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VRBO
New Listing: SH Village Classic, Perfect Location
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Location ~ Location. Perfectly situated in the heart of the Village, one block from restaurants, shopping, and one mile ...
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VRBO
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Expedia
Southampton Home #3
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This classic Victorian home welcomes you with sunlit and airy interiors with all the character and history of a Southamp ...
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Expedia
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VRBO
Southampton Home #4
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This classic Victorian home welcomes you with sunlit and airy interiors with all the character and history of a Southamp ...
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VRBO
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Expedia
Southampton Home #5
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This classic Victorian home welcomes you with sunlit and airy interiors with all the character and history of a Southamp ...
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Expedia
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VRBO
Southampton Home #6
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This classic Victorian home welcomes you with sunlit and airy interiors with all the character and history of a Southamp ...
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VRBO
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Expedia
Newly Renovated Hilltop Villa
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Retreat in Comfort. Nestled atop a hill in the heart of Water Mill, this quiet 5 bed/4 bath modern home's beautiful inte ...
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Expedia
From $1726 per night (USD)
VRBO
New To Market Farm House in Water Mill
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
This home, adjacent to a 105 acre reserve and featuring gorgeous sunsets, offers a first floor open floor plan with larg ...
From $1726 per night (USD)
VRBO
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Expedia
Spectacular Vineyard Setting in Watermill
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Private and serene setting on a cul-de-sac backing directly onto a wine vineyard offers 4 bedrooms and 2.5 baths. This c ...
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Expedia
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VRBO
Just a 15 minute walk to the Village of Southampton!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Enjoy the company of your friends and family in this beautiful, spacious back yard. Majestically surrounded by Mature ...
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VRBO
From $2326 per night (USD)
VRBO
Contemporary Southampton Villa
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Situated just shy of 2 acres and home set on a rise at the end of a 400ft winding driveway, within minutes from local sh ...
From $2326 per night (USD)
VRBO
From $969 per night (USD)
VRBO
Sag Harbor Hamptons hideaway
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
This stylish place to stay is perfect!! Enjoy the peaceful tranquility away from the crowds and the noise. Bucolic setti ...
From $969 per night (USD)
VRBO
From $1356 per night (USD)
VRBO
Perfect SouthHampton getaway
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This is the perfect Hamptons getaway! This resort like 3 bedroom 2 bath gem of a home is conveniently located close to t ...
From $1356 per night (USD)
VRBO
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VRBO
Spacious Home with Heated Pool located in Southampton Village
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Spacious home on North Main Street in the Village of Southampton. Comfortably sleeps 10+. 6 bedrooms, office, 4.5 bat ...
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VRBO
From $2105 per night (USD)
Expedia
Modernist treehouse nestled in nature w/ access to pvt tennis minutes to ocean.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to this modernist, private home nestled in nature . Minutes to all towns of Bridgehampton and Sag Harbor and gorg ...
From $2105 per night (USD)
Expedia
From $3659 per night (USD)
VRBO
Hamptons Style. Close to village restaurants, shops and ocean beach!
Bedrooms:
7
Bathrooms:
7
Sleeps:
14
7 Bedroom, 6.5 Bath, Gourmet Kitchen, Heated Pool/Jacuzzi, Outdoor Fireplace & Grill, Fast Wifi, SONOS + MORE The Willo ...
From $3659 per night (USD)
VRBO
From $576 per night (USD)
Expedia
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Welcome to Whisper in the Woods! Enjoy this large cottage tucked away in the Tuckahoe woods. With 5 bedrooms and 3 bat ...
From $576 per night (USD)
Expedia
From $1188 per night (USD)
VRBO
Gorgeously Renovated SH Village 5 bd w/ Large Pool
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
This is a charming five bedroom four bathroom home with a separate guest house on the property. The house is less than a ...
From $1188 per night (USD)
VRBO
From $1183 per night (USD)
Expedia
Chic Southampton Getaway w/Heated Pool. Minutes away from village & beach.
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Welcome to our home away from home! This newly constructed home is less than a 5 minute drive away from the beach and th ...
From $1183 per night (USD)
Expedia
From $716 per night (USD)
VRBO
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Enjoy a vacation away in this one-level, 4-bedroom, 2-bathroom well decorated beachy cottage, just minutes from the Hamp ...
From $716 per night (USD)
VRBO
From $600 per night (USD)
Expedia
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience the charm of a newly revitalized two-story apartment nestled in the vibrant heart of Southampton Village. The ...
From $600 per night (USD)
Expedia
From $2269 per night (USD)
VRBO
Southampton Village-POOL, TENNIS, BEACH CHAIRS, BEACH BIKES
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
The best of everything the Hamptons has to offer. This home sits behind tall privet hedges in Southampton Village !! Far ...
From $2269 per night (USD)
VRBO
From $3509 per night (USD)
Expedia
Newly Renovated Sag Harbor Estate
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Situated on over 2 private gated acres with close proximity to Sag Harbor, Bridgehampton, and Southampton village’s fame ...
From $3509 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Charming 3-bedroom barn house on 1-acre in Water Mill w/ Fireplace, WiFi, W/D
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Located in Water Mill, this charming barn house locate don 1 acre bordering and overlooking 100 acres of preserve farm f ...
From $314 per night (USD)
VRBO
From $1243 per night (USD)
Expedia
Expansive Sag Harbor Estate with Pool, Tennis, Hot Tub, Close to Sag Harbor...
Bedrooms:
8
Bathrooms:
6
Sleeps:
12
Huckleberry Hideaway Expansive Sag Harbor Estate with Pool, Tennis, Hot Tub, Close to Sag Harbor and Bridgehampton 6BR ...
From $1243 per night (USD)
Expedia
From $3663 per night (USD)
VRBO
Chic Hamptons Retreat in Watermill with Tennis, Pool, Spa, Steam Room, and Gym
Bedrooms:
10
Bathrooms:
7
Sleeps:
20
This wonderful fully loaded estate is available starting mid-September, 2025. Located in Water Mill, the home is nestled ...
From $3663 per night (USD)
VRBO
From $3583 per night (USD)
Expedia
Unparalleled Views in a Hampton's Style Private Escape
Bedrooms:
5
Bathrooms:
6
Sleeps:
11
Embrace the Hamptons' charm in this luxurious Water Mill sanctuary-a perfect balance of elegance, privacy, and breathtak ...
From $3583 per night (USD)
Expedia
From $2814 per night (USD)
VRBO
Beautiful Southampton Village Home, Perfect for Families with Private Pool...
Bedrooms:
5
Bathrooms:
6
Sleeps:
10
The Village Gem Beautiful Southampton Village Home, Perfect for Families with Private Pool in Town 6BR/5.5BA: private ...
From $2814 per night (USD)
VRBO
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VRBO
Beautiful, new design with tons of natural light, heated pool, and great...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Please note that a reservation for this property needs to be approved before it is confirmed. Noyac Luminous Beautiful ...
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VRBO
$Tranquil retreat in the heart of Sag Harbor, 6 bedroom\n11,000 sq ft home$
From $4721 per night (USD)
VRBO
Tranquil retreat in the heart of Sag Harbor, 6 bedroom\n11,000 sq ft home
Bedrooms:
9
Bathrooms:
6
Sleeps:
18
Discover the beauty of Sag Harbor from this phenomenal 6-bedroom estate. With 5 king beds and 1 queen bed, this property ...
From $4721 per night (USD)
VRBO
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Expedia
Luxurious Southampton Retreat with Private Pool and Pool House, Great for...
Bedrooms:
7
Bathrooms:
6
Sleeps:
12
The Southampton Grand Luxurious Southampton Retreat with Private Pool and Pool House, Great for Families 6BR/7.5BA: Pr ...
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Expedia
From $2408 per night (USD)
VRBO
Southampton Paradise with Saltwater Pool & Spa & 3 minutes to Best Beach in USA
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
By day and by night you will enjoy this delightful villa in Southampton Village with 5 bedrooms including 1 king bed, 3 ...
From $2408 per night (USD)
VRBO
From $1318 per night (USD)
Expedia
New Listing - Eclectic home with private pool, decorated loft, gas...
Bedrooms:
4
Bathrooms:
5
Sleeps:
11
Airy Water Mill Ranch New Listing - Eclectic home with private pool, decorated loft, gas fireplace, and ample communal ...
From $1318 per night (USD)
Expedia
From $235 per night (USD)
VRBO
Charming 1-bedroom cottage in the heart of Southampton Village
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Located in the heart of Southampton Village, this intimate, centrally-located cottage is the perfect getaway! Nestled in ...
From $235 per night (USD)
VRBO
From $896 per night (USD)
Expedia
Elegant Coastal Escape with Expansive Yard, Heated Pool, and Outdoor...
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Water Mill Retreat Elegant Coastal Escape with Expansive Yard, Heated Pool, and Outdoor Kitchen in the Heart of Water M ...
From $896 per night (USD)
Expedia
From $1419 per night (USD)
VRBO
Water Mill wonderful farm house
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Enjoy your summer in this fabulous Water Mill farm house, close to the village and beaches. The two story main house fea ...
From $1419 per night (USD)
VRBO
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Expedia
Modern Cottage with a View
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Designer’s own Modern Cottage has bay views and is a short walk to bay beaches. Less than ten minutes to Sag Harbor Vill ...
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Expedia
From $895 per night (USD)
VRBO
Southampton Home with Heated Pool,6 minutes from beach’s
Bedrooms:
3
Bathrooms:
3
Sleeps:
11
Make some memories at this unique and family-friendly place. Enjoy our heated pool and private home theater. Beaches ar ...
From $895 per night (USD)
VRBO
From $8879 per night (USD)
VRBO
Everything in Hamptons special discount available for weekly and monthly renters
Bedrooms:
8
Bathrooms:
6
Sleeps:
12
Idyllic 9000 sq foot estate , centrally located , with everything one could desire. Beautifully decorated interior, wi ...
From $8879 per night (USD)
VRBO
From $428 per night (USD)
VRBO
Stunning Townhouse w Tennis & Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Newly renovated 5-star hotel-quality 2 bedroom, 2.5 bathroom luxury townhouse. South of the high-way, minutes t ...
From $428 per night (USD)
VRBO
From $1088 per night (USD)
Expedia
Sag Harbor August-LD rental! Lets make a deal!!
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
30 day minimum stay only please!!! Updated June 4, 2022 Hello! Welcome to my Paradise! I am currently booked now through ...
From $1088 per night (USD)
Expedia
From $1034 per night (USD)
VRBO
Classic Southampton Village Home with Pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Beautiful Southampton Village cedar shake home set on just shy of a half acre lot featuring four bedrooms, two bathrooms ...
From $1034 per night (USD)
VRBO
From $4346 per night (USD)
VRBO
New Southampton Village Gem. 6 bedroom, 6 + bath and 5 minutes drive to beach.
Bedrooms:
7
Bathrooms:
6
Sleeps:
8
Elegant details in this 5,300 sq ft Southampton Village shingle style traditional 6 bedroom in suite 6 1/2 bath, chef k ...
From $4346 per night (USD)
VRBO
From $500 per night (USD)
VRBO
Southampton Village Walk to All
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming, immaculate one bedroom in the heart of southampton village with an inviting living room space and eat-in kitch ...
From $500 per night (USD)
VRBO
From $2404 per night (USD)
VRBO
Southampton 1 Block From Village, Lovely 4-Bedroom
Bedrooms:
3
Bathrooms:
4
Sleeps:
5
Beautifully decorated and very comfortable, sun-filled Village home. Fully equipped gourmet kitchen, with 4 bedrooms, 2 ...
From $2404 per night (USD)
VRBO
From $591 per night (USD)
VRBO
Chic, Serene, Sunfilled Oasis.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
A country drive leads to this pristine single story home located close to all of Southampton's renowned Golf Courses, t ...
From $591 per night (USD)
VRBO
From $480 per night (USD)
VRBO
Close to Southampton Village and Beaches, Train Station and Hampton Jitney
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Thank you for viewing our listing for our charming three bedroom, two bath home located in Southampton. The house is a r ...
From $480 per night (USD)
VRBO
From $520 per night (USD)
VRBO
1 Block From Southampton Village
Bedrooms:
0
Bathrooms:
2
Sleeps:
2
Beautiful one-bedroom apartment in a Carriage House, 1 block from shops, restaurants and cultural attractions of Main St ...
From $520 per night (USD)
VRBO
From $3248 per night (USD)
VRBO
Luxe Summer House Rental w/ Heated Saltwater Pool; Walk to Beach and Golf.
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Luxurious New Home with Heated Swimming Pool Centrally Located in the Hamptons: This oasis is AVAILABLE FOR 2-4 WEEKS I ...
From $3248 per night (USD)
VRBO
From $5929 per night (USD)
VRBO
Hamptons Oasis 7Bed/7.5 Bath w Pool, Hot Tub and Tennis
Bedrooms:
7
Bathrooms:
7
Sleeps:
10
Idyllic 8500 sq foot estate , centrally located , with everything one could desire. Beautifully decorated interior, with ...
From $5929 per night (USD)
VRBO
From $2318 per night (USD)
VRBO
Charming Southampton Village Guest Home -Walk to Beach, Restaurants, Shops
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Located in the heart of Southampton Village. Walk or Bike to your favorite places in Southampton Village. ...
From $2318 per night (USD)
VRBO
From $1775 per night (USD)
VRBO
Southampton Village South, less than a mile to the beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Charming cape on a half acre in a very quiet neighborhood south of the highway in Southampton Village. New heated saltw ...
From $1775 per night (USD)
VRBO
From $2728 per night (USD)
Expedia
YOU CAN WATCH THE SUNRISE FROM YOUR BALCONY
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
You can watch the sunrise in this custom built stucco villa with circular driveway, wrought iron gate and open large yar ...
From $2728 per night (USD)
Expedia
From $1502 per night (USD)
VRBO
Newly Renovated Pristine Southampton Colonial
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
This newly renovated, spectacular, center hall colonial home is just minutes from Southampton Village, the beautiful bea ...
From $1502 per night (USD)
VRBO
From $16633 per night (USD)
Expedia
Stunning Southampton Village Modern Home
Bedrooms:
9
Bathrooms:
9
Sleeps:
10
This magnificent 14,000+/- sq. ft. modern property is entered through a gated entry with lawns, gardens, and a serpentin ...
From $16633 per night (USD)
Expedia
From $2252 per night (USD)
VRBO
Gracious 6 Bedroom home with a backyard paradise minutes from Main Street
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
A classic Hampton's home located on a quiet lane in the Southampton Meadows Estates. This 6-bedroom, 5.5-bath traditiona ...
From $2252 per night (USD)
VRBO
From $7067 per night (USD)
VRBO
New Luxury Southampton Village Estate- Walk to town! Avail Dates in August!
Bedrooms:
9
Bathrooms:
7
Sleeps:
12
Pristine, 8,000 square foot, brand new home complete with all new furnishings located on a gorgeous sprawling acre lot i ...
From $7067 per night (USD)
VRBO
From $1582 per night (USD)
VRBO
August Gatherings by Pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Open floor plan in this gathering house makes a great place to be together. Spacious kitchen with center island. Two d ...
From $1582 per night (USD)
VRBO

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