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

Southold Hotel with Pool

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Check availability on Southold Hotel with Pool

This weekend
26 Jun - 28 Jun
Next weekend
3 Jul - 5 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, (318 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is HK$698
HK$802 total
includes taxes & fees
28 Jun - 29 Jun
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 HK$2,914
HK$3,330 total
includes taxes & fees
12 Jul - 13 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 HK$631
HK$726 total
includes taxes & fees
8 Jul - 9 Jul
Econo Lodge Inn & Suites Old Saybrook Westbrook
Reception

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 HK$2,089
HK$2,387 total
includes taxes & fees
14 Jul - 15 Jul
The Penny Lane
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, (1,000 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
20 Jul - 21 Jul
Quality Inn Old Saybrook - Westbrook
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, (1,000 reviews)
  • cleanliness
    Swim into serenity with three breathtaking pools and luxurious loungers for perfect poolside days at this resort.
The price is HK$2,893
HK$3,523 total
includes taxes & fees
21 Jul - 22 Jul
Saybrook Point Resort & Marina
Children’s activities

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 HK$1,411
HK$1,612 total
includes taxes & fees
29 Jun - 30 Jun
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, (122 reviews)
  • cleanliness
    Beachside seasonal pool awaits with ocean adventures and relaxing massages nearby.
The price is HK$1,736
HK$2,535 total
includes taxes & fees
1 Jul - 2 Jul
Ocean View Terrace 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, (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 HK$1,792
HK$2,316 total
includes taxes & fees
13 Jul - 14 Jul
Hamlet Inn
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 HK$980
HK$1,120 total
includes taxes & fees
29 Jun - 30 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.
View all properties

Choose what matters most at hotels with a pool in Southold

Breakfast included
4 stars

Top Southold Hotel Reviews

The Hampton Maid

The Hampton Maid

10/10 Excellent
"Our stay at the Hampton maid was absolute perfection from start to finish. The representative at the front desk, went above and beyond to make us feel welcome, ensuring a seamless check-in and offering incredible personalized recommendations for the area. When we opened the door to our room, we could not believe the features that were offered to us for our stay. Refrigerator was filled with cold beverages for purchase also snacks, and other amenities located on the table near the window. The bathroom products they offered were top notch with incredible fragrances. The linens were crisp and clean, and the comforter was amazing. The pool was clean and inviting while the lounge chairs were comfortable, and they also offered pool towels that were extremely large and thirsty. Our first night we dined in the hotel restaurant and took advantage of the happy hour menu, which was extensive and reasonably priced . The presentation of each item that we ordered was flavorful and delicious. The bartender had extensive knowledge of the wine list and suggestions were also offered by the head chef. Upon the completion of our dinner we return to our room and sat outside on our deck. It felt like we were sitting in a mountain like setting as we enjoyed the serenity of the surroundings. We could not have picked a better spot and amore enjoyable two night retreat. This place is worth every penny"
James Vincent Donohue 2-night trip
Posted 1 hour ago
The Hampton Maid

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.

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