A coastal landscape with a beach, ocean waves, and a sunset sky.

Find Hotels with a Pool in Wainscott, NY from CA $230

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Check availability on Wainscott Hotels with a Pool

Tonight
Sep 24 - Sep 25
Tomorrow
Sep 25 - Sep 26
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Wainscott hotels with a pool

A swimming pool with two lounge chairs and a green umbrella.
A wooden building with a white window and a balcony.
A wooden outdoor seating area with a sofa and a table, surrounded by gravel and greenery, with a house in the background.
A beach with pebbles and sand, a sunset, and a calm sea.

1. The Sagaponack

The Sagaponack
Wainscott
  • Take a summer dip in the seasonal outdoor pool with loungers for relaxing in the Hamptons sun.
CA $307
CA $407 total
includes taxes & fees
Sep 28 - Sep 29
The Sagaponack
Two people sitting by a poolside with a dining setup including plates, a bottle, and a wine glass.
A well-maintained garden with a wooden cabin, a small tree, and a paved pathway.
A hotel room with two beds, a kitchenette, a refrigerator, and a wall-mounted shelf with bottles.
A patio with four wicker chairs and a table, a blue umbrella, and a wooden building in the background.

2. Wainscott Woods Retreat

Wainscott Woods Retreat
Wainscott
  • Seasonal outdoor pool at oceanfront hotel offers garden views and nearby vineyard tours for summer retreats.
CA $1,236
CA $1,461 total
includes taxes & fees
Sep 27 - Sep 28
Wainscott Woods Retreat
A swimming pool with a wooden fence, a grassy yard, and a white building in the background.
A spacious living room with a white fireplace, a large mirror, and a view of the outdoors.
A spacious living room with a white sofa, a coffee table, and a dining area with a table and chairs.
An outdoor dining area with a brick fireplace, a table set for four, and a white door in the background.

3. Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!

Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!
Wainscott
CA $1,494
CA $3,234 total
includes taxes & fees
Oct 4 - Oct 5
Rare Two-House Wainscott Estate: Hot Tub, Pool, Walk to Beach!
A swimming pool with lounge chairs and umbrellas, surrounded by a forested area.
A bedroom with two beds, a ceiling fan, a large window, and a view of greenery outside.
An outdoor dining area with a table and chairs, surrounded by tall trees and string lights.
A bathtub surrounded by candles and flower petals.

4. A Room At The Beach

A Room At The Beach
Bridgehampton
  • Soak up sunshine and serene vibes at this Hamptons motel with a stylish outdoor pool.
CA $416
CA $476 total
includes taxes & fees
Oct 4 - Oct 5
A Room At The Beach

5. East Hampton House Resort

East Hampton House Resort
East Hampton North
  • Seasonal outdoor pool creates a refreshing escape at this hotel, with tennis courts and gardens adding to the resort atmosphere.
CA $222
CA $291 total
includes taxes & fees
Oct 19 - Oct 20
East Hampton House Resort
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.
A hotel lobby with a sofa, chairs, tables, and a large window.
A waterfront property with a large house, multiple boats docked, and lush greenery.

6. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
  • Swim into serenity at this charming Sag Harbour retreat with a seasonal outdoor pool and balcony views.
CA $456
CA $521 total
includes taxes & fees
Oct 4 - Oct 5
Sag Harbor Inn
A pool area with lounge chairs and an umbrella, surrounded by lush greenery.
A modern room with a blue accent wall, a sofa, a chair, a bed, and a small table with decorative items.
A modern building with a wooden exterior, a balcony, and a pathway lined with potted plants and stepping stones.
A living room with a fireplace, two sofas, a coffee table, and a chair.

7. Journey East Hampton

Journey East Hampton
East Hampton North
  • Seasonal poolside splendour at East Hampton hotel with complimentary bikes and garden views.
CA $353
CA $443 total
includes taxes & fees
Oct 20 - Oct 21
Journey East Hampton
A backyard with a swimming pool, lounge chairs, and a wooden house.
A wooden cabin with a window, surrounded by a well-maintained lawn and trees.
A spacious dining area with a long wooden table, surrounded by chairs, and a large window offering a view of greenery.
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

8. East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.
A bar area with shelves stocked with various bottles and glasses.
A modern hotel room with a bed, bedside table, and a view of the garden.
A large, white, two-story building with a covered porch and a bicycle parked in front.

9. Topping Rose House

Topping Rose House
Bridgehampton
  • Serene outdoor pool creates luxurious oasis in the Hamptons; perfect for unwinding after coastal adventures.
CA $1,345
CA $1,541 total
includes taxes & fees
Oct 11 - Oct 12
Topping Rose House
A swimming pool with lounge chairs and a sign indicating a depth of 4 feet.
A spacious bar area with a large floral arrangement, seating with cushioned chairs, and a view of the upper level through large windows.
A spacious interior with a wooden staircase, a blue sofa, and a white chair.
A waterfront restaurant with wooden tables and white chairs, set against a backdrop of a marina and calm water.

10. EHP Resort & Marina

EHP Resort & Marina
East Hampton
  • Seasonal outdoor pool flanked by sun loungers invites leisurely afternoons, with poolside cocktail service just steps away.
CA $404
CA $508 total
includes taxes & fees
Sep 29 - Sep 30
EHP Resort & Marina
View all properties

Choose what matters most at hotels with a pool in Wainscott

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Wainscott Hotel Reviews

Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"it was a lovely stay at the Ocean surf resort. We went in September and the weather was spectacular. We really enjoyed watching the sea life from the deck. We saw so many whales, dolphins and seals too. It was quiet enough to get a night's sleep and the mattress was pretty good too. My only issue was the kitchenette- which was there but not usable. There is no counter space at all. I really think that the rooms need to be reconfigured. There was a nice working little fridge. We never used the stove top (I think that it should be taken out) or just mount the microwave. But all in all, we would stay here again."
Donovan 3-night trip
Posted 15 hours ago
Ocean Surf Resort
Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"I really love this hotel! The rooms are beautiful, the service is excellent, and I’ve had a great experience every time I’ve stayed there. I’ve been a few times already and will definitely be coming back next year!"
Veronika 2-night trip
Posted 1 day ago
Montauk Yacht Club
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"The views from the upper level of Building 400 are the best! So tranquil with a clear view of the ocean! The room we stayed in this year was a little dated furniture and appliance wise. Bathroom was updated! The property is very well maintained and the heated pool is great! Would highly recommend staying at The Beachcomber!!"
Michael 2-night trip
Posted 2 days ago
Beachcomber Resort at Montauk
Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"Awesome location by the beach and friendly staff. Great place to stay for a beach getaway!"
Dan 2-night trip
Posted 2 days ago
Ocean Vista Resort
Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"Closest to beach and town"
john 1-night trip
Posted 3 days ago
Ocean Resort Inn
Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent
"Excellent hotel. Comfortable beds. Nice decorated. Very professional and friendly staff."
Miguel 2-night trip
Posted 11 days ago
Faraway Sag Harbor

Frequently asked questions

What are some accommodations with pools in Wainscott?
The Sagaponack: B&B located near The Hamptons Beaches. Features free self parking, a seasonal outdoor pool, and sun loungers. Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and a private beach. The Atlantic Hotel: Provides 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. Offshore Montauk: Hotel, 1-minute walk from The Hamptons Beaches. Features a sauna, a seasonal outdoor pool, and free self parking. Sound View Greenport: Offers a private beach, a seasonal outdoor pool, and 2 bars.
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 with an outdoor swimming pool if you will be visiting Wainscott in the warmest months of August, July, or September when the average temp is 70°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or March when the average temp is 38°F.

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