A wooden gazebo by a pond with a large tree trunk nearby.

Search Hotels with Pool in Shelter Island

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Check availability on Shelter Island Hotels with Pool

Tonight
20 Aug - 21 Aug
Tomorrow
21 Aug - 22 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

Our top choices for Shelter Island hotels with a pool

Property amenity
Property amenity
Front of property – evening/night
Bar (on property)

1. Shelter Island House

Shelter Island House
Shelter Island Heights
  • Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.
฿10,396
฿11,877 total
includes taxes & fees
7 Sept - 8 Sept
Shelter Island House
Pool
Suite, 1 Bedroom, Terrace, Harbour View | Terrace/patio
Suite, 1 Bedroom, Terrace, Harbour View
View from room

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
฿9,148
฿12,154 total
includes taxes & fees
8 Sept - 9 Sept
The Harbor Front Inn
Beach
Parking
Deluxe Room, 1 King Bed
Suite, 1 King Bed, Kitchenette (Living Room) | Bathroom

3. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
  • Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
฿10,305
฿11,774 total
includes taxes & fees
23 Aug - 24 Aug
West Neck Guesthouse
Pool
Terrace/patio
Resort view
Restaurant

4. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
฿8,913
฿13,000 total
includes taxes & fees
15 Sept - 16 Sept
Sound View Greenport
Pool
Balcony
Cottage, 2 Bedrooms, Patio | Living room
Bathroom

5. North Fork Resort

North Fork Resort
Greenport
฿10,562
฿12,067 total
includes taxes & fees
20 Sept - 21 Sept
North Fork Resort
Pool
Terrace/patio
Beach
Terrace/patio

6. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
  • Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
฿17,693
฿22,236 total
includes taxes & fees
13 Sept - 14 Sept
The Pridwin Hotel
Outdoor pool
Beach
Condo | Terrace/patio
Condo

7. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
฿10,075
฿14,441 total
includes taxes & fees
20 Sept - 21 Sept
Cliffside Resort Condominiums
Lobby
Restaurant
Room
Restaurant

8. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
฿10,779
฿13,581 total
includes taxes & fees
7 Sept - 8 Sept
Oyster Estate
Pool
Lobby
Room
Lobby

9. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
  • Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
฿3,325
฿3,824 total
includes taxes & fees
13 Sept - 14 Sept
Quality Inn Old Saybrook - Westbrook
View all properties

Choose what matters most at hotels with a pool in Shelter Island

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Shelter Island Hotel Reviews

Sound View Greenport

Sound View Greenport

8/10 Good
"Stayed here for 2 nights mid-August. Pool was nice (could have been a little cleaner). Restaurant, excellent. Valet staff, excellent. Front desk staff, good. Bar, nice. Breakfast included, very nice. Room, a bit dated but nicely renovated. Through the years I always wanted to stay here - glad I did. The view (and sunset) of the Long Island Sound from the shared balcony cannot be beat. Breathtaking."
Barbara 2-night trip
Posted 6 hours ago
Sound View Greenport
Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good
"I booked through Expedia because I believed the price I was quoted would be the final cost other than incidentals. Additional resort fees and tax were added to the final bill. Over 130.00 in unexpected cost. Be aware when booking."
Debra 1-night trip
Posted 11 hours ago
Water's Edge Resort & Spa
Hampton's Vacation Inn

Hampton's Vacation Inn

10/10 Excellent
"Great place to stay. The closing of the pool at 7pm is a bit early."
Theresa 4-night trip
Posted 1 day ago
Hampton's Vacation Inn
Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"It was a great stay!"
Tynan 2-night trip
Posted 2 days ago
Ocean Resort Inn

Frequently asked questions

What are some accommodation options with pools in Shelter Island?
Pier Blue Inn Old Saybrook - Essex: Offers a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Hotel, 1-minute walk from The Hamptons Beaches. Provides a sauna, a seasonal outdoor pool and free self parking. Offshore Montauk: Hotel located near The Hamptons Beaches. Features 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. The Atlantic Hotel: Offers a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa: Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool and a private beach.
What is there to see and do in Shelter Island?
Surround yourself with nature at Sunset Beach and Crescent Beach. Discover sights such as Mashomack Preserve, Gardiner's Bay Country Club and Shelter Island Historical Society during your stay.
When is the best time to book a hotel with a pool in Shelter Island?
You may want to think about accommodation that has an outdoor pool if you'll be visiting Shelter Island in the hottest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be what you want if you come to town during the coldest months of January, February or March, when the average temperature is 3°C.

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