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

Find Hotels with a Pool in Wainscott, NY

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on Wainscott Hotels with a Pool

Tonight
7 Aug - 8 Aug
Tomorrow
8 Aug - 9 Aug
This weekend
7 Aug - 9 Aug
Next weekend
14 Aug - 16 Aug

Our top choices for Wainscott hotels with a pool

1. The Sagaponack

The Sagaponack
Wainscott
  • Take a summer dip in the seasonal outdoor pool with loungers for relaxing in the Hamptons sun.
SAR 1,409
SAR 1,797 total
includes taxes & fees
7 Sep - 8 Sep
The Sagaponack

2. Wainscott Woods Retreat

Wainscott Woods Retreat
Wainscott
  • Seasonal outdoor pool at oceanfront hotel offers garden views and nearby vineyard tours for summer retreats.
SAR 3,568
SAR 4,077 total
includes taxes & fees
13 Aug - 14 Aug
Wainscott Woods Retreat

3. 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.
SAR 1,277
SAR 1,561 total
includes taxes & fees
7 Sep - 8 Sep
East Hampton House Resort

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.
SAR 2,628
SAR 3,003 total
includes taxes & fees
1 Sep - 2 Sep
A Room At The Beach

5. Journey East Hampton

Journey East Hampton
East Hampton North
  • Seasonal poolside splendor at East Hampton hotel with complimentary bikes and garden views.
SAR 1,671
SAR 2,100 total
includes taxes & fees
7 Sep - 8 Sep
Journey East Hampton

6. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
  • Swim into serenity at this charming Sag Harbor retreat with a seasonal outdoor pool and balcony views.
SAR 1,765
SAR 2,016 total
includes taxes & fees
7 Sep - 8 Sep
Sag Harbor Inn

7. Ocean Vista Resort

Ocean Vista Resort
Amagansett
  • Oceanside sanctuary provides splendid private beach access and indoor pool oasis.
SAR 735
SAR 840 total
includes taxes & fees
7 Sep - 8 Sep
Ocean Vista Resort

8. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
  • Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
SAR 586
SAR 763 total
includes taxes & fees
7 Sep - 8 Sep
The Bentley Hotel Southampton

9. Hamlet Inn

Hamlet Inn
Southampton
  • Serene seasonal pool retreat with private beach access just 2 miles away offers the perfect summer escape on Long Island.
SAR 916
SAR 1,184 total
includes taxes & fees
7 Sep - 8 Sep
Hamlet Inn

10. Topping Rose House

Topping Rose House
Bridgehampton
  • Serene outdoor pool creates luxurious oasis in the Hamptons; perfect for unwinding after coastal adventures.
SAR 3,710
SAR 4,252 total
includes taxes & fees
7 Sep - 8 Sep
Topping Rose House
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

The Pridwin Hotel

The Pridwin Hotel

10/10 Excellent
"We absolutely loved every minute of our stay. Phenomenal property and staff. We can’t wait to come back!"
Cailin 2-night trip
Posted 2 hours ago
The Pridwin Hotel
 Hampton's Vacation Inn

Hampton's Vacation Inn

10/10 Excellent
"I really enjoyed this property as it was well maintained cute cottages totally away from noise and very peaceful"
Rosario 1-night trip
Posted 1 day ago
Hampton's Vacation Inn
Montauk Yacht Club

Montauk Yacht Club

8/10 Good
"like"
chengcheng 1-night trip
Posted 1 day ago
Montauk Yacht Club
Marram

Marram

10/10 Excellent
"This is just a gem. It's a little on the pricey side, but just so relaxing and lovely. An elevated beach bum experience!"
Jonathan 2-night trip
Posted 1 day ago
Marram
Ocean Resort Inn

Ocean Resort Inn

8/10 Good
"Steps from the beach. Nice pool area"
John 2-night trip
Posted 3 days ago
Ocean Resort Inn
Aqualina Inn Montauk

Aqualina Inn Montauk

8/10 Good
"Clean, spacious room, great property, excellent location - one block from beach and in main town."
Danielle 2-night trip
Posted 4 days ago
Aqualina Inn Montauk
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

8/10 Good
"It’s Montauk, you go here for the beach, but if you also like to dip in a pool, it’s inconvenient, plan on walking an entire trail through a parking lot to get to it. I had a prime spot for a room, choose wisely, if it’s not beachfront, you’ll also walk. It’s Gurney’s, known for its spa, it’s truly the best part of the resort, beautiful and services are fine. The staff is very nice here but SLOW. I wouldn’t say in this case you get what you pay for, if you’re looking for a Montauk vacation you’re paying for the name if you’re going for the spa you’re also paying for the spa and personally, it’s not a family vacation spot, no activities. It’s definitely a tourist spot. Dog friendly, plan to hear dogs barking."
Jamie 2-night trip
Posted 7 days ago
Gurney's Montauk Resort & Seawater Spa

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. Sound View Greenport: Offers a private beach, a seasonal outdoor pool, and 2 bars. The Atlantic Hotel: Hotel located near The Hamptons Beaches. Provides 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. Montauk Yacht Club: Hotel, 5-minute walk from The Hamptons Beaches. Features 2 outdoor pools, a children's pool, and a private beach. Offshore Montauk: Hotel, 1-minute walk from The Hamptons Beaches. Offers a sauna, a seasonal outdoor pool, and free self parking.
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.