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
29 Sept - 30 Sept
Tomorrow
30 Sept - 1 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 coastal building with large windows, a deck, and a view of the sea at sunset.
A beach bar with wooden chairs and a small table, overlooking 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$1,941
HK$2,442 total
includes taxes & fees
6 Oct - 7 Oct
Sound View Greenport
A rectangular swimming pool with a view of the sea, surrounded by lounge chairs and a wooden deck.
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.
A balcony with a view of a dock and a boat, a table with a basket of pastries, and a chair.

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
25 Oct - 26 Oct
The Harbor Front Inn
A poolside area with sun loungers, a pool, and a building with a balcony.
A wooden desk with drawers, a chair, a lamp, and a framed picture on the wall.
A hotel room with two beds, a large window, a ceiling fan, and a painting on the wall.
A wooden wall with a wall-mounted lamp, a shelf with decorative items, and a bedside table with a pillow.

3. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
HK$2,197
HK$2,768 total
includes taxes & fees
5 Oct - 6 Oct
Oyster Estate
Outdoor pool
Beach
Room
Room

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
HK$1,850
HK$2,984 total
includes taxes & fees
25 Oct - 26 Oct
Cliffside Resort Condominiums
A poolside area with a hat and towel on a lounge chair.
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.
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.

5. North Fork Resort

North Fork Resort
Greenport
HK$2,090
HK$2,387 total
includes taxes & fees
4 Oct - 5 Oct
North Fork Resort
Property amenity
Property amenity
Terrace/patio
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
4 Oct - 5 Oct
Shelter Island House
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 lobby with multiple seating areas, a kitchen area, and large windows providing natural light.
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.
HK$1,953
HK$2,232 total
includes taxes & fees
30 Oct - 31 Oct
Sag Harbor Inn
A beach with a wooden walkway along the shore, calm water, and a sunset sky.
A hotel room with a large bed, a sofa, a TV on a shelf, and a window with curtains.
A large, light blue two-story house with a steep roof, surrounded by greenery and a gravel driveway.
A backyard with a large chessboard, outdoor furniture, and a house.

8. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
  • Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
HK$2,459
HK$2,810 total
includes taxes & fees
1 Oct - 2 Oct
West Neck Guesthouse
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.
A spacious living room with a fireplace, comfortable seating, and large windows.
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.
HK$3,318
HK$4,170 total
includes taxes & fees
5 Oct - 6 Oct
Faraway Sag Harbor
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.
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 large, white, two-story building with a covered porch and a bicycle parked in front.
A modern hotel room with a bed, bedside table, and a view of the garden.

10. Topping Rose House

Topping Rose House
Bridgehampton
  • Serene outdoor pool creates luxurious oasis in the Hamptons; perfect for unwinding after coastal adventures.
HK$4,906
HK$5,633 total
includes taxes & fees
6 Oct - 7 Oct
Topping Rose House
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

Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Very good"
Rafael 1-night trip
Posted 1 hour 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 23 hours 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 4 days ago
Hilton Garden Inn Riverhead
Budget Host East End

Budget Host East End

8/10 Good
"Staff"
Harvey 2-night trip
Posted 8 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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