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Sag Harbor Vacation Rentals

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189 rentals in Sag Harbor.
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Two Week Stay in August Now Available, (8/24-9/7) Email for more information, vacation rental in Sag Harbor
Two Week Stay in August Now Available, (8/24-9/7) Email for more information, vacation rental in Sag Harbor
Two Week Stay in August Now Available, (8/24-9/7) Email for more information, vacation rental in Sag Harbor

Two Week Stay in August Now Available, (8/24-9/7) Email for more information

Rental Home
7 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Whaling Captain Pierson's Apartment TOO, vacation rental in Sag Harbor
Whaling Captain Pierson's Apartment TOO, vacation rental in Sag Harbor
Whaling Captain Pierson's Apartment TOO, vacation rental in Sag Harbor

Whaling Captain Pierson's Apartment TOO

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful 5 BR, 5 BA home. Walk to town and beaches.  HomeAway/VRBO Exclusive., vacation rental in Sag Harbor
Beautiful 5 BR, 5 BA home. Walk to town and beaches.  HomeAway/VRBO Exclusive., vacation rental in Sag Harbor
Beautiful 5 BR, 5 BA home. Walk to town and beaches.  HomeAway/VRBO Exclusive., vacation rental in Sag Harbor

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

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Charming, Quiet, Peaceful, Warm and Traditional, vacation rental in Sag Harbor
Charming, Quiet, Peaceful, Warm and Traditional, vacation rental in Sag Harbor
Charming, Quiet, Peaceful, Warm and Traditional, vacation rental in Sag Harbor

Charming, Quiet, Peaceful, Warm and Traditional

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Whaling Captain Pierson's Apartment, vacation rental in Sag Harbor
Whaling Captain Pierson's Apartment, vacation rental in Sag Harbor
Whaling Captain Pierson's Apartment, vacation rental in Sag Harbor

Whaling Captain Pierson's Apartment

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Get $1,100 rebate when you book 2 weeks in 2021, see availability, vacation rental in Sag Harbor
Get $1,100 rebate when you book 2 weeks in 2021, see availability, vacation rental in Sag Harbor
Get $1,100 rebate when you book 2 weeks in 2021, see availability, vacation rental in Sag Harbor

Get $1,100 rebate when you book 2 weeks in 2021, see availability

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cove View Manor of Sag Harbor, vacation rental in Sag Harbor
Cove View Manor of Sag Harbor, vacation rental in Sag Harbor
Cove View Manor of Sag Harbor, vacation rental in Sag Harbor

Cove View Manor of Sag Harbor

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Luxury home, great WiFi, Office, Kayaks, Peloton,  Hot Tub & Pool Open, vacation rental in Sag Harbor
Luxury home, great WiFi, Office, Kayaks, Peloton,  Hot Tub & Pool Open, vacation rental in Sag Harbor
Luxury home, great WiFi, Office, Kayaks, Peloton,  Hot Tub & Pool Open, vacation rental in Sag Harbor

Luxury home, great WiFi, Office, Kayaks, Peloton, Hot Tub & Pool Open

Rental Home
7 bedrooms
6 bathrooms
Sleeps 13
Match: Sleeps
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Sag Harbor, Hamptons Hideaway, vacation rental in Sag Harbor
Sag Harbor, Hamptons Hideaway, vacation rental in Sag Harbor
Sag Harbor, Hamptons Hideaway, vacation rental in Sag Harbor

Sag Harbor, Hamptons Hideaway

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sag Harbor Beach House, vacation rental in Sag Harbor
Sag Harbor Beach House, vacation rental in Sag Harbor
Sag Harbor Beach House, vacation rental in Sag Harbor

Sag Harbor Beach House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Historic Sag Harbor Village Gem, vacation rental in Sag Harbor
Historic Sag Harbor Village Gem, vacation rental in Sag Harbor
Historic Sag Harbor Village Gem, vacation rental in Sag Harbor

Historic Sag Harbor Village Gem

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Hamptons Beauty, fully renovated home with a pool, minutes to ocean and town, vacation rental in Sag Harbor
Hamptons Beauty, fully renovated home with a pool, minutes to ocean and town, vacation rental in Sag Harbor
Hamptons Beauty, fully renovated home with a pool, minutes to ocean and town, vacation rental in Sag Harbor

Hamptons Beauty, fully renovated home with a pool, minutes to ocean and town

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Book Sag Harbor Getaway -HOT TUB OPEN THROUGH NEW YEARS!, vacation rental in Sag Harbor
Book Sag Harbor Getaway -HOT TUB OPEN THROUGH NEW YEARS!, vacation rental in Sag Harbor
Book Sag Harbor Getaway -HOT TUB OPEN THROUGH NEW YEARS!, vacation rental in Sag Harbor

Book Sag Harbor Getaway -HOT TUB OPEN THROUGH NEW YEARS!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sag Harbor Home w/Pool Walk to Private Beach/Village HomeAway/VRBO, vacation rental in Sag Harbor
Sag Harbor Home w/Pool Walk to Private Beach/Village HomeAway/VRBO, vacation rental in Sag Harbor
Sag Harbor Home w/Pool Walk to Private Beach/Village HomeAway/VRBO, vacation rental in Sag Harbor

Sag Harbor Home w/Pool Walk to Private Beach/Village HomeAway/VRBO

Rental Home
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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*SAIL* YOUR OWN PRIVATE YACHT !  DAYSAILS ON HAMPTONS  #1 CATAMARAN, vacation rental in Sag Harbor
*SAIL* YOUR OWN PRIVATE YACHT !  DAYSAILS ON HAMPTONS  #1 CATAMARAN, vacation rental in Sag Harbor
*SAIL* YOUR OWN PRIVATE YACHT !  DAYSAILS ON HAMPTONS  #1 CATAMARAN, vacation rental in Sag Harbor

*SAIL* YOUR OWN PRIVATE YACHT ! DAYSAILS ON HAMPTONS #1 CATAMARAN

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Sag Harbor Charmer - 2 Bedroom Cottage; Walk to Town, vacation rental in Sag Harbor
Sag Harbor Charmer - 2 Bedroom Cottage; Walk to Town, vacation rental in Sag Harbor
Sag Harbor Charmer - 2 Bedroom Cottage; Walk to Town, vacation rental in Sag Harbor

Sag Harbor Charmer - 2 Bedroom Cottage; Walk to Town

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sag Harbor Village walk to town and beach, vacation rental in Sag Harbor
Sag Harbor Village walk to town and beach, vacation rental in Sag Harbor
Sag Harbor Village walk to town and beach, vacation rental in Sag Harbor

Sag Harbor Village walk to town and beach

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Perfect Family Hamptons Vacation Retreat in Sag Harbor!, vacation rental in Sag Harbor
Perfect Family Hamptons Vacation Retreat in Sag Harbor!, vacation rental in Sag Harbor
Perfect Family Hamptons Vacation Retreat in Sag Harbor!, vacation rental in Sag Harbor

Perfect Family Hamptons Vacation Retreat in Sag Harbor!

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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Whaling Captain Pierson's Cottage, vacation rental in Sag Harbor
Whaling Captain Pierson's Cottage, vacation rental in Sag Harbor
Whaling Captain Pierson's Cottage, vacation rental in Sag Harbor

Whaling Captain Pierson's Cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Cottage 1865 in Sag Harbor Village, vacation rental in Sag Harbor
Cottage 1865 in Sag Harbor Village, vacation rental in Sag Harbor
Cottage 1865 in Sag Harbor Village, vacation rental in Sag Harbor

Cottage 1865 in Sag Harbor Village

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Charming Sag Harbor House In The Village!, vacation rental in Sag Harbor
Charming Sag Harbor House In The Village!, vacation rental in Sag Harbor
Charming Sag Harbor House In The Village!, vacation rental in Sag Harbor

Charming Sag Harbor House In The Village!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Sag Harbor Luxury Home, Heated Pool, Walk to Private Beach, Walk To Village, vacation rental in Sag Harbor
Sag Harbor Luxury Home, Heated Pool, Walk to Private Beach, Walk To Village, vacation rental in Sag Harbor
Sag Harbor Luxury Home, Heated Pool, Walk to Private Beach, Walk To Village, vacation rental in Sag Harbor

Sag Harbor Luxury Home, Heated Pool, Walk to Private Beach, Walk To Village

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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BRAND NEW SAG HARBOR GORGEOUS  2 Bedroom/2 Bath COTTAGE WITH POOL!, vacation rental in Sag Harbor
BRAND NEW SAG HARBOR GORGEOUS  2 Bedroom/2 Bath COTTAGE WITH POOL!, vacation rental in Sag Harbor
BRAND NEW SAG HARBOR GORGEOUS  2 Bedroom/2 Bath COTTAGE WITH POOL!, vacation rental in Sag Harbor

BRAND NEW SAG HARBOR GORGEOUS 2 Bedroom/2 Bath COTTAGE WITH POOL!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Sag Harbor Ultimate Beach House , 5 min walk to Long Beach, vacation rental in Sag Harbor
Sag Harbor Ultimate Beach House , 5 min walk to Long Beach, vacation rental in Sag Harbor
Sag Harbor Ultimate Beach House , 5 min walk to Long Beach, vacation rental in Sag Harbor

Sag Harbor Ultimate Beach House , 5 min walk to Long Beach

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Book Now for Summer 2021!, vacation rental in Sag Harbor
Book Now for Summer 2021!, vacation rental in Sag Harbor
Book Now for Summer 2021!, vacation rental in Sag Harbor

Book Now for Summer 2021!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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BEHIND SERENE GREEN FARM &  TWO MINUTE DRIVE TO GORGEOUS LONG BEACH, vacation rental in Sag Harbor
BEHIND SERENE GREEN FARM &  TWO MINUTE DRIVE TO GORGEOUS LONG BEACH, vacation rental in Sag Harbor
BEHIND SERENE GREEN FARM &  TWO MINUTE DRIVE TO GORGEOUS LONG BEACH, vacation rental in Sag Harbor

BEHIND SERENE GREEN FARM & TWO MINUTE DRIVE TO GORGEOUS LONG BEACH

Rental Home
4 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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Village Tranquil Traditional With Gunite Pool, hot tub and Lush Gardens, vacation rental in Sag Harbor
Village Tranquil Traditional With Gunite Pool, hot tub and Lush Gardens, vacation rental in Sag Harbor
Village Tranquil Traditional With Gunite Pool, hot tub and Lush Gardens, vacation rental in Sag Harbor

Village Tranquil Traditional With Gunite Pool, hot tub and Lush Gardens

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Sag Harbor Home close to Village, Heated Pool, Sun-filled Decks, 4 Beds/4Baths, vacation rental in Sag Harbor
Sag Harbor Home close to Village, Heated Pool, Sun-filled Decks, 4 Beds/4Baths, vacation rental in Sag Harbor
Sag Harbor Home close to Village, Heated Pool, Sun-filled Decks, 4 Beds/4Baths, vacation rental in Sag Harbor

Sag Harbor Home close to Village, Heated Pool, Sun-filled Decks, 4 Beds/4Baths

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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The Cooper-Burke House, vacation rental in Sag Harbor
The Cooper-Burke House, vacation rental in Sag Harbor
The Cooper-Burke House, vacation rental in Sag Harbor

The Cooper-Burke House

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Beech Tree Cottage, vacation rental in Sag Harbor
Beech Tree Cottage, vacation rental in Sag Harbor
Beech Tree Cottage, vacation rental in Sag Harbor

Beech Tree Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Family waterfront oasis, vacation rental in Sag Harbor
Family waterfront oasis, vacation rental in Sag Harbor
Family waterfront oasis, vacation rental in Sag Harbor

Family waterfront oasis

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Sag Harbor Village Home 4 bed 3 bath Sleeps 8 Salt Water Pool, 2 acres 3K sq ft., vacation rental in Sag Harbor
Sag Harbor Village Home 4 bed 3 bath Sleeps 8 Salt Water Pool, 2 acres 3K sq ft., vacation rental in Sag Harbor
Sag Harbor Village Home 4 bed 3 bath Sleeps 8 Salt Water Pool, 2 acres 3K sq ft., vacation rental in Sag Harbor

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Modern Luxury in Sag Harbor, The Hamptons, vacation rental in Sag Harbor
Modern Luxury in Sag Harbor, The Hamptons, vacation rental in Sag Harbor
Modern Luxury in Sag Harbor, The Hamptons, vacation rental in Sag Harbor

Modern Luxury in Sag Harbor, The Hamptons

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Perfect Sag Harbor  (Unavailable during pandemic. Stay well!), vacation rental in Sag Harbor
Perfect Sag Harbor  (Unavailable during pandemic. Stay well!), vacation rental in Sag Harbor
Perfect Sag Harbor  (Unavailable during pandemic. Stay well!), vacation rental in Sag Harbor

Perfect Sag Harbor (Unavailable during pandemic. Stay well!)

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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A Happy House in the Village, vacation rental in Sag Harbor
A Happy House in the Village, vacation rental in Sag Harbor
A Happy House in the Village, vacation rental in Sag Harbor

A Happy House in the Village

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Newly Remodeled Home Down the Street from the Beach 10min from Vinyards, vacation rental in Sag Harbor
Newly Remodeled Home Down the Street from the Beach 10min from Vinyards, vacation rental in Sag Harbor
Newly Remodeled Home Down the Street from the Beach 10min from Vinyards, vacation rental in Sag Harbor

Newly Remodeled Home Down the Street from the Beach 10min from Vinyards

Rental Home
6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Sag Harbor Cottage Vacation, vacation rental in Sag Harbor
Sag Harbor Cottage Vacation, vacation rental in Sag Harbor
Sag Harbor Cottage Vacation, vacation rental in Sag Harbor

Sag Harbor Cottage Vacation

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Waterview Cottage Overlooking Sag Harbor Bay Beach with Pool, vacation rental in Sag Harbor
Waterview Cottage Overlooking Sag Harbor Bay Beach with Pool, vacation rental in Sag Harbor
Waterview Cottage Overlooking Sag Harbor Bay Beach with Pool, vacation rental in Sag Harbor

Waterview Cottage Overlooking Sag Harbor Bay Beach with Pool

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Historic Georgian Home of Legendary Photographer, vacation rental in Sag Harbor
Historic Georgian Home of Legendary Photographer, vacation rental in Sag Harbor
Historic Georgian Home of Legendary Photographer, vacation rental in Sag Harbor

Historic Georgian Home of Legendary Photographer

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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New Listing: Bay-View Home with Heated Pool, Tennis Court, Steps to..., vacation rental in Sag Harbor
New Listing: Bay-View Home with Heated Pool, Tennis Court, Steps to..., vacation rental in Sag Harbor
New Listing: Bay-View Home with Heated Pool, Tennis Court, Steps to..., vacation rental in Sag Harbor

New Listing: Bay-View Home with Heated Pool, Tennis Court, Steps to...

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
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Renovated Sag Harbor Village home is a short walk to Main Street, vacation rental in Sag Harbor
Renovated Sag Harbor Village home is a short walk to Main Street, vacation rental in Sag Harbor
Renovated Sag Harbor Village home is a short walk to Main Street, vacation rental in Sag Harbor

Renovated Sag Harbor Village home is a short walk to Main Street

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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SAG HARBOR GETAWAY-LONG TERM RENTAL STARTING SEPTEMBER 2020-APRIL 2021, vacation rental in Sag Harbor
SAG HARBOR GETAWAY-LONG TERM RENTAL STARTING SEPTEMBER 2020-APRIL 2021, vacation rental in Sag Harbor
SAG HARBOR GETAWAY-LONG TERM RENTAL STARTING SEPTEMBER 2020-APRIL 2021, vacation rental in Sag Harbor

SAG HARBOR GETAWAY-LONG TERM RENTAL STARTING SEPTEMBER 2020-APRIL 2021

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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Secluded Sag Harbor Oasis: Chic modern getaway 3 mins to Bay, 8 mins to Ocean., vacation rental in Sag Harbor
Secluded Sag Harbor Oasis: Chic modern getaway 3 mins to Bay, 8 mins to Ocean., vacation rental in Sag Harbor
Secluded Sag Harbor Oasis: Chic modern getaway 3 mins to Bay, 8 mins to Ocean., vacation rental in Sag Harbor

Secluded Sag Harbor Oasis: Chic modern getaway 3 mins to Bay, 8 mins to Ocean.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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5 Bedroom Gut Renovated Modern, vacation rental in Sag Harbor
5 Bedroom Gut Renovated Modern, vacation rental in Sag Harbor
5 Bedroom Gut Renovated Modern, vacation rental in Sag Harbor

5 Bedroom Gut Renovated Modern

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Cozy & Luxurious Sag Harbor Village Home - 5 min walk to town, private garden, vacation rental in Sag Harbor
Cozy & Luxurious Sag Harbor Village Home - 5 min walk to town, private garden, vacation rental in Sag Harbor
Cozy & Luxurious Sag Harbor Village Home - 5 min walk to town, private garden, vacation rental in Sag Harbor

Cozy & Luxurious Sag Harbor Village Home - 5 min walk to town, private garden

Rental Home
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
More info
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Secluded Hamptons cottage., vacation rental in Sag Harbor
Secluded Hamptons cottage., vacation rental in Sag Harbor
Secluded Hamptons cottage., vacation rental in Sag Harbor

Secluded Hamptons cottage.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Sag Harbor's Secret by the Bay | Walk to Beach, vacation rental in Sag Harbor
Sag Harbor's Secret by the Bay | Walk to Beach, vacation rental in Sag Harbor
Sag Harbor's Secret by the Bay | Walk to Beach, vacation rental in Sag Harbor

Sag Harbor's Secret by the Bay | Walk to Beach

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Sweet Dreams in Sag Harbor, vacation rental in Sag Harbor
Sweet Dreams in Sag Harbor, vacation rental in Sag Harbor
Sweet Dreams in Sag Harbor, vacation rental in Sag Harbor

Sweet Dreams in Sag Harbor

Rental Home
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
More info
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Secluded Sag Harbor Cottage with a Big Pool w/ Diving Board + Slide, Big Yard!, vacation rental in Sag Harbor
Secluded Sag Harbor Cottage with a Big Pool w/ Diving Board + Slide, Big Yard!, vacation rental in Sag Harbor
Secluded Sag Harbor Cottage with a Big Pool w/ Diving Board + Slide, Big Yard!, vacation rental in Sag Harbor

Secluded Sag Harbor Cottage with a Big Pool w/ Diving Board + Slide, Big Yard!

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Contemporary Oasis in Sag Harbor Village, vacation rental in Sag Harbor
Contemporary Oasis in Sag Harbor Village, vacation rental in Sag Harbor
Contemporary Oasis in Sag Harbor Village, vacation rental in Sag Harbor

Contemporary Oasis in Sag Harbor Village

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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