Southold Hotel Guide - Hotels with Pool in Southold, New York
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4 Sept - 6 SeptOur 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.
€361
includes taxes & fees
15 Sept - 16 Sept
2. The Harbor Front Inn
The Harbor Front InnGreenport
- Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
€315
includes taxes & fees
8 Sept - 9 Sept
3. Cliffside Resort Condominiums
Cliffside Resort CondominiumsGreenport
- Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
€373
includes taxes & fees
21 Sept - 22 Sept
€315
includes taxes & fees
7 Sept - 8 Sept
5. Oyster Estate
Oyster EstateGreenport
- Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
€352
includes taxes & fees
7 Sept - 8 Sept
6. 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.
€579
includes taxes & fees
13 Sept - 14 Sept
7. 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.
€167
includes taxes & fees
28 Sept - 29 Sept
8. 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.
€310
includes taxes & fees
31 Aug - 1 Sept
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Top Southold Hotel Reviews
The Hampton Maid
10/10 Excellent
"Breakfast!"
Water's Edge Resort & Spa
10/10 Excellent
"Just an outstanding hotel in a breathtakingly beautiful setting!! I couldn’t be more impressed & look forward to returning! 10 stars!!"
Sound View Greenport
10/10 Excellent
"Front desk team super nice and accommodating!"
The Pridwin Hotel
8/10 Good
"lovely place. Had an issue with my AC and there was nobody around to fix it"
Budget Host East End
8/10 Good
"We came for the pool and enjoyed every minute of a few relaxing days poolside. Lush green grounds provided some shady picnic tables when it was time to get out of the sun. If you are looking for an inexpensive stay not far from the Hamptons or North Fork this is your place. Staff, especially, front desk, very nice, friendly and informative. Rooms had a mini fridge and comfy bed. A/C worked great. Try to get a poolside room. Hotel includes continental breakfast on weekends. Multiple excellent restaurant options nearby on Main Street. We would recommend Olga's for breakfast, offers outdoor/indoor seating. For dinner there is Cliff's Rendezvous steak house. Call and go when they offer their steak special night. Jerry and the Mermaid for seafood, also has outdoor/indoor seating by the water. There is Tweed's where you can try Buffalo. And a few hidden gems with great water views and outdoor seating -Turkuaz (Turkish food ) and Country Farm Kitchen. There is Atlantis Aquarium nearby, that also offers boat tours of the Peconic by day and booze cruises weekend eves. Suffolk Theatre offers well known artists in concert on the weekends. There are at least 4 breweries a short drive away and homemade ice cream at Snowflake and homemade chocolate at North Fork Chocolate & Eatery. Polish Town is nearby if you want Polish food try the Birchwood Restaurant or groceries from the town's deli's."
Hyatt Place Long Island East End
8/10 Good
"Booked the 2nd time as our first time last year was superb. This year, we booked same type of room and requested for 1st flr room so we'll be closer to the indoor pool but ended up being assigned to a 5th floor room with view of parking lot. Other than that, location was convenient as it's next to the aquarium. Though we might reconsider staying in another hotel next year we go back to the area."