Sag Harbor, New York

Vacation Rentals in Sag Harbor, New York

Discover 144 vacation rental properties in Sag Harbor. From 1 to 8 bedrooms. Average $1500/night. 100% have pools.

144 verified listings Book securely on VRBO Prices updated March 2026

144 properties available

Historic Sag Harbor Village Gem

Historic Sag Harbor Village Gem

1 bed 1 bath
PoolA/CWiFiBalcony
$502/night
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Romantic Studio Cottage, Walk to Town

Romantic Studio Cottage, Walk to Town

1 bed
PoolA/CWiFiBalcony
$352/night
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Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town

Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town

5 beds 4 baths
PoolA/CWiFiBalcony
$1,695/night
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Whaling Captain Pierson's Cottage

Whaling Captain Pierson's Cottage

1 bed 1 bath
PoolA/CWiFiBalcony
$342/night
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Whaling Captain Pierson's Apartment

Whaling Captain Pierson's Apartment

1 bed 1 bath
PoolA/CWiFiBalcony
$326/night
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Whaling Captain Pierson's Apartment TOO

Whaling Captain Pierson's Apartment TOO

2 beds 1 bath
PoolA/CWiFiBalcony
$337/night
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Sag Harbor Charmer - 2 Bedroom Cottage; Walk to Town

Sag Harbor Charmer - 2 Bedroom Cottage; Walk to Town

2 beds 1 bath
PoolA/CWiFiBalcony
$603/night
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Sag Harbor Village Gem

Sag Harbor Village Gem

3 beds 2 baths
PoolA/CWiFiBalcony
$621/night
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The Cooper-Burke House

The Cooper-Burke House

1 bed 1 bath
PoolA/CWiFiBalcony
$362/night
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Sag Harbor Suite by the Beach

Sag Harbor Suite by the Beach

1 bed 1 bath
PoolA/CWiFiBalcony
$433/night
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Unique Modern Barn House in Sag Harbor

Unique Modern Barn House in Sag Harbor

5 beds 5 baths
PoolA/CWiFiBalcony
$2,009/night
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Sag Harbor Village Cottage with Water Views: 3 Bedroom, 1.5 Bath. Walk to town!

Sag Harbor Village Cottage with Water Views: 3 Bedroom, 1.5 Bath. Walk to town!

3 beds 1 bath
PoolA/CWiFiBalcony
$1,256/night
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Beautiful SagHarbour Village W/Heated pool 5 min walk to Beach/Restaurant/Museum

Beautiful SagHarbour Village W/Heated pool 5 min walk to Beach/Restaurant/Museum

3 beds 2 baths
PoolA/CWiFiBalcony
$2,511/night
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Enjoy a lovely summer retreat in Sag Harbor Village, 1 mile to Main Street

Enjoy a lovely summer retreat in Sag Harbor Village, 1 mile to Main Street

3 beds 4 baths
PoolA/CWiFiBalcony
$1,657/night
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Newly renovated home in Sag Harbor Village.

Newly renovated home in Sag Harbor Village.

3 beds 1 bath
PoolA/CWiFiBalcony
$603/night
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Renovated Sag Harbor Village 4 Bedroom With Pool + New Bronco with Beach Pass!

Renovated Sag Harbor Village 4 Bedroom With Pool + New Bronco with Beach Pass!

4 beds 3 baths
PoolA/CWiFiBalcony
$2,009/night
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Sag Harbor Beach 4 Bedroom Home with Pool

Sag Harbor Beach 4 Bedroom Home with Pool

4 beds 2 baths
PoolA/CWiFiBalcony
$1,506/night
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Havens Beach House

Havens Beach House

3 beds 1 bath
PoolA/CWiFiBalcony
$478/night
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Sag Harbor Getaway-Enjoy Hot Tub and Saltwater Pool!

Sag Harbor Getaway-Enjoy Hot Tub and Saltwater Pool!

4 beds 3 baths
PoolA/CWiFiBalcony
$899/night
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Sag Harbor Modern Home, Heated Salt Water Pool, Walk to Beach, Walk to Village

Sag Harbor Modern Home, Heated Salt Water Pool, Walk to Beach, Walk to Village

5 beds 4 baths
PoolA/CWiFiBalcony
$1,741/night
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Sag Harbor Village Chic with water views

Sag Harbor Village Chic with water views

3 beds 2 baths
PoolA/CWiFiBalcony
$1,708/night
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Sag Harbor, Hamptons Summer Compound w/ Pool

Sag Harbor, Hamptons Summer Compound w/ Pool

4 beds 3 baths
PoolA/CWiFiBalcony
$842/night
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Sag Harbor Village, 3 BR, Gunite pool, Pool house

Sag Harbor Village, 3 BR, Gunite pool, Pool house

3 beds 2 baths
PoolA/CWiFiBalcony
$875/night
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PERFECT COTTAGE WITH POOL IN SAG HARBOR VILLAGE

PERFECT COTTAGE WITH POOL IN SAG HARBOR VILLAGE

3 beds 3 baths
PoolA/CWiFiBalcony
$1,314/night
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Our Peaceful, Beach Escape From the City

Our Peaceful, Beach Escape From the City

6 beds 4 baths
PoolA/CWiFiBalcony
$1,085/night
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Sag Harbor Village walk to town and beach

Sag Harbor Village walk to town and beach

4 beds 2 baths
PoolA/CWiFiBalcony
$1,356/night
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Village Tranquil Traditional With Gunite Pool, Hot Tub And Lush Gardens

Village Tranquil Traditional With Gunite Pool, Hot Tub And Lush Gardens

4 beds 3 baths
PoolA/CWiFiBalcony
$1,209/night
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Sag Harbor stunning renovated home with a heated pool, minutes to ocean and town

Sag Harbor stunning renovated home with a heated pool, minutes to ocean and town

4 beds 3 baths
PoolA/CWiFiBalcony
$1,339/night
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Sag Harbor Village Fully Updated Historic Home

Sag Harbor Village Fully Updated Historic Home

3 beds 2 baths
PoolA/CWiFiBalcony
$1,356/night
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Luxury Home in Sag Harbor

Luxury Home in Sag Harbor

3 beds 2 baths
PoolA/CWiFiBalcony
$1,431/night
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Spend Your Summer on a Prestige 500 55ft. Yacht in Beautiful Sag Harbor

Spend Your Summer on a Prestige 500 55ft. Yacht in Beautiful Sag Harbor

3 beds 2 baths
PoolA/CWiFiBalcony
$483/night
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Perfect Sag Harbor Home Away from Home

Perfect Sag Harbor Home Away from Home

4 beds 3 baths
PoolA/CWiFiBalcony
$1,306/night
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Sag Harbor Bay Point Rental

Sag Harbor Bay Point Rental

4 beds 3 baths
PoolA/CWiFiBalcony
$885/night
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Fully Renovated 3BR in Sag Harbor Village w/ Heated Saltwater Pool

Fully Renovated 3BR in Sag Harbor Village w/ Heated Saltwater Pool

3 beds 2 baths
PoolA/CWiFiBalcony
$1,660/night
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Beautiful Sag Harbor Home with Pool and easy walk to private beach or downtown

Beautiful Sag Harbor Home with Pool and easy walk to private beach or downtown

5 beds 4 baths
PoolA/CWiFiBalcony
$1,518/night
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Moments from private beach

Moments from private beach

4 beds 4 baths
PoolA/CWiFiBalcony
$1,773/night
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In the Village proper! Chic & Quintessential 3 bedroom Cottage

In the Village proper! Chic & Quintessential 3 bedroom Cottage

3 beds 2 baths
PoolA/CWiFiBalcony
$1,614/night
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Eclectic and colorful home with a private yard close to town in Sag Harbor.

Eclectic and colorful home with a private yard close to town in Sag Harbor.

4 beds 3 baths
PoolA/CWiFiBalcony
$1,021/night
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Beautiful 5 BR, 5 BA home. Walk to town and beaches. HomeAway/VRBO Exclusive.

Beautiful 5 BR, 5 BA home. Walk to town and beaches. HomeAway/VRBO Exclusive.

5 beds 5 baths
PoolA/CWiFiBalcony
$1,533/night
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Sag Harbor Village Beauty with Heated Salt Water Gunite Pool, blocks to...

Sag Harbor Village Beauty with Heated Salt Water Gunite Pool, blocks to...

4 beds 3 baths
PoolA/CWiFiBalcony
$676/night
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Sag Harbor Village Home 4 bed 3 bath Sleeps 8 Salt Water Pool, 2 acres 3K sq ft.

Sag Harbor Village Home 4 bed 3 bath Sleeps 8 Salt Water Pool, 2 acres 3K sq ft.

4 beds 3 baths
PoolA/CWiFiBalcony
$1,944/night
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Glorious Hamptons Sag Harbor Escape With Pool, 5-minute Walk To Beach And Town

Glorious Hamptons Sag Harbor Escape With Pool, 5-minute Walk To Beach And Town

5 beds 3 baths
PoolA/CWiFiBalcony
$2,511/night
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Quintessential Sag Harbor Village Retreat

Quintessential Sag Harbor Village Retreat

5 beds 3 baths
PoolA/CWiFiBalcony
$1,533/night
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Country Home in Sag Harbor Village

Country Home in Sag Harbor Village

4 beds 2 baths
PoolA/CWiFiBalcony
$1,027/night
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Newly renovated 4- bedroom home in Sag Harbor Village !

Newly renovated 4- bedroom home in Sag Harbor Village !

4 beds 3 baths
PoolA/CWiFiBalcony
$1,909/night
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Remodeled historic Greek Revival house in heart of Sag Harbor.

Remodeled historic Greek Revival house in heart of Sag Harbor.

3 beds 2 baths
PoolA/CWiFiBalcony
$470/night
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Rent your own Beach House

Rent your own Beach House

4 beds 2 baths
PoolA/CWiFiBalcony
$2,588/night
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Sag Harbor Village Pool Hot Tub on Manicured Acre

Sag Harbor Village Pool Hot Tub on Manicured Acre

4 beds 2 baths
PoolA/CWiFiBalcony
$2,529/night
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Showing 48 of 144 properties

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