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Menemsha Holiday Apartments

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49 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
3 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
2 bathrooms
Sleeps 8
Match: Sleeps
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Friendly Hillside Cottage. Private Beach & Pond Access. 3 kayaks & bikes too., holiday rental in Menemsha
Friendly Hillside Cottage. Private Beach & Pond Access. 3 kayaks & bikes too., holiday rental in Menemsha
Friendly Hillside Cottage. Private Beach & Pond Access. 3 kayaks & bikes too., holiday rental in Menemsha

Friendly Hillside Cottage. Private Beach & Pond Access. 3 kayaks & bikes too.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Modern beach house - Walking distance to Philbin Beach, holiday rental in Menemsha
Modern beach house - Walking distance to Philbin Beach, holiday rental in Menemsha
Modern beach house - Walking distance to Philbin Beach, holiday rental in Menemsha

Modern beach house - Walking distance to Philbin Beach

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Isolated Aquinnah Hilltop Home —Stunning Views of Menemsha Pond — Pet Friendly, holiday rental in Menemsha
Isolated Aquinnah Hilltop Home —Stunning Views of Menemsha Pond — Pet Friendly, holiday rental in Menemsha
Isolated Aquinnah Hilltop Home —Stunning Views of Menemsha Pond — Pet Friendly, holiday rental in Menemsha

Isolated 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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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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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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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
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comfortable ranch house overlooking Menemsha Bight, holiday rental in Menemsha
comfortable ranch house overlooking Menemsha Bight, holiday rental in Menemsha
comfortable ranch house overlooking Menemsha Bight, holiday rental in Menemsha

comfortable ranch house overlooking Menemsha Bight

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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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
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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
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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
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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
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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
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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
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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
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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
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Tucked Away on Tea Lane, Chilmark, holiday rental in Menemsha
Tucked Away on Tea Lane, Chilmark, holiday rental in Menemsha
Tucked Away on Tea Lane, Chilmark, holiday rental in Menemsha

Tucked Away on Tea Lane, Chilmark

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Chilmark House w/Sunroom on Martha's Vineyard, holiday rental in Menemsha
Chilmark House w/Sunroom on Martha's Vineyard, holiday rental in Menemsha
Chilmark House w/Sunroom on Martha's Vineyard, holiday rental in Menemsha

Chilmark House w/Sunroom on Martha's Vineyard

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Menemsha Harborside Cottage - STEAMSHIP reservations available for open Aug. wks, holiday rental in Menemsha
Menemsha Harborside Cottage - STEAMSHIP reservations available for open Aug. wks, holiday rental in Menemsha
Menemsha Harborside Cottage - STEAMSHIP reservations available for open Aug. wks, holiday rental in Menemsha

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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
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Quiet home with beach &  peek-a-boo ocean views!, holiday rental in Menemsha
Quiet home with beach &  peek-a-boo ocean views!, holiday rental in Menemsha
Quiet home with beach &  peek-a-boo ocean views!, holiday rental in Menemsha

Quiet home with beach & peek-a-boo ocean views!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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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Beautiful, historic farmhouse on Chilmark Pond, holiday rental in Menemsha
Beautiful, historic farmhouse on Chilmark Pond, holiday rental in Menemsha
Beautiful, historic farmhouse on Chilmark Pond, holiday rental in Menemsha

Beautiful, historic farmhouse on Chilmark Pond

Holiday Rental House
4 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
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EXPERIENCE THE OLD WORLD CHARM OF MARTHA'S VINEYARD IN THIS SEA CAPTAINS HOME, holiday rental in Menemsha
EXPERIENCE THE OLD WORLD CHARM OF MARTHA'S VINEYARD IN THIS SEA CAPTAINS HOME, holiday rental in Menemsha
EXPERIENCE THE OLD WORLD CHARM OF MARTHA'S VINEYARD IN THIS SEA CAPTAINS HOME, holiday rental in Menemsha

EXPERIENCE THE OLD WORLD CHARM OF MARTHA'S VINEYARD IN THIS SEA CAPTAINS HOME

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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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Striking 5BR/4BA Chilmark Contemporary with Views of the Sound, holiday rental in Menemsha
Striking 5BR/4BA Chilmark Contemporary with Views of the Sound, holiday rental in Menemsha
Striking 5BR/4BA Chilmark Contemporary with Views of the Sound, holiday rental in Menemsha

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
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
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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
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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
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Spectacular Site Overlooking Vineyard Sound, holiday rental in Menemsha
Spectacular Site Overlooking Vineyard Sound, holiday rental in Menemsha
Spectacular Site Overlooking Vineyard Sound, holiday rental in Menemsha

Spectacular Site Overlooking Vineyard Sound

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Estate guesthouse, glorious water view, & 2 private beaches!, holiday rental in Menemsha
Estate guesthouse, glorious water view, & 2 private beaches!, holiday rental in Menemsha
Estate guesthouse, glorious water view, & 2 private beaches!, holiday rental in Menemsha

Estate guesthouse, glorious water view, & 2 private beaches!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
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
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Beautiful Secluded Property with Vineyard Sound Views and Private Beach, holiday rental in Menemsha
Beautiful Secluded Property with Vineyard Sound Views and Private Beach, holiday rental in Menemsha
Beautiful Secluded Property with Vineyard Sound Views and Private Beach, holiday rental in Menemsha

Beautiful Secluded Property with Vineyard Sound Views and Private Beach

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Spring Point Cottage With Gorgeous Sunsets Overlooking Vineyard Sound, holiday rental in Menemsha
Spring Point Cottage With Gorgeous Sunsets Overlooking Vineyard Sound, holiday rental in Menemsha
Spring Point Cottage With Gorgeous Sunsets Overlooking Vineyard Sound, holiday rental in Menemsha

Spring Point Cottage With Gorgeous Sunsets Overlooking Vineyard Sound

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Great Deal on Newly Renovated Home in Exclusive Aquinnah., holiday rental in Menemsha
Great Deal on Newly Renovated Home in Exclusive Aquinnah., holiday rental in Menemsha
Great Deal on Newly Renovated Home in Exclusive Aquinnah., holiday rental in Menemsha

Great Deal on Newly Renovated Home in Exclusive Aquinnah.

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Water-view Vacation Home in the Heart of Aquinnah, holiday rental in Menemsha
Water-view Vacation Home in the Heart of Aquinnah, holiday rental in Menemsha
Water-view Vacation Home in the Heart of Aquinnah, holiday rental in Menemsha

Water-view Vacation Home in the Heart of Aquinnah

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Chilmark Cottage With Big Atlantic View;  Private Pond And Beach, holiday rental in Menemsha
Charming Chilmark Cottage With Big Atlantic View;  Private Pond And Beach, holiday rental in Menemsha
Charming Chilmark Cottage With Big Atlantic View;  Private Pond And Beach, holiday rental in Menemsha

Charming Chilmark Cottage With Big Atlantic View; Private Pond And Beach

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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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
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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
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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
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Private Chilmark beach on The Cliffs in your backyard, 3 BR, 3 bath, WiFi, AC, holiday rental in Menemsha
Private Chilmark beach on The Cliffs in your backyard, 3 BR, 3 bath, WiFi, AC, holiday rental in Menemsha
Private Chilmark beach on The Cliffs in your backyard, 3 BR, 3 bath, WiFi, AC, holiday rental in Menemsha

Private Chilmark beach on The Cliffs in your backyard, 3 BR, 3 bath, WiFi, AC

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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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
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Secluded 2-Acre Hideaway | Fireplace, Wraparound Deck | Near Trails & Beaches, holiday rental in Menemsha
Secluded 2-Acre Hideaway | Fireplace, Wraparound Deck | Near Trails & Beaches, holiday rental in Menemsha
Secluded 2-Acre Hideaway | Fireplace, Wraparound Deck | Near Trails & Beaches, holiday rental in Menemsha

Secluded 2-Acre Hideaway | Fireplace, Wraparound Deck | Near Trails & Beaches

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Private Beach front oasis on Martha's Vineyard, holiday rental in Menemsha
Private Beach front oasis on Martha's Vineyard, holiday rental in Menemsha
Private Beach front oasis on Martha's Vineyard, holiday rental in Menemsha

Private Beach front oasis on Martha's Vineyard

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 1
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Frequently Asked Questions about Menemsha