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From $1624 per night (USD)
VRBO
Beautifully Restored Barn, Open First Floor Plan, Historic Charm and...
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Ocean Road Escape Beautifully Restored Barn, Open First Floor Plan, Historic Charm and Updates Furnishings, Close to To ...
From $1624 per night (USD)
VRBO
From $1441 per night (USD)
VRBO
Tastefully Furnished with Upgraded Amenities, Lush Landscaping, Minutes...
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Please note that a reservation for this property needs to be approved before it is confirmed. Dream on Elm Street Tast ...
From $1441 per night (USD)
VRBO
From $1778 per night (USD)
VRBO
Charming Cozy Southampton Village House 4 minutes from the Beach
Bedrooms:
5
Bathrooms:
7
Sleeps:
14
Cozy, spacious charming Southampton Village house great for families and friend groups. The house is 2 minutes from eit ...
From $1778 per night (USD)
VRBO
From $4664 per night (USD)
VRBO
Luxury Villa 7br 7baths with a Private Pool Hamptons
Bedrooms:
7
Bathrooms:
7
Sleeps:
12
Summary: Discover the epitome of serene, luxurious living in the Hamptons. This newly renovated, modern split-level home ...
From $4664 per night (USD)
VRBO
From $1106 per night (USD)
VRBO
SOUTHAMPTON-POOL,3 min to town,1.5 miles to beach. Outdoor kitchen,putting green
Bedrooms:
5
Bathrooms:
1
Sleeps:
8
Gorgeous 4 bedroom, 4.5 bathroom house in prime location. Heated Pool, pool house, sunny, fully fenced in property a mus ...
From $1106 per night (USD)
VRBO
$Large, secluded Watermill\/Southampton estate with pool$
From $2592 per night (USD)
VRBO
Large, secluded Watermill\/Southampton estate with pool
Bedrooms:
9
Bathrooms:
7
Sleeps:
15
Down a long driveway, this wonderfully-appointed compound situated on 2.5+/- acres offers exceptional privacy and seclus ...
From $2592 per night (USD)
VRBO
From $1049 per night (USD)
VRBO
1770's Honeymoon Cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
2
A 1770 country cottage with a modern twist set back on a sprawling 1.5 acres of green lawn. Welcome to our magical oa ...
From $1049 per night (USD)
VRBO
From $1598 per night (USD)
Expedia
SH Village
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Southampton Village Cheerful 3 bed cottage with a private heated pool and community tennis walk to town beach and rest ...
From $1598 per night (USD)
Expedia
Click For Pricing
VRBO
Bridgehampton Private
Bedrooms:
6
Bathrooms:
5
Sleeps:
14
Backed against thousands of acres of private state forest and at the end of a long driveway off a beautiful country road ...
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VRBO
From $2524 per night (USD)
VRBO
Stylish and recently renovated home with pool, sunlit open floor plan,...
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Please note that a reservation for this property needs to be approved before it is confirmed. Chic Southampton Retreat ...
From $2524 per night (USD)
VRBO
From $4054 per night (USD)
VRBO
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Newly furnished, this 5,000 SF+/- Italian villa style residence is situated on 1-acre+/- and comprises of 6 bedrooms and ...
From $4054 per night (USD)
VRBO
From $769 per night (USD)
Expedia
Southampton Beach & Town Cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Charming family friendly beach cottage with large pool. Walking distance to Village of Southampton’s fine dining and sto ...
From $769 per night (USD)
Expedia
From $2164 per night (USD)
VRBO
Southampton Village Luxury Retreat
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Newly renovated Southampton Village home within walking distance to all Southampton Village has to offer. This 3100 squa ...
From $2164 per night (USD)
VRBO
From $3600 per night (USD)
VRBO
Revel in Luxury
Bedrooms:
9
Bathrooms:
8
Sleeps:
25
A very rare find fully renovated in 2021! This prestigious Sag Harbor compound where multiple Hollywood stars and Bravo ...
From $3600 per night (USD)
VRBO
Click For Pricing
VRBO
Heaven in the Hamptons
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
South of Route 27, you will love this amenity-filled oasis near the beach and Bridgehampton village. Modern kitchen, Ros ...
Click For Pricing
VRBO
$HISTORIC FARMHOUSE MINUTES TO VILLAGE IN WATERMILL 5BR, 3 BATH, HEATED POOL \n\n$
From $1843 per night (USD)
VRBO
HISTORIC FARMHOUSE MINUTES TO VILLAGE IN WATERMILL 5BR, 3 BATH, HEATED POOL \n\n
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Experience Water Mill like a local in this 5-bedroom house. Nestled minutes away from Main Street in Bridgehampton Villa ...
From $1843 per night (USD)
VRBO
From $1805 per night (USD)
VRBO
Expansive Sag Harbor Estate with Pool, Tennis, Hot Tub, Close to Sag Harbor...
Bedrooms:
8
Bathrooms:
6
Sleeps:
12
Please note that a reservation for this property needs to be approved before it is confirmed. Huckleberry Hideaway Exp ...
From $1805 per night (USD)
VRBO
From $3238 per night (USD)
Expedia
Newly Renovated, Serene Property with Heated Pool, Tennis, and Resort-Like Spa
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Southampton Serenity Newly Renovated, Serene Property with Heated Pool, Tennis, and Resort-Like Spa 6BR/4BA w/ Vaulted ...
From $3238 per night (USD)
Expedia
From $350 per night (USD)
VRBO
Charming Two-Story Retreat in the Heart of Southampton Village
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 $350 per night (USD)
VRBO
From $1670 per night (USD)
VRBO
Southampton Village-HEATED 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 $1670 per night (USD)
VRBO
From $1637 per night (USD)
VRBO
Newly Renovated Sag Harbor Estate
Bedrooms:
7
Bathrooms:
6
Sleeps:
12
Situated on over 2 private gated acres with close proximity to Sag Harbor, Bridgehampton, and Southampton village’s fame ...
From $1637 per night (USD)
VRBO
From $1263 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 $1263 per night (USD)
VRBO
From $1031 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 $1031 per night (USD)
VRBO
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Expedia
Spacious Home with Heated Pool located in Southampton Village
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Spacious home on North Main Street in the Village of Southampton. Comfortably sleeps 10+. 6 bedrooms, office, 4.5 bat ...
Click For Pricing
Expedia
From $1818 per night (USD)
VRBO
Spacious Southampton Village Home Walking Distance to Town, Private Pool,...
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Southampton Village Luxury Spacious Southampton Village Home Walking Distance to Town, Private Pool, Perfect for Famili ...
From $1818 per night (USD)
VRBO
From $2461 per night (USD)
VRBO
Cozy Home In Southampton With Expansive Yard And Private Pool, Close to...
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Please note that a reservation for this property needs to be approved before it is confirmed. Southampton Beach Villa ...
From $2461 per night (USD)
VRBO
Click For Pricing
VRBO
ARCHITECT’S LIGHT-FILLED ECO-FRIENDLY MODERN HOME
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Am I outside or inside? Huge windows draw the outside in and frame the outside wooded views. Perfect for a summer in ...
Click For Pricing
VRBO
From $3057 per night (USD)
VRBO
Beautiful Home, Backyard, Pool and Patio in Southampton
Bedrooms:
7
Bathrooms:
7
Sleeps:
12
Beautiful home in Southampton Village. Covered patio, huge backyard, pool, pool house and garage. This gorgeous new hous ...
From $3057 per night (USD)
VRBO
Click For Pricing
VRBO
Chic Beach House in the Village of Southampton
Bedrooms:
5
Bathrooms:
7
Sleeps:
10
Enjoy this stylish beach house in The Village of Southampton. This property is perfectly located, within walking distanc ...
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VRBO
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Expedia
Sag Harbor Modern Oasis
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Luxury 5 bedroom, 3 1/2 bathroom home is designed around a central courtyard / pool area. Grill and contemporary seating ...
Click For Pricing
Expedia
From $2759 per night (USD)
VRBO
Designer Gut Renovated Farmhouse on over 1 Acre, Numerous Spacious Living...
Bedrooms:
6
Bathrooms:
4
Sleeps:
8
Water Mill Wooded Escape Designer Gut Renovated Farmhouse on over 1 Acre, Numerous Spacious Living Areas with Modern Am ...
From $2759 per night (USD)
VRBO
Click For Pricing
Expedia
Architect designed house near ocean on huge reserve.
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
There are three private suites- master suite has a huge bathroom with jacuzzi and shower as well as private covered deck ...
Click For Pricing
Expedia
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VRBO
Pristine Southampton Home
Bedrooms:
3
Bathrooms:
5
Sleeps:
5
This is a beautiful home with a huge wall of windows and tons of sunlight, nestled in the trees on a quiet cul de sac ro ...
Click For Pricing
VRBO
From $1311 per night (USD)
VRBO
Gorgeous 4 bed 3 bath home with Pool - walking distance to beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy a serene Hamptons holiday in this bright renovated home. Take a quiet tree lined walk (7 min) to the local beach, ...
From $1311 per night (USD)
VRBO
From $678 per night (USD)
VRBO
Charming Cottage close to Main Street
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Your family will be close to everything when you stay at this centrally-located place with a great outdoor area for you ...
From $678 per night (USD)
VRBO
Click For Pricing
Expedia
SOUTHAMPTON Romantic house like being at a resort
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
My house is romantic, comfortable and very peaceful. One can see where my travels have been. India a favourite. I have 3 ...
Click For Pricing
Expedia
$Luxurious 6bd\/4.5ba on 4 acres with pool & tennis$
From $2009 per night (USD)
VRBO
Luxurious 6bd\/4.5ba on 4 acres with pool & tennis
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Perfect for large families and groups. Completely redone in 2022, this 6 bedroom (2 masters) 4.5 bath house with a larg ...
From $2009 per night (USD)
VRBO
Click For Pricing
Expedia
Just a 15 minute walk to the Village of Southampton!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Enjoy the company of your friends and family in this beautiful, spacious back yard. Majestically surrounded by Mature ...
Click For Pricing
Expedia
From $348 per night (USD)
VRBO
Modern home with large deck, firepit, enclosed yard, & immaculate kitchen
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Contemporary Southampton Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
From $348 per night (USD)
VRBO
Click For Pricing
Expedia
New Listing: SH Village Classic, Perfect Location
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Location ~ Location. Perfectly situated in the heart of the Village, one block from restaurants, shopping, and one mile ...
Click For Pricing
Expedia
From $889 per night (USD)
VRBO
Southampton House Heated Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Just minutes from Southampton Village, Sag Harbor, Water Mill, Long Beach and more. Heated pool and 3 outdoor living spa ...
From $889 per night (USD)
VRBO
From $1745 per night (USD)
VRBO
Southampton House, heated pool, golf, and minutes from town and ocean!
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Make this Hamptons home yours for the summer, a month, or a few weeks. This fully loaded, top-of-the-line house is locat ...
From $1745 per night (USD)
VRBO
From $1007 per night (USD)
VRBO
Hamptons home with heated pool.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
A contemporary house set on 1.2 acres and located a 12 min drive to Sag Harbor and Southampton Villages. Amenities inclu ...
From $1007 per night (USD)
VRBO
$Southampton July 1 to Sept 3,- 50k. Or 30k per July or August. Pool\/Hot Tub$
From $1005 per night (USD)
VRBO
Southampton July 1 to Sept 3,- 50k. Or 30k per July or August. Pool\/Hot Tub
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This lovely home sits on over an acre of private land surrounded by beautiful, mature trees and flowers. The over sized ...
From $1005 per night (USD)
VRBO
From $1566 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 $1566 per night (USD)
VRBO
From $561 per night (USD)
VRBO
Bridgehampton Home on Lush Acre, Heated In-Ground Gunite Pool, Close to...
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Please note that a reservation for this property needs to be approved before it is confirmed. Sandpiper Seclusion Brid ...
From $561 per night (USD)
VRBO
From $1461 per night (USD)
VRBO
Private 2.1 acre gated home with heated pool and tennis & pickleball court
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
Set on 2.1 acres, this gated, contemporary home offers a private retreat for family. Situated at the end of a cul-de-sac ...
From $1461 per night (USD)
VRBO
From $1073 per night (USD)
VRBO
Remarkable Bridgehampton Beach estate just minutes to private beach access
Bedrooms:
5
Bathrooms:
5
Sleeps:
14
Summer availability is from Memorial Day to Labor Day. Stunning 2.5 acre property - meticulously maintained Michael Davi ...
From $1073 per night (USD)
VRBO
From $4275 per night (USD)
VRBO
4 miles -Beach 2 miles -Town, Chef, Gym,2 Pelotons,Heated Pool,hot tub,firepits
Bedrooms:
5
Bathrooms:
7
Sleeps:
20
*We can only accommodate longer term rentals in Weekly & Monthly increments. Monthly Rates: *negotiable July 110k (4 we ...
From $4275 per night (USD)
VRBO
From $6186 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 $6186 per night (USD)
VRBO
From $8725 per night (USD)
VRBO
Newly developed contemporary home situated on 1.5 acres.
Bedrooms:
14
Bathrooms:
10
Sleeps:
15
10 bedroooms & 14.5 baths. Situated in the ocean threshold of South Bridgehampton moments from two pristine beaches is a ...
From $8725 per night (USD)
VRBO
From $2043 per night (USD)
VRBO
Water Mill Hilltop with pool and tennis
Bedrooms:
8
Bathrooms:
6
Sleeps:
12
This spacious two-story traditional is located privately and secluded on a landscaped 2.10-acre property in Water Mill. ...
From $2043 per night (USD)
VRBO
$Southampton Water Mill Towd w\/ Pool House\/Art Studio\/Office & Heated Pool$
From $895 per night (USD)
VRBO
Southampton Water Mill Towd w\/ Pool House\/Art Studio\/Office & Heated Pool
Bedrooms:
4
Bathrooms:
3
Sleeps:
7
Spend your summer entertaining, relaxing, and enjoying this spacious over one acre, beautifully landscaped home with sep ...
From $895 per night (USD)
VRBO
From $17466 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 $17466 per night (USD)
Expedia
$Modern Southampton \/ Watermill Home$
From $2738 per night (USD)
VRBO
Modern Southampton \/ Watermill Home
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Centrally located between Southampton and Sag Harbor villages and close to bay beaches, this recently completed modern a ...
From $2738 per night (USD)
VRBO
Click For Pricing
Expedia
Beautiful Hamptons Home
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Conveniently located between Sag Harbor and Bridgehampton this beautiful home sits on 2.3 acres. Large back porch well s ...
Click For Pricing
Expedia
$ELEGANT HAMPTONS RETREAT W\/ PRIVATE POOL, SERENE SETTING, ON QUIET STREET,...$
From $5904 per night (USD)
VRBO
ELEGANT HAMPTONS RETREAT W\/ PRIVATE POOL, SERENE SETTING, ON QUIET STREET,...
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Please note that a reservation for this property needs to be approved before it is confirmed. Tiffany Elegance ELEGANT ...
From $5904 per night (USD)
VRBO

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