Wainscott Rentals
From $3801 per night (USD)VRBO
Hamptons Compound w/ Golf, Tennis, Pool, Basketball, Bocce, and much more!
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 16
This Compound style property feels secluded, but is close to everything!! Sag Harbor, East Hampton and Wainscott villa ...
From $3801 per night (USD)VRBO
From $1406 per night (USD)VRBO
Family Friendly Home W/ Pool On Pvt Cul-du-sac, Cls To Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Stay in my airy spacious family home, with 3 large bedrooms, 2 updated bathrooms, & a large private deck surrounding the ...
From $1406 per night (USD)VRBO
From $682 per night (USD)VRBO
Newly Renovated, Wainscott Village, Heated Pool+5 min to Beach
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Conveniently located in the town of East Hampton, this newly renovated Wainscott home is only 5 minutes from both East H ...
From $682 per night (USD)VRBO
From $1655 per night (USD)Expedia
Wainscott Southampton Estate Timeless luxury with a private pool,...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Wainscott Hideaway Wainscott Southampton Estate Timeless luxury with a private pool, bikes, ping pong, pool table, and ...
From $1655 per night (USD)Expedia
From $2609 per night (USD)VRBO
Luxury, private, gated heated pool, hot tub, fenced in property! Child friendly!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 13
Gorgeous and ultra-private estate set on 2+ acres. Six bedroom and three bathroom home in the heart of the Hamptons. Pe ...
From $2609 per night (USD)VRBO
From $1637 per night (USD)Expedia
Summer East Hampton Retreat- Heated Pool, Tennis, Hot Tub
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Serenity Stays OutEast, LLC Rental registration certificate number: 26-31 Experience the Ultimate in Luxury and Exclus ...
From $1637 per night (USD)Expedia
From $1567 per night (USD)VRBO
5 Bdrm, 4.5 Bath, Heated Pool, Bike to best Beach & 5 min walk to Wainscott Cntr
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This traditional updated and recently expanded Classic Hampton Saltbox is 3 miles from everything the Hamptons has to o ...
From $1567 per night (USD)VRBO
From $2821 per night (USD)VRBO
Single family home walking distance to the Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
South of the highway modern beach cottage. sleeps 8. All bedrooms have an attached bathroom. The backyard is the ulti ...
From $2821 per night (USD)VRBO
From $4624 per night (USD)VRBO
East Hampton/ Sag Harbor Private Modern 3 Acre Retreat
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Sleek Private 3 Acres This newly built modern 4,000 square foot home is the ultimate family 5BR/5BA vacation home. Un ...
From $4624 per night (USD)VRBO
From $1752 per night (USD)VRBO
Recently Renovated Dream Hamptons Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Perfect Hamptons house. In the middle of it all but quiet and private. New chef's dream kitchen. Four bedrooms, three ba ...
From $1752 per night (USD)VRBO
From $2285 per night (USD)VRBO
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 14
• A complete gut renovation of the interior and a new addition resulting over 5,000 sq ft of lovely living space. 2 ensu ...
From $2285 per night (USD)VRBO
From $5978 per night (USD)VRBO
Gorgeous East Hampton home close to the beach!
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 8
Location! Gorgeous post modern home a short bike ride away from one of the nicest beaches in all of the Hamptons. Walk t ...
From $5978 per night (USD)VRBO
From $1791 per night (USD)VRBO
Immaculate Wainscott House - Walk to Beach! Available this Summer!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 4
Hosted by Diane Vitale (find me on LinkedIn) this fabulous designer house is newly renovated throughout with Anderson wi ...
From $1791 per night (USD)VRBO
From $1941 per night (USD)VRBO
Peaceful, Private, Perfect Family Getaway in prime Wainscott location!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
Privately set down on a long driveway at the end of a quiet cul-de-sac and surrounded on three sides by a nature preserv ...
From $1941 per night (USD)VRBO
From $2129 per night (USD)VRBO
8/6-8/13 special Prime Wainscott Estate South of Highway
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Light filled 5 bedroom and 5.5 bath home in a convenient south-of-the-highway Wainscott location. Two luxurious master s ...
From $2129 per night (USD)VRBO
From $1390 per night (USD)VRBO
Wainscott summer rentals
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Located in Wainscott close to many great restaurants, shops and the beach, this four bedroom, four bath home is tucked a ...
From $1390 per night (USD)VRBO
From $5770 per night (USD)VRBO
Ultimate Hamptons Vacation Mansion
- Bedrooms:
- 10
- Bathrooms:
- 10
- Sleeps:
- 20
Price is based on date, duration of stay, purpose of stay and number of people. TAKE THE VIRTUAL TOUR ON OUR WEBSITE, IT ...
From $5770 per night (USD)VRBO
From $4075 per night (USD)VRBO
Spacious Open Floor Plan on 1.5 Acres
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Enjoy 1.5 private acres surrounded by woods. 5 newly renovated bathrooms The house has an large open loft like floor ...
From $4075 per night (USD)VRBO
From $3516 per night (USD)VRBO
Perfect Location - Walk or Bike to Beach Lane Beach to the Wainscott Beach
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 9
JULY and AUGUST is available for the full month, and another option is from 1st to 15th July or August, and other o ...
From $3516 per night (USD)VRBO
From $2620 per night (USD)Expedia
!! Rare Two-House Wainscott Estate: Walk to Beach, South of Highway, Wainscott !
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to Inis Fada Farm on Sayres Path in Wainscott, NY! Two separate, self-contained homes on a single lot in magnif ...
From $2620 per night (USD)Expedia
From $867 per night (USD)VRBO
Immaculate, Newly Renovated, Sunny, Private, Beautiful pool and decks
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Newly renovated, immaculate 3 bedroom, 3 bathroom house located on quiet, dead end street. New kitchen has high end app ...
From $867 per night (USD)VRBO
From $2053 per night (USD)VRBO
Beautiful Home in East Hampton, walking distance to the ocean with large pool.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
THE PROPERTY IN A SNAPSHOT 5 Bedrooms, including 2 masters, 1 office/ den, which has a sofa-bed, 3 Bathrooms, Sleeps up ...
From $2053 per night (USD)VRBO
From $1629 per night (USD)VRBO
Nature-Preserve Enveloped Sag Harbor/East Hampton Home, 5 BED, 5.5 BATH, POOL
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
5-Bedrooms (4 Ensuites), 5.5 Bathrooms, Office, Pool, Basement Gym. This newly renovated home offers style, proximity, a ...
From $1629 per night (USD)VRBO
From $1373 per night (USD)VRBO
MODERN EAST HAMPTON/WAINSCOTT/CLOSE TO SAG & EAST -POOL FENCE FOR FAMILY W/ KIDS
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
The perfect place for your friends and family to stay throughout the year, including all holidays. Town Of East Hampton ...
From $1373 per night (USD)VRBO
From $1446 per night (USD)VRBO
Contemporary Saltbox Hamptone Home 3 bedrooms, New 20x40 Heated Saltwater Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Great Wainscott location within walking distance to food/wine/Hampton Jitney/beach. Modern contemporary stylishly furni ...
From $1446 per night (USD)VRBO
From $2799 per night (USD)VRBO
Brand New Luxury Home
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 10
This new designer home has it all, no detail has been over looked. This newly completed home leaves nothing to want for. ...
From $2799 per night (USD)VRBO
From $1757 per night (USD)VRBO
Perfect House for Families! Quiet Neighborhood and Close to Everything!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This newer, beautifully appointed home has it all. Beach house but with all of the features and amenities of a full time ...
From $1757 per night (USD)VRBO
From $5129 per night (USD)VRBO
5-ACRES, SALT WATER POOL, TENNIS, BASKETBALL, 5 BEDROOM 7 BATH
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 14
Complete privacy on 5 acres in Wainscott (East Hampton). 5 bedrooms and 7 bathrooms - sleeps 10 max Heated 40’x20’ sal ...
From $5129 per night (USD)VRBO
From $1146 per night (USD)VRBO
Wainscott Private Oasis -Tennis and Pool plus Home Theater
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Just listed first time rental! 4800 sqf Oasis Ideally located between the villages of East Hampton and Sag Harbor is the ...
From $1146 per night (USD)VRBO
From $1729 per night (USD)VRBO
Charming Beach House! Walk to a quaint farmstand and Wainscott beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This charming beach house offers a quintessential easy summer vibe as well as an entertaining atmosphere in one of Wains ...
From $1729 per night (USD)VRBO
From $967 per night (USD)VRBO
Private, Charming, Lovely Farmhouse in Wainscott, East Hampton
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Your Wainscott Oasis The Perfect Hamptons Lifestyle Nestled in the exclusive hamlet of Wainscott within East ...
From $967 per night (USD)VRBO
From $6949 per night (USD)VRBO
5 acre 6 bdrm Estate; large pool and hot tub between Sag Harbor and East Hampton
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Recently updated - 5000sq ft home 1/4mile off route 114 offers true privacy and fantastic convenience (3min to Sag Harbo ...
From $6949 per night (USD)VRBO
From $1176 per night (USD)VRBO
Secluded Wainscott Estate with Heated Pool, Hot Tub, Expansive Yard &...
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
East Gate Estate Secluded Wainscott Estate with Heated Pool, Hot Tub, Expansive Yard & Minutes to the beach 5BR/3BA: H ...
From $1176 per night (USD)VRBO
From $1529 per night (USD)VRBO
Stunning 5+ Bed 5 full bath 3-4 minutes to East Hamp, Bridgehampton &Sag Harbor
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Beautiful 5 1/2 Bedrooms 5 full bath, w Heated Gunite Pool, Stunning Gourmet Kitchen, Living room, Great family room and ...
From $1529 per night (USD)VRBO
From $859 per night (USD)VRBO
Modern Barn-Style Home with State-of-the-Art Finishes, High Ceilings and...
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Please note that a reservation for this property needs to be approved before it is confirmed. Modern Beach Barn Modern ...
From $859 per night (USD)VRBO
From $7378 per night (USD)Expedia
Traditional-style home with a private pool, open-floor living areas, four...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Six Pole Serenity Traditional-style home with a private pool, open-floor living areas, four acres of land, and more! 5 ...
From $7378 per night (USD)Expedia
From $2969 per night (USD)VRBO
Newly Renovated Wainscott Retreat - Bike to the Beach, Central Location!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
*This newly renovated Wainscott retreat features 3,900 sq ft of living space on a beautiful and quiet, dead-end street. ...
From $2969 per night (USD)VRBO
From $2836 per night (USD)VRBO
5 Bedroom Hamptons Beach House w/ heated pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
This sun soaked sanctuary is located south of the Montauk Highway and just a mile to Wainscott Village Beach, one of the ...
From $2836 per night (USD)VRBO
From $5972 per night (USD)VRBO
Beautiful Wainscott Home, Open Layout, Private Pool, Natural Light
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Please note that a reservation for this property needs to be approved before it is confirmed. Wainscott Wonderful Beau ...
From $5972 per night (USD)VRBO
From $1465 per night (USD)VRBO
Wainscott Village Gem- Steps to Shops & Beach Lane
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
This turnkey and stunning house offers 2500 sqft of finest in contemporary luxury living. The home enjoys sunny southern ...
From $1465 per night (USD)VRBO
From $1307 per night (USD)VRBO
Nantucket Style Beach Cottage South of the highway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Charming neighborhood, walk to beach, farm stand, beach, jitney, bakery, wine shop, fish shop, bagel shop and and Barry' ...
From $1307 per night (USD)VRBO
From $1734 per night (USD)Expedia
Charming 3-bedroom house with AC, WiFi and heated pool in lovely Wainscott
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Get ready to relax in this 3-bedroom house in Wainscott. This gorgeous property features 1 king bed, 1 queen bed, and 1 ...
From $1734 per night (USD)Expedia
From $2404 per night (USD)VRBO
Spacious 6-bedroom house in charming Wainscott walking distance to beach
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 14
Light, airy and sun drenched idyllic 6 bedroom estate in a very convenient south-of-the-highway Wainscott location withi ...
From $2404 per night (USD)VRBO
From $3717 per night (USD)VRBO
Beautiful Wainscott Estate with Private Pool and Tennis, Perfect for Families!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Please note that a reservation for this property needs to be approved before it is confirmed. Wainscott Escape Beautif ...
From $3717 per night (USD)VRBO
From $7279 per night (USD)VRBO
Postmodern 4,000 Square-Foot Retreat on Four Acres, Expansive Outdoor...
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Please note that a reservation for this property needs to be approved before it is confirmed. Wainscott Estate Postmod ...
From $7279 per night (USD)VRBO
From $1347 per night (USD)VRBO
Ideally located between East Hampton and Sag Harbor Villages
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Located off of Merchants Path in the estate section of Wainscott on over 2 secluded and private acres at the end of a 12 ...
From $1347 per night (USD)VRBO
From $343 per night (USD)VRBO
Charming East Hampton Home, private yard with fenced in pool, perfect for...
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Please note that a reservation for this property needs to be approved before it is confirmed. The Driftwood House Char ...
From $343 per night (USD)VRBO
From $7155 per night (USD)Expedia
Spacious Wainscott Escape with Private Pool, Spa, and Luxurious...
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 14
Wainscott Seclusion Spacious Wainscott Escape with Private Pool, Spa, and Luxurious Indoor-Outdoor Living - Perfect for ...
From $7155 per night (USD)Expedia
From $2380 per night (USD)VRBO
4-bedroom house in charming Wainscott walking distance to the beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
*NEW* to VRBO after 5 summers of seasonal rentals! Classic Hamptons 4-bed / 3-bath beach house in Wainscott. South of t ...
From $2380 per night (USD)VRBO
From $5709 per night (USD)VRBO
Sundrenched Hamptons Estate with Resort Amenities
- Bedrooms:
- 9
- Bathrooms:
- 7
- Sleeps:
- 12
Escape to this delightful house in picturesque Wainscott. With 7 bedrooms including 5 king beds, 2 sofa beds, and 1 quee ...
From $5709 per night (USD)VRBO
From $631 per night (USD)VRBO
charming one-bedroom bungalow, a perfect escape.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to this charming one-bedroom bungalow, a perfect escape. Step inside to discover an inviting, open-concept livi ...
From $631 per night (USD)VRBO
From $1603 per night (USD)Expedia
Live the good life and escape out east to Sag Harbor/Wainscott!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Merchant Estate Live the good life and escape out east to Sag Harbor/Wainscott! 5BR/ 6.5 BA w/ Tennis on 5 + acres wit ...
From $1603 per night (USD)Expedia
From $2848 per night (USD)VRBO
Merchant Manor - Pool, Tennis Court, Game Room
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Escape Out East to Sag Harbor! Live the good life on this remarkable, 5.4 acre gated compound. There's no doubt you'll f ...
From $2848 per night (USD)VRBO
From $1055 per night (USD)Expedia
Wainscott Gem Large, Modern Home great for families - 1 mile to ocean/easy bike
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
House is available May 1 - June 26th, July 19-30th, and September 1 - 30th. Can rent for 2 week periods in May and June ...
From $1055 per night (USD)Expedia
From $1376 per night (USD)VRBO
Beautifully Renovated EH 4-Bedroom Summer Rental with Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy the perfect Hamptons summer retreat in this beautifully renovated and professionally furnished four-bedroom home s ...
From $1376 per night (USD)VRBO
From $878 per night (USD)VRBO
Rove Travel | Pathside Cove | Villa w/ Outdoor Spaces
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to Pathside Cove, a Rove Travel Home! Rove offers beautifully designed residences with the quality ...
From $878 per night (USD)VRBO
From $1195 per night (USD)VRBO
Modern Wainscott Retreat w/ Heated Pool, Near East Hampton & Sag Harbor, 3BR/2BA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Tucked away on a serene 1‑acre lot in Wainscott, this renovated contemporary retreat offers resort‑style indoor‑outdoor ...
From $1195 per night (USD)VRBO
From $890 per night (USD)VRBO
3-bedroom retreat in beautiful Sag Harbor
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Get ready to relax in this 3-bedroom house in Sag Harbor. The lovely bedrooms include a king bed, a queen bed, and a fun ...
From $890 per night (USD)VRBO
From $683 per night (USD)VRBO
East Hampton-Wainscott South Retreat-Private Acre, Heated Pool, Near Ocean Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
A Private Wainscott Summer Retreat in East Hampton - South of the Highway - Walking distant to Wainscott Beach Tucked a ...
From $683 per night (USD)VRBO