooms 10
- 5 bathrooms
- Sleeps 15 15
- 7 nights min
- Ask about children
- Air conditioning
$1650
from $1650 / night
JORWT - Charming West Tisbury Summer Home, Beautiful Modern Decor, Fabulous
West Tisbury House - 5.8 miles away
- 6 bedrooms 6
- 4 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$543
from $543 / 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
DOUGC - Historic, Arrowhead Farm, Wifi, Some A/C
West Tisbury House - 6.1 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Ask about children
- Air conditioning
$529
from $529 / night
MILLD - Green Home, Private Location, Short Drive to Gorgeous West Tisbury
West Tisbury House - 6.4 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
$272
from $272 / night
SWINL - Private Pool, Landscaped Yard, Wifi
West Tisbury House - 6.6 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Swimming pool
- Ask about children
$515
from $515 / night
CASED - Deep Bottom Pond, Private Heated Pool, Central Air, WiFi, Gorgeous Views
West Tisbury House - 6.8 miles away
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 8 8
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$715
from $715 / 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
BALAR - Vineyard Meadow Farms Home, Close to Gorgeous Long Point Beach
West Tisbury House - 7.4 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$543
from $543 / night
FUNAA - Long Point Beach House, 5 min Drive to the Beach, Large Deck
West Tisbury House - 7.5 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$386
from $386 / 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
ROSSP - Chic Contemporary Luxury Home, Privately Situated on Large Acreage off
West Tisbury House - 7.5 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 7 7
- 7 nights min
- Ask about children
- Air conditioning
$500
from $500 / night
MASCJ - Rustling Oaks, Beautiful New Contemporary Home, Private Yard , Close to
West Tisbury House - 7.7 miles away
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$286
from $286 / night
BLANB - Beachy Keen House at Long Point, A/C, Designer Interior, Large Deck
West Tisbury House - 7.8 miles away
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$250
from $250 / night
SCHEB - Waterfront on Ice House Pond (Old House Pond), Swim, Kayak, Spacious
West Tisbury House - 7.8 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$386
from $386 / night
WOODJ - Gorgeous Retreat, Pool 18 X 36', Lush Landscaped Yard, Expansive Deck
West Tisbury House - 7.9 miles away
- 5 bedrooms 5
- 3 bathrooms
- Sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$658
from $658 / night
SUTUG - Lambert's Cove Rd., Private Beach Access, Hi Speed Internet, Central A/C
West Tisbury House - 8 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 5 5
- 7 nights min
- Ask about children
- Air conditioning
$350
from $350 / night
ACKLB - Longview Country House, 2 Private Decks, 1 Mile to Lambert's Cove
West Tisbury House - 8.1 miles away
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$311
from $311 / night
COHEC - Longview Contemporary, A/C, WiFi, Close to Lambert's Cove Beach
West Tisbury House - 8.1 miles away
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$293
from $293 / night
MARCA - SOUTH BEACH WEST TISBURY, CENTRAL AIR, WIFI INTERNET
West Tisbury House - 8.1 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$593
from $593 / 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
ABBOP - WALK TO PRIVATE BEACH, WIFI INTERNET, AC
West Tisbury House - 8.2 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$208
from $208 / night
ROSSJ - 1.5 Acres of Privacy, Bike Paths Adjacent to House, Association Pool
West Tisbury House - 8.3 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
$286
from $286 / night
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