Southold Hotel with Pool

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Our top choices for Southold hotels with a pool

Hyatt Place Long Island East End

Hyatt Place Long Island East End
3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1,001 reviews)
"Tamara, who checked us in, made a great first impression. She was friendly, helpful, and very accommodating."
United States
Kameron
The price is HK$886
HK$1,012 total
includes taxes & fees
11 Feb - 12 Feb
Hyatt Place Long Island East End

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (609 reviews)
"Nice place"
United States
Mateusz
The price is HK$1,048
HK$1,421 total
includes taxes & fees
4 Feb - 5 Feb
Sound View Greenport

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (564 reviews)
"Everything was Great Immaculate hotel very good location sraff was great"
United States
latoya
The price is HK$1,048
HK$1,420 total
includes taxes & fees
16 Feb - 17 Feb
The Harbor Front Inn

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (15 reviews)
"Wonderful stay"
United States
Judy
Vine & Sand

The Preston House & Hotel

The Preston House & Hotel
3.5 star property
Riverhead
9.8 out of 10, Exceptional, (380 reviews)
"Very comfortable, clean, well-appointed room with a modern yet cozy feel. We stayed one night for a wedding. Would highly recommend!"
United States
Marcia
The price is HK$1,157
HK$1,322 total
includes taxes & fees
1 Mar - 2 Mar
The Preston House & Hotel

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (433 reviews)
"Adorable room"
United States
Martin
The price is HK$906
HK$1,043 total
includes taxes & fees
10 Feb - 11 Feb
The Bentley Hotel Southampton

Hotel Indigo Long Island - East End by IHG

Hotel Indigo Long Island - East End by IHG
3.5 star property
Riverhead
8.8 out of 10, Excellent, (1,002 reviews)
"The places lovely good restaurant. Nice dinner excellent complimentary breakfast."
United States
Caroline
The price is HK$929
HK$1,062 total
includes taxes & fees
16 Feb - 17 Feb
Hotel Indigo Long Island - East End by IHG

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1,002 reviews)
"Wonderful stay in a beautiful setting."
United States
Deborah
The price is HK$2,056
HK$2,559 total
includes taxes & fees
8 Feb - 9 Feb
Saybrook Point Resort & Marina

Residence Inn by Marriott New York Long Island East End

Residence Inn by Marriott New York Long Island East End
3.0 star property
Riverhead
9.0 out of 10, Wonderful, (1,001 reviews)
"great place,I loved it"
United States
Ryan
The price is HK$857
HK$979 total
includes taxes & fees
5 Feb - 6 Feb
Residence Inn by Marriott New York Long Island East End

Holiday Inn Express Hotel & Suites Long Island-East End by IHG

Holiday Inn Express Hotel & Suites Long Island-East End by IHG
2.5 star property
Riverhead
8.6 out of 10, Excellent, (1,004 reviews)
"Quality hotel"
United States
Richard
The price is HK$766
HK$875 total
includes taxes & fees
15 Feb - 16 Feb
Holiday Inn Express Hotel & Suites Long Island-East End by IHG
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.

Choose what matters most at hotels with a pool in Southold

Hotels with pools and free breakfast in Southold

Top Southold Hotel Reviews

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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