Find Hotels with a Pool in Wainscott, NY

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
1 Dec - 2 Dec
Tomorrow
2 Dec - 3 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Wainscott Hotels with a Pool

Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas
The Sagaponack

The Sagaponack

3.0 star property
Wainscott
  • Pool loungers
8.8 out of 10, Excellent, (208)
Sparkling seasonal waters await at this boutique Hamptons bed & breakfast. Guests unwind poolside from May to September, enjoying loungers, umbrellas, and thoughtfully provided beach towels, all steps from renowned Wolffer Estates Vineyard.
The price is SAR 512
SAR 778 total
includes taxes & fees
29 Dec - 30 Dec
The Sagaponack
Outdoor pool, a heated pool
Private, Charming, Lovely Farmhouse in Wainscott, East Hampton

Private, Charming, Lovely Farmhouse in Wainscott, East Hampton

Wainscott
  • Outdoor pool
10.0 out of 10, Exceptional, (112)
The price is SAR 2,701
SAR 5,949 total
includes taxes & fees
2 Dec - 3 Dec
Private, Charming, Lovely Farmhouse in Wainscott, East Hampton
Exterior
Wainscott Woods Retreat

Wainscott Woods Retreat

2.5 star property
Wainscott
  • Near the beach
7.0 out of 10, Good, (9)
Seasonal outdoor pool beckons from May through September with ocean breezes enhancing the experience. Guests appreciate vineyard tours, wine events, and bicycle rentals, all complemented by garden terraces perfect for afternoon relaxation.
The price is SAR 1,123
SAR 1,283 total
includes taxes & fees
7 Dec - 8 Dec
Wainscott Woods Retreat
BBQ/picnic area
Offshore Montauk

Offshore Montauk

2.0 star property
Montauk
  • Outdoor pool
  • Near the beach
9.4 out of 10, Exceptional, (73)
The price is SAR 305
SAR 563 total
includes taxes & fees
14 Dec - 15 Dec
Offshore Montauk
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers
The Harbor Front Inn

The Harbor Front Inn

3.5 star property
Greenport
  • Pool loungers
  • Near the beach
8.8 out of 10, Excellent, (539)
Sunlight dances across the seasonal outdoor pool where comfortable loungers invite leisurely afternoons. After swimming, guests appreciate the 24-hour health club, designer bathroom amenities, and continental breakfast before exploring nearby shops and restaurants.
The price is SAR 391
SAR 631 total
includes taxes & fees
29 Dec - 30 Dec
The Harbor Front Inn
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2.0 star property
Southampton
  • Pool loungers
  • Near private beach
9.6 out of 10, Exceptional, (388)
Swimming awaits at the immaculately clean seasonal outdoor pool where plush loungers invite leisurely afternoons under shady umbrellas. Recently renovated spaces, private beach access just 2 miles away, and proximity to renowned golf courses complete this Southampton retreat.
The price is SAR 441
SAR 508 total
includes taxes & fees
11 Dec - 12 Dec
The Bentley Hotel Southampton
Exterior
Montauk Manor

Montauk Manor

3.5 star property
Montauk
  • Indoor pool
  • Near the beach
  • Hot tub
9.2 out of 10, Wonderful, (1265)
Swimming options abound at this tudor-style retreat where an indoor pool welcomes year-round while a seasonal outdoor pool showcases breathtaking scenic vistas. Guests appreciate the relaxing hot tub, tennis courts, and 24-hour fitness center.
The price is SAR 520
SAR 668 total
includes taxes & fees
2 Dec - 3 Dec
Montauk Manor
Seasonal outdoor pool, pool umbrellas, sun loungers
Kenny's Tipperary Inn

Kenny's Tipperary Inn

2.0 star property
Culloden Shores
  • Pool loungers
  • Near the beach
8.4 out of 10, Very Good, (878)
Surrounded by lush gardens, the seasonal summer pool creates a peaceful retreat for guests seeking sunshine and relaxation. This immaculate motel provides spacious, individually furnished rooms with private decks and premium bedding for complete comfort.
Kenny's Tipperary Inn
Seasonal outdoor pool, pool umbrellas, sun loungers
Sound View Greenport

Sound View Greenport

4.0 star property
Greenport
  • Poolside bar
  • Pool loungers
  • On private beach
8.6 out of 10, Excellent, (596)
Panoramic oceanfront vistas captivate from the seasonal pool area, complete with loungers, umbrellas, and a lively poolside bar. After swimming, guests savor fresh seafood at The Halyard restaurant while watching magnificent sunsets paint the sky.
The price is SAR 601
SAR 871 total
includes taxes & fees
2 Dec - 3 Dec
Sound View Greenport
Property map
North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3.0 star property
Greenport
  • Pool
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
9.4 out of 10, Exceptional, (6)
North Fork Cottages & RV Resort
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.
View all properties

White Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now

Top Wainscott Hotel Reviews

The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"Great hotel for a quick stay - very friendly staff"
Dianne 1-night trip
Posted 7 days ago
The Atlantic Hotel

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodations with pools in Wainscott?
The Sagaponack: Features free self parking, a seasonal outdoor pool, and sun loungers. Wainscott Woods Retreat: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Gurney's Montauk Resort & Seawater Spa: Provides a seasonal outdoor pool, an indoor pool, and a private beach. Montauk Blue Hotel: Features sun loungers, an indoor pool, and complimentary wireless internet access. 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.