Watermill Rentals
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 $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 $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 $329 per night (USD)VRBO
Charming Bridgehampton cottage on 4.5 acre Estate
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Hayground House Cottage is a quaint, serenely private retreat nestled on a gated 4.5 acre historic park-like estate in B ...
From $329 per night (USD)VRBO
From $2609 per night (USD)VRBO
Ultra Modern Bridgehampton Gem, Perfect Location, 6 Beds, Heated Pool, Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 11
First time being rented, available from August 1 to Labor Day! Ultra-modern, new construction gem in the perfect Hampton ...
From $2609 per night (USD)VRBO
From $3577 per night (USD)VRBO
Remarkable Southampton Estate with Resort Amenities, Perfect for Families...
- Bedrooms:
- 11
- Bathrooms:
- 7
- Sleeps:
- 14
Please note that a reservation for this property needs to be approved before it is confirmed. Southampton Extraordinary ...
From $3577 per night (USD)VRBO
From $975 per night (USD)VRBO
Designer Own Elegant Beachy Sag Harbor Home
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Consider this house your home away from home while you visit Sag Harbor. With 5 bedrooms including 3 king beds, 1 queen ...
From $975 per night (USD)VRBO
From $1657 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 $1657 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 $959 per night (USD)VRBO
Bridgehampton Home on Lush Acre, Heated In-Ground Gunite Pool, Close to...
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Please note that a reservation for this property needs to be approved before it is confirmed. Sandpiper Seclusion Brid ...
From $959 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 $2094 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 $2094 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 $1158 per night (USD)VRBO
Traditional Home w/ English Gardens, Pool, Rec Room, Close to Ocean Beaches
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 10
Please note that a reservation for this property needs to be approved before it is confirmed. English Gardens Traditio ...
From $1158 per night (USD)VRBO
From $747 per night (USD)VRBO
SOUTHAMPTON-POOL,3 min to town,1.5 miles to beach. Outdoor kitchen,putting green
- Bedrooms:
- 4
- Bathrooms:
- 1
- Sleeps:
- 8
Gorgeous 4 bedroom, 4.5 bathroom house in prime location. Heated Pool, pool house, sunny, fully fenced in property a mus ...
From $747 per night (USD)VRBO
From $1958 per night (USD)VRBO
Traditional-style home with private pool, sweeping back deck, grand lawn,...
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Please note that a reservation for this property needs to be approved before it is confirmed. Hayground Majestic Tradi ...
From $1958 per night (USD)VRBO
From $924 per night (USD)VRBO
Charming 2-bedroom house with WiFi and AC in wonderful Southampton
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Stay comfortably in Southampton at this 2-bedroom house. The property boasts 2 full beds, 2 bathrooms, and an additional ...
From $924 per night (USD)VRBO
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SOUTHAMPTON LUXURY 4 BED HOME WITH HEATED POOL AND CAC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This 4 bedroom, 2 bath home is nestled on 1.5 acres which abuts a 10 acre preserve, immaculately maintained. Minutes t ...
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From $4887 per night (USD)VRBO
Spacious Sag Harbor Vacation Home with Amazing Outdoor Space, Perfect for...
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 13
Please note that a reservation for this property needs to be approved before it is confirmed. Noyac Hills Haven Spacio ...
From $4887 per night (USD)VRBO
From $1575 per night (USD)VRBO
Great location for US Open golf. Luxurious 4-bedroom house in lovely Sag Harbor.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Located in Sag Harbor, enjoy what this 4-bedroom house has to offer. This amazing property features 1 king bed, 2 queen ...
From $1575 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 $4611 per night (USD)Expedia
Luxurious 7-bedroom estate south of the highway and 5 mins from the ocean!
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 15
FULLY RENOVATED, more photos coming soon! This sophisticated modern farmhouse nestled on renowned Jobs Lane seamlessly m ...
From $4611 per night (USD)Expedia
From $4519 per night (USD)VRBO
Exceptional 5BR/6Bth Luxury Home, Water Mill South, Heated Pool/Spa, Dock Access
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
FIRST TIME OFFERED: A rare opportunity to rent this exceptional, south-of-the-highway Water Mill residence for 7-10 day ...
From $4519 per night (USD)VRBO
From $608 per night (USD)Expedia
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)Expedia
From $3468 per night (USD)VRBO
Prime Water Mill near Mecox Bay
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 10
This former 1800s Parsonage House is located on 1.09 acres south of the highway in prime Water Mill and is seconds from ...
From $3468 per night (USD)VRBO
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Exquisite Brand Newly Renovaged 5-bedroom house Unbeatable location in WaterMill
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Experience Water Mill like a Hamptons socialite in this 5-bedroom house right near the beach. With 2 king beds, 1 twin b ...
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From $235 per night (USD)VRBO
Charming 1-bedroom cottage in the heart of Southampton Village
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Located in the heart of Southampton Village, this intimate, centrally-located cottage is the perfect getaway! Nestled in ...
From $235 per night (USD)VRBO
From $9208 per night (USD)VRBO
Seven Ponds Villa by Rove - 7BR Family Home with Heated Pool
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
Summary: Welcome to Seven Ponds Villa, a Rove Travel Home! Rove offers beautifully designed residences with the quality ...
From $9208 per night (USD)VRBO
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 $1542 per night (USD)VRBO
Charming 5-bedroom cottage with WiFi and AC in Bridgehampton minutes from Sag
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Private Hamptons Villa with Pool – Bridgehampton Escape Tucked away on a gated acre in Bridgehampton, this stylish 5bed ...
From $1542 per night (USD)VRBO
From $4481 per night (USD)VRBO
Private Southampton Oasis with Pool, Spa & Effortless Indoor-Outdoor Living
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 12
Please note that a reservation for this property needs to be approved before it is confirmed. Southampton Solace Priva ...
From $4481 per night (USD)VRBO
From $3740 per night (USD)VRBO
Unparalleled Views in a Hampton's Style Private Escape
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 11
Embrace the Hamptons' charm in this luxurious Water Mill sanctuary-a perfect balance of elegance, privacy, and breathtak ...
From $3740 per night (USD)VRBO
From $716 per night (USD)Expedia
Elegant Coastal Escape with Expansive Yard, Heated Pool, and Outdoor...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Water Mill Retreat Elegant Coastal Escape with Expansive Yard, Heated Pool, and Outdoor Kitchen in the Heart of Water M ...
From $716 per night (USD)Expedia
From $9209 per night (USD)VRBO
Modern Rustic Bridgehampton Escape with Pool, Hot Tub, Gym & Stylish Interiors
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 16
Bridgehampton Dream Modern Rustic Bridgehampton Escape with Pool, Hot Tub, Gym & Stylish Interiors 5BR/6.5BA: Pictures ...
From $9209 per night (USD)VRBO
From $1678 per night (USD)Expedia
Beautiful Southampton Village Home, Perfect for Families with Private Pool...
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
The Village Gem Beautiful Southampton Village Home, Perfect for Families with Private Pool in Town 6BR/5.5BA: private ...
From $1678 per night (USD)Expedia
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Family friendly 4-bedroom house in wonderful Water Mill. Home away from home!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Make yourself at home in this 4-bedroom Water Mill retreat. This peaceful house boasts 3 queen beds and 1 king bed, perf ...
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From $3112 per night (USD)Expedia
1BR Poolside, Daily Breakfast, Serene Double Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Tucked away for privacy and relaxation, the Suite Double offers a tranquil escape with timeless Hamptons charm. This spa ...
From $3112 per night (USD)Expedia
From $2718 per night (USD)VRBO
Luxurious 1BR Poolside, Daily Breakfast, Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover refined comfort in our private Suite King—an elegant Hamptons-style suite featuring a separate master bedroom w ...
From $2718 per night (USD)VRBO
From $2195 per night (USD)Expedia
Spacious 5-bedroom house in gorgeous Water Mill
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 6
Water Mill is waiting for you at this 5-bedroom house. With 3 king beds, 1 full bed, and 1 queen bed, this lovely proper ...
From $2195 per night (USD)Expedia
From $1010 per night (USD)VRBO
Modern Southampton Retreat with Private Pool & Lush Outdoor Oasis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Please note that a reservation for this property needs to be approved before it is confirmed. Southampton Haven Modern ...
From $1010 per night (USD)VRBO
From $1326 per night (USD)VRBO
Hamptons 5 bedroom Hideaway w Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 11
About this space "Unbeatable location." 100% of guests in the past year gave our location a 5-star rating. Our Hamptons ...
From $1326 per night (USD)VRBO
From $1279 per night (USD)VRBO
California King Poolside, Daily Breakfast, Minibar
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Experience the timeless elegance of the Hamptons in this Studi California King Room at The Capri Southampton. Perfectly ...
From $1279 per night (USD)VRBO
From $1465 per night (USD)Expedia
Poolside, Daily Breakfast, Hampstons Style Double
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located directly across from The Bathing Club’s lively pool scene, the Club Double offers a serene yet stylish retreat i ...
From $1465 per night (USD)Expedia
From $561 per night (USD)VRBO
2-bedroom apartment in beautiful Southampton with a beach permit
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Chic Renovated 2BR/2BA Apartment in the Heart of Southampton Village Located on highly sought-after Windmill Lane in th ...
From $561 per night (USD)VRBO
From $7426 per night (USD)VRBO
A Hampton resort lifestyle with private vineyard
- Bedrooms:
- 10
- Bathrooms:
- 8
- Sleeps:
- 20
Covered outdoor living space w/full kitchen, full bar, over sized grill, pizza oven, coffee station, blender station, bi ...
From $7426 per night (USD)VRBO
From $882 per night (USD)VRBO
Chic, Newly Renovated Waterfront Cottage on Mecox Bay with Private Dock &...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Mecox Bay Retreat Chic, Newly Renovated Waterfront Cottage on Mecox Bay with Private Dock & Serene Views 3BR/2.5BA: pr ...
From $882 per night (USD)VRBO
From $495 per night (USD)Expedia
Southampton Village Gem: Shinnecock Open Special
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the heart of Southampton Village, our townhome is exactly that, a home within walking distance to the village ...
From $495 per night (USD)Expedia
From $580 per night (USD)VRBO
Peaceful newly renovated sun filled 5 bedroom home in the heart of Water Mill
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Located at the end of a private driveway is this secluded retreat in the heart of Water Mill. The house sits on just und ...
From $580 per night (USD)VRBO
From $986 per night (USD)Expedia
Spacious Sag Harbor Retreat With Pool, Near Town & Beaches
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 9
Sag Harbor Hideaway Spacious Sag Harbor Retreat With Pool, Near Town & Beaches 5BR/4BA: Private pool, sundeck with cha ...
From $986 per night (USD)Expedia
From $1371 per night (USD)VRBO
Chic Southampton Getaway with Heated Pool & Seamless Indoor-Outdoor Living
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Southampton Paradise Chic Southampton Getaway with Heated Pool & Seamless Indoor-Outdoor Living 4BR/3BA: Private heate ...
From $1371 per night (USD)VRBO
From $1145 per night (USD)VRBO
Tranquil & Private home with tennis & pool with 5 bedrooms and AC
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Escape to this amazing house in picturesque Water Mill. With 5 bedrooms including 1 king, 3 queen, and 3 twin beds, this ...
From $1145 per night (USD)VRBO
From $4854 per night (USD)VRBO
Spacious & chic Southampton estate with heated pool, fire pit &...
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 10
Southampton Manor Spacious & chic Southampton estate with heated pool, fire pit & indoor-outdoor living - perfect for f ...
From $4854 per night (USD)VRBO
From $895 per night (USD)VRBO
Perfect Southampton Escape - Summer Near It All
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome home to this fabulous 3bed/2.5bath new-to-market Summer rental in Southampton. Fabulous layout and larg ...
From $895 per night (USD)VRBO
From $4104 per night (USD)VRBO
Immaculate Victorian in Southampton Village
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: Just completed Spring 24 renovation makes this immaculate Village Victorian the perfect Hamptons Summer escape. ...
From $4104 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