Southold Hotel with Pool

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Check availability on Southold Hotel with Pool

Next weekend
29 May - 31 May
In two weeks
5 Jun - 7 Jun

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)
The price is HK$3,325
HK$3,798 total
includes taxes & fees
28 May - 29 May
Vine & Sand
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (311 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is HK$611
HK$703 total
includes taxes & fees
28 May - 29 May
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, (475 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodation.
The price is HK$623
HK$716 total
includes taxes & fees
25 May - 26 May
Econo Lodge Inn & Suites Old Saybrook Westbrook
Down duvets, 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 price is HK$1,841
HK$2,103 total
includes taxes & fees
26 May - 27 May
The Penny Lane
Seasonal outdoor pool

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (18 reviews)
The price is HK$2,010
HK$2,296 total
includes taxes & fees
26 May - 27 May
North Fork Resort
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)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is HK$926
HK$1,065 total
includes taxes & fees
23 Jun - 24 Jun
Quality Inn Old Saybrook - Westbrook
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, (477 reviews)
  • cleanliness
    Serene seasonal pool retreat with private beach access just 2 miles away offers the perfect summer escape on Long Island.
The price is HK$945
HK$1,221 total
includes taxes & fees
27 May - 28 May
Hamlet Inn
Seasonal outdoor pool

The Hampton Maid

The Hampton Maid
2.5 star property
Hampton Bays
9.2 out of 10, Wonderful, (702 reviews)
  • cleanliness
    Splash into summer at this Hampton motel, where the seasonal pool and massage services await.
The price is HK$1,704
HK$1,947 total
includes taxes & fees
27 May - 28 May
The Hampton Maid
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, (502 reviews)
  • cleanliness
    Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
The price is HK$1,559
HK$1,977 total
includes taxes & fees
27 May - 28 May
The Bentley Hotel Southampton
Seasonal outdoor pool

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (313 reviews)
  • cleanliness
    Dip into pool bliss just steps from the ocean at this resort with heated seasonal swimming and tennis courts.
The price is HK$1,522
HK$1,952 total
includes taxes & fees
25 May - 26 May
Windward Shores Ocean Resort
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

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

4/10 Poor
"The staff were really nice, the breakfast was good. The double beds were uncomfortable. They dipped in the middle and we could feel the springs. We did not have a full roll of tp in the bathroom and had to go ask for it at the front desk. We were in an adjoining room and could hear the people in the next room very clearly."
Phyllis 1-night trip
Posted 3 hours ago
Quality Inn Old Saybrook - Westbrook

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: Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Pier Blue Inn Old Saybrook - Essex: Features a private beach, a seasonal outdoor pool and 2 bars. The Bentley Hotel Southampton: Hotel, 1-minute walk from The Hamptons Beaches. Offers daily, a seasonal outdoor pool and free self parking. Sound View Greenport: Provides a seasonal outdoor pool, an indoor pool and a private beach.
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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