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Greenport Holiday Rentals

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60 rentals in Greenport.
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Charming And Spacious Five Room Suite..Steps To Bay Beach ,Stroll To Village, holiday rental in Greenport
Charming And Spacious Five Room Suite..Steps To Bay Beach ,Stroll To Village, holiday rental in Greenport
Charming And Spacious Five Room Suite..Steps To Bay Beach ,Stroll To Village, holiday rental in Greenport

Charming And Spacious Five Room Suite..Steps To Bay Beach ,Stroll To Village

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Porch On Front~ Greenport Village 1st floor apartment, Easy Walk To Town/Jitney, holiday rental in Greenport
Porch On Front~ Greenport Village 1st floor apartment, Easy Walk To Town/Jitney, holiday rental in Greenport
Porch On Front~ Greenport Village 1st floor apartment, Easy Walk To Town/Jitney, holiday rental in Greenport

Porch On Front~ Greenport Village 1st floor apartment, Easy Walk To Town/Jitney

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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Remodeled Greenport Apartment By Greenport Harbor, holiday rental in Greenport
Remodeled Greenport Apartment By Greenport Harbor, holiday rental in Greenport
Remodeled Greenport Apartment By Greenport Harbor, holiday rental in Greenport

Remodeled Greenport Apartment By Greenport Harbor

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Historic 1830s Greenport Home, holiday rental in Greenport
Historic 1830s Greenport Home, holiday rental in Greenport
Historic 1830s Greenport Home, holiday rental in Greenport

Historic 1830s Greenport Home

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views, holiday rental in Greenport
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views, holiday rental in Greenport
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views, holiday rental in Greenport

Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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'The Gate House' on Beach front Estate, holiday rental in Greenport
'The Gate House' on Beach front Estate, holiday rental in Greenport
'The Gate House' on Beach front Estate, holiday rental in Greenport

'The Gate House' on Beach front Estate

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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First Floor of 1905 Victorian Home In The Heart Of Greenport Village, holiday rental in Greenport
First Floor of 1905 Victorian Home In The Heart Of Greenport Village, holiday rental in Greenport
First Floor of 1905 Victorian Home In The Heart Of Greenport Village, holiday rental in Greenport

First Floor of 1905 Victorian Home In The Heart Of Greenport Village

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Dreamlike Beach House In Greenport - Near EVERYTHING - Bachelorette Paradise, holiday rental in Greenport
Dreamlike Beach House In Greenport - Near EVERYTHING - Bachelorette Paradise, holiday rental in Greenport
Dreamlike Beach House In Greenport - Near EVERYTHING - Bachelorette Paradise, holiday rental in Greenport

Dreamlike Beach House In Greenport - Near EVERYTHING - Bachelorette Paradise

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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One Of A Kind, Resort- Like Waterfront Cottage In Wine Country, holiday rental in Greenport
One Of A Kind, Resort- Like Waterfront Cottage In Wine Country, holiday rental in Greenport
One Of A Kind, Resort- Like Waterfront Cottage In Wine Country, holiday rental in Greenport

One Of A Kind, Resort- Like Waterfront Cottage In Wine Country

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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Spacious apartment, 3 blocks to downtown and steps to fishing pier., holiday rental in Greenport
Spacious apartment, 3 blocks to downtown and steps to fishing pier., holiday rental in Greenport
Spacious apartment, 3 blocks to downtown and steps to fishing pier., holiday rental in Greenport

Spacious apartment, 3 blocks to downtown and steps to fishing pier.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront Condo C204 at The Cliffside Resort, holiday rental in Greenport
Waterfront Condo C204 at The Cliffside Resort, holiday rental in Greenport
Waterfront Condo C204 at The Cliffside Resort, holiday rental in Greenport

Waterfront Condo C204 at The Cliffside Resort

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cottage on Beach front  Estate, holiday rental in Greenport
Cottage on Beach front  Estate, holiday rental in Greenport
Cottage on Beach front  Estate, holiday rental in Greenport

Cottage on Beach front Estate

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Peaceful Retreat with 100 ft private deep water dock, holiday rental in Greenport
Peaceful Retreat with 100 ft private deep water dock, holiday rental in Greenport
Peaceful Retreat with 100 ft private deep water dock, holiday rental in Greenport

Peaceful Retreat with 100 ft private deep water dock

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Downtown Greenport Apt w/Porch Near Shelter Island, holiday rental in Greenport
Downtown Greenport Apt w/Porch Near Shelter Island, holiday rental in Greenport
Downtown Greenport Apt w/Porch Near Shelter Island, holiday rental in Greenport

Downtown Greenport Apt w/Porch Near Shelter Island

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Rose Cottage by the Bay., holiday rental in Greenport
Rose Cottage by the Bay., holiday rental in Greenport
Rose Cottage by the Bay., holiday rental in Greenport

Rose Cottage by the Bay.

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront Estate - One of a Kind Vacation House, holiday rental in Greenport
Waterfront Estate - One of a Kind Vacation House, holiday rental in Greenport
Waterfront Estate - One of a Kind Vacation House, holiday rental in Greenport

Waterfront Estate - One of a Kind Vacation House

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Greenport Village home w/ POOL! Steps to Town Center & Bay Beach!, holiday rental in Greenport
Greenport Village home w/ POOL! Steps to Town Center & Bay Beach!, holiday rental in Greenport
Greenport Village home w/ POOL! Steps to Town Center & Bay Beach!, holiday rental in Greenport

Greenport Village home w/ POOL! Steps to Town Center & Bay Beach!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Cleves Point Estates Home, Private sandy beach, holiday rental in Greenport
Cleves Point Estates Home, Private sandy beach, holiday rental in Greenport
Cleves Point Estates Home, Private sandy beach, holiday rental in Greenport

Cleves Point Estates Home, Private sandy beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Designer's Dream - Charming Boathouse in Greenport Village, holiday rental in Greenport
Designer's Dream - Charming Boathouse in Greenport Village, holiday rental in Greenport
Designer's Dream - Charming Boathouse in Greenport Village, holiday rental in Greenport

Designer's Dream - Charming Boathouse in Greenport Village

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Stunning Greenport Brand New Beach Bungalow for Family Vacationing, holiday rental in Greenport
Stunning Greenport Brand New Beach Bungalow for Family Vacationing, holiday rental in Greenport
Stunning Greenport Brand New Beach Bungalow for Family Vacationing, holiday rental in Greenport

Stunning Greenport Brand New Beach Bungalow for Family Vacationing

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Greenport Waterfront Private Dock, holiday rental in Greenport
Greenport Waterfront Private Dock, holiday rental in Greenport
Greenport Waterfront Private Dock, holiday rental in Greenport

Greenport Waterfront Private Dock

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Greenport Soundfront Estate, holiday rental in Greenport
Greenport Soundfront Estate, holiday rental in Greenport
Greenport Soundfront Estate, holiday rental in Greenport

Greenport Soundfront Estate

Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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NEWLY Renovated Family Home Great Area - Beach - Greenport - Ferry - Restaurants, holiday rental in Greenport
NEWLY Renovated Family Home Great Area - Beach - Greenport - Ferry - Restaurants, holiday rental in Greenport
NEWLY Renovated Family Home Great Area - Beach - Greenport - Ferry - Restaurants, holiday rental in Greenport

NEWLY Renovated Family Home Great Area - Beach - Greenport - Ferry - Restaurants

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Seaside seclusion, salt water sanctuary! Monthly rental discount  fall/winter., holiday rental in Greenport
Seaside seclusion, salt water sanctuary! Monthly rental discount  fall/winter., holiday rental in Greenport
Seaside seclusion, salt water sanctuary! Monthly rental discount  fall/winter., holiday rental in Greenport

Seaside seclusion, salt water sanctuary! Monthly rental discount fall/winter.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Greenport Home w/Furnished Patio - Walk Downtown!, holiday rental in Greenport
Greenport Home w/Furnished Patio - Walk Downtown!, holiday rental in Greenport
Greenport Home w/Furnished Patio - Walk Downtown!, holiday rental in Greenport

Greenport Home w/Furnished Patio - Walk Downtown!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Enchanted Cottage, holiday rental in Greenport
Enchanted Cottage, holiday rental in Greenport
Enchanted Cottage, holiday rental in Greenport

Enchanted Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Available Immediately: Newly renovated Greenport House with Heated Pool 4bd/2bth, holiday rental in Greenport
Available Immediately: Newly renovated Greenport House with Heated Pool 4bd/2bth, holiday rental in Greenport
Available Immediately: Newly renovated Greenport House with Heated Pool 4bd/2bth, holiday rental in Greenport

Available Immediately: Newly renovated Greenport House with Heated Pool 4bd/2bth

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Greenport Waterfront Cottage with Private Community Beach, holiday rental in Greenport
Greenport Waterfront Cottage with Private Community Beach, holiday rental in Greenport
Greenport Waterfront Cottage with Private Community Beach, holiday rental in Greenport

Greenport Waterfront Cottage with Private Community Beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Entire house, private lane, walk to public beach, close to town, holiday rental in Greenport
Entire house, private lane, walk to public beach, close to town, holiday rental in Greenport
Entire house, private lane, walk to public beach, close to town, holiday rental in Greenport

Entire house, private lane, walk to public beach, close to town

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Greenport Village Beauty - with saltwater pool!, holiday rental in Greenport
Greenport Village Beauty - with saltwater pool!, holiday rental in Greenport
Greenport Village Beauty - with saltwater pool!, holiday rental in Greenport

Greenport Village Beauty - with saltwater pool!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Greenport Village home for rent, great for group or extended family, holiday rental in Greenport
Greenport Village home for rent, great for group or extended family, holiday rental in Greenport
Greenport Village home for rent, great for group or extended family, holiday rental in Greenport

Greenport Village home for rent, great for group or extended family

Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Brand Newly Renovated - Walk to Town and Beach, holiday rental in Greenport
Brand Newly Renovated - Walk to Town and Beach, holiday rental in Greenport
Brand Newly Renovated - Walk to Town and Beach, holiday rental in Greenport

Brand Newly Renovated - Walk to Town and Beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Relaxed Village Farmhouse, holiday rental in Greenport
Relaxed Village Farmhouse, holiday rental in Greenport
Relaxed Village Farmhouse, holiday rental in Greenport

Relaxed Village Farmhouse

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Greenport Renovated Farm House, holiday rental in Greenport
Greenport Renovated Farm House, holiday rental in Greenport
Greenport Renovated Farm House, holiday rental in Greenport

Greenport Renovated Farm House

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Greenport Beach House, holiday rental in Greenport
Greenport Beach House, holiday rental in Greenport
Greenport Beach House, holiday rental in Greenport

Greenport Beach House

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Walk to all! Beach/shelter island ferry/LIRR/Jitney/restaurants/shopping, holiday rental in Greenport
Walk to all! Beach/shelter island ferry/LIRR/Jitney/restaurants/shopping, holiday rental in Greenport
Walk to all! Beach/shelter island ferry/LIRR/Jitney/restaurants/shopping, holiday rental in Greenport

Walk to all! Beach/shelter island ferry/LIRR/Jitney/restaurants/shopping

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Greenport Village home, holiday rental in Greenport
Greenport Village home, holiday rental in Greenport
Greenport Village home, holiday rental in Greenport

Greenport Village home

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Sunny Daze-Spacious house in the middle of Long Island Wine Country, holiday rental in Greenport
Sunny Daze-Spacious house in the middle of Long Island Wine Country, holiday rental in Greenport
Sunny Daze-Spacious house in the middle of Long Island Wine Country, holiday rental in Greenport

Sunny Daze-Spacious house in the middle of Long Island Wine Country

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Greenport NY Chic Designer Beach House, steps to water, vineyard views, holiday rental in Greenport
Greenport NY Chic Designer Beach House, steps to water, vineyard views, holiday rental in Greenport
Greenport NY Chic Designer Beach House, steps to water, vineyard views, holiday rental in Greenport

Greenport NY Chic Designer Beach House, steps to water, vineyard views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Beautiful, newly-remodeled home w/ a gas fireplace, patio, & firepit - dogs OK!, holiday rental in Greenport
Beautiful, newly-remodeled home w/ a gas fireplace, patio, & firepit - dogs OK!, holiday rental in Greenport
Beautiful, newly-remodeled home w/ a gas fireplace, patio, & firepit - dogs OK!, holiday rental in Greenport

Beautiful, newly-remodeled home w/ a gas fireplace, patio, & firepit - dogs OK!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Architect Designed Home in Waterfront Village, holiday rental in Greenport
Architect Designed Home in Waterfront Village, holiday rental in Greenport
Architect Designed Home in Waterfront Village, holiday rental in Greenport

Architect Designed Home in Waterfront Village

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Historic Cottage Near Beach!, holiday rental in Greenport
Historic Cottage Near Beach!, holiday rental in Greenport
Historic Cottage Near Beach!, holiday rental in Greenport

Historic Cottage Near Beach!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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'This must be the place', holiday rental in Greenport
'This must be the place', holiday rental in Greenport
'This must be the place', holiday rental in Greenport

'This must be the place'

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW LIST: Luxury Waterfront Condo-Pool, Beach Access, heart of Greenport Village, holiday rental in Greenport
NEW LIST: Luxury Waterfront Condo-Pool, Beach Access, heart of Greenport Village, holiday rental in Greenport
NEW LIST: Luxury Waterfront Condo-Pool, Beach Access, heart of Greenport Village, holiday rental in Greenport

NEW LIST: Luxury Waterfront Condo-Pool, Beach Access, heart of Greenport Village

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Shingled Chic & Modern Light & Bright, holiday rental in Greenport
Shingled Chic & Modern Light & Bright, holiday rental in Greenport
Shingled Chic & Modern Light & Bright, holiday rental in Greenport

Shingled Chic & Modern Light & Bright

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dream Beach House on the North Fork: Waterfront, Private Beach + Stunning Views, holiday rental in Greenport
Dream Beach House on the North Fork: Waterfront, Private Beach + Stunning Views, holiday rental in Greenport
Dream Beach House on the North Fork: Waterfront, Private Beach + Stunning Views, holiday rental in Greenport

Dream Beach House on the North Fork: Waterfront, Private Beach + Stunning Views

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Greenport Escape - Walk to town, Central air! Great for families or couples., holiday rental in Greenport
Greenport Escape - Walk to town, Central air! Great for families or couples., holiday rental in Greenport
Greenport Escape - Walk to town, Central air! Great for families or couples., holiday rental in Greenport

Greenport Escape - Walk to town, Central air! Great for families or couples.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful condo on the Long Island Sound in a resort, holiday rental in Greenport
Beautiful condo on the Long Island Sound in a resort, holiday rental in Greenport
Beautiful condo on the Long Island Sound in a resort, holiday rental in Greenport

Beautiful condo on the Long Island Sound in a resort

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Newly Renovated Summer Retreat, Heated Pool, Walk to Beach, Designer Furnishings, holiday rental in Greenport
Newly Renovated Summer Retreat, Heated Pool, Walk to Beach, Designer Furnishings, holiday rental in Greenport
Newly Renovated Summer Retreat, Heated Pool, Walk to Beach, Designer Furnishings, holiday rental in Greenport

Newly Renovated Summer Retreat, Heated Pool, Walk to Beach, Designer Furnishings

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Charming historic house on Sterling Harbor, waterviews, walk to village, holiday rental in Greenport
Charming historic house on Sterling Harbor, waterviews, walk to village, holiday rental in Greenport
Charming historic house on Sterling Harbor, waterviews, walk to village, holiday rental in Greenport

Charming historic house on Sterling Harbor, waterviews, walk to village

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Frequently Asked Questions about Greenport