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

Hotels with Pool & Resorts in Shelter Island from NZ$162

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Check availability on Shelter Island Hotels with Pool

This weekend
10 Jul - 12 Jul
Next weekend
17 Jul - 19 Jul

Our top choices for Shelter Island hotels with a pool

Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (321 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is NZ$179
includes taxes & fees
13 July - 14 July
Clinton Motel
Lobby sitting area

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,001 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is NZ$238
includes taxes & fees
27 July - 28 July
Quality Inn Old Saybrook - Westbrook
Reception

The Penny Lane

The Penny Lane
3.0 star property
Hampton Bays
9.0 out of 10, Wonderful, (84 reviews)
  • cleanliness
    Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.
The price is NZ$549
includes taxes & fees
20 July - 21 July
The Penny Lane
Seasonal outdoor pool

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (29 reviews)
The price is NZ$695
includes taxes & fees
21 July - 22 July
North Fork Resort
Individually decorated, individually furnished, desk, laptop workspace

Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
Old Saybrook
7.2 out of 10, Good, (482 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodation.
The price is NZ$162
includes taxes & fees
22 July - 23 July
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (487 reviews)
  • cleanliness
    Serene seasonal pool retreat with private beach access just 2 miles away offers the perfect summer escape on Long Island.
The price is NZ$517
includes taxes & fees
13 July - 14 July
Hamlet Inn
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool loungers

Hampton's Vacation Inn

Hampton's Vacation Inn
2.5 star property
Hampton Bays
9.0 out of 10, Wonderful, (341 reviews)
  • cleanliness
    Soak in poolside bliss at this Hampton guesthouse with refreshing seasonal pool, tennis court, and nearby beach activities.
The price is NZ$405
includes taxes & fees
22 July - 23 July
Hampton's Vacation Inn
Seasonal outdoor pool

Budget Host East End

Budget Host East End
2.0 star property
Riverhead
6.8 out of 10, (829 reviews)
  • cleanliness
    Escape summer heat at this serene riverfront motel with a clean, seasonal pool.
The price is NZ$250
includes taxes & fees
13 July - 14 July
Budget Host East End
Seasonal outdoor pool

Ocean View Terrace Inn

Ocean View Terrace Inn
2.0 star property
Hampton Bays
8.6 out of 10, Excellent, (125 reviews)
  • cleanliness
    Beachside seasonal pool awaits with ocean adventures and relaxing massages nearby.
The price is NZ$590
includes taxes & fees
15 July - 16 July
Ocean View Terrace Inn
Outdoor pool, pool umbrellas, pool loungers

Breakers Montauk

Breakers Montauk
3.0 star property
Montauk
8.6 out of 10, Excellent, (208 reviews)
  • cleanliness
    Seaside poolside escape with sun loungers and umbrellas creates a summer sanctuary.
The price is NZ$704
includes taxes & fees
29 July - 30 July
Breakers Montauk
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.
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Choose what matters most at hotels with a pool in Shelter Island

Breakfast included
4 stars

Top Shelter Island Hotel Reviews

Aqualina Inn Montauk

Aqualina Inn Montauk

10/10 Excellent
"absolutely the best stay !! close to all. Cleanest can be and the staff , Amazing . I usually stay at Driftwood but wanted to try in Town. Great choice !! cant wait to book again !"
josephine 2-night trip
Posted 19 hours ago
Aqualina Inn Montauk

Frequently asked questions

What are some accommodation options with pools in Shelter Island?
Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool and a private beach. Offshore Montauk: Hotel, 1-minute walk from The Hamptons Beaches. Offers a sauna, a seasonal outdoor pool and free self parking. Pier Blue Inn Old Saybrook - Essex: Features a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Aparthotel, 14-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool and 3 outdoor tennis courts. Montauk Manor: Features sunloungers, a seasonal outdoor pool and complimentary wireless Internet access.
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.