Search Hotels with Swimming Pool in Shelter Island Heights
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18 Sept - 20 SeptOur top choices for Shelter Island Heights 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.
₹19,084
₹21,802 total
includes taxes & fees
4 Oct - 5 Oct
2. 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.
₹46,525
₹58,470 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.
₹29,728
₹33,964 total
includes taxes & fees
10 Sept - 11 Sept
4. The Harbor Front Inn
The Harbor Front InnGreenport
- Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
₹22,691
₹28,633 total
includes taxes & fees
4 Oct - 5 Oct
5. Sound View Greenport
Sound View GreenportGreenport
- Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
₹22,923
₹28,898 total
includes taxes & fees
1 Oct - 2 Oct
₹28,436
₹32,488 total
includes taxes & fees
10 Sept - 11 Sept
7. Cliffside Resort Condominiums
Cliffside Resort CondominiumsGreenport
- Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
₹27,677
₹40,074 total
includes taxes & fees
30 Sept - 1 Oct
8. Oyster Estate
Oyster EstateGreenport
- Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
₹30,010
₹37,811 total
includes taxes & fees
5 Oct - 6 Oct
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Top Shelter Island Heights Hotel Reviews
Montauk Yacht Club
10/10 Excellent
"Great room, hotel and water views! Fantastic!"
Gurney's Montauk Resort & Seawater Spa
10/10 Excellent
"Very good"
The Hampton Maid
10/10 Excellent
"Our stay at The Hampton Maid was such a great choice. The entire hotel is absolutely charming—you can tell that every corner and every detail has been thoughtfully designed. The front desk staff was wonderful: so friendly, welcoming, and very clear with all the information. We loved the bungalow-style rooms, each with its own deck and parking, which gives you wonderful privacy between rooms. But what truly stole our hearts was the gorgeous, beautifully kept garden—a true green oasis that brings complete peace and lets you fully disconnect from city stress. The room was spotless, and the restaurant was phenomenal—we had breakfast there, and it was spectacular. On top of that, getting a pass to 7 local beaches for just $5 is an incredible perk. You really couldn't ask for more! It’s one of those places where you haven't even left yet, and you're already planning your return. Can't wait to go back!"
Saybrook Point Resort & Marina
10/10 Excellent
"Old Saybrook never disappoints. The rooms have been remodel Edinburgh the last six months but the resort has managed to retain its old world chatm. Eventhough there were three weddings at the property during our visit, the staff were attentive to us and we weren't as re remained their only guests. We will visit again."
Kenny's Tipperary Inn
8/10 Good
"Nice hotel and very clean, and the staff were very courteous and helpful. Beach is walking distance right down the road. Perfect location if you're looking for something by the beach."