Find Hotels with a Pool in Southold, NY

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Check availability on Southold Hotels with a Pool

Tonight
Aug 1 - Aug 2
Tomorrow
Aug 2 - Aug 3
This weekend
Aug 1 - Aug 3
Next weekend
Aug 8 - Aug 10

Top Southold Hotels with a Pool

Clinton Motel
Situated in a landscaped area, this single-story building offers a convenient parking space.

Clinton Motel

2.5 star property
8.6 out of 10, Excellent, (261)
"For the money this reservation was a real win Clean lovely pool area convenient to everything"
The price is ₩110,109
₩126,625 total
includes taxes & fees
Aug 31 - Sep 1
Clinton Motel
Econo Lodge Inn & Suites Old Saybrook Westbrook
Surrounded by lush greenery, a serene pond with a central fountain offers a peaceful escape.

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
7.2 out of 10, Good, (439)
"Room was very comfortable. I would definitely use again."
The price is ₩112,241
₩129,077 total
includes taxes & fees
Aug 10 - Aug 11
Econo Lodge Inn & Suites Old Saybrook Westbrook
Quality Inn Old Saybrook - Westbrook
Relax by the oval-shaped pool surrounded by lounge chairs and a high ceiling with a grid-like pattern.

Quality Inn Old Saybrook - Westbrook

2.5 star property
7.6 out of 10, Good, (1001)
"Great location and pool, close to a wonderful restaurant "
The price is ₩154,013
₩177,115 total
includes taxes & fees
Aug 10 - Aug 11
Quality Inn Old Saybrook - Westbrook
Wainscott Woods Retreat
Exterior

Wainscott Woods Retreat

2.0 star property
10.0 out of 10, Exceptional, (1)
"HIDDEN GEM IN THE HEART OF HAMPTONS! What a special place to stay in the Hamptons! I am so happy we found this wonderful gem! This hotel is clean, quiet and well managed. The pool is beautiful the rooms are modern, sleek and clean! The grounds are beautifully manicured. The location is perfect! This new hotel has the charm of a bed and breakfast. The hotel is a short car ride from either East Hampton or Southampton which is perfect if you chose to explore all the little towns the Hampton's has...
The price is ₩1,630,723
₩1,863,101 total
includes taxes & fees
Aug 3 - Aug 4
Wainscott Woods Retreat
Greenporter Hotel
Relax by the fire pit surrounded by comfortable seating and a serene pool view.

Greenporter Hotel

2.0 star property
9.2 out of 10, Wonderful, (153)
"Great place "
The price is ₩212,064
₩242,283 total
includes taxes & fees
Sep 2 - Sep 3
Greenporter Hotel
Hampton's Vacation Inn
Relax by the pool with lounge chairs and a shaded seating area nearby.

Hampton's Vacation Inn

2.5 star property
9.0 out of 10, Wonderful, (293)
"Great place highly recommended. Quiet and cozy atmosphere. Pool, tennis court, volleyball court and onsite parking made the stay that much better. Amazing staff and super professional. "
The price is ₩332,417
₩379,778 total
includes taxes & fees
Aug 3 - Aug 4
Hampton's Vacation Inn
The Bentley Hotel Southampton
Relax by the pool surrounded by a scenic view and lounge in style on the tiled deck.

The Bentley Hotel Southampton

2.0 star property
9.6 out of 10, Exceptional, (302)
"Great place!"
The price is ₩395,834
₩492,007 total
includes taxes & fees
Aug 19 - Aug 20
The Bentley Hotel Southampton
Budget Host East End Hotel in Riverhead
Relax by the rectangular pool surrounded by a tiled deck and lounge chairs.

Budget Host East End Hotel in Riverhead

2.0 star property
6.6 out of 10, (729)
"Nice place"
The price is ₩144,256
₩164,814 total
includes taxes & fees
Aug 10 - Aug 11
Budget Host East End Hotel in Riverhead
Canoe Place Inn and Cottages
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Canoe Place Inn and Cottages

4.0 star property
10.0 out of 10, Exceptional, (48)
"Wonderful stay! "
The price is ₩809,089
₩979,843 total
includes taxes & fees
Sep 1 - Sep 2
Canoe Place Inn and Cottages
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.

Top Southold Hotel Reviews

Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Staff all very friendly and helpful"
Cynthia 1-night trip
Posted 2 days ago
Hyatt Place Long Island East End

Frequently asked questions

What's it like visiting Southold?
If lounging next to a pool is your idea of the perfect getaway, you may want to check out family-friendly Southold, which has 6 places to stay with pools. While you're visiting, you can explore sights such as Sparkling Pointe and Croteaux Vineyards, and then relax and unwind poolside at one of the accommodations in Southold that guests like for their pools.
What are some accommodations with pools in Southold?
The Shoals Suites and Slips: Offers buffet, a seasonal outdoor pool, and free self parking. Vine & Sand: Provides buffet, an indoor pool, and free self parking. Quality Inn Old Saybrook - Westbrook: Features a private beach, a seasonal outdoor pool, and 2 bars. Greenview Inn Riverhead: Offers 2 outdoor pools, an indoor pool, and a full-service spa. Pier Blue Inn Old Saybrook - Essex: Features 2 outdoor tennis courts, a seasonal outdoor pool, and continental.
How many pool hotels should I expect to find 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 McCabe's Beach and Horton Lane Beach. Discover sights such as Sparkling Pointe, Croteaux Vineyards, and Osprey's Dominion 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 with an outdoor swimming pool if you will be visiting Southold in the warmest months of August, July, or September when the average temp is 70°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or March when the average temp is 38°F.
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 venture out into the surrounding area, ride aboard one of the trains from Southold Station. Southold might not have many public transit options to choose from so consider renting a car to explore more.