A calm lake with a forest in the background during sunset.

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Our top choices for Southold hotels with a pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (318 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is AED 327
AED 376 total
includes taxes & fees
29 Jun - 30 Jun
Clinton Motel

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (25 reviews)
The price is AED 899
AED 1,027 total
includes taxes & fees
28 Jun - 29 Jun
North Fork Resort

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, (481 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.
The price is AED 296
AED 340 total
includes taxes & fees
7 Jul - 8 Jul
Econo Lodge Inn & Suites Old Saybrook Westbrook

The Penny Lane

The Penny Lane
2.0 star property
Hampton Bays
9.0 out of 10, Wonderful, (80 reviews)
  • cleanliness
    Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.
The price is AED 964
AED 1,102 total
includes taxes & fees
14 Jul - 15 Jul
The Penny Lane

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,000 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is AED 434
AED 499 total
includes taxes & fees
19 Jul - 20 Jul
Quality Inn Old Saybrook - Westbrook

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1,000 reviews)
  • cleanliness
    Swim into serenity with three breathtaking pools and luxurious loungers for perfect poolside days at this resort.
The price is AED 1,172
AED 1,439 total
includes taxes & fees
29 Jun - 30 Jun
Saybrook Point Resort & Marina

Hampton's Vacation Inn

Hampton's Vacation Inn
2.5 star property
Hampton Bays
9.0 out of 10, Wonderful, (337 reviews)
  • cleanliness
    Soak in poolside bliss at this Hampton guesthouse with refreshing seasonal pool, tennis court, and nearby beach activities.
The price is AED 661
AED 755 total
includes taxes & fees
29 Jun - 30 Jun
Hampton's Vacation Inn

Ocean View Terrace Inn

Ocean View Terrace Inn
2.0 star property
Hampton Bays
8.6 out of 10, Excellent, (122 reviews)
  • cleanliness
    Beachside seasonal pool awaits with ocean adventures and relaxing massages nearby.
The price is AED 813
AED 1,188 total
includes taxes & fees
1 Jul - 2 Jul
Ocean View Terrace Inn

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (485 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 AED 823
AED 1,064 total
includes taxes & fees
7 Jul - 8 Jul
Hamlet Inn

Budget Host East End

Budget Host East End
2.0 star property
Riverhead
6.8 out of 10, (827 reviews)
  • cleanliness
    Escape summer heat at this serene riverfront motel with a clean, seasonal pool.
The price is AED 459
AED 525 total
includes taxes & fees
28 Jun - 29 Jun
Budget Host East End
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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Frequently asked questions

What's it like visiting Southold?
If lounging next to a pool is your idea of the perfect getaway, you may want to check out family-friendly Southold, which has 5 places to stay with pools. While you're visiting, you can explore sights such as The Hamptons Beaches, and then relax and unwind poolside at one of the accommodations in Southold that travelers like for their pools.
What are some accommodations with pools in Southold?
The Shoals Suites and Slips: Provides a private beach, a seasonal outdoor pool, and 2 bars. Pier Blue Inn Old Saybrook - Essex: Hotel located near The Hamptons Beaches. Features 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. Sound View Greenport: Hotel located near The Hamptons Beaches. Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. The Atlantic Hotel: Features a seasonal outdoor pool, an indoor pool, and a private beach. The Bentley Hotel Southampton: Hotel located near Splish Splash Water Park. Provides a snack bar/deli, a seasonal outdoor pool, and complimentary wired internet access.
How many pool hotels should I expect to find in Southold?
Expedia has 5 hotels in Southold for your poolside break.
What is there to see and do in Southold?
Explore places like The Hamptons Beaches while you're in the area. Make a point to visit attractions like Horton Lane Beach and McCabe's Beach.
When is the best time to book a hotel with a pool in Southold?
You may want to think about a place to stay with an outdoor swimming pool if you will be visiting Southold in the warmest months of August, July, or September when the average temp is 70°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or March when the average temp is 38°F.
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 venture out into the surrounding area, ride aboard one of the trains from Southold Station. Southold might not have many public transit options to choose from so consider renting a car to explore more.