TOP Hotels with Pool in Wainscott Woods, NY for 2026

Q: What are some accommodation options with pools in Wainscott Woods?

Gurney's Montauk Resort & Seawater Spa : Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool and a private beach. Montauk Manor : Aparthotel, 14-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool and 3 outdoor tennis courts. Montauk Yacht Club : Hotel, 5-minute walk from The Hamptons Beaches. Provides 2 outdoor swimming pools, a children's pool and a private beach. The Bentley Hotel Southampton : Hotel located near The Hamptons Beaches. Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Marram : Hotel, 5-minute walk from The Hamptons Beaches. Offers free self parking, a seasonal outdoor pool and sunloungers.

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Our top choices for Wainscott Woods hotels with a pool

Wainscott Woods Retreat

Wainscott

Seasonal outdoor pool at oceanfront hotel offers garden views and nearby vineyard tours for summer retreats.

Rp20.237.807 total

includes taxes & fees

3 Jun - 4 Jun

Breakers Montauk

Montauk

Seaside poolside escape with sun loungers and umbrellas creates a summer sanctuary.

Rp2.767.085 total

includes taxes & fees

2 Jun - 3 Jun

Ocean Resort Inn

Downtown Montauk

Soak in coastal charm at the heated saltwater pool steps from Montauk's sandy shores.

Rp4.392.468 total

includes taxes & fees

15 Jun - 16 Jun

Seasonal outdoor pool, pool umbrellas, pool loungers

Kenny's Tipperary Inn

Culloden Shores

Splash into summer with a serene outdoor pool surrounded by lush gardens and sun-soaked relaxation spaces.

Rp2.910.490 total

includes taxes & fees

2 Jun - 3 Jun

Aqualina Inn Montauk

Downtown Montauk

Dive into poolside luxury at this Montauk motel with summer splash fun and garden views.

Rp3.575.306 total

includes taxes & fees

14 Jun - 15 Jun

Outdoor pool, pool umbrellas, pool loungers

Offshore Montauk

Montauk

Rp6.925.490 total

includes taxes & fees

24 Jun - 25 Jun

Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas

Hamlet Inn

Southampton

Serene seasonal pool retreat with private beach access just 2 miles away offers the perfect summer escape on Long Island.

Rp5.387.188 total

includes taxes & fees

2 Jun - 3 Jun

The Penny Lane

Hampton Bays

Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.

Rp5.258.436 total

includes taxes & fees

8 Jun - 9 Jun

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Choose what matters most at hotels with a pool in Wainscott Woods

Breakfast included

4 stars

Top Wainscott Woods Hotel Reviews

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent

"Amazing resort. We had a great time at gurneys."

The Atlantic Hotel

6/10 Okay

"Overall, I had a pleasant stay at this hotel. The room was comfortable, clean upon arrival, and the staff were friendly and helpful when contacted. The only issue I encountered was that I wasn't aware daily housekeeping was not included during my stay. As a result, I had to call the front desk to have my garbage removed and to request a fresh set of towels. Housekeeping came in the evening, but it would have been helpful if the housekeeping policy had been communicated more clearly at check-in or in the room information. Aside from that, my experience was positive."

Kenny's Tipperary Inn

10/10 Excellent

"We enjoyed our stay there we were there for six days. The place was beautiful. It was very calming beautiful music playing beautiful grounds flowers the pool dog friendly which we love staff was friendly. Nice place was Clean definitely going back next year and definitely would recommend to go there we loved it."

Frequently asked questions

What are some accommodation options with pools in Wainscott Woods?

Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool and a private beach. Montauk Manor: Aparthotel, 14-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool and 3 outdoor tennis courts. Montauk Yacht Club: Hotel, 5-minute walk from The Hamptons Beaches. Provides 2 outdoor swimming pools, a children's pool and a private beach. The Bentley Hotel Southampton: Hotel located near The Hamptons Beaches. Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Marram: Hotel, 5-minute walk from The Hamptons Beaches. Offers free self parking, a seasonal outdoor pool and sunloungers.

What is there to see and do in Wainscott Woods?

Make a point to visit attractions such as Georgica Beach and Guild Hall. 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.

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