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Search Hotels with Swimming Pool in Southold

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Check availability on Southold Hotels with Swimming Pool

Our top choices for Southold hotels with a pool

Seasonal outdoor pool
Vine & Sand

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (13)
"This B&B, and its hosts, were simply amazing. I cannot recommend this place enough."
United States
Sandra
Vine & Sand
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (392)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is ₹10,276
₹11,830 total
includes taxes & fees
14 Dec - 15 Dec
The Bentley Hotel Southampton
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (440)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is ₹8,009
₹10,351 total
includes taxes & fees
12 Dec - 13 Dec
Hamlet Inn
Seasonal outdoor pool
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (296)
"Great staff and clean rooms"
United States
Tyler
The price is ₹7,011
₹8,063 total
includes taxes & fees
11 Dec - 12 Dec
Clinton Motel
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool loungers
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (544)
"Amazing property, rooms, and staff. Book a room with a balcony for amazing views!"
United States
Matthew
The price is ₹11,786
₹17,864 total
includes taxes & fees
24 Dec - 25 Dec
The Harbor Front Inn
Graybarn Cottage | Room amenity
Mill House Inn

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (73)
"We stayed at the Inn for our anniversary last weekend. We are devotees of bed and breakfast hotels and loved this one. We arrived to find a huge, and I mean, huge, bouquet of the most beautiful white roses waiting for us in the suite that they upgraded us to. Totally unexpected. These folks could not do enough for us. Breakfast was extremely nice, cooked to order with quality ingredients. Bed was extremely warm and comfortable. The management, the staff, can't say anything negative about...
United States
margaret
The price is ₹26,965
₹33,889 total
includes taxes & fees
11 Dec - 12 Dec
Mill House 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.
View all properties

Top Southold Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"My stay with Saybrook Point Resort & Marina was amazing. Clean room, amazing staff and amenities! I plan to return again!"
Michelle 2-night trip
Posted 2 days ago
Saybrook Point Resort & Marina

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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 The Old Field Vineyards and Sparkling Pointe, 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, an indoor pool and free self parking. Quality Inn Old Saybrook - Westbrook: Provides a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Features 2 outdoor swimming pools, an indoor pool and a full-service spa. Saybrook Point Resort & Marina: Offers a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa: Offers 2 outdoor tennis courts, a seasonal outdoor pool and free self parking.
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 The Old Field Vineyards, Sparkling Pointe 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 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.