Watermill Rentals
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VRBO
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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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 $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 $3756 per night (USD)Expedia
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)Expedia
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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 ...
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From $3591 per night (USD)Expedia
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)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 $11568 per night (USD)VRBO
Opulent Watermill Retreat: Exclusive Estate with Gourmet Kitchen & Outdoor Oasis
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 14
Welcome to your opulent Hamptons retreat! Nestled in the serene beauty of Watermill, this exclusive estate offers 8 lux ...
From $11568 per night (USD)VRBO
From $1648 per night (USD)VRBO
Spacious 5-bedroom house in beautiful Water Mill NY
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
This Water Mill house boasts 5 inviting bedrooms, each with a king bed. home sits on a 1.85 +/- acre flag lot with a buc ...
From $1648 per night (USD)VRBO
From $1071 per night (USD)Expedia
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)Expedia
From $712 per night (USD)VRBO
Amazing Beachfront Water Mill Home with Private Pool and Hot Tub, Perfect...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Water Mill Waterfront Wonder Amazing Beachfront Water Mill Home with Private Pool and Hot Tub, Perfect for Families 3B ...
From $712 per night (USD)VRBO
From $23121 per night (USD)VRBO
12,000 sq ft of Luxury, Modern Design, Full Gym, Indoor and Outdoor Dining...
- Bedrooms:
- 9
- Bathrooms:
- 8
- Sleeps:
- 6
Please note that a reservation for this property needs to be approved before it is confirmed. Cobb Road Daydream 12,00 ...
From $23121 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 $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 $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 $1550 per night (USD)VRBO
Private chic 3BR/2.5BA Hamptons cottage with pool - South of Highway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
This exquisitely renovated summer beach cottage is nestled down a quiet lane in the West Mecox Bay waterfront community ...
From $1550 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 $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 $1979 per night (USD)VRBO
Charming 4 BR +2 waterfront--pool, privacy, views, gazebo, boats, near beaches
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 8
Our cottage-style house is located on an acre of land on an arm of Mecox Bay--an easy boat ride or bike ride to the ocea ...
From $1979 per night (USD)VRBO
From $1751 per night (USD)Expedia
Amazing Hampton's Styled Getaway
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
This 3500 sq ft Hampton's styled home has a large light filled living room with fireplace and sliding glass doors to the ...
From $1751 per night (USD)Expedia
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 $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 $1658 per night (USD)VRBO
Classic Farm House in the heart of Water Mill, 2.7mi To Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy this charming 4 bedroom, 2.5 bath, dutch colonial farm house with NEWLY RENOVATED POOL HOUSE, complete kitchen, pa ...
From $1658 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 $6478 per night (USD)VRBO
Hamptons Mecox Bay neighborhood located in Water Mill / Bridgehampton
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
Hamptons Mecox Bay neighborhood located in Water Mill / Bridgehampton, this south-of-the-highway renovated historic Publ ...
From $6478 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 $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 $1755 per night (USD)VRBO
Best sunsets in the Hamptons. This home has it all. Best location in Water Mill.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Hamptons Estate on one of the most desirable streets in Water Mill (5 bedrooms, 5000 sqfeet). This home has it all: Spa, ...
From $1755 per night (USD)VRBO
From $3336 per night (USD)VRBO
Mint condition Water Mill South of the Highway with Mecox Bay access
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Spend your final moments of the summer in style at this brand new 5 bedroom 5.5 bathroom home. Prime location on a one w ...
From $3336 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 $1161 per night (USD)VRBO
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)VRBO
From $2328 per night (USD)VRBO
West Mecox | Bay Front with Southern Water Views
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This wonderful 4+ bedroom, 4 bath home, sited on a full acre, sits directly on Mecox Bay with a heated pool and rolling ...
From $2328 per night (USD)VRBO
From $723 per night (USD)VRBO
Modern Spacious House located 5 minutes from the beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Modern Spacious house with three bedrooms three baths. This unique property is like no other in the Hamptons. The pic ...
From $723 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 $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 $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 $2969 per night (USD)VRBO
Luxury French Villa in Water Mill
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
SEND AN INQUIRY FOR OFF SEASON & EXTENDED STAY SPECIALS! Welcome to this new custom built home in the highly coveted ha ...
From $2969 per night (USD)VRBO
From $3014 per night (USD)Expedia
LABOR DAY WEEK Special.Luxury Water Mill S.Mecox Bay/Pool/Dock/Fabulous Gardens
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
A gem in one of the most lovely, private areas of the Hamptons, tucked between Southampton and Bridgehampton, south of t ...
From $3014 per night (USD)Expedia
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)Expedia
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)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 $4121 per night (USD)VRBO
Luxury Water Mill Modern Retreat with Tennis, Pool, Minutes to Ocean Beaches
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Featured in various European magazines, this inspired modernist home combines zen-like simplicity with masterful design. ...
From $4121 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
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Watermill Farm Views Offer Great Spot For Family
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Well-appointed 2-story Watermill home with spectacular farm views, breathtaking sunsets, pool, sizeable yard, and CedarW ...
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NEW LISTING : SOUTHAMPTON PRIVATE HOME!!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful Southampton home with 4 bedrooms and 3 full baths! Private one acre lot backing to a preserve area. Home has ...
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From $3427 per night (USD)Expedia
Heated Pool and Tennis Court
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Gorgeous like new condition open-floor plan home in the heart of the Hamptons. Close to everything; Flying Point Beach, ...
From $3427 per night (USD)Expedia
From $1624 per night (USD)VRBO
Exclusive Designer Retreat in Water Mill
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Completely transformed in 2022 by an award-winning designer, this stunning property masterfully combines the timeless el ...
From $1624 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
From $5839 per night (USD)VRBO
BRAND NEW 7BR7BA Southampton Estate - Heated Salt Pool, Mins to Beach & Town
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 14
Welcome to The Water Millin’ House — a private, luxury 7 bedroom + bunk room Hamptons retreat with a heated saltwater po ...
From $5839 per night (USD)VRBO
From $7908 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 $7908 per night (USD)VRBO
From $2882 per night (USD)VRBO
Stunning 5 bedroom Vicente Wolf Designed Home South of Highway in Water Mill
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Introducing a luxurious 5,000 sq ft modern ranch nestled on a highly sought-after private lane in Water Mill South. Th ...
From $2882 per night (USD)VRBO
From $1077 per night (USD)VRBO
Modern Hamptons Farmhouse on Beautiful Horse Farm
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Located in the heart of the Hamptons in Watermill, NY, the neighborhood offers the best of the Hamptons. The home is on ...
From $1077 per night (USD)VRBO
From $819 per night (USD)VRBO
Beautiful Contemporary Water Mill Home Centrally Located with Private Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Please note that a reservation for this property needs to be approved before it is confirmed. Old Trail Tranquility Be ...
From $819 per night (USD)VRBO
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\" 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 ...
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From $1637 per night (USD)VRBO
Brand New Contemproraty House in Southampton
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 6
Brand new stunning contemporary house is now available for immediate occupancy. Amazing floor plan consists of four bed ...
From $1637 per night (USD)VRBO
Click For PricingExpedia
Amazing winter get away, \\ Gym. Hot tub. Special Offer for Dec, Jan. Feb, March
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
Your dream vacation. House is well appointed, open spacious, and relaxing. Perfect for large dinners and small cocktail ...
Click For PricingExpedia
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 $15010 per night (USD)VRBO
Expansive Bridgehampton Estate on almost 3 acres, Private Pool and Tennis,...
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 14
Please note that a reservation for this property needs to be approved before it is confirmed. Bridgehampton Escape Exp ...
From $15010 per night (USD)VRBO
From $423 per night (USD)VRBO
Recently Renovated Southampton Home, Modern Design, Perfect for Families
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Please note that a reservation for this property needs to be approved before it is confirmed. Southampton Ranch Modern ...
From $423 per night (USD)VRBO
From $1537 per night (USD)Expedia
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)Expedia
From $1768 per night (USD)VRBO
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)VRBO
From $460 per night (USD)VRBO
Unique Southampton Getaway w/ Rooftop Deck!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Looking to get away from city stresses? Leave them all behind and head to this newly remodeled 3-bedroom, 2.5-bathroom S ...
From $460 per night (USD)VRBO
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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 ...
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Harmony in the Hamptons!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
Lots of beautiful space in this wonderful private home surrounded by lush gardens in the heart of the Hamptons. Five bed ...
Click For PricingExpedia
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
From $755 per night (USD)Expedia
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)Expedia
From $1387 per night (USD)VRBO
Family Getaway With Pool, Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This cozy getaway is located off of Deerfield Road in Water Mill, in the township of Southampton and provides easy acces ...
From $1387 per night (USD)VRBO
From $3810 per night (USD)Expedia
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)Expedia
From $1625 per night (USD)VRBO
Stunning Private 4 acre Estate on Preserve near Village/Beach with Heated Pool.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Amazing views of open fields with expansive lawn and 20 flowering grape cherry trees in spring. Ultimate privacy on 4 a ...
From $1625 per night (USD)VRBO
From $1107 per night (USD)VRBO
Southampton Stunner: Modern & Bright, Pool, Beach & More!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful light and airy modern home, nestled in amongst the trees on a beautiful property. High ceilings and windowed w ...
From $1107 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
From $1183 per night (USD)VRBO
Private & Tranquil 1.03 Acre Estate in the Heart of Southampton
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This well-appointed and maintained 2,200 sq.ft., 4 bedroom, 3 bath Contemporary has a bright sunlit breakfast area direc ...
From $1183 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 $1559 per night (USD)VRBO
August Availability- Hamptons Summer Family Escape, Modern Farmhouse retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
On full acre, modern farmhouse style with new fully renovated primary bathroom and home, where coastal interior meets a ...
From $1559 per night (USD)VRBO
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Bridgehampton private estate home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Hidden at the end of an 1100 ft driveway on 5 private acres of high rolling meadow with distant oceanviews and overlooki ...
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From $1577 per night (USD)VRBO
Sag Harbor Resort Area Sanctuary, Privacy, Seclusion Heat Pool, Spa
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 18
A 5,000 square foot post modern estate secluded 8 bedrooms on the second floor with 4 1/2 baths, with detailed crown/ba ...
From $1577 per night (USD)VRBO
From $663 per night (USD)VRBO
SAG HARBOR SUMMER PARADISE AWAITS YOU!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
: SUMMER SEASON IS APPROACHING! Reserve Now! Bright, Sun-Filled 6 bedroom, 4.5 bath home with double height foyer and l ...
From $663 per night (USD)VRBO
From $1877 per night (USD)VRBO
Tastefully Decorated and Lushly Landscaped Family Retreat with 60' Pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
This comfortable, light filled five bedroom house sits on two beautifully landscaped acres north of the highway in Bridg ...
From $1877 per night (USD)VRBO
From $1733 per night (USD)VRBO
Conveniently Located Home 2 Miles from Village
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 13
Location, luxury and privacy abound in this rental. Located on a private street and features 6 bedrooms all en suite, p ...
From $1733 per night (USD)VRBO
From $3585 per night (USD)Expedia
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Hamptons Intl Film Festival Oct 3-13, 2025 (https://hamptonsfilmfest.org/) Immerse yourself in the allure of this stun ...
From $3585 per night (USD)Expedia
From $1626 per night (USD)VRBO
Beautiful, Private & Spacious, Cozy Hamptons Retreat, Sleeps 15, Peloton Bike+
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 15
Gracious living in this 3000 sq ft, 6 bedroom home with heated outdoor gunite pool (pool open from Friday of Memorial da ...
From $1626 per night (USD)VRBO
From $1167 per night (USD)Expedia
Stunning Private Sunny Modern Southampton home-5 beds Last minute discounts
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
This elegant property boasts nearly 2 acres of Relais Chateaux style gardens. The home sits amidst magnificent, lush lan ...
From $1167 per night (USD)Expedia
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 $1125 per night (USD)VRBO
August Deal: Luxe w/ Pool, Private, Amazing Garden, Outdoor Kitchen, Game Room
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Experience classic Southampton luxury with a twist of playful charm at our Sanctuary by the Beach. This 4-bedroom, 5-bat ...
From $1125 per night (USD)VRBO
From $1628 per night (USD)VRBO
Just renovated, Amazing oasis, heated pool-spa, between Sag Harbor -Southampton
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
A beautiful newly renovated house on a quiet street off Noyack road and close to all the Hamptons has to offer (just ber ...
From $1628 per night (USD)VRBO
From $2873 per night (USD)VRBO
JUST BECAME AVAILABLE FOR LABOR DAY. DIRECTLY ACROSS FROM THE 2023 CLASSIC.
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 8
Stunning contemporary beautifully appointed perfectly for all seasons. Interiors filled with beautiful art. Three firep ...
From $2873 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 $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 $1140 per night (USD)VRBO
\nGorgeous Southampton Home- Pool, Spa, Putting Green, Walk to Beach & Tennis/PB
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Indulge in a fabulous stay at a luxurious beach house in a private community in Southampton. This home features five bea ...
From $1140 per night (USD)VRBO
From $1285 per night (USD)VRBO
Southampton Home - Farm Views and Close Proximity to Village
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Traditional Hamptons cape-style house is located on a charming, quiet cul de sac in Southampton, just seconds from the V ...
From $1285 per night (USD)VRBO
From $764 per night (USD)VRBO
Beautiful ,Sag Harbor 4 bedroom, 31/2 bath Heated Pool rental\n
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful 4 bedroom 31/2 en-suite bath home , 3200 square feet with heated pool, on one acre property, in beautiful ups ...
From $764 per night (USD)VRBO
From $3202 per night (USD)VRBO
>> Prime Waterfront Location, Private, Dock, 5 minute Walk to Ocean & Beach <<
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Fabulous location! 5 minute WALK (no permit to access the beach needed) to the ocean - beach Very private, beautiful B ...
From $3202 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 $1371 per night (USD)VRBO
3 Story Contemporary
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Spacious 5 bedroom, three bathroom, contemporary Southampton home offers an open kitchen/ living room floor plan which i ...
From $1371 per night (USD)VRBO
From $1826 per night (USD)VRBO
Spacious 5 bedroom Family House with Heated Pool and Padel Court
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
This beautifully landscaped Gambrel on 1 acre offers 5,000 square feet of living space with 5 bedrooms, 5.5 baths, den w ...
From $1826 per night (USD)VRBO
From $1734 per night (USD)VRBO
Southampton Private Retreat is on the market for sale.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
THIS HOME CAN ONLY BE RESERVED BY CONTACTING THE OWNER DIRECTLY Private four bedroom (two en-suite) three bath home wit ...
From $1734 per night (USD)VRBO
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 $963 per night (USD)VRBO
Bright Beautiful Southampton - 4 Br near village 5 min & ocean beaches
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Our Southampton 4 bedroom classic shingle home with stylish decor is ideally located near Southampton Village (5 minutes ...
From $963 per night (USD)VRBO