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Search Hotels with Pool in Wainscott Woods

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Check availability on Wainscott Woods Hotels with Pool

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Wainscott Woods hotels with a pool

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 Rp6.070.063
Rp6.935.046 total
includes taxes & fees
1 Jan - 2 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, (91)
"Hotel was beautiful !!"
United States
Erica
The price is Rp1.944.095
Rp3.177.687 total
includes taxes & fees
12 Jan - 13 Jan 2026
Offshore Montauk
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, (880)
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn
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, (445)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is Rp1.461.839
Rp1.889.506 total
includes taxes & fees
31 Dec - 1 Jan 2026
Hamlet Inn
Exterior
Montauk Manor

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1274)
"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 Rp2.320.857
Rp2.979.270 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, (554)
"Room and staff were amazing. "
United States
Manuel
The price is Rp2.263.087
Rp3.004.203 total
includes taxes & fees
29 Jan - 30 Jan 2026
The Harbor Front Inn
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)
"Great view but a gas station has a better breakfast. "
United States
Michael
The price is Rp2.414.619
Rp3.214.000 total
includes taxes & fees
8 Jan - 9 Jan 2026
Sound View Greenport
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, (412)
"Adorable boutique hotel with charming unique touches. "
United States
Mary
The price is Rp2.064.924
Rp2.375.964 total
includes taxes & fees
22 Jan - 23 Jan 2026
The Bentley Hotel Southampton
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.
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Top Wainscott Woods Hotel Reviews

Frequently asked questions

What are some accommodation options with pools in Wainscott Woods?
Wainscott Woods Retreat: Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Gurney's Montauk Resort & Seawater Spa: Offers a seasonal outdoor pool, an indoor pool and a private beach. Montauk Blue Hotel: Provides sunloungers, an indoor pool and complimentary wireless Internet access. Offshore Montauk: Features free self parking, an outdoor pool and complimentary wireless Internet access. The Bentley Hotel Southampton: Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access.
What is there to see and do in Wainscott Woods?
Make a point to visit attractions such as Georgica Beach and Railroad Museum of Long Island. During your stay, visit sights such as Wolffer Estates Vineyard, The Jewish Center of the Hamptons and East Hampton Main Beach.
When is the best time to book a hotel with a pool in Wainscott Woods?
You may want to consider accommodation with an outdoor swimming pool if you plan to visit Wainscott Woods in the hottest months of August, July or September, when the average temperature is 21°C. Accommodation with an indoor pool may be what you want if you are visiting during the coldest months of January, February or March, when the average temperature is 3°C.