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

Find Hotels with a Pool in Shelter Island, NY

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Check availability on Shelter Island Hotels with a Pool

Tonight
22 Sep - 23 Sep
Tomorrow
23 Sep - 24 Sep
This weekend
25 Sep - 27 Sep
Next weekend
2 Oct - 4 Oct

Our top choices for Shelter Island hotels with a pool

Property amenity
Terrace/patio
Bar (on property)
Property amenity

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.
AED 739
AED 844 total
includes taxes & fees
4 Oct - 5 Oct
Shelter Island House
Suite, 1 Bedroom, Terrace, Harbor View | Frette Italian sheets, premium bedding, down comforters, pillowtop beds
Suite, 1 Bedroom, Terrace, Harbor View | Terrace/patio
Studio (Suite, King) | Frette Italian sheets, premium bedding, down comforters, pillowtop beds
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
AED 879
AED 1,109 total
includes taxes & fees
12 Oct - 13 Oct
The Harbor Front Inn
Seasonal outdoor pool, pool umbrellas, sun loungers
Private beach, sun loungers, beach umbrellas, beach towels
Resort view
Lunch, dinner and brunch served

3. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
AED 898
AED 1,131 total
includes taxes & fees
14 Oct - 15 Oct
Sound View Greenport
Beach nearby
Suite, 1 King Bed, Kitchenette (Living Room) | Bathroom | Combined shower/tub, free toiletries, bathrobes, towels
Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, WiFi (free), bed sheets
Free self parking

4. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
  • Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
AED 1,151
AED 1,316 total
includes taxes & fees
1 Oct - 2 Oct
West Neck Guesthouse
Seasonal outdoor pool
Balcony
Flat-screen TV
Cottage, 2 Bedrooms, Patio | Living room | Flat-screen TV

5. North Fork Resort

North Fork Resort
Greenport
AED 1,040
AED 1,188 total
includes taxes & fees
18 Oct - 19 Oct
North Fork Resort
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas
Condo | 2 bedrooms, iron/ironing board, WiFi (free), individually decorated
Private beach
Condo | Terrace/patio

6. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
AED 1,067
AED 1,627 total
includes taxes & fees
28 Sep - 29 Sep
Cliffside Resort Condominiums
Seasonal outdoor pool, open 9:00 AM to 8:30 PM, pool umbrellas
Restaurant
Bay King | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Exterior

7. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
AED 1,103
AED 1,389 total
includes taxes & fees
5 Oct - 6 Oct
Oyster Estate
Outdoor pool
Free daily continental breakfast
Building design
Lobby lounge

8. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
  • Swim into serenity at this charming Sag Harbor retreat with a seasonal outdoor pool and balcony views.
AED 1,190
AED 1,360 total
includes taxes & fees
4 Oct - 5 Oct
Sag Harbor Inn
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Property grounds
Restaurant
Lobby lounge

9. Hamlet Inn

Hamlet Inn
Southampton
  • Serene seasonal pool retreat with private beach access just 2 miles away offers the perfect summer escape on Long Island.
AED 466
AED 602 total
includes taxes & fees
23 Sep - 24 Sep
Hamlet Inn
Seasonal outdoor pool
Cribs (free), rollaway beds (surcharge), WiFi (free), bed sheets
Free self parking
Cribs (free), rollaway beds (surcharge), WiFi (free), bed sheets

10. Clinton Motel

Clinton Motel
Clinton
  • Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
AED 286
AED 329 total
includes taxes & fees
23 Sep - 24 Sep
Clinton Motel
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

Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"Awesome location by the beach and friendly staff. Great place to stay for a beach getaway!"
Dan 2-night trip
Posted 1 hour ago
Ocean Vista Resort
Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"Closest to beach and town"
john 1-night trip
Posted 19 hours ago
Ocean Resort Inn
Ocean Surf Resort

Ocean Surf Resort

8/10 Good
"All good, however booking through Expedia cost me 300$ more than me booking straight with hotel… service fees at hotel as well…"
Jude 2-night trip
Posted 2 days ago
Ocean Surf Resort

Frequently asked questions

What are some accommodations with pools in Shelter Island?
Pier Blue Inn Old Saybrook - Essex: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and a private beach. Gurney's Montauk Resort & Seawater Spa: Hotel, 1-minute walk from The Hamptons Beaches. Provides a sauna, a seasonal outdoor pool, and free self parking. Offshore Montauk: Features a seasonal outdoor pool, an indoor pool, and a private beach. Water's Edge Resort & Spa: Offers 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. The Atlantic Hotel: Features a private beach, a seasonal outdoor pool, and 2 bars.
What is there to see and do in Shelter Island?
Surround yourself with nature at Sunset Beach and Mashomack Preserve. Discover sights such as Shelter Island Historical Society, Crescent Beach, and Gardiner's Bay Country Club during your stay.
When is the best time to book a hotel with a pool in Shelter Island?
You may want to think about an accommodation that has an outdoor pool if you will be visiting Shelter Island in the hottest months of August, July, or September when the average temp is 70°F. Lodging 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 38°F.