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From $2139 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 $2139 per night (USD)
VRBO
From $2424 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 $2424 per night (USD)
VRBO
From $4593 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 $4593 per night (USD)
VRBO
From $708 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 $708 per night (USD)
Expedia
From $810 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 $810 per night (USD)
VRBO
From $956 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 $956 per night (USD)
Expedia
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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 $3477 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 $3477 per night (USD)
VRBO
From $903 per night (USD)
VRBO
Charming 3-bedroom Country home in the Southampton
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Charming 3-bedroom country home on a quiet tree lined cul-de-sac. This 1984 home has been newly renovated with a modern ...
From $903 per night (USD)
VRBO
From $594 per night (USD)
Expedia
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 $594 per night (USD)
Expedia
From $1848 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 $1848 per night (USD)
VRBO
From $1218 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 $1218 per night (USD)
VRBO
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VRBO
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 ...
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VRBO
From $781 per night (USD)
VRBO
Designer Gut Renovated Farmhouse on over 1 Acre, Numerous Spacious Living...
Bedrooms:
6
Bathrooms:
4
Sleeps:
8
Please note that a reservation for this property needs to be approved before it is confirmed. Water Mill Wooded Escape ...
From $781 per night (USD)
VRBO
From $5051 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 $5051 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $862 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 $862 per night (USD)
VRBO
From $671 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 $671 per night (USD)
VRBO
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VRBO
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
VRBO
From $2790 per night (USD)
Expedia
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 $2790 per night (USD)
Expedia
From $2467 per night (USD)
VRBO
Cozy Home In Southampton With Expansive Yard And Private Pool, Close to...
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Southampton Beach Villa Cozy Home In Southampton With Expansive Yard And Private Pool, Close to Fowlers Beach, Perfect ...
From $2467 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
$HISTORIC FARMHOUSE MINUTES TO VILLAGE IN WATERMILL 5BR, 3 BATH, HEATED POOL \n\n$
From $1811 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 $1811 per night (USD)
VRBO
From $601 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 $601 per night (USD)
Expedia
From $674 per night (USD)
VRBO
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 $674 per night (USD)
VRBO
From $297 per night (USD)
Expedia
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 $297 per night (USD)
Expedia
From $1115 per night (USD)
VRBO
Southampton Village-HEATED POOL, TENNIS, BEACH CHAIRS, BEACH BIKES
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
The best of Fall in the Hamptons !! Farm stands, apple picking, corn mazes and Hank’s Pumpkin Town ! Bring the kids, th ...
From $1115 per night (USD)
VRBO
From $1672 per night (USD)
Expedia
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 $1672 per night (USD)
Expedia
From $2500 per night (USD)
VRBO
New Construction Newly Renovated Southampton Village Summer Oasis
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Bright and sunny Southampton Village home is perfect for creating summer memories. Resort-style outdoors is brand new c ...
From $2500 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
From $303 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 $303 per night (USD)
VRBO
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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 ...
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Expedia
$Luxurious 6bd\/4.5ba on 4 acres with pool & tennis$
From $1024 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 $1024 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 ...
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Expedia
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VRBO
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 ...
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VRBO
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Expedia
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 ...
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Expedia
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
Click For Pricing
Expedia
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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Expedia
From $682 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 $682 per night (USD)
VRBO
From $586 per night (USD)
Expedia
Bridgehampton Home on Lush Acre, Heated In-Ground Gunite Pool, Close to...
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Sandpiper Seclusion Bridgehampton Home on Lush Acre, Heated In-Ground Gunite Pool, Close to Atlantic Ocean and Sagg Pon ...
From $586 per night (USD)
Expedia
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 $704 per night (USD)
Expedia
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 $704 per night (USD)
Expedia
From $1217 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 $1217 per night (USD)
VRBO
From $423 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 $423 per night (USD)
VRBO
From $805 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 $805 per night (USD)
VRBO
From $7233 per night (USD)
VRBO
New house with Tennis, basketball, GYM, heated pool and Spa
Bedrooms:
8
Bathrooms:
7
Sleeps:
17
Secluded luxury newly constructed house nested atop a knoll in a 5.2 acres wooded area perfectly located between Sag Har ...
From $7233 per night (USD)
VRBO
From $955 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 $955 per night (USD)
VRBO
$Southampton July 1 to Sept 3,- 55k. Or 35k per July or August. Pool\/Hot Tub.$
From $1006 per night (USD)
VRBO
Southampton July 1 to Sept 3,- 55k. Or 35k 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 $1006 per night (USD)
VRBO
From $5329 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 $5329 per night (USD)
VRBO
From $2029 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 $2029 per night (USD)
VRBO
From $17499 per night (USD)
VRBO
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 $17499 per night (USD)
VRBO
$Modern Southampton \/ Watermill Home$
From $2628 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 $2628 per night (USD)
VRBO
$Southampton Water Mill Towd w\/ Pool House\/Art Studio\/Office & Heated Pool$
From $420 per night (USD)
VRBO
Southampton Water Mill Towd w\/ Pool House\/Art Studio\/Office & Heated Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Spend your summer entertaining, relaxing, and enjoying this spacious over one acre, beautifully landscaped home with sep ...
From $420 per night (USD)
VRBO
From $679 per night (USD)
VRBO
Four Bedroom Home in Amazing Bridgehampton Location
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Amazing South of the Highway location, a stone throw from the beach and centrally located near all the amenities Bridgeh ...
From $679 per night (USD)
VRBO
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VRBO
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 ...
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VRBO
From $2908 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 $2908 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
$ELEGANT HAMPTONS RETREAT W\/ PRIVATE POOL, SERENE SETTING, ON QUIET STREET,...$
From $2751 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 $2751 per night (USD)
VRBO

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