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Holiday Rentals in Menemsha

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50 rentals in Menemsha.
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Rebuilt Private Menemsha Home! Chilmark Ma., holiday rental in Menemsha
Rebuilt Private Menemsha Home! Chilmark Ma., holiday rental in Menemsha
Rebuilt Private Menemsha Home! Chilmark Ma., holiday rental in Menemsha

Rebuilt Private Menemsha Home! Chilmark Ma.

Holiday Rental House
3 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
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Magical House in the Trees with Water View - Secluded Area, holiday rental in Menemsha
Magical House in the Trees with Water View - Secluded Area, holiday rental in Menemsha
Magical House in the Trees with Water View - Secluded Area, holiday rental in Menemsha

Magical House in the Trees with Water View - Secluded Area

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Martha's Vineyard Cozy Getaway near picturesque Philbin Beach, holiday rental in Menemsha
Martha's Vineyard Cozy Getaway near picturesque Philbin Beach, holiday rental in Menemsha
Martha's Vineyard Cozy Getaway near picturesque Philbin Beach, holiday rental in Menemsha

Martha's Vineyard Cozy Getaway near picturesque Philbin Beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice, holiday rental in Menemsha
Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice, holiday rental in Menemsha
Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice, holiday rental in Menemsha

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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Serenity and calm. Private Ocean Beach/Menemsha Pond Access. Kayak Use Included, holiday rental in Menemsha
Serenity and calm. Private Ocean Beach/Menemsha Pond Access. Kayak Use Included, holiday rental in Menemsha
Serenity and calm. Private Ocean Beach/Menemsha Pond Access. Kayak Use Included, holiday rental in Menemsha

Serenity and calm. Private Ocean Beach/Menemsha Pond Access. Kayak Use Included

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Newly Renovated Home in Menemsha, holiday rental in Menemsha
Spectacular Newly Renovated Home in Menemsha, holiday rental in Menemsha
Spectacular Newly Renovated Home in Menemsha, holiday rental in Menemsha

Spectacular Newly Renovated Home in Menemsha

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Exclusive Aquinnah Hilltop Home —Stunning Views of Menemsha Pond — Pet Friendly, holiday rental in Menemsha
Exclusive Aquinnah Hilltop Home —Stunning Views of Menemsha Pond — Pet Friendly, holiday rental in Menemsha
Exclusive Aquinnah Hilltop Home —Stunning Views of Menemsha Pond — Pet Friendly, holiday rental in Menemsha

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

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

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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!, holiday rental in Menemsha
Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!, holiday rental in Menemsha
Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!, holiday rental in Menemsha

Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Ideal Menemsha House with Private Beach and Breathtaking Sunset Views, holiday rental in Menemsha
Ideal Menemsha House with Private Beach and Breathtaking Sunset Views, holiday rental in Menemsha
Ideal Menemsha House with Private Beach and Breathtaking Sunset Views, holiday rental in Menemsha

Ideal Menemsha House with Private Beach and Breathtaking Sunset Views

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Secluded Guest House overlooking Menemsha pond. Dogs welcome. Path to pond!, holiday rental in Menemsha
Secluded Guest House overlooking Menemsha pond. Dogs welcome. Path to pond!, holiday rental in Menemsha
Secluded Guest House overlooking Menemsha pond. Dogs welcome. Path to pond!, holiday rental in Menemsha

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Quintessential Chilmark Retreat With Water Views In Martha's Vineyard, holiday rental in Menemsha
Quintessential Chilmark Retreat With Water Views In Martha's Vineyard, holiday rental in Menemsha
Quintessential Chilmark Retreat With Water Views In Martha's Vineyard, holiday rental in Menemsha

Quintessential Chilmark Retreat With Water Views In Martha's Vineyard

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Luminous rural retreat with spectacular ocean views., holiday rental in Menemsha
Luminous rural retreat with spectacular ocean views., holiday rental in Menemsha
Luminous rural retreat with spectacular ocean views., holiday rental in Menemsha

Luminous rural retreat with spectacular ocean views.

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Private Beach Oceanfront Cottage, holiday rental in Menemsha
Private Beach Oceanfront Cottage, holiday rental in Menemsha
Private Beach Oceanfront Cottage, holiday rental in Menemsha

Private Beach Oceanfront Cottage

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby, holiday rental in Menemsha
Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby, holiday rental in Menemsha
Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby, holiday rental in Menemsha

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Fully Appointed Water View House  Ten Minutes Walk from Beach, holiday rental in Menemsha
Fully Appointed Water View House  Ten Minutes Walk from Beach, holiday rental in Menemsha
Fully Appointed Water View House  Ten Minutes Walk from Beach, holiday rental in Menemsha

Fully Appointed Water View House Ten Minutes Walk from Beach

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Chilmark home with water views and key to Black Point Beach, holiday rental in Menemsha
Chilmark home with water views and key to Black Point Beach, holiday rental in Menemsha
Chilmark home with water views and key to Black Point Beach, holiday rental in Menemsha

Chilmark home with water views and key to Black Point Beach

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Menemsha Village - Davis Cottage, holiday rental in Menemsha
Menemsha Village - Davis Cottage, holiday rental in Menemsha
Menemsha Village - Davis Cottage, holiday rental in Menemsha

Menemsha Village - Davis Cottage

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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"Over South", Family farm house in Chilmark, holiday rental in Menemsha
"Over South", Family farm house in Chilmark, holiday rental in Menemsha
"Over South", Family farm house in Chilmark, holiday rental in Menemsha

"Over South", Family farm house in Chilmark

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Pet-Friendly Historic Chilmark Cottage, holiday rental in Menemsha
Pet-Friendly Historic Chilmark Cottage, holiday rental in Menemsha
Pet-Friendly Historic Chilmark Cottage, holiday rental in Menemsha

Pet-Friendly Historic Chilmark Cottage

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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3 Bedroom House with Guest Cottage on 3 Acres off Middle Road, holiday rental in Menemsha
3 Bedroom House with Guest Cottage on 3 Acres off Middle Road, holiday rental in Menemsha
3 Bedroom House with Guest Cottage on 3 Acres off Middle Road, holiday rental in Menemsha

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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In Menemsha Village - Sunset House, holiday rental in Menemsha
In Menemsha Village - Sunset House, holiday rental in Menemsha
In Menemsha Village - Sunset House, holiday rental in Menemsha

In Menemsha Village - Sunset House

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Iconic mid-century home with gorgeous ocean views, private pool and decks!, holiday rental in Menemsha
Iconic mid-century home with gorgeous ocean views, private pool and decks!, holiday rental in Menemsha
Iconic mid-century home with gorgeous ocean views, private pool and decks!, holiday rental in Menemsha

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Pet-Friendly Historic Chilmark House, holiday rental in Menemsha
Pet-Friendly Historic Chilmark House, holiday rental in Menemsha
Pet-Friendly Historic Chilmark House, holiday rental in Menemsha

Pet-Friendly Historic Chilmark House

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Chilmark Vista and Lucy Vincent Beach, holiday rental in Menemsha
Chilmark Vista and Lucy Vincent Beach, holiday rental in Menemsha
Chilmark Vista and Lucy Vincent Beach, holiday rental in Menemsha

Chilmark Vista and Lucy Vincent Beach

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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Airey Two Bedroom Menemsha cottage, holiday rental in Menemsha
Airey Two Bedroom Menemsha cottage, holiday rental in Menemsha
Airey Two Bedroom Menemsha cottage, holiday rental in Menemsha

Airey Two Bedroom Menemsha cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Peaceful Chilmark Farmhouse by Menemsha Beach, holiday rental in Menemsha
Peaceful Chilmark Farmhouse by Menemsha Beach, holiday rental in Menemsha
Peaceful Chilmark Farmhouse by Menemsha Beach, holiday rental in Menemsha

Peaceful Chilmark Farmhouse by Menemsha Beach

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Menemsha Harborside Cottage, holiday rental in Menemsha
Menemsha Harborside Cottage, holiday rental in Menemsha
Menemsha Harborside Cottage, holiday rental in Menemsha

Menemsha Harborside Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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437 State Road,, holiday rental in Menemsha
437 State Road,, holiday rental in Menemsha
437 State Road,, holiday rental in Menemsha

437 State Road,

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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CLASSIC VINEYARD FISHING VILLAGE VIEWS FROM THIS QUINTESSENTIAL COTTAGE, holiday rental in Menemsha
CLASSIC VINEYARD FISHING VILLAGE VIEWS FROM THIS QUINTESSENTIAL COTTAGE, holiday rental in Menemsha
CLASSIC VINEYARD FISHING VILLAGE VIEWS FROM THIS QUINTESSENTIAL COTTAGE, holiday rental in Menemsha

CLASSIC VINEYARD FISHING VILLAGE VIEWS FROM THIS QUINTESSENTIAL COTTAGE

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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CHARMING HOME W/VIEWS OF VINEYARD SOUND & ELIZABETH ISLANDS, holiday rental in Menemsha
CHARMING HOME W/VIEWS OF VINEYARD SOUND & ELIZABETH ISLANDS, holiday rental in Menemsha
CHARMING HOME W/VIEWS OF VINEYARD SOUND & ELIZABETH ISLANDS, holiday rental in Menemsha

CHARMING HOME W/VIEWS OF VINEYARD SOUND & ELIZABETH ISLANDS

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Gracious and Spacious Chilmark Home with a Pool, holiday rental in Menemsha
Gracious and Spacious Chilmark Home with a Pool, holiday rental in Menemsha
Gracious and Spacious Chilmark Home with a Pool, holiday rental in Menemsha

Gracious and Spacious Chilmark Home with a Pool

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Family friendly beach house sleeps 12, holiday rental in Menemsha
Family friendly beach house sleeps 12, holiday rental in Menemsha
Family friendly beach house sleeps 12, holiday rental in Menemsha

Family friendly beach house sleeps 12

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Up-Island Treehouse with Roofdeck and Waterviews, holiday rental in Menemsha
Up-Island Treehouse with Roofdeck and Waterviews, holiday rental in Menemsha
Up-Island Treehouse with Roofdeck and Waterviews, holiday rental in Menemsha

Up-Island Treehouse with Roofdeck and Waterviews

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
More info
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Walk to Beach Beautiful Ocean Views, holiday rental in Menemsha
Walk to Beach Beautiful Ocean Views, holiday rental in Menemsha
Walk to Beach Beautiful Ocean Views, holiday rental in Menemsha

Walk to Beach Beautiful Ocean Views

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
More info
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Aquinnah Skye Ln:Private Custom Post & Beam,Walk to Beach,Water View,Central A/C, holiday rental in Menemsha
Aquinnah Skye Ln:Private Custom Post & Beam,Walk to Beach,Water View,Central A/C, holiday rental in Menemsha
Aquinnah Skye Ln:Private Custom Post & Beam,Walk to Beach,Water View,Central A/C, holiday rental in Menemsha

Aquinnah Skye Ln:Private Custom Post & Beam,Walk to Beach,Water View,Central A/C

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Beautiful Chilmark Farmhouse W/ Private South Shore Beach and Outdoor Pool, holiday rental in Menemsha
Beautiful Chilmark Farmhouse W/ Private South Shore Beach and Outdoor Pool, holiday rental in Menemsha
Beautiful Chilmark Farmhouse W/ Private South Shore Beach and Outdoor Pool, holiday rental in Menemsha

Beautiful Chilmark Farmhouse W/ Private South Shore Beach and Outdoor Pool

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Private Oceanfront Compound, 1/3 mi Private Beach, AC, Chilmark, WiFi, holiday rental in Menemsha
Private Oceanfront Compound, 1/3 mi Private Beach, AC, Chilmark, WiFi, holiday rental in Menemsha
Private Oceanfront Compound, 1/3 mi Private Beach, AC, Chilmark, WiFi, holiday rental in Menemsha

Private Oceanfront Compound, 1/3 mi Private Beach, AC, Chilmark, WiFi

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Cozy efficiency apartment/heated pool, holiday rental in Menemsha
Cozy efficiency apartment/heated pool, holiday rental in Menemsha
Cozy efficiency apartment/heated pool, holiday rental in Menemsha

Cozy efficiency apartment/heated pool

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming Oceanfront Cottage in Chilmark, holiday rental in Menemsha
Charming Oceanfront Cottage in Chilmark, holiday rental in Menemsha
Charming Oceanfront Cottage in Chilmark, holiday rental in Menemsha

Charming Oceanfront Cottage in Chilmark

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Menemsha Pond waterfront cottage, holiday rental in Menemsha
Menemsha Pond waterfront cottage, holiday rental in Menemsha
Menemsha Pond waterfront cottage, holiday rental in Menemsha

Menemsha Pond waterfront cottage

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Oceanfront Chilmark Home, Stairs to Private Beach, AC, WiFi, Pet Friendly, holiday rental in Menemsha
Oceanfront Chilmark Home, Stairs to Private Beach, AC, WiFi, Pet Friendly, holiday rental in Menemsha
Oceanfront Chilmark Home, Stairs to Private Beach, AC, WiFi, Pet Friendly, holiday rental in Menemsha

Oceanfront Chilmark Home, Stairs to Private Beach, AC, WiFi, Pet Friendly

Holiday Rental House
8 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
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PRIVATE CHILMARK HOME, 5BR,5 bath, 2 outdoor showers, AC, holiday rental in Menemsha
PRIVATE CHILMARK HOME, 5BR,5 bath, 2 outdoor showers, AC, holiday rental in Menemsha
PRIVATE CHILMARK HOME, 5BR,5 bath, 2 outdoor showers, AC, holiday rental in Menemsha

PRIVATE CHILMARK HOME, 5BR,5 bath, 2 outdoor showers, AC

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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Peaceful Enclave with Chilmark Association Beach and Tennis Courts, holiday rental in Menemsha
Peaceful Enclave with Chilmark Association Beach and Tennis Courts, holiday rental in Menemsha
Peaceful Enclave with Chilmark Association Beach and Tennis Courts, holiday rental in Menemsha

Peaceful Enclave with Chilmark Association Beach and Tennis Courts

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Menemsha pond views & access! Mid-century renovated 60's beach house. Dogs ok., holiday rental in Menemsha
Menemsha pond views & access! Mid-century renovated 60's beach house. Dogs ok., holiday rental in Menemsha
Menemsha pond views & access! Mid-century renovated 60's beach house. Dogs ok., holiday rental in Menemsha

Menemsha pond views & access! Mid-century renovated 60's beach house. Dogs ok.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Modern Luxury Waterview Home, Private Beach Access, 4 BR, 3 bath, holiday rental in Menemsha
Modern Luxury Waterview Home, Private Beach Access, 4 BR, 3 bath, holiday rental in Menemsha
Modern Luxury Waterview Home, Private Beach Access, 4 BR, 3 bath, holiday rental in Menemsha

Modern Luxury Waterview Home, Private Beach Access, 4 BR, 3 bath

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Amazing Water Views in Chilmark, 4-BR, Waterfront, Key to Zak’s Beach in GAYHEAD, holiday rental in Menemsha
Amazing Water Views in Chilmark, 4-BR, Waterfront, Key to Zak’s Beach in GAYHEAD, holiday rental in Menemsha
Amazing Water Views in Chilmark, 4-BR, Waterfront, Key to Zak’s Beach in GAYHEAD, holiday rental in Menemsha

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Waterfront Compound - Heated Pool, Hot Tub, Tennis Court, Private Beach, 7 BR, holiday rental in Menemsha
Waterfront Compound - Heated Pool, Hot Tub, Tennis Court, Private Beach, 7 BR, holiday rental in Menemsha
Waterfront Compound - Heated Pool, Hot Tub, Tennis Court, Private Beach, 7 BR, holiday rental in Menemsha

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

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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Peaceful House on Menemsha Hill - 2 min from beach!, holiday rental in Menemsha
Peaceful House on Menemsha Hill - 2 min from beach!, holiday rental in Menemsha
Peaceful House on Menemsha Hill - 2 min from beach!, holiday rental in Menemsha

Peaceful House on Menemsha Hill - 2 min from beach!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails, holiday rental in Menemsha
Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails, holiday rental in Menemsha
Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails, holiday rental in Menemsha

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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