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

Southold Hotels with Swimming Pool

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Check availability on Southold Hotels with Swimming Pools

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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 coastal building with large windows, a deck, and a view of the sea at sunset.
A spacious room with wicker furniture, large windows, and a view of the sea.

1. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
RM731
RM952 total
includes taxes & fees
16 Nov - 17 Nov
Sound View Greenport
A swimming pool with lounge chairs and umbrellas, surrounded by a wooden deck and a view of boats.
A neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
RM731
RM952 total
includes taxes & fees
4 Nov - 5 Nov
The Harbor Front Inn
A poolside area with lounge chairs and yellow umbrellas.
A wooden cabinet with a newspaper, a coffee maker, and a mug on top. There is a small stool and a window with blinds.
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.
A wooden desk with drawers, a chair, a lamp, and a framed picture on the wall.

3. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
RM919
RM1,157 total
includes taxes & fees
25 Oct - 26 Oct
Oyster Estate
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 living room with a sofa, a dining table, and a kitchen area in the background.
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.

4. North Fork Resort

North Fork Resort
Greenport
RM1,312
RM1,499 total
includes taxes & fees
22 Oct - 23 Oct
North Fork Resort
Outdoor pool
Room
Beach
Room

5. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
RM690
RM1,241 total
includes taxes & fees
12 Nov - 13 Nov
Cliffside Resort Condominiums
Property amenity
Front of property – evening/night
Property amenity
Terrace/patio

6. 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.
RM822
RM939 total
includes taxes & fees
25 Oct - 26 Oct
Shelter Island House
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.
A waterfront property with a large house, multiple boats docked, and lush greenery.
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.

7. 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 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.

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.
RM551
RM630 total
includes taxes & fees
31 Oct - 1 Nov
The Bentley Hotel Southampton
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.
A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.
A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.

9. 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 swimming pool with lounge chairs and umbrellas, surrounded by a forested area.
Beach
A bathtub surrounded by candles and flower petals.
A bedroom with two beds, a ceiling fan, a large window, and a view of greenery outside.

10. 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
22 Oct - 23 Oct
A Room At The Beach
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

Sound View Greenport

Sound View Greenport

8/10 Good
"Great ocean sounds through the pen window!"
Eric 3-night trip
Posted 5 hours ago
Sound View Greenport
Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"."
Marcelia 1-night trip
Posted 2 days ago
Hyatt Place Long Island East End
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

8/10 Good
"Room was spacious, comfortable and clean. Overall the hotel was nice. The decorating was a bit off putting and looked like it had been done in the 1970’s and never changed; orange and avocado green with brown carpet. If you can get past that it was a good place to stay. Breakfast was very nice with plenty of hot and cold choices. For me, the fact that it was open from 7:30 til 10 am was very nice. I would stay here again."
Brenda 4-night trip
Posted 2 days ago
Quality Inn Old Saybrook - Westbrook
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"This hotel was so conveniently located on a main road, right off the 495, near so many restaurants and stores and a few minute drive to the wineries and farms. The property was spotless and very nice and accommodating. We had a 2 queen room for a family of 4 and it was perfectly spacious. We have small kids so we used the pool and hot tub. The pool was a little too cold for my liking but my kids had a blast. The hotel was great all around. I am sure we will be back again next fall!"
Jenna 1-night trip
Posted 2 days ago
Hilton Garden Inn Riverhead
The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"We were 4 girls and the room was two bedrooms and another bed also so it accommodated all of us. 😊"
Grace 1-night trip
Posted 2 days ago
The Atlantic Hotel
The Hampton Maid

The Hampton Maid

10/10 Excellent
"Property and room was incredible. However, didn’t like the restaurant food. It was lacking flavor and the dessert choices weren’t good. Lastly, the pillows weren’t the best."
Delise 2-night trip
Posted 3 days ago
The Hampton Maid

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: Features a seasonal outdoor pool, an indoor pool and a private beach. Pier Blue Inn Old Saybrook - Essex: Offers a private beach, a seasonal outdoor pool and 2 bars. Water's Edge Resort & Spa: Features 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. Sound View Greenport: Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access. The Atlantic Hotel: Hotel, 3-minute walk from The Hamptons Beaches. Offers 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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