Southold Hotels with Swimming Pool

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Check availability on Southold Hotels with Swimming Pools

Tonight
27 Jan - 28 Jan
Tomorrow
28 Jan - 29 Jan
This weekend
30 Jan - 1 Feb
Next weekend
6 Feb - 8 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, pool umbrellas, pool loungers

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (608 reviews)
"Nice place"
United States
Mateusz
The price is RM532
RM722 total
includes taxes & fees
28 Jan - 29 Jan
Sound View Greenport
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, (563 reviews)
"Everything was Great Immaculate hotel very good location sraff was great"
United States
latoya
The price is RM465
RM645 total
includes taxes & fees
28 Jan - 29 Jan
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, (448 reviews)
"Room was in good condition however I found the shower to be extremely small despite having great water pressure and extremely nice temperature."
United States
gail
The price is RM343
RM443 total
includes taxes & fees
28 Jan - 29 Jan
Hamlet 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, (431 reviews)
"Adorable boutique hotel with charming unique touches. "
United States
Mary
The price is RM437
RM503 total
includes taxes & fees
2 Feb - 3 Feb
The Bentley Hotel Southampton
Indoor pool, open 9:00 AM to 9:00 PM, pool loungers

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,001 reviews)
"Was a clean room and the pool was warm and kids had fun. Breakfast was good and plenty of choices "
United States
pieter
The price is RM385
RM442 total
includes taxes & fees
15 Feb - 16 Feb
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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Top Southold Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"All was good at the hotel. No complaints"
Isabel 1-night trip
Posted 8 days ago
Saybrook Point Resort & Marina

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.

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