Hotels with a Pool in Southold
Free cancellation options if plans change
Earn rewards on every night you stay
Save more with Member Prices
Check prices for these dates
Hotels with a Pool in Southold
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, (1,000 reviews)
8.8/10
Excellent
(1,000 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 $303
$303
$365 total
includes taxes & fees
Jul 8 - Jul 9
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, (321 reviews)
8.6/10
Excellent
(321 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 $89
$89
$102 total
includes taxes & fees
Jul 13 - Jul 14
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, (1,001 reviews)
7.8/10
Good
(1,001 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
Jul 28 - Jul 29
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, (1,007 reviews)
9.6/10
Exceptional
(1,007 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 $399
$399
$484 total
includes taxes & fees
Jul 21 - Jul 22
9.2 out of 10, Wonderful, (722 reviews)
9.2/10
Wonderful
(722 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 8 - Jul 9
8.8 out of 10, Excellent, (319 reviews)
8.8/10
Excellent
(319 reviews)
Beachfront bliss awaits at this pristine resort where a seasonal pool, 2 tennis courts, and ocean views create perfect relaxation. Individually furnished rooms feature full kitchens, while attentive staff ensure a seamless stay.
Beachfront bliss awaits at this pristine resort where a seasonal pool, 2 tennis courts, and ocean views create perfect relaxation. Individually furnished rooms feature full kitchens, while attentive staff ensure a seamless stay.
The price is $472
$472
$567 total
includes taxes & fees
Jul 8 - Jul 9
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, (91 reviews)
9.6/10
Exceptional
(91 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 $592
$592
$744 total
includes taxes & fees
Jul 12 - Jul 13
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, (29 reviews)
9.4/10
Exceptional
(29 reviews)
The price is $372
$372
$425 total
includes taxes & fees
Jul 8 - Jul 9
Journey East Hampton
Journey East Hampton4.0 star property
East Hampton North
- Pool loungers
- Near the beach
9.2 out of 10, Wonderful, (185 reviews)
9.2/10
Wonderful
(185 reviews)
Sparkling waters of the seasonal pool (April-October) invite summer splashes amid lush garden surroundings. Families appreciate sun loungers, pool umbrellas, and the nearby playground, while adventurous souls can borrow bicycles to explore scenic Hamptons beaches.
Sparkling waters of the seasonal pool (April-October) invite summer splashes amid lush garden surroundings. Families appreciate sun loungers, pool umbrellas, and the nearby playground, while adventurous souls can borrow bicycles to explore scenic Hamptons beaches.
The price is $617
$617
$775 total
includes taxes & fees
Jul 21 - Jul 22
8.8 out of 10, Excellent, (620 reviews)
8.8/10
Excellent
(620 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 $422
$422
$534 total
includes taxes & fees
Jul 28 - Jul 29
Cliffside Resort Condominiums
Cliffside Resort Condominiums3.0 star property
Greenport
- Pool loungers
- On private beach
9.0 out of 10, Wonderful, (266 reviews)
9.0/10
Wonderful
(266 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 $374
$374
$470 total
includes taxes & fees
Jul 23 - Jul 24
9.0 out of 10, Wonderful, (84 reviews)
9.0/10
Wonderful
(84 reviews)
Crystal-blue water beckons from the seasonal outdoor pool, surrounded by loungers for soaking up sunshine between May and October. Seaside adventures continue with barbecue gatherings in the garden before retreating to air-conditioned comfort.
Crystal-blue water beckons from the seasonal outdoor pool, surrounded by loungers for soaking up sunshine between May and October. Seaside adventures continue with barbecue gatherings in the garden before retreating to air-conditioned comfort.
The price is $311
$311
$356 total
includes taxes & fees
Jul 20 - Jul 21
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, (1,002 reviews)
9.2/10
Wonderful
(1,002 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 $292
$292
$334 total
includes taxes & fees
Aug 2 - Aug 3
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, (830 reviews)
6.8/10
(830 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 9 - Jul 10
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, (482 reviews)
7.2/10
Good
(482 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 14 - Jul 15
9.4 out of 10, Exceptional, (642 reviews)
9.4/10
Exceptional
(642 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 $469
$469
$536 total
includes taxes & fees
Jul 13 - Jul 14
The Bentley Hotel Southampton
The Bentley Hotel Southampton2.0 star property
Southampton
- Pool loungers
- Near private beach
9.6 out of 10, Exceptional, (544 reviews)
9.6/10
Exceptional
(544 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 $305
$305
$373 total
includes taxes & fees
Jul 14 - Jul 15
Hotel Indigo Long Island - East End by IHG
Hotel Indigo Long Island - East End by IHG3.5 star property
Riverhead
- Pool loungers
8.8 out of 10, Excellent, (1,005 reviews)
8.8/10
Excellent
(1,005 reviews)
Sparkling waters await at this Art Deco retreat's sun-drenched pool area, complete with comfortable loungers and shady umbrellas. Guests rave about the clean facilities, excellent drink service, and convenient poolside dining at Bistro 72.
Sparkling waters await at this Art Deco retreat's sun-drenched pool area, complete with comfortable loungers and shady umbrellas. Guests rave about the clean facilities, excellent drink service, and convenient poolside dining at Bistro 72.
The price is $296
$296
$338 total
includes taxes & fees
Jul 12 - Jul 13
8.6 out of 10, Excellent, (583 reviews)
8.6/10
Excellent
(583 reviews)
Poolside perfection awaits at the seasonal outdoor oasis, complete with umbrellas and a beach bar. Beyond swimming, guests discover tennis courts, bicycles for rent, and an arcade room, all minutes from Cooper's Beach.
Poolside perfection awaits at the seasonal outdoor oasis, complete with umbrellas and a beach bar. Beyond swimming, guests discover tennis courts, bicycles for rent, and an arcade room, all minutes from Cooper's Beach.
The price is $441
$441
$531 total
includes taxes & fees
Jul 26 - Jul 27
9.8 out of 10, Exceptional, (16 reviews)
9.8/10
Exceptional
(16 reviews)
Seasonal swimming beckons from May through September at this sun-drenched Hamptons haven. Loungers surround the refreshing outdoor pool, while beach umbrellas await at the private shoreline just a mile away.
Seasonal swimming beckons from May through September at this sun-drenched Hamptons haven. Loungers surround the refreshing outdoor pool, while beach umbrellas await at the private shoreline just a mile away.
The price is $615
$615
$703 total
includes taxes & fees
Jul 8 - Jul 9
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.
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.
Corey Creek Winery
9.6/10 (5 reviews)
Travelers might want a tour of Corey Creek Winery, just one of the places to visit, and located 1.7 mi (2.7 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 Mattebella Vineyards, both within a short walk.