Find Hotels with a Pool in Southold, NY

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Check availability on Southold Hotels with a Pool

Tonight
May 5 - May 6
Tomorrow
May 6 - May 7
This weekend
May 8 - May 10
Next weekend
May 15 - May 17

Our top choices for Southold hotels with a pool

Seasonal outdoor pool

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.8 out of 10, Exceptional, (16 reviews)
"Our room and the entire home was beautifully and charmingly renovated, breakfast was delicious, the room was filled with thoughtful touches, and the pool and hot tub were lovely."
United States
Michelle
$353 nightly
The price is $403
May 6 - May 7
Total with taxes and fees
Vine & Sand
A heated pool

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Southold
$363 nightly
The price is $415
May 6 - May 7
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
A heated pool

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Southold
10.0 out of 10, Exceptional, (1 review)
"Great experience. Wonderful hosts. "
United States
Mark L.
$363 nightly
The price is $415
May 6 - May 7
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Outdoor pool, a heated pool

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Southold
10.0 out of 10, Exceptional, (1 review)
"Pool and hot tub divine."
United States
Jessica P.
$396 nightly
The price is $452
May 6 - May 7
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
A heated pool

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Southold
$396 nightly
The price is $452
May 6 - May 7
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (308 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
"The pool was great"
United States
Michelle
$77 nightly
The price is $89
May 6 - May 7
Total with taxes and fees
Clinton Motel
Individually decorated, individually furnished, desk, laptop workspace

Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
Old Saybrook
7.2 out of 10, Good, (472 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.
"Pool was open and, while small, it was clean and refreshing. The woman at the front desk was very kind and helpful - made me feel welcome. The property itself is a bit outdated but it looks like they are working to update it. the room was very clean and comfortable for our family of 3. Only issue was the AC system was VERY loud and woke me up every 20 minutes when it went off. I had to shut it off around 3 am and try to salvage my nights sleep. Not sure if this is all rooms or just bad luck on...
United States
Melissa
$76 nightly
The price is $87
May 12 - May 13
Total with taxes and fees
Econo Lodge Inn & Suites Old Saybrook Westbrook
Down comforters, free WiFi, bed sheets

The Penny Lane

The Penny Lane
2.0 star property
Hampton Bays
9.0 out of 10, Wonderful, (77 reviews)
  • cleanliness
    Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.
"The hotel was very clean and the location was very good. It was close to restaurants and beach."
United States
Anonymous traveler
$199 nightly
The price is $227
May 7 - May 8
Total with taxes and fees
The Penny Lane
Seasonal outdoor pool

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"Cabin was clean, well appointed and very comfortable. The staff immediately responded at 7am when we called to reset the hot water heater. The Solo fire pit looked very tempting but we did not have the time to enjoy that. will be back!"
United States
Kenn
$186 nightly
The price is $213
May 13 - May 14
Total with taxes and fees
North Fork Cottages & RV Resort
Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,005 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
"the pool was so relaxing"
United States
Kathleen
$118 nightly
The price is $136
May 26 - May 27
Total with taxes and fees
Quality Inn Old Saybrook - Westbrook
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.
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Choose what matters most at hotels with a pool in Southold

Breakfast included
4 stars

Hotels with pools and free breakfast in Southold

Interior
Vine & Sand

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.8 out of 10, Exceptional, (16)
$353 nightly
The price is $403
May 6 - May 7
Total with taxes and fees
Vine & Sand
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

Top Southold Hotel Reviews

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

8/10 Good
"Good value "
Joseph 2-night trip
Posted 1 day ago
Quality Inn Old Saybrook - Westbrook

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 5 places to stay with pools. While you're visiting, you can explore sights such as Sparkling Pointe and Mattebella 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: Features a private beach, a seasonal outdoor pool, and 2 bars. Sound View Greenport: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. The Bentley Hotel Southampton: Hotel, 1-minute walk from The Hamptons Beaches. Features daily, a seasonal outdoor pool, and free self parking. Sag Harbor Inn: Offers a seasonal outdoor pool, an indoor pool, and a private beach.
How many pool hotels should I expect to find 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 Horton Lane Beach and McCabe's Beach. Discover sights such as Sparkling Pointe, Mattebella Vineyards, and Croteaux Vineyards 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.

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