Find Hotels with a Pool in Shelter Island, NY
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Sep 15 - Sep 16Tomorrow
Sep 16 - Sep 17This weekend
Sep 18 - Sep 20Next weekend
Sep 25 - Sep 27Our 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.
NT$6,368
NT$7,276 total
includes taxes & fees
Oct 4 - Oct 5
2. The Harbor Front Inn
The Harbor Front InnGreenport
- Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
NT$7,979
NT$10,023 total
includes taxes & fees
Oct 15 - Oct 16
3. Sound View Greenport
Sound View GreenportGreenport
- Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
NT$8,441
NT$10,552 total
includes taxes & fees
Oct 1 - Oct 2
4. West Neck Guesthouse
West Neck GuesthouseShelter Island Heights
- Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
NT$9,920
NT$11,334 total
includes taxes & fees
Oct 1 - Oct 2
NT$10,167
NT$11,616 total
includes taxes & fees
Sep 16 - Sep 17
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.
NT$19,202
NT$24,132 total
includes taxes & fees
Sep 16 - Sep 17
7. Cliffside Resort Condominiums
Cliffside Resort CondominiumsGreenport
- Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
NT$9,181
NT$13,322 total
includes taxes & fees
Oct 5 - Oct 6
8. Oyster Estate
Oyster EstateGreenport
- Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
NT$10,931
NT$13,772 total
includes taxes & fees
Oct 5 - Oct 6
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Top Shelter Island Hotel Reviews
Sound View Greenport
10/10 Excellent
"Great place on the water. Piano Bar is nice; good food & drink. All the staff was very friendly and helpful."
Ocean Surf Resort
10/10 Excellent
"Our room was poolside. Behind the pool were lounge chairs with a view of the ocean. Doesn't get any better than that! Pool doesn't close Labor Day. Stays open til mid October and is heated. Off the pool deck, is a pathway down to the beach. Slept with the door open so we could listen to the waves. Room had a stovetop, microwave, coffeemaker and mini fridge. Plates, glasses, pots, pans and utensils available for use. Bring your own food and drinks instead of paying for overpriced restaurant meals. Rooms were updated, clean, and comfy. Table for two right outside the sliding door. A few blocks away from Montauk village. Plenty of folks staying here but still quiet and peaceful."
Sun N Sound
8/10 Good
"Very nice and clean. Pool was excellent. Only complaint was that the bathroom sink and shower drains were slow to drain. I'll give it a 8/10"
Gurney's Montauk Resort & Seawater Spa
10/10 Excellent
"Absolutely gorgeous stay!"
Faraway Sag Harbor
10/10 Excellent
"Excellent hotel. Comfortable beds. Nice decorated. Very professional and friendly staff."
Kenny's Tipperary Inn
10/10 Excellent
"Very clean. Friendly and helpful staff."
Beachcomber Resort at Montauk
10/10 Excellent
"Very peaceful. See the ocean from the deck, Sauna is clean. Only AC was too loud & Shower water pressure was low. Uber to get around was expensive."
Water's Edge Resort & Spa
10/10 Excellent
"Everything is perfect of what we need for short getaway to wind down labor day weekend. Short ride to New York . Thank you Waters edge resort and Spa . Westbrook Ct ."
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- Elizabeth A. Morton National Wildlife Refuge
- Corey Creek Winery
- Off the Rocker
- Sparkling Pointe
- Visit Noyack
- Orient Beach State Park
- Railroad Museum of Long Island
- Sag Harbor Whaling and Historical Museum
- Greenport Carousel
- Orient Vacations
- Visit Peconic
- Longhouse Reserve
- Greenport Farmers' Market
- Visit Cutchogue
- The Style Bar
- Cedar Point County Park
- Croteaux Vineyards
- Shelter Island Historical Society
- Sunset Beach
- 67 Steps Beach
- Truman's Beach
- Kaplan Meadows Sanctuary
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