A calm lake with a forest in the background during sunset.

Find Hotels with a Pool in Southold, NY from CA $130

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Check availability on Southold Hotels with a Pool

Our top choices for Southold hotels with a pool

Seasonal outdoor pool, pool umbrellas, sun loungers

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (667 reviews)
  • cleanliness
    Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
The price is CA $439
CA $622 total
includes taxes & fees
Aug 10 - Aug 11
Sound View Greenport
Suite, 1 Bedroom, Terrace, Harbour View | Terrace/patio

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (630 reviews)
  • cleanliness
    Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
The price is CA $491
CA $633 total
includes taxes & fees
Aug 4 - Aug 5
The Harbor Front Inn
Seasonal outdoor pool

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (34 reviews)
The price is CA $587
CA $670 total
includes taxes & fees
Jul 26 - Jul 27
North Fork Resort
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (325 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is CA $137
CA $158 total
includes taxes & fees
Jul 22 - Jul 23
Clinton Motel
Property amenity

Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (61 reviews)
  • cleanliness
    Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.
The price is CA $443
CA $507 total
includes taxes & fees
Aug 13 - Aug 14
Shelter Island House
Desk, laptop workspace, iron/ironing board, rollaway beds (surcharge)

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, (483 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.
The price is CA $113
CA $130 total
includes taxes & fees
Jul 27 - Jul 28
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (273 reviews)
  • cleanliness
    Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
The price is CA $582
CA $726 total
includes taxes & fees
Jul 29 - Jul 30
Cliffside Resort Condominiums
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, (1,004 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is CA $178
CA $204 total
includes taxes & fees
Aug 18 - Aug 19
Quality Inn Old Saybrook - Westbrook
Seasonal outdoor pool, pool umbrellas, sun loungers

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (94 reviews)
  • cleanliness
    Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
The price is CA $963
CA $1,211 total
includes taxes & fees
Aug 20 - Aug 21
The Pridwin Hotel
Beach nearby

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very good, (42 reviews)
  • cleanliness
    Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
The price is CA $440
CA $502 total
includes taxes & fees
Jul 27 - Jul 28
West Neck Guesthouse
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

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"We enjoyed a beautiful, spacious room, excellent food, and both the indoor and outdoor pools, together with the sauna and stream rom. All were first-rate."
Matthew 2-night trip
Posted 8 hours 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 $130 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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