Hotels with a Pool in Southold
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Hotels with a Pool in Southold
Sound View Greenport
Sound View Greenport4.0 star property
Greenport
- Poolside bar
- Pool loungers
- On private beach
8.4 out of 10, Very Good, (667 reviews)
8.4/10
Very Good
(667 reviews)
Poolside paradise meets oceanfront splendor at this beachfront retreat featuring a seasonal outdoor pool with loungers and umbrellas. Sip cocktails from the poolside bar while admiring spectacular sunsets before enjoying fresh seafood at the waterfront restaurant.
Poolside paradise meets oceanfront splendor at this beachfront retreat featuring a seasonal outdoor pool with loungers and umbrellas. Sip cocktails from the poolside bar while admiring spectacular sunsets before enjoying fresh seafood at the waterfront restaurant.
The price is $320
$320
$451 total
includes taxes & fees
Aug 18 - Aug 19
8.8 out of 10, Excellent, (629 reviews)
8.8/10
Excellent
(629 reviews)
Dive into relaxation at the seasonal outdoor pool featuring stunning harbor vistas, plush loungers, and refreshing waters. Guests rave about the hotel's prime location, steps from shops and restaurants, plus the indulgent Italian linens and pillowtop mattresses awaiting after a swim.
Dive into relaxation at the seasonal outdoor pool featuring stunning harbor vistas, plush loungers, and refreshing waters. Guests rave about the hotel's prime location, steps from shops and restaurants, plus the indulgent Italian linens and pillowtop mattresses awaiting after a swim.
The price is $392
$392
$499 total
includes taxes & fees
Aug 5 - Aug 6
Cliffside Resort Condominiums
Cliffside Resort Condominiums3.0 star property
Greenport
- Pool loungers
- On private beach
9.0 out of 10, Wonderful, (274 reviews)
9.0/10
Wonderful
(274 reviews)
Swimming season shines at this bayside retreat's outdoor pool, complete with plush loungers for maximum relaxation. Beyond the refreshing waters, guests treasure direct beach access and stunning sunset views from furnished balconies.
Swimming season shines at this bayside retreat's outdoor pool, complete with plush loungers for maximum relaxation. Beyond the refreshing waters, guests treasure direct beach access and stunning sunset views from furnished balconies.
The price is $463
$463
$572 total
includes taxes & fees
Jul 29 - Jul 30
The Pridwin Hotel
The Pridwin Hotel4.0 star property
Shelter Island Heights
- Poolside bar
- Pool loungers
- On private beach
- Full-service spa
9.6 out of 10, Exceptional, (94 reviews)
9.6/10
Exceptional
(94 reviews)
Mountain biking adventures lead to refreshing dips in the seasonal outdoor pool, complete with luxurious loungers and cocktail service. After swimming, guests retreat to the spa for hydrotherapy or explore the private beach just steps away.
Mountain biking adventures lead to refreshing dips in the seasonal outdoor pool, complete with luxurious loungers and cocktail service. After swimming, guests retreat to the spa for hydrotherapy or explore the private beach just steps away.
The price is $646
$646
$812 total
includes taxes & fees
Jul 27 - Jul 28
Clinton Motel
Clinton Motel2.5 star property
Clinton
- Pool
- Free parking
- Free WiFi
- Air conditioning
- 24/7 front desk
8.6 out of 10, Excellent, (325 reviews)
8.6/10
Excellent
(325 reviews)
Refreshing dips await in the seasonal outdoor pool, open July through September at this well-maintained Connecticut retreat. Spacious, clean rooms feature refrigerators and coffee makers, while barbecue grills and garden views complete the experience.
Refreshing dips await in the seasonal outdoor pool, open July through September at this well-maintained Connecticut retreat. Spacious, clean rooms feature refrigerators and coffee makers, while barbecue grills and garden views complete the experience.
The price is $92
$92
$106 total
includes taxes & fees
Aug 23 - Aug 24
North Fork Resort
North Fork Resort3.0 star property
Greenport
- Pool
- Laundry facilities
- Pet friendly
- Free parking
- Free WiFi
- Air conditioning
9.4 out of 10, Exceptional, (34 reviews)
9.4/10
Exceptional
(34 reviews)
The price is $409
$409
$467 total
includes taxes & fees
Jul 28 - Jul 29
8.4 out of 10, Very Good, (61 reviews)
8.4/10
Very Good
(61 reviews)
Swim laps in the seasonal outdoor pool followed by handcrafted cocktails at the poolside bar. After exploring hiking trails on rental bicycles, guests can indulge in massage services before retiring to premium bedding.
Swim laps in the seasonal outdoor pool followed by handcrafted cocktails at the poolside bar. After exploring hiking trails on rental bicycles, guests can indulge in massage services before retiring to premium bedding.
The price is $316
$316
$361 total
includes taxes & fees
Jul 30 - Jul 31
8.2 out of 10, Very Good, (42 reviews)
8.2/10
Very Good
(42 reviews)
Cyclists and swimmers rejoice at this spotless bed & breakfast offering free bicycle rentals and a sparkling seasonal pool open May through September. Garden views and picnic areas complete the tranquil summer sanctuary.
Cyclists and swimmers rejoice at this spotless bed & breakfast offering free bicycle rentals and a sparkling seasonal pool open May through September. Garden views and picnic areas complete the tranquil summer sanctuary.
The price is $314
$314
$358 total
includes taxes & fees
Jul 26 - Jul 27
Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook2.5 star property
Old Saybrook
- Indoor pool
- Pool loungers
7.8 out of 10, Good, (1,006 reviews)
7.8/10
Good
(1,006 reviews)
Sparkling clean waters welcome swimmers from 9:00 AM to 9:00 PM daily in this serene indoor retreat. After enjoying hiking trails nearby, guests can unwind poolside before savoring American cuisine at The Comfort Cafe.
Sparkling clean waters welcome swimmers from 9:00 AM to 9:00 PM daily in this serene indoor retreat. After enjoying hiking trails nearby, guests can unwind poolside before savoring American cuisine at The Comfort Cafe.
The price is $118
$118
$136 total
includes taxes & fees
Aug 23 - Aug 24
The Bentley Hotel Southampton
The Bentley Hotel Southampton2.0 star property
Southampton
- Pool loungers
- Near private beach
9.6 out of 10, Exceptional, (548 reviews)
9.6/10
Exceptional
(548 reviews)
Pool enthusiasts delight in the pristine seasonal swimming spot, complete with sun loungers and umbrellas. Located near The Hamptons Beaches, this freshly remodeled hotel offers individually furnished rooms, plus nearby sailing and kayaking adventures.
Pool enthusiasts delight in the pristine seasonal swimming spot, complete with sun loungers and umbrellas. Located near The Hamptons Beaches, this freshly remodeled hotel offers individually furnished rooms, plus nearby sailing and kayaking adventures.
The price is $346
$346
$420 total
includes taxes & fees
Jul 29 - Jul 30
9.4 out of 10, Exceptional, (647 reviews)
9.4/10
Exceptional
(647 reviews)
Seasonal outdoor poolside lounging awaits at this harbor-adjacent retreat where clean, spacious rooms open to private balconies. Guests rave about the peaceful atmosphere, continental breakfast with a view, and proximity to Hamptons beaches.
Seasonal outdoor poolside lounging awaits at this harbor-adjacent retreat where clean, spacious rooms open to private balconies. Guests rave about the peaceful atmosphere, continental breakfast with a view, and proximity to Hamptons beaches.
The price is $509
$509
$582 total
includes taxes & fees
Aug 3 - Aug 4
Budget Host East End
Budget Host East End2.0 star property
Riverhead
- Pool
- Free parking
- Free WiFi
- Air conditioning
- 24/7 front desk
6.8 out of 10, (838 reviews)
6.8/10
(838 reviews)
Dive into the inviting seasonal pool, consistently praised by guests for its crystal-clear waters and clean surroundings. Beyond swimming, this well-maintained motel offers barbecue grills, laundry services, and comfortable rooms with 32-inch TVs.
Dive into the inviting seasonal pool, consistently praised by guests for its crystal-clear waters and clean surroundings. Beyond swimming, this well-maintained motel offers barbecue grills, laundry services, and comfortable rooms with 32-inch TVs.
The price is $125
$125
$143 total
includes taxes & fees
Jul 26 - Jul 27
Econo Lodge Inn & Suites Old Saybrook Westbrook
Econo Lodge Inn & Suites Old Saybrook Westbrook2.0 star property
Old Saybrook
- Near the beach
7.2 out of 10, Good, (484 reviews)
7.2/10
Good
(484 reviews)
Swimming pool waters beckon with refreshing relief after exploring Old Saybrook's city center. Recently refreshed rooms await with modern comforts, while the peaceful garden and terrace create perfect spots for afternoon unwinding.
Swimming pool waters beckon with refreshing relief after exploring Old Saybrook's city center. Recently refreshed rooms await with modern comforts, while the peaceful garden and terrace create perfect spots for afternoon unwinding.
The price is $81
$81
$93 total
includes taxes & fees
Jul 29 - Jul 30
Water's Edge Resort & Spa
Water's Edge Resort & Spa3.5 star property
Westbrook Center
- Indoor pool
- Pool loungers
- On private beach
- Hot tub
8.8 out of 10, Excellent, (1,003 reviews)
8.8/10
Excellent
(1,003 reviews)
Pool perfection awaits at this beachfront sanctuary featuring sparkling indoor and outdoor pools framed by private cabanas. Guests savor Italian cuisine at 3 on-site restaurants after rejuvenating with facials and massages at the spa.
Pool perfection awaits at this beachfront sanctuary featuring sparkling indoor and outdoor pools framed by private cabanas. Guests savor Italian cuisine at 3 on-site restaurants after rejuvenating with facials and massages at the spa.
The price is $319
$319
$384 total
includes taxes & fees
Jul 29 - Jul 30
Hyatt Place Long Island East End
Hyatt Place Long Island East End3.0 star property
Riverhead
- Outdoor pool
- Indoor pool
- Poolside bar
9.2 out of 10, Wonderful, (1,001 reviews)
9.2/10
Wonderful
(1,001 reviews)
Poolside perfection awaits with dual swimming options for year-round enjoyment. After swimming laps, guests can sip refreshing beverages at the poolside bar, then explore nearby kayaking adventures or relax in spotlessly clean rooms.
Poolside perfection awaits with dual swimming options for year-round enjoyment. After swimming laps, guests can sip refreshing beverages at the poolside bar, then explore nearby kayaking adventures or relax in spotlessly clean rooms.
The price is $273
$273
$312 total
includes taxes & fees
Aug 2 - Aug 3
8.6 out of 10, Excellent, (126 reviews)
8.6/10
Excellent
(126 reviews)
Kayak through gentle waves or practice beach yoga before cooling off in the seasonal outdoor pool. Sun loungers and beach umbrellas create perfect relaxation spots, while attentive staff ensure a carefree coastal getaway.
Kayak through gentle waves or practice beach yoga before cooling off in the seasonal outdoor pool. Sun loungers and beach umbrellas create perfect relaxation spots, while attentive staff ensure a carefree coastal getaway.
The price is $258
$258
$370 total
includes taxes & fees
Aug 5 - Aug 6
9.2 out of 10, Wonderful, (735 reviews)
9.2/10
Wonderful
(735 reviews)
Splash into summer relaxation at the seasonal outdoor pool, complete with comfortable seating and attentive towel service. Beyond aquatic enjoyment, guests savor international cuisine at R.AIRE restaurant after exploring hiking trails or kayaking adventures.
Splash into summer relaxation at the seasonal outdoor pool, complete with comfortable seating and attentive towel service. Beyond aquatic enjoyment, guests savor international cuisine at R.AIRE restaurant after exploring hiking trails or kayaking adventures.
The price is $435
$435
$497 total
includes taxes & fees
Jul 27 - Jul 28
Saybrook Point Resort & Marina
Saybrook Point Resort & Marina3.5 star property
Old Saybrook Center
- 2 outdoor pools
- Indoor pool
- Pool loungers
- Near the beach
- Hot tub
9.6 out of 10, Exceptional, (1,013 reviews)
9.6/10
Exceptional
(1,013 reviews)
Dive into 2 scenic outdoor pools or the indoor swimming sanctuary at this wellness-focused hotel. Beyond the refreshing waters, guests savor ocean views at Fresh Salt restaurant and indulge in rejuvenating spa treatments after kayaking adventures.
Dive into 2 scenic outdoor pools or the indoor swimming sanctuary at this wellness-focused hotel. Beyond the refreshing waters, guests savor ocean views at Fresh Salt restaurant and indulge in rejuvenating spa treatments after kayaking adventures.
The price is $409
$409
$505 total
includes taxes & fees
Aug 5 - Aug 6
8.6 out of 10, Excellent, (492 reviews)
8.6/10
Excellent
(492 reviews)
Poolside lounging takes center stage at this sun-soaked retreat with umbrella-shaded relaxation from May through September. Beyond the refreshing waters, guests discover hiking trails, water sports, and pristine beaches within minutes.
Poolside lounging takes center stage at this sun-soaked retreat with umbrella-shaded relaxation from May through September. Beyond the refreshing waters, guests discover hiking trails, water sports, and pristine beaches within minutes.
The price is $247
$247
$319 total
includes taxes & fees
Aug 3 - Aug 4
Holiday Inn Express & Suites Riverhead - Long Island by IHG
Holiday Inn Express & Suites Riverhead - Long Island by IHG2.5 star property
Riverhead
- Pool loungers
8.6 out of 10, Excellent, (1,000 reviews)
8.6/10
Excellent
(1,000 reviews)
Dive into the seasonal outdoor pool, complete with plush loungers and umbrellas for perfect summer relaxation. Beyond aquatic enjoyment, this hotel offers a 24-hour fitness center, free breakfast buffet, and easy access to local kayaking adventures.
Dive into the seasonal outdoor pool, complete with plush loungers and umbrellas for perfect summer relaxation. Beyond aquatic enjoyment, this hotel offers a 24-hour fitness center, free breakfast buffet, and easy access to local kayaking adventures.
The price is $210
$210
$240 total
includes taxes & fees
Aug 2 - Aug 3
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.
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 landmarks in Southold
Croteaux Vineyards
10.0/10 (12 reviews)
Travelers might want a tour of Croteaux Vineyards, just one of the places to visit, and located 1.5 mi (2.4 km) from central Southold.
Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy your tour, head to Mattebella Vineyards or Corey Creek Winery, both within a short walk.
Mattebella Vineyards
8.0/10 (4 reviews)
Travelers might want a tour of Mattebella Vineyards, just one of the places to visit, and located 1.4 mi (2.3 km) from central Southold.
Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy your tour, head to Croteaux Vineyards or Corey Creek Winery, both within a short walk.
Osprey's Dominion
9.6/10 (5 reviews)
Travelers might want a tour of Osprey's Dominion, just one of the places to visit, and located 1.9 mi (3 km) from central Southold.
Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy your tour, head to Sannino's Bella Vita Vineyard or Corey Creek Winery, both within a short walk.