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Chilmark Holiday Apartments

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28 rentals in Chilmark.
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Private oceanfront compound , 1/3 mi Private Beach, AC, Chilmark, WiFi, holiday 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, holiday 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, holiday 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, holiday 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!, holiday 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, holiday 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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Menemsha Harborside Cottage - STEAMSHIP reservations available for open Aug. wks, holiday 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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Airey Two Bedroom Menemsha cottage, holiday rental in Chilmark

Airey Two Bedroom Menemsha cottage

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Tucked Away on Tea Lane, Chilmark, holiday rental in Chilmark

Tucked Away on Tea Lane, Chilmark

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Fully Appointed Water View House  Ten Minutes Walk from Beach, holiday 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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Beautiful, historic farmhouse on Chilmark Pond, holiday rental in Chilmark

Beautiful, historic farmhouse on Chilmark Pond

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Family friendly beach house sleeps 12, holiday rental in Chilmark

Family friendly beach house sleeps 12

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Chilmark Farmhouse with access to Hancock Beach, holiday 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, holiday 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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Gracious and Spacious Chilmark Home with a Pool, holiday rental in Chilmark

Gracious and Spacious Chilmark Home with a Pool

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Chilmark Hilltop Ocean View, holiday rental in Chilmark

Spectacular Chilmark Hilltop Ocean View

5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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CLASSIC VINEYARD FISHING VILLAGE VIEWS FROM THIS QUINTESSENTIAL COTTAGE, holiday rental in Chilmark

CLASSIC VINEYARD FISHING VILLAGE VIEWS FROM THIS QUINTESSENTIAL COTTAGE

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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ARCHITECTURAL AWARD WINNING HOME WITH PANORAMIC VIEWS OF THE VINEYARD SOUND, holiday 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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Secluded 4.5-Acre Estate w/ Huge Screened Porch & Quansoo Beach Access, holiday 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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Striking 5BR/4BA Chilmark Contemporary with Views of the Sound, holiday 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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SPACIOUS AND COMFORTABLE CHILMARK CAPE WITH CENTRAL AIR CONDITIONING, holiday rental in Chilmark

SPACIOUS AND COMFORTABLE CHILMARK CAPE WITH CENTRAL AIR CONDITIONING

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Expanded Cape on Wade's Cove & Key to Hancock Beach, holiday 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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Ideal Menemsha House with Private Beach and Breathtaking Sunset Views, holiday 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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comfortable ranch house overlooking Menemsha Bight, holiday rental in Chilmark

comfortable ranch house overlooking Menemsha Bight

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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CHARMING COUNTRY HOME IN CHILMARK, holiday rental in Chilmark

CHARMING COUNTRY HOME IN CHILMARK

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Home with Waterviews of Vineyard Sound and Elizabeth Islands, holiday 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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CHARMING HOME W/VIEWS OF VINEYARD SOUND & ELIZABETH ISLANDS, holiday rental in Chilmark

CHARMING HOME W/VIEWS OF VINEYARD SOUND & ELIZABETH ISLANDS

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

Spring Point Cottage With Gorgeous Sunsets Overlooking Vineyard Sound

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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