North Sea Rentals
- From $713 per night (USD)
VRBO
Newly remodeled Southampton Village Retreated with heated pool & tennis courts.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
AVAILABLE: SEPTEMBER RENTAL. This house is a bright and airy, very clean second home with private heated pool and commun ...
From $713 per night (USD)VRBO
- From $15000 per night (USD)
VRBO
Stunning Southampton Village Modern Home
- Bedrooms:
- 9
- Bathrooms:
- 7
- Sleeps:
- 16
This magnificent 14,000+/- sq. ft. modern property is entered through a gated entry with lawns, gardens, and a serpentin ...
From $15000 per night (USD)VRBO
- From $1236 per night (USD)
VRBO
Beautiful Southampton Home Minutes from Beaches, Nature Preserve, Golf...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Tuckahoe Woods Wonder Beautiful Southampton Home Minutes from Beaches, Nature Preserve, Golf Courses, Town Shopping and ...
From $1236 per night (USD)VRBO
- From $941 per night (USD)
VRBO
Charming Waterfront Cottage with Sunset Views!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
This historic home has been enjoyed by six generations of our family, and we're so excited to share it with you. This be ...
From $941 per night (USD)VRBO
- Click For Pricing
VRBO
Private Oasis in Sag Harbor
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Minutes from Long Beach, Mecox Beach, and the charming village of Sag Harbor, this spacious 3 level home offers indoor a ...
Click For PricingVRBO
- From $542 per night (USD)
VRBO
Immaculate newly renovated home in beach community
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
First Weekend in JUNE availability. Enjoy summer in the Hamptons in this newly renovated, spacious and serene family hom ...
From $542 per night (USD)VRBO
- From $2533 per night (USD)
VRBO
Villa Southampton Village
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 8
A beautifully renovated and expanded historical mansion has been brought into the 21st century and exquisitely decorated ...
From $2533 per night (USD)VRBO
- Click For Pricing
VRBO
Southampton Waterfront in Unique Location
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
4 BR, 4 Baths Southampton Home on 2 thirds of an acre secluded waterfront property, close to opening into Great Peconic ...
Click For PricingVRBO
- From $1403 per night (USD)
VRBO
Professionally renovated estate in the heart of Southampton with Private...
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 14
The Wythe Professionally renovated estate in the heart of Southampton with Private Pool, Hot Tub, Outdoor Shower, Gym, ...
From $1403 per night (USD)VRBO
- From $950 per night (USD)
VRBO
Newly renovated house in Southampton with pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our newly renovated 3-bedroom retreat in Southampton! With a pool, dedicated office, and room for 8 adults, i ...
From $950 per night (USD)VRBO
- From $1346 per night (USD)
VRBO
Tennis and Pool in Watermill- South of the Highway
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
A rare find with a hartru tennis court and pool in Watermill. The property is situated south of the highway and is a 5 m ...
From $1346 per night (USD)VRBO
- From $1950 per night (USD)
Expedia
Designer Southampton House family friendly near Shinnecock Golf Course
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Escape the hustle and bustle of summer traffic with this beautifully situated Southampton summer house, conveniently loc ...
From $1950 per night (USD)Expedia
- From $986 per night (USD)
VRBO
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 $986 per night (USD)VRBO
- From $15000 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 $15000 per night (USD)Expedia
- From $600 per night (USD)
VRBO
Catherine’s Place
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Farmhouse meets the bay in a beach comminity. Includes, tennis, basketball courts, private beach passes, 5-10 minutes wa ...
From $600 per night (USD)VRBO
- From $2982 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 $2982 per night (USD)VRBO
- From $4275 per night (USD)
VRBO
Southampton Summer Bayfront w\/Boat Dock + Saltwater Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Discover the extraordinary allure of Southampton's Edgemere Estate, a sanctuary that epitomizes grandeur and tranquility ...
From $4275 per night (USD)VRBO
- From $1580 per night (USD)
Expedia
Newly Renovated Pristine Southampton Colonial
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
This newly renovated, spectacular, center hall colonial home is just minutes from Southampton Village, the beautiful bea ...
From $1580 per night (USD)Expedia
- From $910 per night (USD)
VRBO
Beautiful Southampton Home centrally located close to Sag Harbor,...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Peconic Hills Hideaway Beautiful Southampton Home centrally located close to Sag Harbor, Southampton, and Bridgehampton ...
From $910 per night (USD)VRBO
- From $854 per night (USD)
VRBO
Southampton Luxury Escape - Sauna, Pool, Hot Tub, Tennis and More!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
NEWLY RENOVATED, SERENE PROPERTY WITH HEATED POOL, TENNIS, AND RESORT-LIKE SPA 6BR/4BA Vaulted Ceilings, Large Media Ro ...
From $854 per night (USD)VRBO
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- Click For Pricing
VRBO
Charming Southampton Villa-ge Minutes to the Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Located right in the heart of the village, minutes away from the train station and close to SH beaches, be ready for a t ...
Click For PricingVRBO
- From $2310 per night (USD)
VRBO
Modern Luxury Southampton Home
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Modern luxury living, 6,000+ sq ft across two stories + finished basement. Brand new house built in 2020 includes 5 bedr ...
From $2310 per night (USD)VRBO
- From $1327 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 or enjoying the tranquility of this over one acre, nicely landscaped home with separate p ...
From $1327 per night (USD)VRBO
- From $3600 per night (USD)
VRBO
Quintessential Sag Harbor Escape close to beach & town
- Bedrooms:
- 8
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to 2244 Noyack Rd, a stunning vacation retreat nestled in the serene beauty of Sag Harbor. This exquisite proper ...
From $3600 per night (USD)VRBO
- From $1133 per night (USD)
VRBO
Pool, Privacy & Peace in Stylish & Cozy Cottage in Sag Harbor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Pool is open! At the end of a quiet cul-de-sac, you will arrive at our peaceful escape. This sun drenched home (with A/C ...
From $1133 per night (USD)VRBO
- From $3156 per night (USD)
VRBO
Rosemorran Retreat Awaits With 5 Bedrooms, Tennis Crt, Pool & Jacuzzi. Stunning
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 10
This .95 acre residence is a very special property, featuring park-like grounds with Har-Tru tennis court, pool, Jacuzzi ...
From $3156 per night (USD)VRBO
- From $1365 per night (USD)
VRBO
Beautiful Southampton Waterfront Home with pool and private steps to the beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Please note that a reservation for this property needs to be approved before it is confirmed. Bayside Sensation in Sout ...
From $1365 per night (USD)VRBO
- Click For Pricing
VRBO
Private spacious home in the Southampto
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
Private spacious home in Southampton. The house is beautifully situated on a private 1 acre lot and has a heated gunite ...
Click For PricingVRBO
- From $4000 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 $4000 per night (USD)VRBO
- Click For Pricing
Expedia
Wonderful Southampton Cottage w\/ Private Pool - Unwind & Relax
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lovingly known as The Birds Nest. Kick back and relax in a calm, stylish space. This chic Southampton cottage with an ...
Click For PricingExpedia
- From $639 per night (USD)
Expedia
Stylish Southampton Waterfront
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy pure peacefulness while overlooking Little Fresh Pond in Southampton. The home is western facing, offering majesti ...
From $639 per night (USD)Expedia
- From $2600 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 $2600 per night (USD)VRBO
- From $1429 per night (USD)
VRBO
Southampton - Perfect Family Holiday Home!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Fabulous family vacation home nestled in a quiet cul-de-sac. Hamptons hideaway ideal for relaxing with family and friend ...
From $1429 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Lovely 2 story house minutes from village and beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
2story house with 4bedrooms and 2 baths. Hardwood floors. Eat in Kitchen with granite countertops. Gas range, dishwa ...
From $350 per night (USD)VRBO
- From $750 per night (USD)
Expedia
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 $750 per night (USD)Expedia
- From $775 per night (USD)
VRBO
Southampton Waterfront - kayaks included!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Southampton serenity awaits you with this stunning waterfront home! Perfectly located to beaches & Sag Harbor and Southa ...
From $775 per night (USD)VRBO
- From $1245 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 $1245 per night (USD)Expedia
- Click For Pricing
VRBO
Cozy, Coastal, Colorful, Cottage. Great for beach lovers and families.
- Bedrooms:
- 3
- 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 PricingVRBO
- Click For Pricing
Expedia
Tranquil Sag Harbor Retreat with water sunset views and access steps away
- Bedrooms:
- 5
- 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 PricingExpedia
- From $1087 per night (USD)
VRBO
BEACHY WATERFRONT HOME WITH DIRECT ACCESS TO PECONIC BAY AND PRIVATE DOCK,...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Fish Cove Waterfront BEACHY WATERFRONT HOME WITH DIRECT ACCESS TO PECONIC BAY AND PRIVATE DOCK, CENTRALLY LOCATED 3BR/ ...
From $1087 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- Click For Pricing
VRBO
Escape the City to this Spectacular Summer Rental in Southampton\n
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Indulge in the beauty of Summer every day at this stunning retreat in Southampton, which has been recently renovated to ...
Click For PricingVRBO
- From $722 per night (USD)
Expedia
Newly Renovated Southampton Home with Heated Pool
- 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 $722 per night (USD)Expedia
- From $1094 per night (USD)
VRBO
Private Bayfront Living, Water Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Shore Road Serenity Private Bayfront Living, Water Views 3BR/2BA, Lovely Outdoor Spaces, Short Drive to Sag Harbor & S ...
From $1094 per night (USD)VRBO
- From $2200 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 $2200 per night (USD)VRBO
- From $1487 per night (USD)
VRBO
Southampton Retreat close to towns of Southampton, Sag Harbor, amazing...
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 11
Please note that a reservation for this property needs to be approved before it is confirmed. North Sea Serenity South ...
From $1487 per night (USD)VRBO
- From $3152 per night (USD)
Expedia
Beautiful Southampton Home Walking Distance to Town and Short Bike Ride to...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Southampton Village Vibrance Beautiful Southampton Home Walking Distance to Town and Short Bike Ride to Beaches 5BR/4B ...
From $3152 per night (USD)Expedia
- From $7581 per night (USD)
VRBO
9 Bedroom Water Mill Estate
- Bedrooms:
- 13
- 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 $7581 per night (USD)VRBO
- From $1785 per night (USD)
Expedia
Dog-friendly estate with amazing pool, deck, & game room at new reduced rate
- Bedrooms:
- 8
- Bathrooms:
- 6
- Sleeps:
- 14
Island in the Sky Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1785 per night (USD)Expedia
- From $921 per night (USD)
VRBO
2 acre serene haven in Sag Harbor, recently renovated
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Special two acre property with a one-of-kind landscape featuring amazing pine trees. Beautiful sun room to enjoy in shou ...
From $921 per night (USD)VRBO
- From $1387 per night (USD)
Expedia
Beautiful, new design with tons of natural light, beautiful pool, and great...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Noyac Luminous Beautiful, new design with tons of natural light, beautiful pool, and great location in Sag Harbor 3BR/ ...
From $1387 per night (USD)Expedia
- From $749 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 $749 per night (USD)VRBO
- From $945 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 $945 per night (USD)VRBO
- Click For Pricing
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 PricingVRBO
- From $1948 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 $1948 per night (USD)VRBO
- From $391 per night (USD)
VRBO
Tucked into the quiet woods of Sag Harbor.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Want to wake up with the sound of birds and breeze passing through the trees? Come spend a night in this cozy cottage tu ...
From $391 per night (USD)VRBO
- From $700 per night (USD)
Expedia
coziest place to spend Thanksgiving, huge yard and proper dining room for family
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
On a quiet plot of land, enjoy a classic family cottage fit for a small family and furry friend, large yard and only 2 m ...
From $700 per night (USD)Expedia
- From $1650 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 $1650 per night (USD)VRBO
- From $1000 per night (USD)
Expedia
HIDDEN GEM AVAILABLE FOR MD to LD! NEW SWIMMING POOL AND CENTRAL AIR!!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
3 Minutes to Private Beach! This 4 bedroom, 2 bath home is nestled on 1.5 acres which abuts a 10 acre preserve, immac ...
From $1000 per night (USD)Expedia
- From $1270 per night (USD)
VRBO
Designer beach house with private beach rights, pool and brand new everything
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
The moment you step inside, you will be welcomed by a bright and airy living room, adorned with large windows that allow ...
From $1270 per night (USD)VRBO
- From $1326 per night (USD)
Expedia
Elegant estate with beach access, pool, kayaks, & fireplace
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 9
Cedar Crest Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $1326 per night (USD)Expedia
- Click For Pricing
Expedia
Elegant home near area's beaches with paddle boards & hot tub - dog-friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Mod & Sun Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
Click For PricingExpedia
- From $1840 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 $1840 per night (USD)VRBO
- From $4036 per night (USD)
VRBO
The Prospect Estate - Spacious Historic House minutes from SH Village
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 18
AVAILABILITY NOTICE : PLEASE INQUIRE FOR MOST UP-TO-DATE AVAILABILITY BEFORE MAKING A "RESERVATION REQUEST". POSTED CALE ...
From $4036 per night (USD)VRBO
- From $1536 per night (USD)
Expedia
Chic Southampton Getaway w\/Heated Pool. Minutes away from village & beach.
- Bedrooms:
- 7
- 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 $1536 per night (USD)Expedia
- From $550 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 $550 per night (USD)VRBO
- From $624 per night (USD)
Expedia
Dog-friendly house near beach with private heated pool, tennis & fireplace
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 9
Southampton Serenity Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $624 per night (USD)Expedia
- From $1100 per night (USD)
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 ...
From $1100 per night (USD)VRBO
- From $1327 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 $1327 per night (USD)VRBO
- From $3325 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 $3325 per night (USD)VRBO
- From $575 per night (USD)
Expedia
Delightful Southampton Retreat with Pool & Outdoor Shower 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 $575 per night (USD)Expedia
- From $1767 per night (USD)
VRBO
Spacious Southampton Home with Heated Pool, Walking Distance to Southampton...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Please note that a reservation for this property needs to be approved before it is confirmed. Southampton Village Vista ...
From $1767 per night (USD)VRBO
- Click For Pricing
Expedia
Modernist Glass House secluded and private close to ocean beaches
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 2
Imagine enjoying your day and evenings surrounded by complete privacy and nature. Walls of glass open up to the natural ...
Click For PricingExpedia
- From $4326 per night (USD)
VRBO
Expansive Southampton Home with Harbor Water Views, Private Pool, Modern...
- Bedrooms:
- 9
- Bathrooms:
- 6
- Sleeps:
- 12
Harbor View Modern Expansive Southampton Home with Harbor Water Views, Private Pool, Modern Design and Layout, Perfect ...
From $4326 per night (USD)VRBO
- From $1045 per night (USD)
VRBO
Sag Harbor - Beautiful 5BR, 3.5BR home with heated pool, wooded private backyard
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Sag Harbor Oasis!! Beautiful 5 bedroom, 3.5BR home on private wooded lot with heated pool The home provides for ample ...
From $1045 per night (USD)VRBO
- From $1200 per night (USD)
VRBO
Charming 4-bedroom house with WiFi and AC in delightful Southampton
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This 4-bedroom house is perfect for your escape to Southampton. Nestled in a tranquil neighborhood, our adorable propert ...
From $1200 per night (USD)VRBO
- From $1995 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 $1995 per night (USD)Expedia
- From $2500 per night (USD)
VRBO
SUNNY CONTEMPORARY W POOL AND SPACE FOR ALL
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
OLDER CONTEMPORARY HOME WITH LARGE OPEN SPACES. This house is good for an easy living Hamptons experience. Comfy not f ...
From $2500 per night (USD)VRBO
- From $1800 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 $1800 per night (USD)Expedia
- From $4198 per night (USD)
VRBO
Stunning, Contemporary Southampton Home Near Town Beaches and Downtown
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Please note that a reservation for this property needs to be approved before it is confirmed. Whites Lane Wonder Stunn ...
From $4198 per night (USD)VRBO
- From $1600 per night (USD)
Expedia
Modernist Glass House nestled in tall pines and nature offering total privacy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Imagine enjoying your day and evenings surrounded by complete privacy and nature. Walls of glass open up to the natural ...
From $1600 per night (USD)Expedia
- From $1785 per night (USD)
VRBO
Lush Hamptons Beach House, minutes to ocean, bay, and farm stands.\n\n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Located in charming Watermill, this stunning property spans across 6 acres, conveniently situated equidistant from Sag H ...
From $1785 per night (USD)VRBO
- From $1033 per night (USD)
Expedia
Charming Home in the Village of Southampton
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your summer retreat in the charming Village of Southampton. LOCATION HIGHLIGHTS: Nestled in a prime location ...
From $1033 per night (USD)Expedia
- From $2358 per night (USD)
VRBO
Open Professional Kitchen, Full Kitchen with Bar, Oversized Heated Pool,...
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
Please note that a reservation for this property needs to be approved before it is confirmed. Turtle Pond Open Profess ...
From $2358 per night (USD)VRBO
- From $2375 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 $2375 per night (USD)Expedia
- From $2420 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 $2420 per night (USD)VRBO
- From $1735 per night (USD)
Expedia
Spacious and Cozy Water Mill Home with Private Pool, Centrally Located,...
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Water Mill Retreat Spacious and Cozy Water Mill Home with Private Pool, Centrally Located, Perfect for Families 4BR/2B ...
From $1735 per night (USD)Expedia
- From $1314 per night (USD)
VRBO
Custom, private home with pool, tennis, near water
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled across from the serene Cold Spring Pond, this exquisite modern home offers the perfect blend of luxury and natur ...
From $1314 per night (USD)VRBO
- From $2157 per night (USD)
VRBO
Amenities Galore: Gorgeous Southampton Rental
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Villa Kivasa is a gorgeous family home offering 6 spacious bedrooms, 4.5 bathrooms, a large open backyard that includes ...
From $2157 per night (USD)VRBO
- From $1450 per night (USD)
VRBO
Southampton Village Family Tradition\nMint 5BR-5BR. Walkable location.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Relaxation starts right here in this beautiful location. Private, quiet, delightful. Attention to detail welcomes gues ...
From $1450 per night (USD)VRBO
- From $700 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 $700 per night (USD)Expedia
- From $4850 per night (USD)
VRBO
Southampton Retreat NEW Listing
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
Gorgeous Newly listed Rental on over an acre decorated with high furnishings of Restoration Hardware, Mitch gold and con ...
From $4850 per night (USD)VRBO
- From $1918 per night (USD)
Expedia
Southampton Village home with Pool, beach chairs, bikes and Tennis !
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This is a spacious designer furnished 4 bedroom 4 bath (all en-suite) home. Completely renovated with a gorgeous kitchen ...
From $1918 per night (USD)Expedia
- From $1200 per night (USD)
VRBO
Secluded Southampton Home That Has It All
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Secluded, warm, beautiful, and amenity-filled property features an expansive 5,000+/- s/f of immaculate interior living ...
From $1200 per night (USD)VRBO
- From $1017 per night (USD)
Expedia
Expansive Waterfront Home in Southampton with Private Dock, Amazing Views,...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
Southampton Waterfront Spectacular Expansive Waterfront Home in Southampton with Private Dock, Amazing Views, Perfect f ...
From $1017 per night (USD)Expedia
- From $7548 per night (USD)
VRBO
Spectacular un Hamptons Hideaway w Grand piano and sunsets over freshwater lake
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 8
High end luxury w fun. New construction. Award winning architect. Peaceful. Private. Nature abounds. On private road. A ...
From $7548 per night (USD)VRBO
- From $4668 per night (USD)
Expedia
Waterfront Luxury with Pickleball and Dock, Separate Barn and More!!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Rare and absolutely private, this 2+ acre waterfront retreat boasts water access with dock, gunite pool and pickleball. ...
From $4668 per night (USD)Expedia
- From $1039 per night (USD)
VRBO
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 $1039 per night (USD)VRBO
- From $1000 per night (USD)
VRBO
Hamptons Gated Privacy
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Retreat to this contemporary home located on a beautiful Hamptons country road. Enjoy the privacy of 2 +/- landscaped ac ...
From $1000 per night (USD)VRBO