Southold Hotels with Swimming Pool
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6 Sept - 7 SeptTomorrow
7 Sept - 8 SeptNext weekend
11 Sept - 13 SeptIn two weeks
18 Sept - 20 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.
RM1,183
RM1,698 total
includes taxes & fees
28 Sept - 29 Sept
2. The Harbor Front Inn
The Harbor Front InnGreenport
- Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
RM1,052
RM1,317 total
includes taxes & fees
4 Oct - 5 Oct
3. 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.
RM814
RM930 total
includes taxes & fees
4 Oct - 5 Oct
4. Cliffside Resort Condominiums
Cliffside Resort CondominiumsGreenport
- Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
RM1,180
RM1,709 total
includes taxes & fees
27 Sept - 28 Sept
RM1,300
RM1,485 total
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.
RM2,153
RM2,706 total
includes taxes & fees
7 Sept - 8 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.
RM582
RM767 total
includes taxes & fees
5 Oct - 6 Oct
8. Oyster Estate
Oyster EstateGreenport
- Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
RM1,391
RM1,753 total
includes taxes & fees
5 Oct - 6 Oct
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Top Southold Hotel Reviews
Budget Host East End
10/10 Excellent
"Clean room, accommodating staff Helpful front desk"
The Hampton Maid
10/10 Excellent
"Restaurant was exceptional"
Hampton's Vacation Inn
10/10 Excellent
"The property was beautiful. We can’t wait to go back!"
Hyatt Place Long Island East End
10/10 Excellent
"Everything was great. Breakfast is a highlight"
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."