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29 Aug - 30 AugTomorrow
30 Aug - 31 AugNext weekend
4 Sep - 6 SepIn two weeks
11 Sep - 13 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.
฿9,710
฿13,931 total
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.
฿9,147
฿12,153 total
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.
฿10,001
฿14,377 total
includes taxes & fees
21 Sept - 22 Sept
฿11,736
฿13,408 total
includes taxes & fees
8 Sept - 9 Sept
5. 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.
฿17,647
฿22,177 total
includes taxes & fees
14 Sept - 15 Sept
6. Oyster Estate
Oyster EstateGreenport
- Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
฿10,700
฿13,482 total
includes taxes & fees
7 Sept - 8 Sept
7. 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.
฿10,396
฿11,878 total
includes taxes & fees
10 Sept - 11 Sept
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.
฿4,997
฿6,531 total
includes taxes & fees
15 Sept - 16 Sept
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Top Southold Hotel Reviews
Hampton's Vacation Inn
10/10 Excellent
"A short stay to visit our daughter turned into a mini vacation. Lovely grounds comfortable and clean amenities, all well maintained. Did not see staff in person but responsive by text and phone."
Budget Host East End
10/10 Excellent
"Todo me gustó bonito lugar para ospedarse"
The Hampton Maid
10/10 Excellent
"The staff was welcoming. Room was spotless. Water pressure in the shower phenomenal. Proximity to Ponquogue & Tiana Beaches excellent. Beds and pillows very comfortable. Will definitely return!"
Saybrook Point Resort & Marina
10/10 Excellent
"The best of the best! This was our 5th stay at Saybrook point and each year we look forward to going back. I can’t say enough good things. Do take advantage of all the amenities the hotel has to offer. Scenic bike ride, passes to the beach, shuttle services to and from town, amazing restaurants and the pool facilities. It’s a gem of a hotel and the town itself is even better."
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"
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."