Search Hotels with Swimming Pool in Shelter Island
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Shelter Island Hotels with Swimming Pool
Tonight
7 Sept - 8 SeptTomorrow
8 Sept - 9 SeptThis weekend
11 Sept - 13 SeptNext weekend
18 Sept - 20 SeptOur 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.
₹19,017
₹21,726 total
includes taxes & fees
4 Oct - 5 Oct
2. West Neck Guesthouse
West Neck GuesthouseShelter Island Heights
- Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
₹29,624
₹33,846 total
includes taxes & fees
9 Sept - 10 Sept
3. The Harbor Front Inn
The Harbor Front InnGreenport
- Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
₹22,858
₹28,814 total
includes taxes & fees
4 Oct - 5 Oct
4. Sound View Greenport
Sound View GreenportGreenport
- Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
₹25,152
₹36,834 total
includes taxes & fees
28 Sept - 29 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.
₹50,726
₹63,750 total
includes taxes & fees
13 Sept - 14 Sept
₹28,336
₹32,374 total
includes taxes & fees
24 Sept - 25 Sept
7. Cliffside Resort Condominiums
Cliffside Resort CondominiumsGreenport
- Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
₹27,579
₹39,933 total
includes taxes & fees
4 Oct - 5 Oct
8. Oyster Estate
Oyster EstateGreenport
- Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
₹33,731
₹42,500 total
includes taxes & fees
15 Sept - 16 Sept
View all properties
Top Shelter Island Hotel Reviews
Hampton's Vacation Inn
10/10 Excellent
"Wonderful stay!! Loved this property and the staff. Clean, well kept. Beds were slightly uncomfortable but that wasn’t a big deal. Great location!"
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."
Water's Edge Resort & Spa
8/10 Good
"Excellent staff and location. The food was mediocre"
Sound View Greenport
10/10 Excellent
"A Beautiful and Peaceful Stay at Sound View Greenport I had a wonderful stay at Sound View Greenport and would highly recommend it to anyone looking for a relaxing getaway on the North Fork of Long Island. It’s a great place for couples, families, or anyone who simply wants to escape the busy city and enjoy some quiet time by the water. Greenport is also nearby, making it convenient to explore the local restaurants, shops, vineyards, and other attractions. If you’re planning a trip to Greenport or the North Fork, Sound View is definitely a place worth considering. I would happily stay here again! 🌅🌊❤️"
Budget Host East End
10/10 Excellent
"Came out for the 80th Annual powwow n Shinnecock and stayed here and not disappointed. From checking in to check out Thurs place was home for the night. Will be returning next year again and booking this place again."
The Hampton Maid
10/10 Excellent
"Absolutely beautiful hotel, in peaceful setting with lovely amenities."
Montauk Yacht Club
10/10 Excellent
"Great!"
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."
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."