Find Hotels with a Pool in Southold, NY from CA $105

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Check availability on Southold Hotels with a Pool

Tonight
Feb 28 - Mar 1
Tomorrow
Mar 1 - Mar 2
Next weekend
Mar 6 - Mar 8
In two weeks
Mar 13 - Mar 15

Our top choices for Southold hotels with a pool

Seasonal outdoor pool

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (15 reviews)
"Wonderful stay"
United States
Judy
Vine & Sand
A heated pool

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Southold
The price is CA $428
CA $556 total
includes taxes & fees
Mar 1 - Mar 2
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
A heated pool

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Southold
10.0 out of 10, Exceptional, (1 review)
"Great experience. Wonderful hosts. "
United States
Mark L.
The price is CA $428
CA $556 total
includes taxes & fees
Mar 1 - Mar 2
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Outdoor pool, a heated pool

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Southold
10.0 out of 10, Exceptional, (1 review)
"Must like historical houses and little sausage-shaped dogs. A seamless blend of old and mod. Room is meticulously shiny clean. Substantial bedding designed for a good night’s sleep. High-end details (furnishings, footed tub with heat lamp and fluffy robes), culture (gallery), included breakfast is simple perfection due to high-quality ingredients/sourcing (fresh pastries, eggs, butter, fruit). Pool and hot tub divine. Our hosts are upbeat and fun and really went beyond for us. There are great...
United States
Jessica P.
The price is CA $471
CA $613 total
includes taxes & fees
Mar 1 - Mar 2
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
A heated pool

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Southold
The price is CA $471
CA $613 total
includes taxes & fees
Mar 1 - Mar 2
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (302 reviews)
"The room was comfortable and clean. A good value for the money."
United States
Michael
The price is CA $106
CA $122 total
includes taxes & fees
Mar 1 - Mar 2
Clinton Motel
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, (453 reviews)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is CA $146
CA $189 total
includes taxes & fees
Mar 1 - Mar 2
Hamlet Inn
Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,001 reviews)
"Hotel was very clean, staff was wonderful and the pool was so relaxing. It was a quick visit but definitely would stay again if I was in that area. "
United States
Kathleen
The price is CA $138
CA $159 total
includes taxes & fees
Mar 9 - Mar 10
Quality Inn Old Saybrook - Westbrook
Exterior

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
Southampton
8.6 out of 10, Excellent, (207 reviews)
"Staff was amazing. The room was very clean. I've stayed here numerous times, even on the night before my wedding as I was married in the Hamptons and I highly recommend! "
United States
Martine
The price is CA $162
CA $194 total
includes taxes & fees
Mar 29 - Mar 30
Southampton Long Island Hotel
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, (467 reviews)
"All good it met our expectations as a budget hotel. Large clean room bed was comfortable although the pillows were past it. "
United States
Hilary
The price is CA $91
CA $105 total
includes taxes & fees
Mar 9 - Mar 10
Econo Lodge Inn & Suites Old Saybrook Westbrook
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

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Hotels with pools and free breakfast in Southold

Interior
Vine & Sand

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (15)
Vine & Sand
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

Top Southold Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Great room clean and comfortable."
Jeffrey 3-night trip
Posted 1 day ago
Saybrook Point Resort & Marina

Frequently asked questions

What are the best hotels in Southold with outdoor pools?
Vine & Sand is a charming 3-star hotel in Southold that offers a delightful outdoor pool, great for families looking to relax after a day of adventure. Guests rave about the lovely rooms, making it a comfortable choice for travellers of all kinds.

In addition to its inviting pool, Vine & Sand provides a range of amenities that enhance the stay for families. Enjoy complimentary breakfast on weekends, and take advantage of free WiFi to stay connected or plan your excursions. The hotel also offers self-parking at no extra cost, making it convenient for those driving to the area. With bicycles available for guests, exploring the beautiful surroundings becomes an enjoyable family activity.
How much does a hotel with outdoor pool in Southold cost?
Enjoy staying in a hotel in Southold with an outdoor pool. You can find a great deal from CA $105 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Are there hotels in Southold with outdoor pool cabanas or loungers?
Vine & Sand is a charming 3-star hotel in Southold that offers a delightful outdoor pool area, superb for families looking to relax in the sun. Guests have praised the lovely rooms, making it a cozy retreat after a day of adventure.

The outdoor pool features beach sun loungers, allowing you to soak up the sun comfortably while enjoying the serene surroundings. Additionally, the hotel provides convenient amenities like free WiFi and complimentary breakfast on weekends, enhancing your stay with quality and value.
Is it cheaper to book flights and a hotel in Southold as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package.
How can I save on a hotel in Southold with Expedia?
Before booking your Southold hotel, remember to join Expedia's free travel rewards program—One Key™. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel with an outdoor pool in Southold for you.

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