Find Hotels with a Pool in Southold, NY from CA $113

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Check availability on Southold Hotels with a Pool

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 CA $470
CA $537 total
includes taxes & fees
Apr 21 - Apr 22
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 $440
CA $569 total
includes taxes & fees
Apr 19 - Apr 20
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)
The price is CA $440
CA $569 total
includes taxes & fees
Apr 19 - Apr 20
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)
The price is CA $479
CA $619 total
includes taxes & fees
Apr 19 - Apr 20
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 $479
CA $619 total
includes taxes & fees
Apr 19 - Apr 20
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, (306 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is CA $109
CA $125 total
includes taxes & fees
Apr 19 - Apr 20
Clinton Motel
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, (1,000 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is CA $139
CA $160 total
includes taxes & fees
Apr 27 - Apr 28
Quality Inn Old Saybrook - Westbrook
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, (470 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.
The price is CA $98
CA $113 total
includes taxes & fees
Apr 23 - Apr 24
Econo Lodge Inn & Suites Old Saybrook Westbrook
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 CA $255
CA $292 total
includes taxes & fees
Apr 19 - Apr 20
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, (469 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 CA $153
CA $198 total
includes taxes & fees
Apr 30 - May 1
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

Hotels with pools and free breakfast in Southold

Interior
Vine & Sand

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.8 out of 10, Exceptional, (16)
The price is CA $470
CA $537 total
includes taxes & fees
Apr 21 - Apr 22
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
"Everything was super clean and staff was friendly and helpful. "
Katherine 1-night trip
Posted 2 days 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 $113 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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