Hotels with Swimming Pool in Southold, New York
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Aug 23 - Aug 24Tomorrow
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Aug 28 - Aug 30In two weeks
Sep 4 - Sep 6Our 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.
P16,733
P24,406 total
includes taxes & fees
Sep 15 - Sep 16
2. The Harbor Front Inn
The Harbor Front InnGreenport
- Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
P17,048
P22,650 total
includes taxes & fees
Sep 8 - Sep 9
3. Cliffside Resort Condominiums
Cliffside Resort CondominiumsGreenport
- Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
P18,914
P27,112 total
includes taxes & fees
Sep 7 - Sep 8
P19,828
P22,654 total
includes taxes & fees
Sep 7 - Sep 8
5. Oyster Estate
Oyster EstateGreenport
- Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
P20,088
P25,309 total
includes taxes & fees
Sep 7 - Sep 8
6. Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - WestbrookOld Saybrook
- Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
P6,242
P7,179 total
includes taxes & fees
Sep 13 - Sep 14
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.
P32,972
P41,438 total
includes taxes & fees
Sep 13 - Sep 14
8. 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.
P9,380
P12,260 total
includes taxes & fees
Sep 20 - Sep 21
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Top Southold Hotel Reviews
The Hampton Maid
8/10 Good
"The hotel has a sort of New England charm. The rooms are good sized and ours had a nice balcony overlooking the gardens. Prices were pretty reasonable for the Hamptons in the middle of Summer, although someone else staying there told us that the breakfast was not particularly good and yet expensive. We decided to take breakfast elsewhere. I would certainly return to the Hampton Maid if I ever go back to the area."
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."
Sound View Greenport
10/10 Excellent
"The views are amazing! The breakfast was a great perk. Short drive to town but you really don't need to leave the grounds with bar/restaurant/beach/pool all there."
Faraway Sag Harbor
10/10 Excellent
"Great vibe and decor. Super Cozy and elegant. Best Hamptons stay! Can’t wait to come back next year."