A calm lake with a forest in the background during sunset.

Search Hotels with Swimming Pool in Southold

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Check availability on Southold Hotels with Swimming Pool

Tonight
16 Sept - 17 Sept
Tomorrow
17 Sept - 18 Sept
This weekend
18 Sept - 20 Sept
Next weekend
25 Sept - 27 Sept

Our top choices for Southold hotels with a pool

A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.
A spacious room with wicker furniture, large windows, and a view of the sea.
A coastal building with large windows, a deck, and a view of the sea at sunset.

1. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
₹23,198
₹29,244 total
includes taxes & fees
1 Oct - 2 Oct
Sound View Greenport
A rectangular swimming pool with a deck area, surrounded by lounge chairs and umbrellas.
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.
A balcony with a view of a dock and a boat, a table with a basket of pastries, and a chair.
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
₹24,096
₹30,270 total
includes taxes & fees
15 Oct - 16 Oct
The Harbor Front Inn
A poolside area with a hat and towel on a lounge chair.
A modern house with a deck, outdoor seating, and a fire pit.
A modern bathroom with a black bathtub, white sink, and shower area. There are framed pictures on the wall and a potted plant on the counter.
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

3. North Fork Resort

North Fork Resort
Greenport
₹28,656
₹32,740 total
includes taxes & fees
24 Sept - 25 Sept
North Fork Resort

4. Shelter Island House

Shelter Island House
Shelter Island Heights
  • Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.
₹19,231
₹21,971 total
includes taxes & fees
4 Oct - 5 Oct
Shelter Island House

5. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
₹27,725
₹40,230 total
includes taxes & fees
5 Oct - 6 Oct
Cliffside Resort Condominiums
A pool area with lounge chairs and umbrellas, a mural on the wall, and a clear view of the sky.
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.
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 lounge area with a pool view, white furniture, and contemporary lighting fixtures.

6. 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.
₹13,036
₹17,293 total
includes taxes & fees
5 Oct - 6 Oct
The Bentley Hotel Southampton
A rectangular swimming pool with a fenced area, surrounded by trees and a concrete deck with white metal loungers.
A hotel room with a large bed, two bedside tables, a desk with chairs, a TV, and a small table with flowers.
A motel with a large parking lot and multiple rooms.
A parking lot with a building in the background.

7. Clinton Motel

Clinton Motel
Clinton
  • Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
₹7,549
₹8,682 total
includes taxes & fees
17 Sept - 18 Sept
Clinton Motel
A swimming pool with a tiled edge, surrounded by lounge chairs and umbrellas, with a grassy area and trees in the background.
A spacious living room with a white sofa, a coffee table, and a fireplace. There are large windows offering a view of the outdoors.
A room with a wicker sofa, a small table with a potted plant, and a bed with a wooden ladder.
A house with a covered porch, a garden with various plants and flowers, and a 'OPEN' sign on the window.

8. 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.
₹12,112
₹15,655 total
includes taxes & fees
30 Sept - 1 Oct
Hamlet Inn
A poolside area with lounge chairs and yellow umbrellas.
A cozy interior with a wooden bench, a sofa, and a bar area.
A bedroom with a large bed, bedside tables, a window with curtains, and wooden shelving with various items.
A modern outdoor seating area with a sofa, cushions, a wooden coffee table with a fire feature, and a decorative wall with geometric patterns.

9. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
₹29,914
₹37,690 total
includes taxes & fees
7 Oct - 8 Oct
Oyster Estate
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of the sea.
A beach with rows of white lounge chairs and umbrellas, a wooden table with a drink, and a person walking along the shore.
A person sitting on a bench with a drink, overlooking a waterfront with a flag and a view of the water.

10. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
  • Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
₹52,488
₹65,965 total
includes taxes & fees
17 Sept - 18 Sept
The Pridwin Hotel
View all properties

Choose what matters most at hotels with a pool in Southold

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Southold Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"It was the perfect getaway- close to home. The property was beautiful, clean and peaceful. The beach could have been cleaner, but overall we loved our stay. The food served in their variety of restaurants was delicious. We will definitely return."
Jennifer 3-night trip
Posted 6 hours ago
Water's Edge Resort & Spa
Budget Host East End

Budget Host East End

10/10 Excellent
"Excelente"
Jenifer 1-night trip
Posted 7 hours ago
Budget Host East End
The Hampton Maid

The Hampton Maid

10/10 Excellent
"Excellent stay. Very peaceful. Breakfast and dinner were absolutely amazing! Mateo at the front desk was very helpful and made our stay more enjoyable! Highly recommended."
Diana 2-night trip
Posted 9 hours ago
The Hampton Maid
The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"I had room facing the busy street, but the room was well insulated and I did not hear the traffic from outside. Also, the floor plan was very functional. Linen was clean CLEAN, bed was SO comfortable And the amenities of small fridge, coffee maker, iron, -and 2 water bottles provided with each room clean was especially helpful. Parking spaces were wide with ample space to unload and open passenger doors."
barbara 5-night trip
Posted 10 hours ago
The Atlantic Hotel
Sound View Greenport

Sound View Greenport

10/10 Excellent
"Great place on the water. Piano Bar is nice; good food & drink. All the staff was very friendly and helpful."
Joseph 3-night trip
Posted 1 day ago
Sound View Greenport
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"Friendly staff, comfortable and clean room. Modern and bright."
Danielle 1-night trip
Posted 1 day ago
Hilton Garden Inn Riverhead
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 2 days ago
Faraway Sag Harbor

Frequently asked questions

What's it like visiting Southold?
If laying by the pool is your idea of the perfect getaway, you may want to consider family-friendly Southold, which offers 5 places to stay with pools. During your visit, you can explore sights such as The Hamptons Beaches, and then kick back and relax poolside at one of the accommodation options in Southold that travellers like for their pools.
What are some accommodation options with pools in Southold?
The Shoals Suites and Slips: Provides a private beach, a seasonal outdoor pool and 2 bars. Pier Blue Inn Old Saybrook - Essex: Features a seasonal outdoor pool, an indoor pool and a private beach. Sound View Greenport: Offers 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. Water's Edge Resort & Spa: Provides free self parking, a seasonal outdoor pool and complimentary wireless Internet access. The Atlantic Hotel: Hotel, 3-minute walk from The Hamptons Beaches. Features spa services, a seasonal outdoor pool and a snack bar/deli.
How many pool hotels are there in Southold?
Expedia has 5 hotels in Southold for your poolside break.
What is there to see and do in Southold?
Enjoy a stroll along the shore at McCabe's Beach and Horton Lane Beach. Discover sights such as Sparkling Pointe, Croteaux Vineyards and Sannino's Bella Vita Vineyard during your stay.
When is the best time to book a hotel with a pool in Southold?
You may want to think about a place to stay that offers an outdoor pool if you plan to visit Southold in the warmest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be the way to go if you visit during the coldest months of January, February or March, when the average temp is 3°C.
What's the best way to travel around Southold?
Knowing the transportation options in Southold can help you enjoy the area beyond your hotel pool. To see more of the larger area, hop on a train at Southold Station. Southold may not have many public transport options to choose from, so consider renting a car to explore more.

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