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

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Check availability on Southold Hotels with Pool

This weekend
3 Jul - 5 Jul
Next weekend
10 Jul - 12 Jul

Our top choices for Southold hotels with a pool

Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (319 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is Rp1.595.058
Rp1.834.317 total
includes taxes & fees
30 Jun - 1 Jul
Clinton Motel
Seasonal outdoor pool

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (25 reviews)
The price is Rp4.887.329
Rp5.583.775 total
includes taxes & fees
1 Jul - 2 Jul
North Fork Resort
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, (481 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodation.
The price is Rp1.443.259
Rp1.659.748 total
includes taxes & fees
5 Jul - 6 Jul
Econo Lodge Inn & Suites Old Saybrook Westbrook
Reception

The Penny Lane

The Penny Lane
3.0 star property
Hampton Bays
9.0 out of 10, Wonderful, (81 reviews)
  • cleanliness
    Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.
The price is Rp4.776.034
Rp5.456.619 total
includes taxes & fees
14 Jul - 15 Jul
The Penny Lane
Lobby sitting area

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 Rp2.117.484
Rp2.435.107 total
includes taxes & fees
20 Jul - 21 Jul
Quality Inn Old Saybrook - Westbrook
Seasonal outdoor pool

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 Rp2.240.250
Rp2.559.486 total
includes taxes & fees
2 Jul - 3 Jul
Budget Host East End
Indoor pool, 2 outdoor pools, open 5:00 AM to 10:00 PM, pool umbrellas

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1,003 reviews)
  • cleanliness
    Swim into serenity with three breathtaking pools and luxurious loungers for perfect poolside days at this resort.
The price is Rp6.613.218
Rp8.053.251 total
includes taxes & fees
21 Jul - 22 Jul
Saybrook Point Resort & Marina
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, (486 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 Rp3.855.022
Rp4.982.674 total
includes taxes & fees
6 Jul - 7 Jul
Hamlet Inn
Children’s activities

Hampton's Vacation Inn

Hampton's Vacation Inn
2.5 star property
Hampton Bays
9.0 out of 10, Wonderful, (340 reviews)
  • cleanliness
    Soak in poolside bliss at this Hampton guesthouse with refreshing seasonal pool, tennis court, and nearby beach activities.
The price is Rp3.629.205
Rp4.146.434 total
includes taxes & fees
12 Jul - 13 Jul
Hampton's Vacation Inn
Seasonal outdoor pool

Ocean View Terrace Inn

Ocean View Terrace Inn
2.0 star property
Hampton Bays
8.6 out of 10, Excellent, (123 reviews)
  • cleanliness
    Beachside seasonal pool awaits with ocean adventures and relaxing massages nearby.
The price is Rp4.161.488
Rp6.041.685 total
includes taxes & fees
15 Jul - 16 Jul
Ocean View Terrace 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.
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Choose what matters most at hotels with a pool in Southold

Breakfast included
4 stars

Top Southold Hotel Reviews

Hotel Indigo Long Island - East End by IHG

Hotel Indigo Long Island - East End by IHG

8/10 Good
"Everything was great breakfast could have been better choices, more protein ideas less carbs ... Very carb heavy breakfast"
Grace 2-night trip
Posted 4 hours ago
Hotel Indigo Long Island - East End by IHG

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 The Hamptons Beaches, and then kick back and relax poolside at one of the accommodation options in Southold that travellers like for their pools.
What are some accommodation options 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 high-speed (wired) Internet access.
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?
Explore places such as The Hamptons Beaches while you're in the area. Make a point to visit attractions such as 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 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.