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

Southold Hotel with Pool

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Check availability on Southold Hotel with Pool

Tonight
30 Sept - 1 Oct
Tomorrow
1 Oct - 2 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

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 beach bar with wooden chairs and a small table, overlooking the sea.
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.
HK$1,942
HK$2,442 total
includes taxes & fees
6 Oct - 7 Oct
Sound View Greenport
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.
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 balcony with a view of a dock and a boat, a table with a basket of pastries, and a chair.
Pool

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
HK$1,758
HK$2,233 total
includes taxes & fees
26 Oct - 27 Oct
The Harbor Front Inn
Outdoor pool
Terrace/patio
Beach
Room

3. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
HK$1,851
HK$2,985 total
includes taxes & fees
25 Oct - 26 Oct
Cliffside Resort Condominiums
A poolside area with a hat and towel on a lounge chair.
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 modern living room with a sofa, a dining table, and a kitchen area in the background.
A modern house with a deck, outdoor seating, and a fire pit.

4. North Fork Resort

North Fork Resort
Greenport
HK$2,090
HK$2,388 total
includes taxes & fees
1 Oct - 2 Oct
North Fork Resort
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 lounge area with a pool view, white furniture, and contemporary lighting fixtures.
A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.

5. 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.
HK$963
HK$1,324 total
includes taxes & fees
6 Oct - 7 Oct
The Bentley Hotel Southampton
Property amenity
Terrace/patio
Front of property – evening/night
Bar (on property)

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.
HK$1,579
HK$1,804 total
includes taxes & fees
13 Oct - 14 Oct
Shelter Island House
A rectangular swimming pool with a fenced area, surrounded by trees and a concrete deck with white metal loungers.
A motel with a large parking lot and multiple rooms.
A hotel room with two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.
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.
HK$612
HK$704 total
includes taxes & fees
1 Oct - 2 Oct
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 house with a covered porch, a garden with various plants and flowers, and a 'OPEN' sign on the window.
A glass-top table with a vase of flowers, surrounded by white-covered chairs, in a bright indoor setting with plants and a fireplace 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.

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.
HK$1,053
HK$1,361 total
includes taxes & fees
1 Oct - 2 Oct
Hamlet Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a wooden fence and trees.
A sign for 'The Atlantic Southampton' with a stylized logo and text.
A modern kitchen with a central island, a dining area with a black and white striped sofa, and a living area with a black leather couch.
A kitchen counter with a coffee maker, thermos, fruits, and breakfast items.

9. The Atlantic Hotel

The Atlantic Hotel
Southampton
  • Splash into summer at this modern hotel with tennis courts and a seasonal pool for sunny relaxation.
HK$700
HK$996 total
includes taxes & fees
28 Oct - 29 Oct
The Atlantic Hotel
A pool area with lounge chairs and a covered seating area, surrounded by greenery and a view of neighboring houses.
Two Adirondack chairs facing a beach with a clear view of the sea and a distant island.
An outdoor seating area with Adirondack chairs and a table, surrounded by American flags and flowers, with a view of houses and a body of water in the background.
A bedroom with a bed, a desk, a chair, a window with a view of trees and a body of water.

10. Ocean View Terrace Inn

Ocean View Terrace Inn
Hampton Bays
  • Beachside seasonal pool awaits with ocean adventures and relaxing massages nearby.
HK$863
HK$1,418 total
includes taxes & fees
1 Oct - 2 Oct
Ocean View Terrace Inn
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

The Hampton Maid

The Hampton Maid

10/10 Excellent
"Muy lindo lugar!! El staff muy ayento y el restaurante super delicioso!! El cafe de la mañana uff 👍👍👍"
Armida 2-night trip
Posted 10 hours ago
The Hampton Maid
Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Very good"
Rafael 1-night trip
Posted 16 hours ago
Hyatt Place Long Island East End
Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Front desk helpful! Indoor bar area nice area for single traveler plenty of space."
Toni and Zak 1-night trip
Posted 2 days ago
Water's Edge Resort & Spa
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Absolutely lovely resort, food and the spa is wonderful!"
Christa 2-night trip
Posted 3 days ago
Saybrook Point Resort & Marina
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

8/10 Good
"Good hotel benefited by a good lobby and the delightful Annabel who welcomed us when we arrived after a long journey and managed to arrange food for my family just before the kitchen closed. She looked after us and friends over our stay and made us all very welcome Rooms were spacious though a little dark and we were surprised that given the cost of the hotel room they were only cleaned every other day Facilities are good though and it’s a great base to visit this lovely island. Would happily stay here again"
LOUISE M 3-night trip
Posted 5 days ago
Hilton Garden Inn Riverhead
Budget Host East End

Budget Host East End

8/10 Good
"Staff"
Harvey 2-night trip
Posted 9 days ago
Budget Host East End
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 weeks 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: 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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