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

Search Hotels with Swimming Pool in Shelter Island

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Shelter Island Hotels with Swimming Pool

Our top choices for Shelter Island hotels with a pool

Seasonal outdoor pool, pool umbrellas, pool loungers

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (94 reviews)
  • cleanliness
    Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
The price is ₹64,330
₹80,846 total
includes taxes & fees
24 Aug - 25 Aug
The Pridwin Hotel
Property amenity

Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (61 reviews)
  • cleanliness
    Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.
The price is ₹30,541
₹34,893 total
includes taxes & fees
30 Jul - 31 Jul
Shelter Island House
Beach nearby

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very good, (42 reviews)
  • cleanliness
    Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
The price is ₹30,275
₹34,590 total
includes taxes & fees
27 Jul - 28 Jul
West Neck Guesthouse
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (275 reviews)
  • cleanliness
    Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
The price is ₹39,938
₹49,825 total
includes taxes & fees
30 Jul - 31 Jul
Cliffside Resort Condominiums
Suite, 1 Bedroom, Terrace, Harbour View | Terrace/patio

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (631 reviews)
  • cleanliness
    Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
The price is ₹40,757
₹51,529 total
includes taxes & fees
23 Aug - 24 Aug
The Harbor Front Inn
Outdoor pool

Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (649 reviews)
  • cleanliness
    Swim into serenity at this charming Sag Harbour retreat with a seasonal outdoor pool and balcony views.
The price is ₹49,155
₹56,159 total
includes taxes & fees
10 Aug - 11 Aug
Sag Harbor Inn
Seasonal outdoor pool, pool umbrellas, pool loungers

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (667 reviews)
  • cleanliness
    Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
The price is ₹72,211
₹90,776 total
includes taxes & fees
14 Aug - 15 Aug
Sound View Greenport
Seasonal outdoor pool

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (35 reviews)
The price is ₹47,617
₹54,403 total
includes taxes & fees
24 Aug - 25 Aug
North Fork Resort
Seasonal outdoor pool, pool cabanas (surcharge), pool umbrellas

Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (297 reviews)
  • cleanliness
    Dive into summer splendour at a tranquil pool retreat with chic cabanas and luxe loungers.
The price is ₹91,743
₹115,298 total
includes taxes & fees
26 Jul - 27 Jul
Faraway Sag Harbor
Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,007 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is ₹11,410
₹13,121 total
includes taxes & fees
23 Aug - 24 Aug
Quality Inn Old Saybrook - Westbrook
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

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

Breakfast included
4 stars

Top Shelter Island Hotel Reviews

Hampton's Vacation Inn

Hampton's Vacation Inn

10/10 Excellent
"Excellent!! Would stay again in a heartbeat!"
Delaney 1-night trip
Posted less than an hour ago
Hampton's Vacation Inn

Frequently asked questions

What are some accommodation options 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, 5-minute walk from The Hamptons Beaches. Provides 2 outdoor swimming pools, a children's pool and a private beach. Montauk Yacht Club: Features a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Offers a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa: Hotel located near The Hamptons Beaches. Features 2 outdoor tennis courts, a seasonal outdoor pool and free self parking.
What is there to see and do in Shelter Island?
Explore places such as The Hamptons Beaches while you're in the area. Make a point to visit attractions such as Sunset Beach and Shelter Island Whale's Tail.
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.