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Find Hotels with a Pool in Wainscott Woods, NY

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Check availability on Wainscott Woods Hotels with a Pool

Our top choices for Wainscott Woods hotels with a pool

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)
"We had a great stay at the house - it's perfect for a family and the kids love the pool ! Would definitely stay again and perfect for long term rental as well."
United States
Amy P.
The price is ￥111,953
￥246,401 total
includes taxes & fees
Dec 13 - Dec 14
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 ￥35,068
￥40,065 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Wainscott Woods Retreat
Outdoor pool
Offshore Montauk

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (79)
"Nice decoration, clean amenities, good stay"
United States
weihao
The price is ￥18,052
￥29,507 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Offshore Montauk
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, (394)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is ￥18,304
￥21,069 total
includes taxes & fees
Dec 21 - Dec 22
The Bentley Hotel Southampton
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, (441)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is ￥13,854
￥17,906 total
includes taxes & fees
Dec 14 - Dec 15
Hamlet Inn
Seasonal outdoor pool, pool umbrellas, sun 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, (878)
"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, (1266)
"Great ambience. Very kind and friendly service. Wonderful luxe suite. Very homey and cozy. I really enjoyed my stay here. Just lovely. "
United States
Violet
The price is ￥21,551
￥27,664 total
includes taxes & fees
Dec 22 - Dec 23
Montauk Manor
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (546)
"Awesome stay!!! Great Location "
United States
Bryan
The price is ￥20,388
￥30,903 total
includes taxes & fees
Dec 25 - Dec 26
The Harbor Front Inn
Seasonal outdoor pool, pool umbrellas, sun loungers
Hero Beach Club

Hero Beach Club

Hero Beach Club
4.0 star property
Montauk
9.0 out of 10, Wonderful, (202)
"Great weekend trip "
United States
Timothy
The price is ￥22,254
￥41,234 total
includes taxes & fees
Dec 21 - Dec 22
Hero Beach Club
Exterior
Daunt's Albatross Motel

Daunt's Albatross Motel

Daunt's Albatross Motel
2.0 star property
Downtown Montauk
9.0 out of 10, Wonderful, (288)
"The staff is the best, made my birthday stay extra special. Love the room and how clean and cute it was. Best hotel in town."
United States
Tiffany
Daunt's Albatross Motel
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

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"EVERYTHING about our stay at Gurneys was wonderful. The staff was outstanding and so accommodating. The room was beautiful looking out at the ocean. We have decided to make a family tradition to go to stay."
Rachel 1-night trip
Posted 5 days ago
Gurney's Montauk Resort & Seawater Spa

Frequently asked questions

What are some accommodations 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 sun loungers, an indoor pool, and complimentary wireless internet access. Sound View Greenport: Features a private beach, a seasonal outdoor pool, and 2 bars. The Atlantic Hotel: Offers 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking.
What is there to see and do in Wainscott Woods?
Make a point to visit attractions like Georgica Beach and Railroad Museum of Long Island. During your stay, check out 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 an accommodation that offers an outdoor pool if you plan to visit Wainscott Woods in the hottest months of August, July, or September when the average temperature is 70°F. Lodging with an indoor pool may be what you want if you visit during the coldest months of January, February, or March when the average temperature is 38°F.