Find Hotels with a Pool in Southold, NY

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Check availability on Southold Hotels with a Pool

Check prices for these dates

Tonight
Aug 7 - Aug 8
Tomorrow
Aug 8 - Aug 9
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Top Southold Hotels with a Pool

Ocean Vista Resort
Indoor pool, a waterfall pool

Ocean Vista Resort

2.5 star property
9.0 out of 10, Wonderful, (184)
"It waa great for traveling with kids. Close to the beach and my kids loved the indoor pool!"
$195 nightly
The price is $222
Sep 1 - Sep 2
Total includes taxes and fees
Ocean Vista Resort
Windward Shores Ocean Resort
Seasonal outdoor pool

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (290)
"Easy checking in and out Easy access few steps to beach from first floor unit "
$237 nightly
The price is $271
Sep 2 - Sep 3
Total includes taxes and fees
Windward Shores Ocean Resort
Ocean theme Balcony-View Studio Apt w/ 1 BTH & Tub
A heated pool

Ocean theme Balcony-View Studio Apt w/ 1 BTH & Tub

10.0 out of 10, Exceptional, (1)
"Great stay. Unfortunately, they told us there was pickleball but there wasn’t. "
$470 nightly
The price is $526
Sep 4 - Sep 5
Total includes taxes and fees
Ocean theme Balcony-View Studio Apt w/ 1 BTH & Tub
Unit 823 - Ocean Colony Beach and Tennis Club
A heated pool

Unit 823 - Ocean Colony Beach and Tennis Club

10.0 out of 10, Exceptional, (1)
"We loved the ocean colony resort as it was centrally located but also felt very calm and peaceful - close to nature. We loved the apartment, and the amenities - though it was too cold for the pool. The proximity to the beach was unmatched and the services they provide (chairs, umbrellas, towels) are so nice. The section of beach is private, serene, and just gorgeous. Because we were so close to the water, we could fall asleep to the sound of waves and enjoy coffee on the porch overlooking the...
$482 nightly
The price is $540
Sep 1 - Sep 2
Total includes taxes and fees
Unit 823 - Ocean Colony Beach and Tennis Club
White Studio Apt w/ Balcony, Tub & Ocean view!
A heated pool

White Studio Apt w/ Balcony, Tub & Ocean view!

$482 nightly
The price is $540
Sep 4 - Sep 5
Total includes taxes and fees
White Studio Apt w/ Balcony, Tub & Ocean view!
The King 1BR Beachside Home | Tennis+Ocean+WiFiPKG
A heated pool

The King 1BR Beachside Home | Tennis+Ocean+WiFiPKG

10.0 out of 10, Exceptional, (1)
$575 nightly
The price is $645
Sep 1 - Sep 2
Total includes taxes and fees
The King 1BR Beachside Home | Tennis+Ocean+WiFiPKG
1 BR Beach Studio and Relax Balcony in Amangansett
A heated pool

1 BR Beach Studio and Relax Balcony in Amangansett

$575 nightly
The price is $645
Sep 1 - Sep 2
Total includes taxes and fees
1 BR Beach Studio and Relax Balcony in Amangansett
Pristine 1BR w/ loft, Corner Unit + Heated Pool
A heated pool

Pristine 1BR w/ loft, Corner Unit + Heated Pool

10.0 out of 10, Exceptional, (3)
"Loved it! Highly recommend! Beautiful property."
$695 nightly
The price is $779
Sep 3 - Sep 4
Total includes taxes and fees
Pristine 1BR w/ loft, Corner Unit + Heated Pool
A Touch of Ocean Studio, 1 BTH & Balcony Apt!
A heated pool

A Touch of Ocean Studio, 1 BTH & Balcony Apt!

10.0 out of 10, Exceptional, (5)
"Love the Ocean Colony. The unit was great for me and my husband. Love that it has its own private beach… and that they provide chairs and umbrellas. We will definitely be back"
$818 nightly
The price is $916
Aug 26 - Aug 27
Total includes taxes and fees
A Touch of Ocean Studio, 1 BTH & Balcony Apt!
Cozy Pad 2BR Beachside Home | TennisPoolFreePKG
A heated pool

Cozy Pad 2BR Beachside Home | TennisPoolFreePKG

$894 nightly
The price is $1,002
Sep 2 - Sep 3
Total includes taxes and fees
Cozy Pad 2BR Beachside Home | TennisPoolFreePKG
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.

Top Southold Hotel Reviews

Sound View Greenport

Sound View Greenport

10/10 Excellent
"Our stay was everything we were looking for, waterfront, easy on/off the beach from our room, lounge chairs and umbrellas on the beach and nearby pool. Sunsets were amazing, lobster rolls in the piano bar were incredible. One day there was an issue with the kitchen and they brough complimentary spread to the pool area. July is expensive but it was definitely worth it. We live on Long Island and didn't have to deal with flying issues. Just a 2 hour drive and 4 days of relaxing sun....."
Brian 3-night trip
Posted 2 days ago
Sound View Greenport

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 6 places to stay with pools. While you're visiting, you can explore sights such as Sparkling Pointe and Croteaux Vineyards, and then relax and unwind poolside at one of the accommodations in Southold that guests like for their pools.
What are some accommodations 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. Greenview Inn Riverhead: Offers 2 outdoor pools, an indoor pool, and a full-service spa. Sound View Greenport: Features 2 outdoor tennis courts, a seasonal outdoor pool, and continental. Saybrook Point Resort & Marina: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access.
How many pool hotels should I expect to find in Southold?
Expedia has 6 hotels in Southold for your poolside break.
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 Osprey's Dominion 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.