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

Search Hotels with Pool in Southold

  • 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 Southold Hotels with Pool

Tonight
12 Oct - 13 Oct
Tomorrow
13 Oct - 14 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 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 spacious room with wicker furniture, large windows, and a view of the sea.
A beach bar with wooden chairs and a small table, overlooking the sea.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.

1. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
4.960.438 ₫
6.406.204 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Sound View Greenport
A swimming pool with lounge chairs and umbrellas, surrounded by a wooden deck and a view of boats.
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.
A neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
4.631.088 ₫
6.029.923 ₫ total
includes taxes & fees
2 Nov - 3 Nov
The Harbor Front Inn
Outdoor pool
Room
Room
Beach

3. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
4.372.885 ₫
7.866.381 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums
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 rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

4. North Fork Resort

North Fork Resort
Greenport
6.892.301 ₫
7.874.454 ₫ total
includes taxes & fees
13 Oct - 14 Oct
North Fork Resort
A poolside area with lounge chairs and yellow umbrellas.
A wooden shower enclosure with a tiled wall, a showerhead, and a toilet visible through the door.
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.

5. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
5.827.668 ₫
7.342.684 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Oyster Estate
Property amenity
Terrace/patio
Front of property – evening/night
Property amenity

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.
5.206.740 ₫
5.948.490 ₫ total
includes taxes & fees
13 Oct - 14 Oct
Shelter Island House
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A waterfront property with a large house, multiple boats docked, and lush greenery.
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.

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.
5.665.968 ₫
6.473.369 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn
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 hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.
A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.

8. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Dive into summer splendour at a tranquil pool retreat with chic cabanas and luxe loungers.
9.779.616 ₫
12.290.623 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Faraway Sag Harbor
A pool area with lounge chairs and umbrellas, a mural on the wall, and a clear view of the sky.
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.
A modern outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.

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.
3.699.696 ₫
4.226.903 ₫ total
includes taxes & fees
28 Oct - 29 Oct
The Bentley Hotel Southampton
A poolside area with lounge chairs, umbrellas, and a view of boats in the background.
A marina with boats docked, a fire feature, and outdoor seating with a bottle and glasses.
A modern hotel with a glass facade, a covered entrance, and a sign indicating it is a Hyatt Place.
A dining area with wooden paneling, a patterned floor, and a view of outdoor seating through large windows.

10. Hyatt Place Long Island East End

Hyatt Place Long Island East End
Riverhead
  • Take a dip in two refreshing pools at this Long Island hotel, where poolside relaxation meets marina adventure and family fun.
3.285.744 ₫
3.753.963 ₫ total
includes taxes & fees
3 Nov - 4 Nov
Hyatt Place Long Island East End
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
"Beautiful place. Staff were very helpful and polite."
Deborah 1-night trip
Posted 12 hours ago
Water's Edge Resort & Spa
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

10/10 Excellent
"The hotel is a little dated but clean. The staff are nice and the breakfast was good."
Dana 2-night trip
Posted 15 hours ago
Quality Inn Old Saybrook - Westbrook
Budget Host East End

Budget Host East End

10/10 Excellent
"La habitación estaba limpia, el baño también. Las camas talvez deberían ser más firmes, pero por lo demás la estadía en el hotel estuvo muy cómoda"
Juan 2-night trip
Posted 18 hours ago
Budget Host East End
The Hampton Maid

The Hampton Maid

10/10 Excellent
"Beautiful property. Lovely rooms."
Meredith 1-night trip
Posted 20 hours ago
The Hampton Maid
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"We changed our plans and spent all three afternoons at the spa and pool because it was so relaxing and lovely. The outdoor pool overlooked the marina and the indoor pool, sauna and whirpool helped invigorate us. The duck and risotto at the restaurant was excellent. The staff was incredibly helpful and attentive. We will be back again."
Leslie 2-night trip
Posted 21 hours ago
Saybrook Point Resort & Marina
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

8/10 Good
"Staff were very helpful, they printed some documents for me at the front desk. And, my room had reading lights over the bed. May not matter to most, but those lights are great for those of us who like to read in bed."
Darla 1-night trip
Posted 2 days ago
Hilton Garden Inn Riverhead
Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent
"We were pleased with the excellent location to Sag Harbor's Main Street and the Zagaya restaurant *upstairs. It was superb! The staff was very friendly and helpful. The rooms were small and the baths particularly small so just a heads up on that although the toiletries were really nice. The hotel has a great vibe at night with live music in the bar area on Thursday evenings. The weather was cool...absolutely gorgeous for early October so we didn't use the pool/cabanas (although it was heated). I did peek in the fitness room and it was very nice. Not enough time to check out the spa but there's always next time!"
SUSAN 4-night trip
Posted 3 days ago
Faraway Sag Harbor
Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Parking wasn’t convenient."
Carl 1-night trip
Posted 6 days ago
Hyatt Place Long Island East End

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.
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.

Explore a world of travel with Expedia