Hotels with Swimming Pools in Shelter Island
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28 Aug - 30 AugOur top choices for Shelter Island hotels with a pool
1. 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.
S$462
includes taxes & fees
25 Aug - 26 Aug
2. The Harbor Front Inn
The Harbor Front InnGreenport
- Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
S$449
includes taxes & fees
8 Sept - 9 Sept
3. West Neck Guesthouse
West Neck GuesthouseShelter Island Heights
- Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
S$458
includes taxes & fees
23 Aug - 24 Aug
4. Sound View Greenport
Sound View GreenportGreenport
- Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
S$482
includes taxes & fees
15 Sept - 16 Sept
S$459
includes taxes & fees
13 Sept - 14 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.
S$858
includes taxes & fees
14 Sept - 15 Sept
7. Cliffside Resort Condominiums
Cliffside Resort CondominiumsGreenport
- Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
S$561
includes taxes & fees
13 Sept - 14 Sept
8. Oyster Estate
Oyster EstateGreenport
- Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
S$498
includes taxes & fees
7 Sept - 8 Sept
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Top Shelter Island Hotel Reviews
Kenny's Tipperary Inn
10/10 Excellent
"Very clean rooms and pet friendly! Good location"
Hampton's Vacation Inn
10/10 Excellent
"Great place to stay. The closing of the pool at 7pm is a bit early."
Sound View Greenport
10/10 Excellent
"Hotel very well situated with a nice beach and a great pool. The rooms were clean and spacious. There were a lot of families so we couldn’t just sit and enjoy the view with toddlers running around - but that was me 20 years ago. I would recommend but next time I would want to book the private patio rooms. Continental breakfast was great - all around fantastic stay."
Ocean Resort Inn
10/10 Excellent
"It was a great stay!"
Water's Edge Resort & Spa
8/10 Good
"Nice resort, very convenient. However, a little pricey and every time you turned around there was a gratuity. Food was ok, not great for the price paid though."
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