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Chilmark Vacation Rentals

Chilmark Vacation Rentals

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71 rentals in Chilmark.
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Classic,upscale Chilmark Farmhouse and private beach, vacation rental in Chilmark
Classic,upscale Chilmark Farmhouse and private beach, vacation rental in Chilmark
Classic,upscale Chilmark Farmhouse and private beach, vacation rental in Chilmark

Classic,upscale Chilmark Farmhouse and private beach

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
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, vacation rental in Chilmark
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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Classic Cape in ideal, Chilmark location, Pet Friendly, vacation rental in Chilmark
Classic Cape in ideal, Chilmark location, Pet Friendly, vacation rental in Chilmark
Classic Cape in ideal, Chilmark location, Pet Friendly, vacation rental in Chilmark

Classic Cape in ideal, Chilmark location, Pet Friendly

Rental Home
4 bedrooms
3 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, vacation rental in Chilmark
Spectacular Newly Renovated Home in Menemsha, vacation rental in Chilmark

Spectacular Newly Renovated Home in Menemsha

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Vintage 1920s House W/Beach Path & Glorious Sunset Water Views, vacation rental in Chilmark
Vintage 1920s House W/Beach Path & Glorious Sunset Water Views, vacation rental in Chilmark
Vintage 1920s House W/Beach Path & Glorious Sunset Water Views, vacation rental in Chilmark

Vintage 1920s House W/Beach Path & Glorious Sunset Water Views

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!, vacation rental in Chilmark
Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!, vacation rental in Chilmark
Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!, vacation rental in Chilmark

Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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10 minutes walk to Lucy Vincent Beach, vacation rental in Chilmark
10 minutes walk to Lucy Vincent Beach, vacation rental in Chilmark
10 minutes walk to Lucy Vincent Beach, vacation rental in Chilmark

10 minutes walk to Lucy Vincent Beach

Rental Home
4 bedrooms
4 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, vacation rental in Chilmark
Ideal Menemsha House with Private Beach and Breathtaking Sunset Views, vacation rental in Chilmark

Ideal Menemsha House with Private Beach and Breathtaking Sunset Views

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded Guest House overlooking Menemsha pond. Dogs welcome. Path to pond!, vacation rental in Chilmark
Secluded Guest House overlooking Menemsha pond. Dogs welcome. Path to pond!, vacation rental in Chilmark
Secluded Guest House overlooking Menemsha pond. Dogs welcome. Path to pond!, vacation rental in Chilmark

Secluded Guest House overlooking Menemsha pond. Dogs welcome. Path to pond!

Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Exclusive Aquinnah Hilltop Home —Stunning Views of Menemsha Pond — Pet Friendly, vacation rental in Chilmark
Exclusive Aquinnah Hilltop Home —Stunning Views of Menemsha Pond — Pet Friendly, vacation rental in Chilmark
Exclusive Aquinnah Hilltop Home —Stunning Views of Menemsha Pond — Pet Friendly, vacation rental in Chilmark

Exclusive Aquinnah Hilltop Home —Stunning Views of Menemsha Pond — Pet Friendly

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Spectacular Oceanfront, 4 BR/4 bath, Hottub, Private Beach, Tennis, AC, WiFi, vacation rental in Chilmark
Spectacular Oceanfront, 4 BR/4 bath, Hottub, Private Beach, Tennis, AC, WiFi, vacation rental in Chilmark
Spectacular Oceanfront, 4 BR/4 bath, Hottub, Private Beach, Tennis, AC, WiFi, vacation rental in Chilmark

Spectacular Oceanfront, 4 BR/4 bath, Hottub, Private Beach, Tennis, AC, WiFi

Rental Home
4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Cool, Mid Century House --  Lots of Light!!, vacation rental in Chilmark
Cool, Mid Century House --  Lots of Light!!, vacation rental in Chilmark
Cool, Mid Century House --  Lots of Light!!, vacation rental in Chilmark

Cool, Mid Century House -- Lots of Light!!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Rebuilt Private Menemsha Home! Chilmark Ma., vacation rental in Chilmark
Rebuilt Private Menemsha Home! Chilmark Ma., vacation rental in Chilmark
Rebuilt Private Menemsha Home! Chilmark Ma., vacation rental in Chilmark

Rebuilt Private Menemsha Home! Chilmark Ma.

Rental Home
3 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
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Contemporary Cottage with Breathtaking Views, vacation rental in Chilmark
Contemporary Cottage with Breathtaking Views, vacation rental in Chilmark
Contemporary Cottage with Breathtaking Views, vacation rental in Chilmark

Contemporary Cottage with Breathtaking Views

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
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, vacation rental in Chilmark
Quintessential Chilmark Retreat With Water Views In Martha's Vineyard, vacation rental in Chilmark

Quintessential Chilmark Retreat With Water Views In Martha's Vineyard

Rental Home
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Peaceful Wooded Retreat, Short Car Ride to Everything. Week is Friday to Friday, vacation rental in Chilmark
Peaceful Wooded Retreat, Short Car Ride to Everything. Week is Friday to Friday, vacation rental in Chilmark
Peaceful Wooded Retreat, Short Car Ride to Everything. Week is Friday to Friday, vacation rental in Chilmark

Peaceful Wooded Retreat, Short Car Ride to Everything. Week is Friday to Friday

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby, vacation rental in Chilmark
Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby, vacation rental in Chilmark
Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby, vacation rental in Chilmark

Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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, vacation rental in Chilmark
Striking 5BR/4BA Chilmark Contemporary with Views of the Sound, vacation rental in Chilmark

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

Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
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, vacation rental in Chilmark
Fully Appointed Water View House  Ten Minutes Walk from Beach, vacation rental in Chilmark

Fully Appointed Water View House Ten Minutes Walk from Beach

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Best deal in Chilmark (Open Memorial Day weekend-Nov. 15), vacation rental in Chilmark
Best deal in Chilmark (Open Memorial Day weekend-Nov. 15), vacation rental in Chilmark
Best deal in Chilmark (Open Memorial Day weekend-Nov. 15), vacation rental in Chilmark

Best deal in Chilmark (Open Memorial Day weekend-Nov. 15)

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Chilmark home with water views and key to Black Point Beach, vacation rental in Chilmark
Chilmark home with water views and key to Black Point Beach, vacation rental in Chilmark
Chilmark home with water views and key to Black Point Beach, vacation rental in Chilmark

Chilmark home with water views and key to Black Point Beach

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Menemsha Village - Davis Cottage, vacation rental in Chilmark
Menemsha Village - Davis Cottage, vacation rental in Chilmark
Menemsha Village - Davis Cottage, vacation rental in Chilmark

Menemsha Village - Davis Cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Pet-Friendly Historic Chilmark Cottage, vacation rental in Chilmark
Pet-Friendly Historic Chilmark Cottage, vacation rental in Chilmark
Pet-Friendly Historic Chilmark Cottage, vacation rental in Chilmark

Pet-Friendly Historic Chilmark Cottage

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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3 Bedroom House with Guest Cottage on 3 Acres off Middle Road, vacation rental in Chilmark
3 Bedroom House with Guest Cottage on 3 Acres off Middle Road, vacation rental in Chilmark
3 Bedroom House with Guest Cottage on 3 Acres off Middle Road, vacation rental in Chilmark

3 Bedroom House with Guest Cottage on 3 Acres off Middle Road

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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In Menemsha Village - Sunset House, vacation rental in Chilmark
In Menemsha Village - Sunset House, vacation rental in Chilmark
In Menemsha Village - Sunset House, vacation rental in Chilmark

In Menemsha Village - Sunset House

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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3 BR, 3 bath, Private Chilmark Home, Hot tub, pet friendly, large yard & patio, vacation rental in Chilmark
3 BR, 3 bath, Private Chilmark Home, Hot tub, pet friendly, large yard & patio, vacation rental in Chilmark
3 BR, 3 bath, Private Chilmark Home, Hot tub, pet friendly, large yard & patio, vacation rental in Chilmark

3 BR, 3 bath, Private Chilmark Home, Hot tub, pet friendly, large yard & patio

Rental Home
3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks, vacation rental in Chilmark
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks, vacation rental in Chilmark
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks, vacation rental in Chilmark

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Chilmark beach house with private Abel's Hill beach access, vacation rental in Chilmark
Charming Chilmark beach house with private Abel's Hill beach access, vacation rental in Chilmark
Charming Chilmark beach house with private Abel's Hill beach access, vacation rental in Chilmark

Charming Chilmark beach house with private Abel's Hill beach access

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Enjoy privacy and tranquility on the shores of the Tisbury Great Pond, vacation rental in Chilmark
Enjoy privacy and tranquility on the shores of the Tisbury Great Pond, vacation rental in Chilmark
Enjoy privacy and tranquility on the shores of the Tisbury Great Pond, vacation rental in Chilmark

Enjoy privacy and tranquility on the shores of the Tisbury Great Pond

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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, vacation rental in Chilmark
Striking 5BR/4BA Chilmark Contemporary with Views of the Sound, vacation rental in Chilmark

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

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Chilmark Vista and Lucy Vincent Beach, vacation rental in Chilmark
Chilmark Vista and Lucy Vincent Beach, vacation rental in Chilmark
Chilmark Vista and Lucy Vincent Beach, vacation rental in Chilmark

Chilmark Vista and Lucy Vincent Beach

Rental Home
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Airey Two Bedroom Menemsha cottage, vacation rental in Chilmark
Airey Two Bedroom Menemsha cottage, vacation rental in Chilmark
Airey Two Bedroom Menemsha cottage, vacation rental in Chilmark

Airey Two Bedroom Menemsha cottage

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

Tucked Away on Tea Lane, Chilmark

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Peaceful Chilmark Farmhouse by Menemsha Beach, vacation rental in Chilmark
Peaceful Chilmark Farmhouse by Menemsha Beach, vacation rental in Chilmark
Peaceful Chilmark Farmhouse by Menemsha Beach, vacation rental in Chilmark

Peaceful Chilmark Farmhouse by Menemsha Beach

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Menemsha Harborside Cottage, vacation rental in Chilmark
Menemsha Harborside Cottage, vacation rental in Chilmark
Menemsha Harborside Cottage, vacation rental in Chilmark

Menemsha Harborside Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Quiet Home with Beach & Peek-A-Boo Ocean Views, Free WiFi, Washer/Dryer, vacation rental in Chilmark
Quiet Home with Beach & Peek-A-Boo Ocean Views, Free WiFi, Washer/Dryer, vacation rental in Chilmark
Quiet Home with Beach & Peek-A-Boo Ocean Views, Free WiFi, Washer/Dryer, vacation rental in Chilmark

Quiet Home with Beach & Peek-A-Boo Ocean Views, Free WiFi, Washer/Dryer

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded Mid-Century Home w/Large Deck, Yard, Gas Grill, and Partial A/C, vacation rental in Chilmark
Secluded Mid-Century Home w/Large Deck, Yard, Gas Grill, and Partial A/C, vacation rental in Chilmark
Secluded Mid-Century Home w/Large Deck, Yard, Gas Grill, and Partial A/C, vacation rental in Chilmark

Secluded Mid-Century Home w/Large Deck, Yard, Gas Grill, and Partial A/C

Rental Home
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful house on Chilmark Pond with water view, pool & access to private beach, vacation rental in Chilmark
Beautiful house on Chilmark Pond with water view, pool & access to private beach, vacation rental in Chilmark
Beautiful house on Chilmark Pond with water view, pool & access to private beach, vacation rental in Chilmark

Beautiful house on Chilmark Pond with water view, pool & access to private beach

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Chilmark Farmhouse with access to Hancock Beach, vacation rental in Chilmark
Chilmark Farmhouse with access to Hancock Beach, vacation rental in Chilmark
Chilmark Farmhouse with access to Hancock Beach, vacation rental in Chilmark

Chilmark Farmhouse with access to Hancock Beach

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful, Historic Farmhouse & Guest House on Chilmark Pond, vacation rental in Chilmark
Beautiful, Historic Farmhouse & Guest House on Chilmark Pond, vacation rental in Chilmark
Beautiful, Historic Farmhouse & Guest House on Chilmark Pond, vacation rental in Chilmark

Beautiful, Historic Farmhouse & Guest House on Chilmark Pond

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

Family friendly beach house sleeps 12

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Chilmark two bedroom, one bath cottage with waterfront and private beach, vacation rental in Chilmark
Chilmark two bedroom, one bath cottage with waterfront and private beach, vacation rental in Chilmark
Chilmark two bedroom, one bath cottage with waterfront and private beach, vacation rental in Chilmark

Chilmark two bedroom, one bath cottage with waterfront and private beach

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Clay Cliffs in your Backyard, Private Beach in Chilmark, 3 BR, 3 bath, WiFi, AC, vacation rental in Chilmark
Clay Cliffs in your Backyard, Private Beach in Chilmark, 3 BR, 3 bath, WiFi, AC, vacation rental in Chilmark
Clay Cliffs in your Backyard, Private Beach in Chilmark, 3 BR, 3 bath, WiFi, AC, vacation rental in Chilmark

Clay Cliffs in your Backyard, Private Beach in Chilmark, 3 BR, 3 bath, WiFi, AC

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming Oceanfront Cottage in Chilmark, vacation rental in Chilmark
Charming Oceanfront Cottage in Chilmark, vacation rental in Chilmark
Charming Oceanfront Cottage in Chilmark, vacation rental in Chilmark

Charming Oceanfront Cottage in Chilmark

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Chilmark pondside cottage with private beach, sweeping views, vacation rental in Chilmark
Chilmark pondside cottage with private beach, sweeping views, vacation rental in Chilmark
Chilmark pondside cottage with private beach, sweeping views, vacation rental in Chilmark

Chilmark pondside cottage with private beach, sweeping views

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Amazing Water Views in Chilmark, 4-BR, Waterfront, Key to Zak’s Beach in GAYHEAD, vacation rental in Chilmark
Amazing Water Views in Chilmark, 4-BR, Waterfront, Key to Zak’s Beach in GAYHEAD, vacation rental in Chilmark
Amazing Water Views in Chilmark, 4-BR, Waterfront, Key to Zak’s Beach in GAYHEAD, vacation rental in Chilmark

Amazing Water Views in Chilmark, 4-BR, Waterfront, Key to Zak’s Beach in GAYHEAD

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Waterfront Compound - Heated Pool, Hot Tub, Tennis Court, Private Beach, 7 BR, vacation rental in Chilmark
Waterfront Compound - Heated Pool, Hot Tub, Tennis Court, Private Beach, 7 BR, vacation rental in Chilmark
Waterfront Compound - Heated Pool, Hot Tub, Tennis Court, Private Beach, 7 BR, vacation rental in Chilmark

Waterfront Compound - Heated Pool, Hot Tub, Tennis Court, Private Beach, 7 BR

Rental Home
7 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails, vacation rental in Chilmark
Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails, vacation rental in Chilmark
Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails, vacation rental in Chilmark

Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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CHARMING COUNTRY HOME IN CHILMARK, vacation rental in Chilmark
CHARMING COUNTRY HOME IN CHILMARK, vacation rental in Chilmark
CHARMING COUNTRY HOME IN CHILMARK, vacation rental in Chilmark

CHARMING COUNTRY HOME IN CHILMARK

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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, vacation rental in Chilmark
CHARMING HOME W/VIEWS OF VINEYARD SOUND & ELIZABETH ISLANDS, vacation rental in Chilmark

CHARMING HOME W/VIEWS OF VINEYARD SOUND & ELIZABETH ISLANDS

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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