Southold Hotels with Swimming Pool

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Check availability on Southold Hotels with Swimming Pools

Tonight
28 Apr - 29 Apr
Tomorrow
29 Apr - 30 Apr
This weekend
1 May - 3 May
Next weekend
8 May - 10 May

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 RM1,425
RM1,628 total
includes taxes & fees
29 Apr - 30 Apr
Vine & Sand
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (307 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is RM308
RM355 total
includes taxes & fees
29 Apr - 30 Apr
Clinton Motel
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, (1,003 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is RM467
RM537 total
includes taxes & fees
27 May - 28 May
Quality Inn Old Saybrook - Westbrook
Down duvets, in-room safe, iron/ironing board, free cots/infant beds

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 RM792
RM905 total
includes taxes & fees
29 Apr - 30 Apr
The Penny Lane
Seasonal outdoor pool

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
The price is RM735
RM840 total
includes taxes & fees
29 Apr - 30 Apr
North Fork Cottages & RV Resort
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, (473 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 RM441
RM570 total
includes taxes & fees
30 Apr - 1 May
Hamlet 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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good
"It is a lovely hotel."
Kathleen 1-night trip
Posted 11 hours ago
Water's Edge Resort & Spa

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 Sparkling Pointe and Mattebella 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: Offers buffet, a seasonal outdoor pool and free self parking. Vine & Sand: Features a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access. The Bentley Hotel Southampton: Hotel, 1-minute walk from The Hamptons Beaches. Features daily, a seasonal outdoor pool and free self parking. Sag Harbor Inn: Offers 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 Sparkling Pointe, Mattebella Vineyards and Croteaux Vineyards 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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