A lighthouse on a rocky coastline with a clear blue sky.

Wainscott Woods Hotels with Swimming Pool

  • 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 Woods Hotels with Swimming Pools

Tonight
19 Oct - 20 Oct
Tomorrow
20 Oct - 21 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Wainscott Woods hotels with a pool

A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A hotel lobby with a sofa, chairs, tables, and a large window.
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

1. 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.
RM894
RM1,021 total
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn
A pool area with lounge chairs and an umbrella, surrounded by lush greenery.
A living room with a fireplace, two sofas, a coffee table, and a chair.
A modern kitchen with a central island, pendant lights, and a view of the outdoors.
A modern room with a blue accent wall, a sofa, a chair, a bed, and a small table with decorative items.

2. Journey East Hampton

Journey East Hampton
East Hampton North
  • Seasonal poolside splendour at East Hampton hotel with complimentary bikes and garden views.
RM1,010
RM1,270 total
includes taxes & fees
3 Nov - 4 Nov
Journey East Hampton
A swimming pool with two lounge chairs and a green umbrella.
Two bicycles with wicker baskets labeled "Sophie & Co." parked in front of a building with a dark door and white columns.
A beach with pebbles and sand, a sunset, and a calm sea.
A wooden building with a white window and a balcony.

3. The Sagaponack

The Sagaponack
Wainscott
  • Take a summer dip in the seasonal outdoor pool with loungers for relaxing in the Hamptons sun.
RM792
RM1,068 total
includes taxes & fees
26 Oct - 27 Oct
The Sagaponack
Outdoor pool
Living area
Terrace/patio
Room

4. 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.
RM590
RM785 total
includes taxes & fees
2 Nov - 3 Nov
East Hampton House Resort
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.

5. 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.
RM1,209
RM1,381 total
includes taxes & fees
21 Oct - 22 Oct
A Room At The Beach
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.
A spacious living room with a fireplace, comfortable seating, and large windows.

6. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Dive into summer splendour at a tranquil pool retreat with chic cabanas and luxe loungers.
RM1,506
RM1,893 total
includes taxes & fees
16 Nov - 17 Nov
Faraway Sag Harbor
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.
A large, white, two-story building with a covered porch and a bicycle parked in front.
A bar setting with a bartender and a customer. The bar has shelves with various bottles and glasses. There is a cushioned bench in the foreground.
A modern hotel room with a bed, bedside table, and a view of the garden.

7. Topping Rose House

Topping Rose House
Bridgehampton
  • Serene outdoor pool creates luxurious oasis in the Hamptons; perfect for unwinding after coastal adventures.
RM2,553
RM2,931 total
includes taxes & fees
20 Oct - 21 Oct
Topping Rose House
A house with a sloped roof, large windows, and a pathway leading to the entrance.
A covered porch with white railings, green cushioned chairs, hanging flower baskets, and pendant lights.
A wooden gate leading to a pathway surrounded by lush greenery and trees.
A dining area with a chandelier, a large table, chairs, and a vase with flowers.

8. Mill House Inn

Mill House Inn
Pantigo Road Historic District
  • Soak in serene poolside moments at this charming Colonial B&B with a garden terrace for ultimate relaxation.
RM1,326
RM1,917 total
includes taxes & fees
20 Oct - 21 Oct
Mill House Inn
A pool area with lounge chairs and umbrellas, a mural on the wall, and a clear view of the sky.
A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.
A modern outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.
A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.

9. 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.
RM551
RM630 total
includes taxes & fees
31 Oct - 1 Nov
The Bentley Hotel Southampton
A swimming pool with a white fence, a table with chairs, and a building with a white picket fence in the background.
A living room with a wooden entertainment center, a sofa, a coffee table, and a lamp.
A living room area with a sofa, a dining table, and a separate queen bedroom.
A bedroom with a bed, bedside tables, a chair, a desk, and a bathroom visible through an open door.

10. Southampton Long Island Hotel

Southampton Long Island Hotel
Southampton
  • Luxurious poolside retreat with seasonal outdoor oasis and plush sun loungers, just minutes from Cooper's Beach in the Hamptons.
RM649
RM774 total
includes taxes & fees
20 Oct - 21 Oct
Southampton Long Island Hotel
View all properties

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

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Wainscott Woods Hotel Reviews

Sound View Greenport

Sound View Greenport

8/10 Good
"This was our third stay at Soundview. We stay there because all of the rooms face the sound and the natural view can’t be beat. The rooms are lodgy but spacious and depending on your room, there are public/private balconies."
Danielle 1-night trip
Posted 19 hours ago
Sound View Greenport
Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"Beautiful place to stay . Room has a full kitchen. Also included in the room glasses silverware and dishes . Easy access to the beach. Most enjoyable time ."
John 2-night trip
Posted 2 days ago
Ocean Vista Resort
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Great place in Montauk. Beautiful view and room was spacious."
fred 4-night trip
Posted 3 days ago
Beachcomber Resort at Montauk
The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"Lots of parking, rooms were clean and smelt nice"
miranda 1-night trip
Posted 3 days ago
The Atlantic Hotel

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. Offshore Montauk: Hotel, 1-minute walk from The Hamptons Beaches. Offers a sauna, a seasonal outdoor pool and free self parking. The Atlantic Hotel: Provides 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. Sound View Greenport: Features a private beach, a seasonal outdoor pool and 2 bars. Montauk Blue Hotel: Hotel, 1-minute walk from The Hamptons Beaches. Offers sunloungers, an indoor pool and complimentary wireless Internet access.
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.

Explore a world of travel with Expedia