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From $524 per night (USD)
VRBO
Bright & Modern Pool House
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The unique landscape of this compound creates distinct areas for relaxation creating the effect of being nestled into th ...
From $524 per night (USD)
VRBO
From $1761 per night (USD)
VRBO
Private Southampton Retreat with Pool, Tennis & Resort Style...
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Please note that a reservation for this property needs to be approved before it is confirmed. Southampton Serene Priva ...
From $1761 per night (USD)
VRBO
From $608 per night (USD)
VRBO
Charming 3-bedroom house in enchanting Southampton Village
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Unwind in Southampton at this adorable house. With 3 cozy bedrooms including a king, queen, and twin bed, guests can rel ...
From $608 per night (USD)
VRBO
From $1012 per night (USD)
Expedia
Minutes from the beach, brand new 4 bedroom
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Miller Manor! - Newly renovated - Family friendly - Fully fenced in yard - Central air - 4 bed, 3 bath retrea ...
From $1012 per night (USD)
Expedia
From $1071 per night (USD)
VRBO
Fully Renovated and Re-Designed Water Mill Home with Sweeping Horse Farm...
Bedrooms:
5
Bathrooms:
6
Sleeps:
13
Please note that a reservation for this property needs to be approved before it is confirmed. Meadow's Edge Fully Reno ...
From $1071 per night (USD)
VRBO
From $3853 per night (USD)
Expedia
Spacious Southampton Home Minutes to Town, Private Pool, Perfect for Families
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Southampton Village Classic Spacious Southampton Home Minutes to Town, Private Pool, Perfect for Families 4BR/3BA: pri ...
From $3853 per night (USD)
Expedia
From $3591 per night (USD)
VRBO
Water Mill Perfection: Tennis, Saltwater Pool, Winery, Art Museum, Kids Oasis
Bedrooms:
7
Bathrooms:
7
Sleeps:
14
This one of a kind property runs against the backside of Duckwalk Vineyards and is just a short 5-minute walk to wine ta ...
From $3591 per night (USD)
VRBO
$\ The Bungalow\ Southampton Village - walk to town, train, Jitney$
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Expedia
\" The Bungalow\" Southampton Village - walk to town, train, Jitney
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A former hangout of many East End artists, "The Bungalow" is a charming Southampton Village house located minutes from t ...
Click For Pricing
Expedia
From $1537 per night (USD)
VRBO
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
The home has four bedrooms, three full bathrooms with an open living room and sitting room (with flat screen tv on the w ...
From $1537 per night (USD)
VRBO
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Expedia
Premium Hamptons location minutes from ocean or bay beaches ,
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Comfortable 3 Br home located on a magnificent 2acre property with a heated salt water lap pool Airy and bright home wit ...
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Expedia
From $1587 per night (USD)
VRBO
Gorgeous Brand New Modern Farmhouse
Bedrooms:
5
Bathrooms:
5
Sleeps:
11
This Board and Batten Napa Farmhouse sits on 2/3 of landscaped acreage to be completed by May 31st of 2020. This is the ...
From $1587 per night (USD)
VRBO
From $1768 per night (USD)
Expedia
Beautiful Southampton Village home, new reno, Heated pool!
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Recently renovated, Four Bedrooms, Two Full Baths, and a finished basement with ample room for all are located in the he ...
From $1768 per night (USD)
Expedia
From $2101 per night (USD)
VRBO
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Southampton Village Oasis Contemporary Southampton Village Home Walking Distance to Town, Pool, Perfect for Families or ...
From $2101 per night (USD)
VRBO
Click For Pricing
Expedia
Southampton Village Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in Southampton Village, enjoy carefree, beautifully landscaped pool and tennis courts. Light-filled condo with ...
Click For Pricing
Expedia
From $1869 per night (USD)
VRBO
South of Hwy Dream! Walk to Duck Walk Vineyard, Parrish Art Museum, and Lunch!
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Rental Permit RP241274 FULL SUMMER PRICING *June 32k *July 45k *Aug - $50K - RENTED *WEEKLY -$13,000 per week with 2 we ...
From $1869 per night (USD)
VRBO
From $670 per night (USD)
Expedia
Charming Modern Home - Winter and Summer Retreat
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Beautiful home on a quiet street. Immaculately maintained. Summer and winter retreat. In addition to five bedrooms and t ...
From $670 per night (USD)
Expedia
From $903 per night (USD)
VRBO
Walk to the Village! Charming modern farmhouse.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Kick back and relax in this calm, stylish space. House in the village but feels like you’re on your own retreat. House i ...
From $903 per night (USD)
VRBO
Click For Pricing
Expedia
5+ Bedrooms , 4.5 Bathrooms Pet's OK, Water Mill
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Watermill North - Serenity and beauty in this amazing Contemporary Modern designed home has 5,760 Sq. Ft. (approx.) on 3 ...
Click For Pricing
Expedia
From $1100 per night (USD)
VRBO
Private, Tennis and Pool Minutes to Southampton Village and Beaches
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
PLEASE CONTACT HOMEOWNER BEFORE BOOKING THIS HOME. THIS HOME DOES NOT ALLOW INSTANT BOOKING: Kathleen/katdoherty1@gmail ...
From $1100 per night (USD)
VRBO
From $969 per night (USD)
Expedia
Home page of Southampton Village
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Charming home in Southampton Village. Walking distance to Jobs Lane and Main Street Village shops. About a mile to the ...
From $969 per night (USD)
Expedia
From $2746 per night (USD)
VRBO
Southampton Village New Rental
Bedrooms:
10
Bathrooms:
8
Sleeps:
16
Great back yard with long swimming pool, outdoor gas grill and plenty of very comfortable outdoor seating, Every bedroo ...
From $2746 per night (USD)
VRBO
Click For Pricing
Expedia
Beautiful Home In Great Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Great neighborhood! 5-mins to bay, 12-mins to ocean. Near many hiking trails. Property is located approx 2.5 miles fr ...
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Expedia
From $3756 per night (USD)
VRBO
Yellowstone In The Hamptons ~ 18-Acre Estate Surrounded By A Nature Preserve
Bedrooms:
7
Bathrooms:
4
Sleeps:
6
This Just In! Please inquire about discounts for longer stays. Located in the prime, prestigious, heart of the Hampto ...
From $3756 per night (USD)
VRBO
Click For Pricing
Expedia
Luxury Sunset Shores Summer Getaway - 8min to town
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Beautiful Luxury Sunset Shores Summer House. Recently updated with new hardwood floors, hot tub, paint, lighting, new ba ...
Click For Pricing
Expedia
From $4090 per night (USD)
VRBO
Ultimate Hamptons luxury with Private Tennis and Pool
Bedrooms:
7
Bathrooms:
8
Sleeps:
20
Don't miss out on the best rental with tennis, new deck, and pool on a sprawling 5-acre property! Stunning and Very Priv ...
From $4090 per night (USD)
VRBO
From $696 per night (USD)
VRBO
Like Tuscany, private Vineyard Home, Southampton
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Like Tuscany, truly surrounded by vineyards. Gorgeous views from every room. Open concept kitchen, travertine floors, hi ...
From $696 per night (USD)
VRBO
From $1143 per night (USD)
VRBO
Beautiful Private, Secluded Southampton All Season Retreat, Close To Beaches
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Beautiful newly furnished and decorated 4 BR colonial with open concept living space and sprawling deck that overlooks a ...
From $1143 per night (USD)
VRBO
From $1072 per night (USD)
VRBO
Southampton House Perfect for Families and Entertaining
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Come enjoy this south of the highway home in Southampton set on a gorgeous .7 acre lot in an unbeatable location. Situat ...
From $1072 per night (USD)
VRBO
From $411 per night (USD)
VRBO
Peaceful Quiet Updated Modern Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Situated off of a quiet lane on a half-acre of land, this designer, updated, modern residence offers a peaceful and quie ...
From $411 per night (USD)
VRBO
From $763 per night (USD)
VRBO
Perfect Southampton Getaway
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
All utilities included in rental price - we do not accept instant bookings - please send a message first. Situated in ...
From $763 per night (USD)
VRBO
From $4219 per night (USD)
VRBO
Family Friendly, Estate Like Home, Heated Pool Seconds to Bay!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
A perfect getaway for a family at this Sag Harbor step back in time farmhouse. 1.5 acres of privacy with a heated pool ...
From $4219 per night (USD)
VRBO
From $3441 per night (USD)
VRBO
Luxury Private Water Mill Home w/ pool - 14 day rental 8/22-9/5 2022
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
12 min. from beach. Located at the end of a dead end street, down a long private drive overlooking the expansive grounds ...
From $3441 per night (USD)
VRBO
From $1622 per night (USD)
VRBO
Southampton Village Cottage SOH Backyard Paradise 20 x 40 OLYMPIC SIZED POOL!!!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Backyard enclosed with two BBQ's. This one level ranch house has a convenient in the Village of Southampton location. So ...
From $1622 per night (USD)
VRBO
From $887 per night (USD)
VRBO
Hampton Beach Barn w/ Infrared Sauna and Heated Pool - Dog friendly.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
3,000sf (approximate) Post & Beam Beach Barn, located in the upscale hamlet of Water Mill in Southampton, NY. POOL OP ...
From $887 per night (USD)
VRBO
From $2295 per night (USD)
VRBO
Hamptons Escape
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Experience luxury at its finest in this stunning retreat house located in the heart of Southampton/Watermill Horse Count ...
From $2295 per night (USD)
VRBO
From $6534 per night (USD)
VRBO
GORGEOUS, 10K SF PRIVATE VILLA - Seasonal rental only.
Bedrooms:
7
Bathrooms:
6
Sleeps:
12
Offered for the very first time this season, we pride ourselves on providing the ultimate hospitality and comfort and th ...
From $6534 per night (USD)
VRBO
From $1463 per night (USD)
VRBO
Idyllic quiet retreat, golf course views, newly renovated in Hamptons style.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Peaceful Quiet retreat in Southampton with golf course views, tastefully renovated, very sunny and spacious. Newly Ren ...
From $1463 per night (USD)
VRBO
From $527 per night (USD)
Expedia
Pools tennis gym golf pickelball
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Book soon ! Fun charming and updated bright and lovely chic 2 bedroom 3 bathroom condo minutes bike or drive to Southamp ...
From $527 per night (USD)
Expedia
From $5683 per night (USD)
VRBO
Southampton Village New Construction
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
New modern home with fantastic décor and amenities. Really enjoy your vacation in this stylish and feel good environment ...
From $5683 per night (USD)
VRBO
From $2027 per night (USD)
VRBO
Southampton exclusive private location with beautiful heated salt water pool
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Welcome to the Hamptons! The perfect peaceful and quiet Hamptons getaway. Exclusive private location close to Sebonac Go ...
From $2027 per night (USD)
VRBO
From $3599 per night (USD)
VRBO
Southampton Village 5 minute walk to Main Steet 10 minute walk to Coopers Beach
Bedrooms:
5
Bathrooms:
7
Sleeps:
14
This home offers state-of-the-art systems including Sonos, Honeywell Alarm, Radio-Ra, High-speed wifi, Cat-6 in every ro ...
From $3599 per night (USD)
VRBO
From $1575 per night (USD)
VRBO
Gorgeous Southampton Village Charmer, French Country Style
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful picturesque French-country style house is minutes away from the beach, village shops and village tennis court, ...
From $1575 per night (USD)
VRBO
From $2252 per night (USD)
VRBO
Perfect fall family retreat in Water Mill with new Gym and Media Room
Bedrooms:
4
Bathrooms:
6
Sleeps:
9
The ideal family vacation home. Looking for a family who will enjoy and love our house. Close to Southampton, Sag Habor ...
From $2252 per night (USD)
VRBO
From $1487 per night (USD)
VRBO
Idyllic views in Water Mill with pool and tennis
Bedrooms:
5
Bathrooms:
6
Sleeps:
11
*** Please note 2-week minimum stay *** Idyllic 1.5 acre property with tennis and pool south of the highway in Water ...
From $1487 per night (USD)
VRBO
From $2054 per night (USD)
VRBO
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The pool is open! Reliable WiFi and cell phone service. Renovated Village classic with a secluded garden, walking distan ...
From $2054 per night (USD)
VRBO
From $1722 per night (USD)
VRBO
Summer Rental with Private Heated Pool &Tennis Near Beach & Village
Bedrooms:
3
Bathrooms:
4
Sleeps:
13
A great home in a great location in the Village of Southampton. Home offers an open floor plan for entertaining. Home b ...
From $1722 per night (USD)
VRBO
From $1472 per night (USD)
VRBO
Southampton Village Charmer - South of Highway
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
A beautifully renovated designer home in one of Southampton's most desirable locations. The house was recently completel ...
From $1472 per night (USD)
VRBO
From $1485 per night (USD)
VRBO
Avail 7/10-9/05! Gorgeous, classy 3 bdrm near beach, private pool, in Village!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Village of Southampton chic! Navy cedar-shingled 3 bedroom, 2.5 bath 2-story beach house w/ new, heated salt-water pool ...
From $1485 per night (USD)
VRBO
From $755 per night (USD)
VRBO
Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Enjoy your stay in this “beachy chic” renovated historic home. White oak flooring and antique wood beams add to the coo ...
From $755 per night (USD)
VRBO
From $616 per night (USD)
VRBO
Newly Renovated, Professionally Decorated Hamptons Home bordered by a reserve
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This completely renovated and professionally decorated home provides the perfect summer retreat. Sitting on three peacef ...
From $616 per night (USD)
VRBO
From $3810 per night (USD)
VRBO
Hamptons House - 4 Bedroom House + 4 Bedroom Cottage with pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
20
Ideal Location!! House is flawless and perfect! This 3 acre property has 4 bedroom and 3 bath full bathrooms. Located in ...
From $3810 per night (USD)
VRBO
From $2897 per night (USD)
VRBO
Spacious and Conveniently Located Home in Southampton / Water Mill
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Amazing location and home in the heart of Water Mill. 3 min from ocean beaches (Cooper's and Flying Point), 3 min from S ...
From $2897 per night (USD)
VRBO
From $5941 per night (USD)
VRBO
Ultimate Hamptons Vacation Estate
Bedrooms:
9
Bathrooms:
10
Sleeps:
22
Situated on 2 1/2 private acres you can do whatever you desire, all bedrooms include en-suite private full bath, cable t ...
From $5941 per night (USD)
VRBO
From $2023 per night (USD)
VRBO
COVETED Millfarm Lane -3 min to Southampton
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Modern, spacious, clean , professionally decorated family home w farm views on the border of Watermill / Southampton. HO ...
From $2023 per night (USD)
VRBO
From $915 per night (USD)
VRBO
Southampton Village Gem
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
On a quiet street in Southampton Village, this newly renovated home is the perfect summer getaway. Bright, stylish inter ...
From $915 per night (USD)
VRBO
From $504 per night (USD)
Expedia
Escape and enjoy a peaceful vacation at this Southampton Estate with Pool...
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Whites Lane Escape Escape and enjoy a peaceful vacation at this Southampton Estate with Pool and Tennis! 4BR/3.5BA w/ ...
From $504 per night (USD)
Expedia
From $1097 per night (USD)
VRBO
Chic Southampton Home, close to Village and Ocean Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Situated privately on a quiet road sits this crisp newly renovated three bedroom, two and one half bath contemporary hou ...
From $1097 per night (USD)
VRBO
From $514 per night (USD)
VRBO
Dreaming of summer fun or an off-season adventure? Enjoy both!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Book for summer fun or have an incredible off-season experience! Stunning Flying Point and Scott Cameron beaches + charm ...
From $514 per night (USD)
VRBO
From $2132 per night (USD)
VRBO
Swim in a sea of hydrangeas on this peaceful, bucolic property.
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Enjoy this comfortable cottage traditional, with an open floor plan, in a bucolic setting that is surrounded by nearby f ...
From $2132 per night (USD)
VRBO
From $1161 per night (USD)
Expedia
New Fully Remodeled Post Modern Home, Perfect getaway for a family!
Bedrooms:
5
Bathrooms:
6
Sleeps:
10
Fully remodeled 6 bedroom 5.5 Bath house. •Modern, clean, and spacious •Quiet, comfortable, and peaceful •Lots of out ...
From $1161 per night (USD)
Expedia
From $2504 per night (USD)
VRBO
Sag harbor/ Bridgehampton High End Furniture House 5 bed/7ba w POOL very private
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
LUXURY Sag Harbor 5/6 bedroom House. Mature Families only, no party groups , 2 weeks minimum (may consider to do weekly ...
From $2504 per night (USD)
VRBO
From $2304 per night (USD)
VRBO
Incredible Location, Family and Dog Friendly , minutes to flying point
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
This oversized, casual and inviting beach house sits next 100 acres of west facing preserve. Phenomenal sunrises and s ...
From $2304 per night (USD)
VRBO
From $1024 per night (USD)
VRBO
Private Village Home-South Of Hill Street, Walk To Coopers Beach or Village
Bedrooms:
2
Bathrooms:
5
Sleeps:
7
Located in the village of Southampton, this renovated historic home puts you at Coopers Beach, village shopping and rest ...
From $1024 per night (USD)
VRBO
From $2875 per night (USD)
VRBO
Luxury - 5 bdrs, 6 baths, Tennis Crt, Heated Pool, Basketball, Hot tub, 2.4 acrs
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Stunning Modern Estate in Sag Harbor – Fully Renovated in 2023-24 Welcome to your private oasis in Sag Harbor. This lux ...
From $2875 per night (USD)
VRBO
From $1073 per night (USD)
VRBO
Southampton House South of Highway Perfect for Families
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Southampton home perfect for your summer get away with the family and friends. Two story home features 3 bedrooms upstai ...
From $1073 per night (USD)
VRBO
From $1268 per night (USD)
VRBO
Centrally Located Southampton / Water Mill <br>Bright, Open Floor, Saltwater Pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
4 bedrooms. 3 1/2 baths, Master Bedroom on first floor (Sleeps 8). Master has a king size bed. Relaxing, Spacious, Br ...
From $1268 per night (USD)
VRBO
From $2122 per night (USD)
VRBO
Perfection in the Heart of Southampton Village; Walk to Town, Bike to Beaches
Bedrooms:
4
Bathrooms:
3
Sleeps:
7
Enjoy this stunning 3 bedroom, 4 bathroom village home with gourmet kitchen, den, media room and two-zone central air-co ...
From $2122 per night (USD)
VRBO
From $3020 per night (USD)
VRBO
Modern Home in Southampton Village w/Gunite Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Excellent rental property located in Southampton Village. Well designed and completely rebuilt in 2015, this four bedroo ...
From $3020 per night (USD)
VRBO
From $2236 per night (USD)
VRBO
Southampton Village Charmer with gunite pool and spacious renovated pool house
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Beautifully renovated home located on a private and quiet street in Southampton Village. Walking or biking distance to s ...
From $2236 per night (USD)
VRBO
From $2344 per night (USD)
VRBO
Southampton Village Estate with Tennis, Heated Pool and Spa
Bedrooms:
5
Bathrooms:
7
Sleeps:
12
Beautifully renovated seven bedroom, five bath, two-story home that holds on to its 19th century architectural roots whi ...
From $2344 per night (USD)
VRBO
Click For Pricing
VRBO
Cozy, Coastal, Colorful, Cottage. Great for beach lovers and families.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your dream vacation rental in Southampton. This cozy condo offers everything you need for your August Hampton ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Tranquil Sag Harbor Retreat with water sunset views and access steps away
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Wonderful Sag Harbor/Noyac home for rent, with pool, tennis, views of Peconic Bay and access to secluded beach just 150' ...
Click For Pricing
Expedia
From $4439 per night (USD)
VRBO
The Prospect Estate - Spacious Historic House minutes from SH Village
Bedrooms:
7
Bathrooms:
7
Sleeps:
18
AVAILABILITY NOTICE : PLEASE INQUIRE FOR MOST UP-TO-DATE AVAILABILITY BEFORE MAKING A "RESERVATION REQUEST". POSTED CALE ...
From $4439 per night (USD)
VRBO
From $6284 per night (USD)
VRBO
9 Bedroom Water Mill Estate
Bedrooms:
12
Bathrooms:
9
Sleeps:
16
Luxurious 13,000 square foot estate features 9 bedrooms and12.5 baths in the heart of Water Mill farmlands. All bedrooms ...
From $6284 per night (USD)
VRBO
From $551 per night (USD)
VRBO
Beautiful Home In SH Village!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Enjoy this charming home perfectly located within a 3 minute drive or 10 minute walk to Main Street Southampton, grocery ...
From $551 per night (USD)
VRBO
From $514 per night (USD)
VRBO
Open Floor Plan, Private Tennis Court, Close to Ocean Beaches and...
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Please note that a reservation for this property needs to be approved before it is confirmed. Southampton w/ Tennis & P ...
From $514 per night (USD)
VRBO
From $574 per night (USD)
VRBO
Cozy 3 Bedroom Southampton Village Oasis
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Escape to your beach chic haven in Southampton Village, where contemporary luxury meets timeless elegance. Unwind in the ...
From $574 per night (USD)
VRBO
From $843 per night (USD)
VRBO
Think Big Blue Skies, 4 Bedroom, 4 Bath Water Mill
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This rental doesn't come on the market very often, as usually leases turn into long term leases. Next availability star ...
From $843 per night (USD)
VRBO
From $912 per night (USD)
VRBO
In the Heart of SH Village, Salt Water Heated Pool with Incredible Outdoor Space
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
In the Heart of SH Village, Salt Water Heated Pool with Incredible Outdoor Space Immaculate, charming ranch home surroun ...
From $912 per night (USD)
VRBO
From $3218 per night (USD)
Expedia
Walk-to-Beach, Newly Built Smart Home with Heated Salt Water Pool, Near...
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Sag Harbor Luxe Walk-to-Beach, Newly Built Smart Home with Heated Salt Water Pool, Near Noyac Golf Club 5BR/5BA: Priva ...
From $3218 per night (USD)
Expedia
From $2060 per night (USD)
VRBO
Spacious Open Design for dates in August/LDW
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
This Sag Harbor contemporary home has 4 spacious bedrooms, including 2 king beds, 4 twin beds, a queen bed, and 2 full b ...
From $2060 per night (USD)
VRBO
From $554 per night (USD)
Expedia
Charming 3-bedroom gem in Southampton village
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Escape to this stylish 3-bedroom gem in Southampton Village, where modern comfort meets classic charm. This inviting ret ...
From $554 per night (USD)
Expedia
From $557 per night (USD)
VRBO
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a Large two-bedroom two-bath house that is one mile to Southampton village. Private space with fenced yard and ...
From $557 per night (USD)
VRBO
From $5883 per night (USD)
Expedia
New Hamptons House in Sag harbor + Pool + 8 bedroom
Bedrooms:
7
Bathrooms:
8
Sleeps:
18
New house in Sag Harbor with pool. Everything is brand new. 8 bedrooms and 6.5 bathrooms. 6,000sf, 20x40 pool, very priv ...
From $5883 per night (USD)
Expedia
$Charming Southampton Village Home 4 Bedroom, 2 Bath \n5 minutes from the beach$
From $355 per night (USD)
VRBO
Charming Southampton Village Home 4 Bedroom, 2 Bath \n5 minutes from the beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Halsey House…. A charming, 2 story home in the heart of Southampton Village. Located on a quiet lane within w ...
From $355 per night (USD)
VRBO
From $1634 per night (USD)
Expedia
Beautiful Hampton Retreat- Sag Harbor Tennis and Pool on 2 private acres
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Relaxing private getaway nestled deep in the woods. Beautifully updated private home tucked away in Sag Harbor with tenn ...
From $1634 per night (USD)
Expedia
From $1085 per night (USD)
VRBO
Southampton Village Luxury with Pool House Spa - Guest Cottage. Walk to Town!
Bedrooms:
6
Bathrooms:
4
Sleeps:
10
Sea Rose - Located in Southampton Village, you'll find this completely renovated fully equipped home featuring a gorgeou ...
From $1085 per night (USD)
VRBO
From $7426 per night (USD)
VRBO
A Hampton resort lifestyle with private vineyard
Bedrooms:
10
Bathrooms:
8
Sleeps:
20
Covered outdoor living space w/full kitchen, full bar, over sized grill, pizza oven, coffee station, blender station, bi ...
From $7426 per night (USD)
VRBO
From $1790 per night (USD)
VRBO
Water Mill classic overlooking horse farm
Bedrooms:
5
Bathrooms:
6
Sleeps:
8
Newly renovated Water Mill classic with horse farm views. Perfect Hamptons getaway for large families. Three floors of ...
From $1790 per night (USD)
VRBO
From $495 per night (USD)
Expedia
Southampton Village Gem: Shinnecock Open Special
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located in the heart of Southampton Village, our townhome is exactly that, a home within walking distance to the village ...
From $495 per night (USD)
Expedia
From $580 per night (USD)
VRBO
Peaceful newly renovated sun filled 5 bedroom home in the heart of Water Mill
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Located at the end of a private driveway is this secluded retreat in the heart of Water Mill. The house sits on just und ...
From $580 per night (USD)
VRBO
From $4621 per night (USD)
VRBO
Steps away from Southampton Village Main Street
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
You will love this location! Situated on a lovely tree lined street only 300 steps to quaint, historic Main Street, you ...
From $4621 per night (USD)
VRBO
From $2897 per night (USD)
VRBO
Newly Built 6 Bed/5.5 Bath Modern Farmhouse with Pool and Hot tub
Bedrooms:
5
Bathrooms:
6
Sleeps:
10
Just completed construction Summer 2022! Gorgeous 6 bedrooms, 5.5 baths, designer decorated, perfect for a large or mul ...
From $2897 per night (USD)
VRBO
From $1044 per night (USD)
VRBO
Sag Harbor Waterfront Post and Beam Chalet with Deep Water Dock
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Located on a peninsula of a private, tree-lined street this waterfront home will be the quiet retreat you've been lookin ...
From $1044 per night (USD)
VRBO
From $1026 per night (USD)
VRBO
Cottage in Southampton Village; Relax in your own private park!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
The Perfect Getaway Strolling distance to the village and the Long Island Railroad, come and rest, relax and decompress ...
From $1026 per night (USD)
VRBO
From $2473 per night (USD)
VRBO
Southampton Village Luxury Retreat
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Newly renovated Southampton Village home within walking distance to all Southampton Village has to offer. This 3100 squa ...
From $2473 per night (USD)
VRBO
From $3426 per night (USD)
VRBO
Southampton Village, Complete Privacy, Gunite Pool & and 3 minute walk to town!!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Discover the epitome of sophisticated living in Southampton with this extraordinary house for rent. Set amidst a picture ...
From $3426 per night (USD)
VRBO
From $4022 per night (USD)
VRBO
Stunning secluded Southampton Village property near restaurants, shops and beach
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
This spectacular classic Hamptons home built in 2017 with a significant renovation in 2024. Furnished by a high-end int ...
From $4022 per night (USD)
VRBO
From $2404 per night (USD)
VRBO
Southampton estate with 5 bedrooms, pool, gym and community tennis
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Southampton village estate, close to amenities and beach. Community tennis. Game room, gym, family friendly, 20x40 heate ...
From $2404 per night (USD)
VRBO
From $3856 per night (USD)
Expedia
Chic Hamptons Retreat in Watermill with Tennis, Pool, Spa, Steam Room, and Gym
Bedrooms:
9
Bathrooms:
7
Sleeps:
20
This wonderful fully loaded estate is available starting mid-September, 2025. Located in Water Mill, the home is nestled ...
From $3856 per night (USD)
Expedia

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