Watermill Rentals
- From $3516 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 rentals in Weekly & Monthly increments. Monthly Rates: *negotiable July 110k (4 weeks) Aug 110 ...
From $3516 per night (USD)VRBO
- From $8999 per night (USD)
VRBO
Elegantly Appointed Estate, Large Living and Dining Areas, Music and Movie...
- Bedrooms:
- 9
- Bathrooms:
- 7
- Sleeps:
- 10
Please note that a reservation for this property needs to be approved before it is confirmed. Bridgehampton Gem Elegan ...
From $8999 per night (USD)VRBO
- From $1441 per night (USD)
VRBO
Beautifully Restored Barn, Open First Floor Plan, Historic Charm and...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Ocean Road Escape Beautifully Restored Barn, Open First Floor Plan, Historic Charm and Updates Furnishings, Close to To ...
From $1441 per night (USD)VRBO
- From $1555 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 $1555 per night (USD)VRBO
- From $2263 per night (USD)
VRBO
Pristine estate sited on 4 acres of land, 1,700 SF pool pavilion with...
- Bedrooms:
- 9
- Bathrooms:
- 8
- Sleeps:
- 16
Please note that a reservation for this property needs to be approved before it is confirmed. Deerfield Dream House Pr ...
From $2263 per night (USD)VRBO
- From $1496 per night (USD)
VRBO
Modern Hamptons Farmhouse on Beautiful Horse Farm
- Bedrooms:
- 5
- 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 $1496 per night (USD)VRBO
- From $1462 per night (USD)
VRBO
♥♥♥Hampton's Modern Barn Retreat NEW CONSTRUCTION!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
ARCH&Co® presents: ♥♥♥Hampton's Modern Barn Retreat NEW CONSTRUCTION! 6 bed suites, 6 bathrooms- pool with deck, ...
From $1462 per night (USD)VRBO
- From $3371 per night (USD)
VRBO
Eclectic-style home with full amenities including a private pool, bluetooth...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Bridgehampton Beach Walk Eclectic-style home with full amenities including a private pool, bluetooth speaker system, ga ...
From $3371 per night (USD)VRBO
- From $4079 per night (USD)
VRBO
New Pool House, Backyard with Heated Pool, Close to Village Shopping and Beaches
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 14
The Village Heart New Pool House, Backyard with Heated Pool, Close to Village Shopping and Beaches 6BR/6BA w/ Luxury I ...
From $4079 per night (USD)VRBO
- From $1600 per night (USD)
Expedia
Escape to Southampton and enjoy this gorgeous and newly renovated...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Wireless Way Escape to Southampton and enjoy this gorgeous and newly renovated traditional home! 5BR/4.5BA w/ 600 Mb. ...
From $1600 per night (USD)Expedia
- From $6543 per night (USD)
VRBO
Elegant Watefront home with Oversized Gunite Heated Pool, Tennis, Living...
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 8
Please note that a reservation for this property needs to be approved before it is confirmed. Water Mill Waterfront Com ...
From $6543 per night (USD)VRBO
- From $1800 per night (USD)
VRBO
Breathtaking Mecox Bay Waterfront - Water Water Water
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Premier Waterfront Home. New to Market - Never Been Available - Best Waterfront on Pointe Mecox - Boaters DREAM Premier ...
From $1800 per night (USD)VRBO
- Click For Pricing
VRBO
Water Mill South of Highway 5 Bedroom Modern Home
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to this newly constructed Contemporary Barn set on 1.2 +/- acres of sprawling lawn. The first floor has a striki ...
Click For PricingVRBO
- From $776 per night (USD)
VRBO
Stylish Respite For Grown Ups, But Kids Will Love It, Too!
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 6
This home is located in the desirable Hampton Park area, just a few minutes from Southampton Village and a few minutes ...
From $776 per night (USD)VRBO
- From $1500 per night (USD)
VRBO
Beautiful, Spacious, Private, Family- Friendly Home In Water Mill (4000 SF)
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy over 60 acres of protected farmfield vistas from this charming and recently renovated 5-bedroom Hampton home. Priv ...
From $1500 per night (USD)VRBO
- From $3796 per night (USD)
VRBO
Charming Bridgehampton Vacation Home on 2 acres, private heated pool,...
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Bridgehampton Jewel Charming Bridgehampton Vacation Home on 2 acres, private heated pool, minutes from beaches and fine ...
From $3796 per night (USD)VRBO
- From $1667 per night (USD)
VRBO
Post Modern on Mature Landscaping, Master Bedroom with Separate...
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Northside Seclusion Post Modern on Mature Landscaping, Master Bedroom with Separate Office/Two-Tiered Mahogany Deck, Co ...
From $1667 per night (USD)VRBO
- From $996 per night (USD)
Expedia
NEW LISTING! Chic, Affordably Priced Southampton home, convenient location.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Get a taste of the Hamptons life with this affordably priced Southampton home. 4 bedrooms, 3 full baths, sleeps 8. Ful ...
From $996 per night (USD)Expedia
- Click For Pricing
VRBO
-Heated pool, bike to town .Coopers Beach-Pups Welcome
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful, spacious property, heated pool, separate apartment for guests with deck and all outdoor furniture. Great loca ...
Click For PricingVRBO
- From $2199 per night (USD)
VRBO
Luxury French Villa in the Heart of The Hamptons
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this new custom built home in the highly coveted hamlet of Water Mill in The Hamptons. This home features 400 ...
From $2199 per night (USD)VRBO
- From $5586 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 $5586 per night (USD)VRBO
- From $2100 per night (USD)
Expedia
Great location in Southampton Village close to beach and shopping
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
On a charming tree-lined street, this 3 bedroom renovated home has been painstakingly restored. Features include top of ...
From $2100 per night (USD)Expedia
- Click For Pricing
VRBO
Prime SH Village Location: Expertly Renovated & Furnished Townhouse.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Available Summer 2024: Make this newly renovated and expertly decorated townhouse with brand new furnishings, in the hea ...
Click For PricingVRBO
- From $900 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 $900 per night (USD)VRBO
- From $1500 per night (USD)
VRBO
Elegant, Charming, Very Private Home on 2 Magnificent Acres.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
The best of both worlds exist in this 4 bedroom traditional in Water Mill with an old fashion wrap around porch outside. ...
From $1500 per night (USD)VRBO
- Click For Pricing
Expedia
YOU CAN WATCH THE SUNRISE FROM YOUR BALCONY
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
You can watch the sunrise in this custom built stucco villa with circular driveway, wrought iron gate and open large yar ...
Click For PricingExpedia
- Click For Pricing
VRBO
Bridgehampton Private
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 14
Backed against thousands of acres of private state forest and at the end of a long driveway off a beautiful country road ...
Click For PricingVRBO
- Click For Pricing
VRBO
Bridgehampton Enchanting Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Perfect home and pool with enchanting landscape on 1.2 private acres on quiet cul-de-sac, 1/2 mile south of the highway ...
Click For PricingVRBO
- From $2007 per night (USD)
VRBO
Newly Built 6 Bed\/5.5 Bath Modern Farmhouse with Pool and Hot tub
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 10
Just completed construction Summer 2022! Gorgeous 6 bedrooms, 5.5 baths, designer decorated, perfect for a large or mul ...
From $2007 per night (USD)VRBO
- From $2603 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 $2603 per night (USD)VRBO
- From $648 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 $648 per night (USD)VRBO
- From $1200 per night (USD)
VRBO
Water mill cottage on a 5 acre estate near beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cottage on a beautiful estate with with fenced in swimming pool and own driveway access. Private cottage and beautiful ...
From $1200 per night (USD)VRBO
- Click For Pricing
VRBO
Immaculate 3 BR Ranch Home WestHampton
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Spend your summer in the Hamptons in this immaculate, beautifully appointed, completely renovated contemporary- ...
Click For PricingVRBO
- From $6949 per night (USD)
Expedia
Six Bedroom Designer Home Southhampton
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
Summary: This custom home sits on 0.60 of an acre and features 3,800 + square feet with 5 bedrooms, five full baths and ...
From $6949 per night (USD)Expedia
- From $999 per night (USD)
VRBO
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 $999 per night (USD)VRBO
- Click For Pricing
Expedia
5,200 sf Sag Harbor Grand Villa w Pool near Beach
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 7
Welcome to a one-of-a-kind property located off Deerfield Road in the desirable private community of Northside Hills, a ...
Click For PricingExpedia
- From $3250 per night (USD)
VRBO
Hamptons, Rare Find, Best location. Water Mill S. Pool, Special Aug.19-Sept. 2.\n
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
A gem in one of the most lovely, private areas of the Hamptons,tucked between Southampton and Bridgehampton. South of th ...
From $3250 per night (USD)VRBO
- Click For Pricing
VRBO
Beautiful Waterfront Condo
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Spacious 3 BR 3.5 Bath with large dining space, A/V in all rooms and deck, and easy access to all Water Mill, Southampto ...
Click For PricingVRBO
- 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 $2587 per night (USD)
Expedia
Get out of town and relax in this stunning home in Bridgehampton!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Luxury on Lumber Get out of town and relax in this stunning home in Bridgehampton! 5BR/4BA w/ a great room, den, sunro ...
From $2587 per night (USD)Expedia
- 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
- Click For Pricing
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 ...
Click For PricingVRBO
- From $3857 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 $3857 per night (USD)VRBO
- From $263 per night (USD)
VRBO
Southampton Village Ensuite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Luxury hotel-like stay in idyllic Southampton Village steps from the train station. Light, bright & airy, this freshly ...
From $263 per night (USD)VRBO
- From $1095 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 $1095 per night (USD)VRBO
- From $843 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 $843 per night (USD)VRBO
- From $15000 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 $15000 per night (USD)VRBO
- From $3652 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 $3652 per night (USD)VRBO
- Click For Pricing
VRBO
Heaven in the Hamptons
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
South of Route 27, you will love this amenity-filled oasis near the beach and Bridgehampton village. Modern kitchen, Ros ...
Click For PricingVRBO
- 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 $960 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 $960 per night (USD)VRBO
- From $666 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 $666 per night (USD)VRBO
- From $3786 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 $3786 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 $2345 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 $2345 per night (USD)VRBO
- From $1288 per night (USD)
Expedia
South of the Highway Southampton Home \/ Two minute drive to Southampton Village!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our charming vacation rental home in Southampton, NY! Nestled just a two-minute drive away from Southampton V ...
From $1288 per night (USD)Expedia
- From $2650 per night (USD)
VRBO
Stunning 5 bedroom Vicente Wolf Designed Home South of Highway in Water Mill
- Bedrooms:
- 6
- 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 $2650 per night (USD)VRBO
- From $1214 per night (USD)
VRBO
New Listing - Eclectic home with private pool, decorated loft, gas...
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 11
Please note that a reservation for this property needs to be approved before it is confirmed. Airy Water Mill Ranch Ne ...
From $1214 per night (USD)VRBO
- 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
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 $2182 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 $2182 per night (USD)VRBO
- Click For Pricing
Expedia
Mecox Bay with Panoramic Bay and Reserve Views - Water Mill South
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Tranquil bay and reserve views are the hallmarks of this classic home on an inlet just off Mecox Bay, South of the Highw ...
Click For PricingExpedia
- From $3159 per night (USD)
VRBO
Beautiful Southampton Home Walking Distance to Town and Short Bike Ride to...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Please note that a reservation for this property needs to be approved before it is confirmed. Southampton Village Vibra ...
From $3159 per night (USD)VRBO
- From $5500 per night (USD)
VRBO
Water Mill Estate
- Bedrooms:
- 13
- Bathrooms:
- 9
- Sleeps:
- 14
Luxurious 13,000 square foot estate with 9 bedrooms, 12.5 baths in the heart of Water Mill farmlands. All bedrooms are o ...
From $5500 per night (USD)VRBO
- From $2715 per night (USD)
VRBO
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 $2715 per night (USD)VRBO
- From $799 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 $799 per night (USD)VRBO
- 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 $600 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 $600 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 $1879 per night (USD)
Expedia
Beautiful Contemporary Water Mill Home Centrally Located with Private Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Old Trail Tranquility Beautiful Contemporary Water Mill Home Centrally Located with Private Pool 5BR + office/4BA: cen ...
From $1879 per night (USD)Expedia
- From $1000 per night (USD)
VRBO
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)VRBO
- From $1800 per night (USD)
VRBO
Christmas At the Beach in The Hamptons' \"Christmas Village\"
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
A classic Hamptons farmhouse, fully decorated for Christmas if you want, on a quiet road, 3/4 mile from ocean beaches, 1 ...
From $1800 per night (USD)VRBO
- From $692 per night (USD)
VRBO
Spacious coastal retreat with a pool, bikes, wood fireplace, and games - dogs ok
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 11
Seashell Collector Estate Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $692 per night (USD)VRBO
- From $1486 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 $1486 per night (USD)VRBO
- From $4207 per night (USD)
VRBO
The Prospect Estate - Spacious Historic House minutes from SH Village
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 16
AVAILABILITY NOTICE : PLEASE INQUIRE FOR MOST UP-TO-DATE AVAILABILITY BEFORE MAKING A "RESERVATION REQUEST". POSTED CALE ...
From $4207 per night (USD)VRBO
- From $600 per night (USD)
Expedia
Cozy Southampton house to enjoy a weekend away! 5 minutes drive to main street.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Enjoy a weekend away in this one-level, 4-bedroom, 2-bathroom well decorated beachy cottage, just minutes from the Hampt ...
From $600 per night (USD)Expedia
- From $496 per night (USD)
VRBO
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 $496 per night (USD)VRBO
- From $2449 per night (USD)
Expedia
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 $2449 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 $1214 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 $1214 per night (USD)VRBO
- From $1800 per night (USD)
VRBO
Unique peaceful and private Modern Tree House nestled in natures glory
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Completely private and secluded, modern tree house, nestled in nature. Access to private shared tennis court and pool p ...
From $1800 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 $775 per night (USD)
VRBO
1940s Fisherman’s Cottage close to beach. Right next to the Water Mill museum.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Stay at one of the last remaining 1940s fisherman's cottages, perfectly restored on a private and secluded property. Clo ...
From $775 per night (USD)VRBO
- From $1025 per night (USD)
VRBO
Sag Harbor - Beautiful 5BR, 3.5BR home with heated pool, 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 $1025 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 $1694 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 $1694 per night (USD)Expedia
- From $1800 per night (USD)
VRBO
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)VRBO
- From $3178 per night (USD)
VRBO
Newly Renovated Decor, Open Great Room, Heated Pool in Open Lawn, Short...
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 9
Please note that a reservation for this property needs to be approved before it is confirmed. Elegant and head turning, ...
From $3178 per night (USD)VRBO
- From $1600 per night (USD)
VRBO
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)VRBO
- 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 $3000 per night (USD)
VRBO
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 $3000 per night (USD)VRBO
- From $2972 per night (USD)
Expedia
Newly Renovated, Serene Property with Heated Pool, Tennis, and Resort-Like Spa
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Southampton Serenity Newly Renovated, Serene Property with Heated Pool, Tennis, and Resort-Like Spa 6BR/4BA w/ Vaulted ...
From $2972 per night (USD)Expedia
- From $1686 per night (USD)
VRBO
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 $1686 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO