Search Hotels with Pool in Shelter Island Heights

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Check availability on Shelter Island Heights Hotels with Pool

Our top choices for Shelter Island Heights 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, (85 reviews)
  • cleanliness
    Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
The price is Rp5.637.554
Rp7.084.920 total
includes taxes & fees
14 May - 15 May
The Pridwin Hotel
Beach nearby

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.0 out of 10, Very good, (37 reviews)
  • cleanliness
    Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
The price is Rp3.837.098
Rp4.384.003 total
includes taxes & fees
10 Jun - 11 Jun
West Neck Guesthouse
Property amenity

Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (57 reviews)
  • cleanliness
    Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.
The price is Rp3.527.711
Rp4.030.268 total
includes taxes & fees
17 May - 18 May
Shelter Island House
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (309 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is Rp1.367.262
Rp1.572.351 total
includes taxes & fees
14 May - 15 May
Clinton Motel
Seasonal outdoor pool, pool loungers

Ocean Resort Inn

Ocean Resort Inn
2.0 star property
Downtown Montauk
9.6 out of 10, Exceptional, (492 reviews)
  • cleanliness
    Soak in coastal charm at the heated saltwater pool steps from Montauk's sandy shores.
The price is Rp2.350.890
Rp2.686.110 total
includes taxes & fees
20 May - 21 May
Ocean Resort Inn
Down duvets, free WiFi, bed sheets

The Penny Lane

The Penny Lane
2.0 star property
Hampton Bays
9.0 out of 10, Wonderful, (77 reviews)
  • cleanliness
    Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.
The price is Rp4.780.143
Rp5.461.312 total
includes taxes & fees
15 May - 16 May
The Penny Lane
Seasonal outdoor pool

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
9.0 out of 10, Wonderful, (14 reviews)
The price is Rp5.206.113
Rp5.947.985 total
includes taxes & fees
27 May - 28 May
North Fork Cottages & RV Resort
Outdoor pool, pool umbrellas, pool loungers

Offshore Montauk

Offshore Montauk
4.0 star property
Montauk
9.4 out of 10, Exceptional, (132 reviews)
The price is Rp3.950.749
Rp6.503.281 total
includes taxes & fees
25 May - 26 May
Offshore Montauk
Exterior

Sun N Sound

Sun N Sound
2.5 star property
Culloden Shores
9.0 out of 10, Wonderful, (269 reviews)
  • cleanliness
    Splash into refreshing waters at this beach-adjacent retreat with sun-soaked outdoor pool.
The price is Rp3.142.950
Rp3.876.538 total
includes taxes & fees
14 May - 15 May
Sun N Sound
Seasonal outdoor pool, pool loungers

Aqualina Inn Montauk

Aqualina Inn Montauk
2.5 star property
Downtown Montauk
9.6 out of 10, Exceptional, (496 reviews)
  • cleanliness
    Dive into poolside luxury at this Montauk motel with summer splash fun and garden views.
The price is Rp2.350.890
Rp2.686.110 total
includes taxes & fees
19 May - 20 May
Aqualina Inn 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 Heights

Breakfast included
4 stars

Top Shelter Island Heights Hotel Reviews

Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Had a great stay here! Nice location just off the beach, conveniently in the middle of town. The room was spotless (it was in the first week or two of the season) on the small side but has everything you need including a tiny kitchen."
Nick 1-night trip
Posted 2 hours ago
Ocean Surf Resort

Frequently asked questions

What's it like visiting Shelter Island Heights?
If taking it easy by the pool is your idea of a great getaway, you may want to consider Shelter Island Heights, which offers 10 places to stay with pools. During your trip, you can explore sights such as Sunset Beach and Crescent Beach, and then relax poolside at one of the accommodation options in Shelter Island Heights that guests like for their pools.
What are some accommodation options with pools in Shelter Island Heights?
The Pridwin Hotel: Features a private beach, a seasonal outdoor pool and a full-service spa. Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool and a private beach. Montauk Manor: Aparthotel, 14-minute walk from The Hamptons Beaches. Provides a seasonal outdoor pool, an indoor pool and 3 outdoor tennis courts. Montauk Yacht Club: Hotel, 5-minute walk from The Hamptons Beaches. Features 2 outdoor swimming pools, a children's pool and a private beach. The Bentley Hotel Southampton: Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access.
How many pool hotels will I find in Shelter Island Heights?
Expedia has 10 hotels in Shelter Island Heights for your poolside break.
What is there to see and do in Shelter Island Heights?
Spend some time experiencing the great outdoors at Sunset Beach and Crescent Beach. Discover sights such as Shelter Island Country Club, Sylvester Manor and Menhadden Lane Beach during your stay. Take in the natural beauty of Shelter Island Heights with the island views and beaches.
When is the best time to book a hotel with a pool in Shelter Island Heights?
You may want to think about a place to stay that has an outdoor pool if you plan to visit Shelter Island Heights in the warmest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be the way to go if you come to town during the coldest months of January, February or March, when the average temp is 3°C.