Find Hotels with a Pool in Southold, NY
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18 Sep - 20 SepOur top choices for Southold hotels with a pool
1. Sound View Greenport
Sound View GreenportGreenport
- Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
SAR 918
SAR 1,156 total
includes taxes & fees
1 Oct - 2 Oct
2. The Harbor Front Inn
The Harbor Front InnGreenport
- Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
SAR 899
SAR 1,134 total
includes taxes & fees
4 Oct - 5 Oct
3. Cliffside Resort Condominiums
Cliffside Resort CondominiumsGreenport
- Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
SAR 1,096
SAR 1,587 total
includes taxes & fees
30 Sep - 1 Oct
4. Shelter Island House
Shelter Island HouseShelter Island Heights
- Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.
SAR 756
SAR 863 total
includes taxes & fees
4 Oct - 5 Oct
SAR 1,126
SAR 1,287 total
includes taxes & fees
15 Sep - 16 Sep
6. The Bentley Hotel Southampton
The Bentley Hotel SouthamptonSouthampton
- Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
SAR 562
SAR 736 total
includes taxes & fees
27 Sep - 28 Sep
7. The Pridwin Hotel
The Pridwin HotelShelter Island Heights
- Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
SAR 1,904
SAR 2,393 total
includes taxes & fees
13 Sep - 14 Sep
8. Clinton Motel
Clinton MotelClinton
- Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
SAR 293
SAR 337 total
includes taxes & fees
14 Sep - 15 Sep
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Top Southold Hotel Reviews
Quality Inn Old Saybrook - Westbrook
10/10 Excellent
"Enjoyed the stay, staff were friendly and pleasant the whole time, Breakfast was excellent!"
The Hampton Maid
10/10 Excellent
"Our stay at The Hampton Maid was such a great choice. The entire hotel is absolutely charming—you can tell that every corner and every detail has been thoughtfully designed. The front desk staff was wonderful: so friendly, welcoming, and very clear with all the information. We loved the bungalow-style rooms, each with its own deck and parking, which gives you wonderful privacy between rooms. But what truly stole our hearts was the gorgeous, beautifully kept garden—a true green oasis that brings complete peace and lets you fully disconnect from city stress. The room was spotless, and the restaurant was phenomenal—we had breakfast there, and it was spectacular. On top of that, getting a pass to 7 local beaches for just $5 is an incredible perk. You really couldn't ask for more! It’s one of those places where you haven't even left yet, and you're already planning your return. Can't wait to go back!"
Saybrook Point Resort & Marina
10/10 Excellent
"Old Saybrook never disappoints. The rooms have been remodel Edinburgh the last six months but the resort has managed to retain its old world chatm. Eventhough there were three weddings at the property during our visit, the staff were attentive to us and we weren't as re remained their only guests. We will visit again."
Hilton Garden Inn Riverhead
10/10 Excellent
"Bartender was great. I got in late a wanted a beer so she took her time cleaning up so i could relax and have a beer! Great service."
Faraway Sag Harbor
8/10 Good
"Faraway has been renovated Beautifully. The food has improved since Baron's Cove. The pool would benefit improving service and perhaps combining the food / drinks servers and pool attendants. In addition since we have been guests of the older Hotel, Baron's Cove for 16 years it would have been meaningful to have the new staff welcome guests and perhaps give a priority rate or welcome massage etc."