Watermill Rentals
Click For PricingVRBO
Airy Luxury Hamptons Retreat with Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This light-flooded immaculate contemporary is the perfect combination of location and charm! Located minutes to the Jitn ...
Click For PricingVRBO
From $6039 per night (USD)Expedia
Hamptons Oasis 7Bed\/7.5 Bath w Pool, Hot Tub and Tennis
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 10
Idyllic 8500 sq foot estate , centrally located , with everything one could desire. Beautifully decorated interior, with ...
From $6039 per night (USD)Expedia
From $1588 per night (USD)VRBO
Secluded Kid friendly Hampton’s home
- Bedrooms:
- 8
- Bathrooms:
- 6
- Sleeps:
- 8
Beautiful kid friendly home with in-laws suite above second family room. Flat fenced in backyard with new pool. wake up ...
From $1588 per night (USD)VRBO
Click For PricingExpedia
Centrally located Water Mill home near towns and beaches
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
4 Bedroom 3.5 bedroom home in Watermill situated among Water Mill farmland. Borders 30 acre reserved property with rear ...
Click For PricingExpedia
From $1343 per night (USD)VRBO
Gorgeous 4 bed 3 bath home with Pool - walking distance to beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy a serene Hamptons holiday in this bright renovated home. Take a quiet tree lined walk (7 min) to the local beach, ...
From $1343 per night (USD)VRBO
From $1721 per night (USD)Expedia
Majestic estate on over one acre of lush land, beautiful landscaping,...
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Please note that a reservation for this property needs to be approved before it is confirmed. North Side Serene Majest ...
From $1721 per night (USD)Expedia
From $771 per night (USD)VRBO
Southampton Village Gem - Walk to Main Street
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Your family will be close to everything when you stay at this centrally-located place with a great outdoor area for you ...
From $771 per night (USD)VRBO
Click For PricingExpedia
Private family getaway
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 18
Gunite pool and spa. Huge deck. Large dining area, lots of musical instruments like piano,guitar,drums. Close to Beache ...
Click For PricingExpedia
From $1738 per night (USD)VRBO
Southampton Village South, less than a mile to the beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Charming cape on a half acre in a very quiet neighborhood south of the highway in Southampton Village. New heated saltw ...
From $1738 per night (USD)VRBO
Click For PricingExpedia
Hamptons Cottage with Spa
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the peaceful seclusion of this charming, updated 3 bedroom, 2 bath cottage located on a private, acre-sized flag-l ...
Click For PricingExpedia
From $5617 per night (USD)VRBO
Ultimate Water Mill Southampton Escape– Stunning 7BR Estate for Family & Friends
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
A stunning 7-bedroom, 7-bathroom estate designed for multigenerational family gatherings and friend retreats. This stunn ...
From $5617 per night (USD)VRBO
From $2964 per night (USD)Expedia
Hamptons Escape
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 6
Experience luxury at its finest in this stunning retreat house located in the heart of Southampton/Watermill Horse Count ...
From $2964 per night (USD)Expedia
From $1908 per night (USD)VRBO
Sunset Bayview, Master Suite with Private Balcony, Private Gated Residence,...
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
Little Peconic Bayview Sunset Bayview, Master Suite with Private Balcony, Private Gated Residence, One of the Highest E ...
From $1908 per night (USD)VRBO
From $1303 per night (USD)Expedia
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 $1303 per night (USD)Expedia
From $1622 per night (USD)VRBO
Southampton Village Cottage SOH Backyard Paradise 20 x 40 OLYMPIC SIZED POOL!!!
- Bedrooms:
- 2
- Bathrooms:
- 4
- 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 $4038 per night (USD)Expedia
Pool oasis, tennis court, hot tub, pool table, , luxury kitchen appliances, etc.
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 15
This private Hamptons estate on 8 very private and idyllic acres is a little piece of paradise! The home was newly renov ...
From $4038 per night (USD)Expedia
From $1614 per night (USD)VRBO
Hampton Beach Barn w\/ Infrared Sauna and Heated Pool - Dog friendly.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
3,000sf (approximate) Post & Beam Beach Barn, located in the upscale hamlet of Water Mill in Southampton, NY. POOL OP ...
From $1614 per night (USD)VRBO
From $2038 per night (USD)Expedia
\nGorgeous Southampton Home- Pool, Spa, Putting Green, Walk to Beach & Tennis\/PB
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 8
Indulge in a fabulous stay at a luxurious beach house in a private community in Southampton. This home features five bea ...
From $2038 per night (USD)Expedia
Click For PricingVRBO
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 ...
Click For PricingVRBO
From $2857 per night (USD)Expedia
Water Mill Perfection: Tennis, Saltwater Pool, Winery, Art Museum, Kids Oasis
- Bedrooms:
- 8
- 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 $2857 per night (USD)Expedia
From $1482 per night (USD)VRBO
Charming Cape Cod in Southampton
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully refreshed Cape Cod in a peaceful neighborhood just off of North Main Street in Southampton. The kitchen was ...
From $1482 per night (USD)VRBO
From $4142 per night (USD)Expedia
Heated Pool and Tennis Court
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
Gorgeous like new condition open-floor plan home in the heart of the Hamptons. Close to everything; Flying Point Beach, ...
From $4142 per night (USD)Expedia
From $6298 per night (USD)VRBO
Exclusive Bridgehampton Retreat - Private Estate
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
This exquisite 6 Bedroom / 6.5 Bathroom house is immaculately appointed throughout to provide you with every possible lu ...
From $6298 per night (USD)VRBO
Click For PricingExpedia
Chic Beach House in the Village of Southampton
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 10
Enjoy this stylish beach house in The Village of Southampton. This property is perfectly located, within walking distanc ...
Click For PricingExpedia
From $1143 per night (USD)VRBO
Like Tuscany, private Vineyard Home, Southampton
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
Like Tuscany, truly surrounded by vineyards. Gorgeous views from every room. Open concept kitchen, travertine floors, hi ...
From $1143 per night (USD)VRBO
Click For PricingExpedia
Sag Harbor Modern Oasis
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Luxury 5 bedroom, 3 1/2 bathroom home is designed around a central courtyard / pool area. Grill and contemporary seating ...
Click For PricingExpedia
From $3588 per night (USD)VRBO
Designer Gut Renovated Farmhouse on over 1 Acre, Numerous Spacious Living...
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
Water Mill Wooded Escape Designer Gut Renovated Farmhouse on over 1 Acre, Numerous Spacious Living Areas with Modern Am ...
From $3588 per night (USD)VRBO
From $1550 per night (USD)Expedia
Private chic 3BR\/2.5BA Hamptons cottage with pool - South of Highway
- Bedrooms:
- 3
- 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)Expedia
From $6284 per night (USD)VRBO
Ultimate Hamptons luxury with Private Tennis and Pool
- Bedrooms:
- 8
- 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 $6284 per night (USD)VRBO
Click For PricingExpedia
\" 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 PricingExpedia
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 $1609 per night (USD)VRBO
Bright Beautiful Southampton - 4 Br near village 5 min & ocean beaches
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Our Southampton 4 bedroom classic shingle home with stylish decor is ideally located near Southampton Village (5 minutes ...
From $1609 per night (USD)VRBO
From $3441 per night (USD)Expedia
Luxury Private Water Mill Home w\/ pool - 14 day rental 8\/22-9\/5 2022
- Bedrooms:
- 5
- 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)Expedia
From $714 per night (USD)VRBO
Perfect Southampton Village 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 $714 per night (USD)VRBO
From $2392 per night (USD)Expedia
Charming Cozy Southampton Village House 4 minutes from the Beach
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
Cozy, spacious charming Southampton Village house great for families and friend groups. The house is 2 minutes from eit ...
From $2392 per night (USD)Expedia
From $7067 per night (USD)VRBO
New Luxury Southampton Village Estate- Walk to town! Avail Dates in August!
- Bedrooms:
- 9
- Bathrooms:
- 7
- Sleeps:
- 12
Pristine, 8,000 square foot, brand new home complete with all new furnishings located on a gorgeous sprawling acre lot i ...
From $7067 per night (USD)VRBO
From $5074 per night (USD)VRBO
4 miles -Beach 2 miles -Town, Chef, Gym,2 Pelotons,Heated Pool,hot tub,firepits
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 20
*We can only accommodate longer term rentals in Weekly & Monthly increments due to Southampton rental code restrictions. ...
From $5074 per night (USD)VRBO
From $6572 per night (USD)VRBO
Elegantly Appointed Estate, Large Living and Dining Areas, Music and Movie...
- Bedrooms:
- 9
- Bathrooms:
- 7
- Sleeps:
- 10
Bridgehampton Gem Elegantly Appointed Estate, Large Living and Dining Areas, Music and Movie Rooms Ideal for Entertaini ...
From $6572 per night (USD)VRBO
From $2821 per night (USD)Expedia
Beautifully Restored Barn, Open First Floor Plan, Historic Charm and...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Ocean Road Escape Beautifully Restored Barn, Open First Floor Plan, Historic Charm and Updates Furnishings, Close to To ...
From $2821 per night (USD)Expedia
From $1691 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 $1691 per night (USD)VRBO
From $1903 per night (USD)Expedia
Modern Hamptons Farmhouse on Beautiful Horse Farm
- Bedrooms:
- 5
- Bathrooms:
- 5
- 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 $1903 per night (USD)Expedia
From $894 per night (USD)VRBO
Hamptons Modern Retreat NEW CONS
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
ARCH&Co® presents: ♥♥♥Hampton's Modern Barn Retreat NEW CONSTRUCTION! 6 bedroom suites, 6 bathrooms- pool with deck, ...
From $894 per night (USD)VRBO
From $7036 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 $7036 per night (USD)VRBO
From $2394 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 $2394 per night (USD)VRBO
From $4902 per night (USD)Expedia
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 $4902 per night (USD)Expedia
From $1967 per night (USD)VRBO
Post Modern on Mature Landscaping, Master Bedroom with Separate...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
Please note that a reservation for this property needs to be approved before it is confirmed. Northside Seclusion Post ...
From $1967 per night (USD)VRBO
From $1105 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 $1105 per night (USD)Expedia
Click For PricingVRBO
-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 $3000 per night (USD)Expedia
Luxury French Villa in Water Mill
- Bedrooms:
- 4
- 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 $3000 per night (USD)Expedia
From $5904 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 $5904 per night (USD)VRBO
From $1128 per night (USD)Expedia
1770's Honeymoon Cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 3
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 $1128 per night (USD)Expedia
From $2728 per night (USD)VRBO
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 ...
From $2728 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
From $2281 per night (USD)VRBO
BRIDGEHAMPTON Enchanted Home \nSouth of Highway Private and Peaceful
- 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 ...
From $2281 per night (USD)VRBO
From $3468 per night (USD)Expedia
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 $3468 per night (USD)Expedia
From $1312 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 $1312 per night (USD)VRBO
From $4729 per night (USD)Expedia
Six Bedroom Designer Home Southhampton
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 10
Summary: (Currently by Request Only; contact us for date requests) This custom home sits on 0.60 of an acre and feature ...
From $4729 per night (USD)Expedia
From $1826 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 $1826 per night (USD)VRBO
Click For PricingExpedia
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 $4390 per night (USD)VRBO
Price reduction Luxury Water Mill South \/Mecox Bay\/ Pool\/ Dock\/Fabulous Gardens
- 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 t ...
From $4390 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
From $3594 per night (USD)VRBO
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 $3594 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
From $5390 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 $5390 per night (USD)VRBO
From $954 per night (USD)Expedia
Southampton Beach & Town Cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Charming family friendly beach cottage with large pool. Walking distance to Village of Southampton’s fine dining and sto ...
From $954 per night (USD)Expedia
From $18424 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 $18424 per night (USD)VRBO
From $3139 per night (USD)Expedia
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 $3139 per night (USD)Expedia
Click For PricingVRBO
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
Click For PricingExpedia
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 PricingExpedia
From $630 per night (USD)VRBO
Southampton Water Mill Towd w\/ Pool House\/Art Studio\/Office & Heated Pool
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 7
Spend your summer entertaining, relaxing, and enjoying this spacious over one acre, beautifully landscaped home with sep ...
From $630 per night (USD)VRBO
From $4798 per night (USD)Expedia
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 $4798 per night (USD)Expedia
From $3448 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 $3448 per night (USD)VRBO
From $2882 per night (USD)Expedia
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 $2882 per night (USD)Expedia
Click For PricingVRBO
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
From $2258 per night (USD)Expedia
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 $2258 per night (USD)Expedia
Click For PricingVRBO
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 PricingVRBO
From $6185 per night (USD)Expedia
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 $6185 per night (USD)Expedia
From $2806 per night (USD)VRBO
Dog-friendly estate with amazing pool, deck, & game room at new reduced rate
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 14
Island in the Sky Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $2806 per night (USD)VRBO
From $1740 per night (USD)Expedia
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 $1740 per night (USD)Expedia
From $1784 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 $1784 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
From $3007 per night (USD)VRBO
Beautiful Contemporary Water Mill Home Centrally Located with Private Pool
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Old Trail Tranquility Beautiful Contemporary Water Mill Home Centrally Located with Private Pool 5BR + office/4BA: cen ...
From $3007 per night (USD)VRBO
Click For PricingExpedia
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 ...
Click For PricingExpedia
Click For PricingVRBO
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 ...
Click For PricingVRBO
From $17219 per night (USD)Expedia
Newly developed contemporary home situated on 1.5 acres.
- Bedrooms:
- 14
- Bathrooms:
- 10
- Sleeps:
- 15
10 bedroooms & 14.5 baths. Situated in the ocean threshold of South Bridgehampton moments from two pristine beaches is a ...
From $17219 per night (USD)Expedia
From $1904 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 $1904 per night (USD)VRBO
From $4462 per night (USD)Expedia
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 $4462 per night (USD)Expedia
From $762 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 $762 per night (USD)VRBO
Click For PricingExpedia
ARCHITECT’S LIGHT-FILLED ECO-FRIENDLY MODERN HOME
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Am I outside or inside? Huge windows draw the outside in and frame the outside wooded views. Perfect for a summer in ...
Click For PricingExpedia
From $1596 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 $1596 per night (USD)VRBO
From $1048 per night (USD)Expedia
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 $1048 per night (USD)Expedia
From $1034 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 $1034 per night (USD)VRBO
Click For PricingExpedia
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 ...
Click For PricingExpedia
From $2880 per night (USD)VRBO
Spacious Southampton Village Home Walking Distance to Town, Private Pool,...
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Southampton Village Luxury Spacious Southampton Village Home Walking Distance to Town, Private Pool, Perfect for Famili ...
From $2880 per night (USD)VRBO
From $2105 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 $2105 per night (USD)Expedia
From $1846 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 $1846 per night (USD)VRBO
From $4965 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 $4965 per night (USD)Expedia
From $3316 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 $3316 per night (USD)VRBO
From $515 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 $515 per night (USD)Expedia