Search Hotels with Pool in Shelter Island
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28 Aug - 30 AugNext weekend
4 Sep - 6 SepOur top choices for Shelter Island hotels with a pool
1. The Harbor Front Inn
The Harbor Front InnGreenport
- Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
฿9,081
฿12,065 total
includes taxes & fees
8 Sept - 9 Sept
2. Sound View Greenport
Sound View GreenportGreenport
- Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
฿9,640
฿13,831 total
includes taxes & fees
15 Sept - 16 Sept
3. West Neck Guesthouse
West Neck GuesthouseShelter Island Heights
- Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
฿10,282
฿11,748 total
includes taxes & fees
31 Aug - 1 Sept
4. 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.
฿10,372
฿11,851 total
includes taxes & fees
7 Sept - 8 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.
฿17,606
฿22,127 total
includes taxes & fees
14 Sept - 15 Sept
฿11,709
฿13,377 total
includes taxes & fees
8 Sept - 9 Sept
7. Oyster Estate
Oyster EstateGreenport
- Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
฿11,160
฿14,061 total
includes taxes & fees
22 Sept - 23 Sept
8. Cliffside Resort Condominiums
Cliffside Resort CondominiumsGreenport
- Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
฿9,929
฿14,274 total
includes taxes & fees
21 Sept - 22 Sept
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Top Shelter Island Hotel Reviews
Montauk Yacht Club
10/10 Excellent
"Thank you for good service"
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."