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Chilmark Vacation Rentals

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40 rentals in Chilmark.
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Private oceanfront compound , 1/3 mi Private Beach, AC, Chilmark, WiFi, vacation rental in Chilmark

Private oceanfront compound , 1/3 mi Private Beach, AC, Chilmark, WiFi

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice, vacation rental in Chilmark

Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Newly Renovated Home in Menemsha, vacation rental in Chilmark

Spectacular Newly Renovated Home in Menemsha

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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In Menemsha Village - Sunset House, vacation rental in Chilmark

In Menemsha Village - Sunset House

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Iconic mid-century home with gorgeous ocean views, private pool and decks!, vacation rental in Chilmark

Iconic mid-century home with gorgeous ocean views, private pool and decks!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Quintessential Chilmark Retreat With Water Views In Martha's Vineyard, vacation rental in Chilmark

Quintessential Chilmark Retreat With Water Views In Martha's Vineyard

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Tucked Away on Tea Lane, Chilmark, vacation rental in Chilmark

Tucked Away on Tea Lane, Chilmark

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Menemsha Harborside Cottage - STEAMSHIP reservations available for open Aug. wks, vacation rental in Chilmark

Menemsha Harborside Cottage - STEAMSHIP reservations available for open Aug. wks

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Fully Appointed Water View House  Ten Minutes Walk from Beach, vacation rental in Chilmark

Fully Appointed Water View House Ten Minutes Walk from Beach

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Airey Two Bedroom Menemsha cottage, vacation rental in Chilmark

Airey Two Bedroom Menemsha cottage

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful, historic farmhouse on Chilmark Pond, vacation rental in Chilmark

Beautiful, historic farmhouse on Chilmark Pond

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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HORNP - Squibnocket Farm Waterfront, Private Beach,, vacation rental in Chilmark

HORNP - Squibnocket Farm Waterfront, Private Beach,

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Family friendly beach house sleeps 12, vacation rental in Chilmark

Family friendly beach house sleeps 12

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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CLASSIC VINEYARD FISHING VILLAGE VIEWS FROM THIS QUINTESSENTIAL COTTAGE, vacation rental in Chilmark

CLASSIC VINEYARD FISHING VILLAGE VIEWS FROM THIS QUINTESSENTIAL COTTAGE

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Chilmark Farmhouse with access to Hancock Beach, vacation rental in Chilmark

Chilmark Farmhouse with access to Hancock Beach

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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4 Bedroom on 5 Acres of Woodlands with Fresh Eggs and Chickens, vacation rental in Chilmark

4 Bedroom on 5 Acres of Woodlands with Fresh Eggs and Chickens

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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SUDRL - Ocean View House! Luxury Main and Guest, Waterfront on the Vineyard Soun, vacation rental in Chilmark

SUDRL - Ocean View House! Luxury Main and Guest, Waterfront on the Vineyard Soun

7 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Chilmark Hilltop Ocean View, vacation rental in Chilmark

Spectacular Chilmark Hilltop Ocean View

5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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SEFER - Pinkletink House! Custom New home on Prospect Hill , Chilmark,  Gorgeous, vacation rental in Chilmark

SEFER - Pinkletink House! Custom New home on Prospect Hill , Chilmark, Gorgeous

4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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BLASD - A Gem in Chilmark, Impeccably Maintained Home,  Multiple Decks and Patio, vacation rental in Chilmark

BLASD - A Gem in Chilmark, Impeccably Maintained Home, Multiple Decks and Patio

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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ARCHITECTURAL AWARD WINNING HOME WITH PANORAMIC VIEWS OF THE VINEYARD SOUND, vacation rental in Chilmark

ARCHITECTURAL AWARD WINNING HOME WITH PANORAMIC VIEWS OF THE VINEYARD SOUND

6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Gracious and Spacious Chilmark Home with a Pool, vacation rental in Chilmark

Gracious and Spacious Chilmark Home with a Pool

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Expanded Cape on Wade's Cove & Key to Hancock Beach, vacation rental in Chilmark

Luxury Expanded Cape on Wade's Cove & Key to Hancock Beach

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Striking 5BR/4BA Chilmark Contemporary with Views of the Sound, vacation rental in Chilmark

Striking 5BR/4BA Chilmark Contemporary with Views of the Sound

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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CHARMING COUNTRY HOME IN CHILMARK, vacation rental in Chilmark

CHARMING COUNTRY HOME IN CHILMARK

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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PERRG - North Slope Hilltop House.  Private yard, Screeened  Porch and Patio,  8, vacation rental in Chilmark

PERRG - North Slope Hilltop House. Private yard, Screeened Porch and Patio, 8

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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SPACIOUS AND COMFORTABLE CHILMARK CAPE WITH CENTRAL AIR CONDITIONING, vacation rental in Chilmark

SPACIOUS AND COMFORTABLE CHILMARK CAPE WITH CENTRAL AIR CONDITIONING

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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SPANM - Sweet Chilmark Cottage, Spacious Screened Porch and Deck Area, Private L, vacation rental in Chilmark

SPANM - Sweet Chilmark Cottage, Spacious Screened Porch and Deck Area, Private L

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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HERGT - Luxury Retreat Chilmark, Key to Quansoo Private Association Beach, Set o, vacation rental in Chilmark

HERGT - Luxury Retreat Chilmark, Key to Quansoo Private Association Beach, Set o

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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WEBSL - Menemsha, vacation rental in Chilmark

WEBSL - Menemsha

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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CHARMING HOME W/VIEWS OF VINEYARD SOUND & ELIZABETH ISLANDS, vacation rental in Chilmark

CHARMING HOME W/VIEWS OF VINEYARD SOUND & ELIZABETH ISLANDS

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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LORUJ - Spacious Ocean View Home,  Private Association Beach - South Shore - Inq, vacation rental in Chilmark

LORUJ - Spacious Ocean View Home, Private Association Beach - South Shore - Inq

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Ideal Menemsha House with Private Beach and Breathtaking Sunset Views, vacation rental in Chilmark

Ideal Menemsha House with Private Beach and Breathtaking Sunset Views

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded 4.5-Acre Estate w/ Huge Screened Porch & Quansoo Beach Access, vacation rental in Chilmark

Secluded 4.5-Acre Estate w/ Huge Screened Porch & Quansoo Beach Access

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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WINGR -  Designer Luxury with Oustanding Atlantic Ocean Views,  Private Beaches,, vacation rental in Chilmark

WINGR - Designer Luxury with Oustanding Atlantic Ocean Views, Private Beaches,

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Spectacular Home with Waterviews of Vineyard Sound and Elizabeth Islands, vacation rental in Chilmark

Spectacular Home with Waterviews of Vineyard Sound and Elizabeth Islands

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spring Point Cottage With Gorgeous Sunsets Overlooking Vineyard Sound, vacation rental in Chilmark

Spring Point Cottage With Gorgeous Sunsets Overlooking Vineyard Sound

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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WATTL - Cottage with Screened Porch, Close to Menemsha Village Area and just a S, vacation rental in Chilmark

WATTL - Cottage with Screened Porch, Close to Menemsha Village Area and just a S

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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comfortable ranch house overlooking Menemsha Bight, vacation rental in Chilmark

comfortable ranch house overlooking Menemsha Bight

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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SIDMC - Outstanding Chilmark Home,  Heated Pool 18 x 36 with Patio Surround, Exc, vacation rental in Chilmark

SIDMC - Outstanding Chilmark Home, Heated Pool 18 x 36 with Patio Surround, Exc

0 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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