Southold Hotels with Swimming Pool

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Check availability on Southold Hotels with Swimming Pools

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
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, (468 reviews)
"All good it met our expectations as a budget hotel. Large clean room bed was comfortable although the pillows were past it. "
United States
Hilary
The price is RM263
RM303 total
includes taxes & fees
22 Mar - 23 Mar
Econo Lodge Inn & Suites Old Saybrook Westbrook
Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,002 reviews)
"nice area and quiet...eat and drink in the same place"
United States
michael
The price is RM364
RM418 total
includes taxes & fees
22 Mar - 23 Mar
Quality Inn Old Saybrook - Westbrook
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (303 reviews)
"I enjoyed my stay at the Clinton Motel. The room had everything I needed for my one night stay. The front desk personnel were helpful and courteous. "
United States
william
The price is RM306
RM352 total
includes taxes & fees
24 Mar - 25 Mar
Clinton Motel
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, (572 reviews)
"Room was beautiful and everyone who worked there was very nice. We’d love to go back! "
United States
Mary
The price is RM526
RM714 total
includes taxes & fees
15 Mar - 16 Mar
The Harbor Front Inn
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (458 reviews)
"Excellent host & very clean stay! Host was very helpful with info about area & very accommodating!!"
United States
Lisa
The price is RM385
RM498 total
includes taxes & fees
14 Mar - 15 Mar
Hamlet Inn
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

Top Southold Hotel Reviews

Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"The bar and amenities and food were good"
oriana 2-night trip
Posted 9 hours ago
Hilton Garden Inn Riverhead

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 Croteaux Vineyards and Horton Lane Beach, 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: Offers buffet, a seasonal outdoor pool and free self parking. Vine & Sand: Provides a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa: Features a seasonal outdoor pool, an indoor pool and 2 hot tubs. Residence Inn by Marriott New York Long Island East End: Offers a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access.
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 Horton Lane Beach and McCabe's Beach. Discover sights such as Croteaux Vineyards, Osprey's Dominion 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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