Wainscott Hotel with Pool

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Check availability on Wainscott Hotel with Pool

Tonight
26 Dec - 27 Dec
Tomorrow
27 Dec - 28 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Wainscott hotels with a pool

Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas
The Sagaponack

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (215)
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is HK$1,203
HK$1,686 total
includes taxes & fees
29 Dec - 30 Dec
The Sagaponack
Outdoor pool, a heated pool
Private, Charming, Lovely Farmhouse in Wainscott, East Hampton

Private, Charming, Lovely Farmhouse in Wainscott, East Hampton

Private, Charming, Lovely Farmhouse in Wainscott, East Hampton
Wainscott
10.0 out of 10, Exceptional, (112)
"Very clean rooms! Great place to stay! Great area and privacy! Host was wonderful. Would stay there again!"
United States
DAVID K.
The price is HK$5,599
HK$12,366 total
includes taxes & fees
27 Dec - 28 Dec
Private, Charming, Lovely Farmhouse in Wainscott, East Hampton
Exterior
Wainscott Woods Retreat

Wainscott Woods Retreat

Wainscott Woods Retreat
2.5 star property
Wainscott
7.0 out of 10, Good, (9)
"Newly Renovated and extremely clean, well kept, and inviting rooms. Staff could not be nicer and more accommodating. Location is ideally situated close to lots of shops, Goldbergs for bagels, East Hampton Beaches etc. Highly recommend this accommodation to anyone staying in the area."
United States
Ivan
The price is HK$2,762
HK$3,156 total
includes taxes & fees
2 Jan - 3 Jan 2026
Wainscott Woods Retreat
BBQ/picnic Area
Offshore Montauk

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (86)
"Hotel was beautiful !!"
United States
Erica
The price is HK$903
HK$1,476 total
includes taxes & fees
8 Jan - 9 Jan 2026
Offshore Montauk
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (444)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is HK$693
HK$895 total
includes taxes & fees
28 Dec - 29 Dec
Hamlet Inn
Seasonal outdoor pool, pool umbrellas, pool loungers
Kenny's Tipperary Inn

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very good, (879)
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn
Exterior
Montauk Manor

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1273)
"The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable "
United States
Kathleen
The price is HK$1,078
HK$1,383 total
includes taxes & fees
5 Jan - 6 Jan 2026
Montauk Manor
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool loungers
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (551)
"Awesome stay!!! Great Location "
United States
Bryan
The price is HK$1,051
HK$1,412 total
includes taxes & fees
25 Jan - 26 Jan 2026
The Harbor Front Inn
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (405)
"Room was beautiful and spacious. Staff was courteous and on point. "
United States
Ron
The price is HK$973
HK$1,119 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Bentley Hotel Southampton
Seasonal outdoor pool, pool umbrellas, pool loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (601)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is HK$1,014
HK$1,370 total
includes taxes & fees
29 Dec - 30 Dec
Sound View Greenport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Wainscott Hotel Reviews

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Everything was perfect. Staff, room, experience. Will definitely stay again. "
Kristy 1-night trip
Posted 12 days ago
Gurney's Montauk Resort & Seawater Spa

Frequently asked questions

What are some accommodation options with pools in Wainscott?
The Sagaponack: Features free self parking, a seasonal outdoor pool and sunloungers. Wainscott Woods Retreat: Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Gurney's Montauk Resort & Seawater Spa: Provides a seasonal outdoor pool, an indoor pool and a private beach. Montauk Blue Hotel: Features sunloungers, an indoor pool and complimentary wireless Internet access. Offshore Montauk: Offers free self parking, an outdoor pool and complimentary wireless Internet access.
What is there to see and do in Wainscott?
The picturesque setting of The Hamptons Beaches showcases the area's natural beauty. Discover sights such as Georgica Beach, Wolffer Estates Vineyard and East Hampton Main Beach during your stay. Take in the natural beauty of Wainscott with the beaches.
When is the best time to book a hotel with a pool in Wainscott?
You may want to think about a place to stay that offers an outdoor pool if you plan to visit Wainscott in the warmest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be the way to go if you visit during the coldest months of January, February or March, when the average temp is 3°C.

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