Find Hotels with a Pool in Southold, NY

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Check prices for these dates

Tonight
15 Nov - 16 Nov
Tomorrow
16 Nov - 17 Nov
Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov

Our top choices for Southold hotels with a pool

A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.

1. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (768 reviews)
  • cleanliness
    Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
The price is AED 546
AED 729 total
includes taxes & fees
14 Dec - 15 Dec
Sound View Greenport
A swimming pool with lounge chairs and umbrellas, surrounded by a wooden deck and a view of boats.

2. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
9.0 out of 10, Wonderful, (676 reviews)
  • cleanliness
    Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
The price is AED 472
AED 644 total
includes taxes & fees
13 Dec - 14 Dec
The Harbor Front Inn
A poolside area with sun loungers, a pool, and a building with a balcony.

3. Oyster Estate

Oyster Estate
4.0 star property
Greenport
9.2 out of 10, Wonderful, (302 reviews)
  • cleanliness
    Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
The price is AED 661
AED 833 total
includes taxes & fees
2 Dec - 3 Dec
Oyster Estate
Terrace/patio

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (300 reviews)
  • cleanliness
    Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
The price is AED 706
AED 1,214 total
includes taxes & fees
26 Nov - 27 Nov
Cliffside Resort Condominiums
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.

5. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (689 reviews)
  • cleanliness
    Swim into serenity at this charming Sag Harbor retreat with a seasonal outdoor pool and balcony views.
The price is AED 804
AED 919 total
includes taxes & fees
16 Nov - 17 Nov
Sag Harbor Inn
A poolside area with a hat and towel on a lounge chair.

6. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
The price is AED 1,145
AED 1,308 total
includes taxes & fees
23 Nov - 24 Nov
North Fork Resort
Pool

7. Seven - A Resort Style Inn

Seven - A Resort Style Inn
2.0 star property
Shelter Island Heights
The price is AED 1,336
AED 1,527 total
includes taxes & fees
21 Nov - 22 Nov
Seven - A Resort Style Inn
A pool area with umbrellas, potted plants, and a pathway leading to a building.

8. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (322 reviews)
  • cleanliness
    Dive into summer splendor at a tranquil pool retreat with chic cabanas and luxe loungers.
The price is AED 1,072
AED 1,347 total
includes taxes & fees
16 Dec - 17 Dec
Faraway Sag Harbor
A pool area with lounge chairs and umbrellas, a mural on the wall, and a clear view of the sky.

9. The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (619 reviews)
  • cleanliness
    Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
The price is AED 433
AED 495 total
includes taxes & fees
22 Nov - 23 Nov
The Bentley Hotel Southampton
A swimming pool with lounge chairs and umbrellas, surrounded by a forested area.

10. A Room At The Beach

A Room At The Beach
3.0 star property
Bridgehampton
9.2 out of 10, Wonderful, (107 reviews)
  • cleanliness
    Soak up sunshine and serene vibes at this Hamptons motel with a stylish outdoor pool.
The price is AED 1,088
AED 1,243 total
includes taxes & fees
16 Nov - 17 Nov
A Room At The Beach
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

A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
Sag Harbor Inn

Sag Harbor Inn

Sag Harbor Inn
Sag Harbor

10/10 Excellent

My stay was perfect. This family run hotel is outstanding, and great value for the money. Room (facing pool) was large, quiet and in perfect condition. Small private terrace with lounge chairs a big plus. Bathroom is large and modern with 5 star amenities (I appreciate that). Entire hotel feels like it was recently renovated. Will definitely stay here again!
United States
Anonymous traveler
Reviewed April 30, 2021
Sag Harbor Inn

Frequently Asked Questions

How many pool hotels should I expect to find in Southold?

Expedia has 5 hotels in Southold for your poolside break.

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: Features a seasonal outdoor pool, an indoor pool, and a private beach. Pier Blue Inn Old Saybrook - Essex: Offers a private beach, a seasonal outdoor pool, and 2 bars. Water's Edge Resort & Spa: Features 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. Sound View Greenport: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. The Atlantic Hotel: Hotel, 3-minute walk from The Hamptons Beaches. Offers spa services, a seasonal outdoor pool, and a snack bar/deli.

What is there to see and do in Southold?

Enjoy a stroll along the shore at McCabe's Beach and Horton Lane Beach. Discover sights such as Sparkling Pointe, Croteaux Vineyards, 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 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.