Southold Hotels with Swimming Pool

  • 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 Swimming Pools

Tonight
3 Feb - 4 Feb
Tomorrow
4 Feb - 5 Feb
This weekend
6 Feb - 8 Feb
Next weekend
13 Feb - 15 Feb

Our top choices for Southold hotels with a pool

Seasonal outdoor pool

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (15 reviews)
"Wonderful stay"
United States
Judy
Vine & Sand
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool loungers

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (564 reviews)
"Everything was Great Immaculate hotel very good location sraff was great"
United States
latoya
The price is RM529
RM718 total
includes taxes & fees
9 Feb - 10 Feb
The Harbor Front Inn
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (433 reviews)
"Adorable room"
United States
Martin
The price is RM458
RM527 total
includes taxes & fees
10 Feb - 11 Feb
The Bentley Hotel Southampton
Indoor pool, outdoor pool

Hyatt Place Long Island East End

Hyatt Place Long Island East End
3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1,001 reviews)
"Tamara, who checked us in, made a great first impression. She was friendly, helpful, and very accommodating."
United States
Kameron
The price is RM424
RM484 total
includes taxes & fees
4 Feb - 5 Feb
Hyatt Place Long Island East End
Seasonal outdoor pool

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (305 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
The price is RM522
RM682 total
includes taxes & fees
4 Feb - 5 Feb
Windward Shores Ocean Resort
Seasonal outdoor pool, pool umbrellas, pool loungers

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (609 reviews)
"Nice place"
United States
Mateusz
The price is RM529
RM718 total
includes taxes & fees
9 Feb - 10 Feb
Sound View Greenport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Choose what matters most at hotels with a pool in Southold

4 stars
5 stars

Top Southold Hotel Reviews

Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Tamara, who checked us in, made a great first impression. She was friendly, helpful, and very accommodating."
Kameron 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 6 places to stay with pools. During your visit, you can explore sights such as Sparkling Pointe and Croteaux Vineyards, and then kick back and relax poolside at one of the accommodation options in Southold that guests like for their pools.
What are some accommodation options with pools in Southold?
The Shoals Suites and Slips: Features a private beach, a seasonal outdoor pool and 2 bars. Pier Blue Inn Old Saybrook - Essex: Offers an indoor pool, an outdoor pool and a snack bar/deli. Sound View Greenport: Features a seasonal outdoor pool, an indoor pool and a private beach. Hilton Garden Inn Riverhead: Offers a seasonal outdoor pool, an indoor pool and 2 hot tubs. Water's Edge Resort & Spa: Provides an indoor pool, an outdoor pool and 2 bars.
How many pool hotels are there in Southold?
Expedia has 6 hotels in Southold for your poolside break.
What is there to see and do in Southold?
Enjoy a stroll along the shore at Horton Lane Beach and McCabe's 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