Shelter Island Heights Hotels with Swimming Pool

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Check availability on Shelter Island Heights Hotels with Swimming Pools

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 RM1,371
RM1,723 total
includes taxes & fees
27 May - 28 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 RM866
RM989 total
includes taxes & fees
31 May - 1 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 RM796
RM909 total
includes taxes & fees
19 May - 20 May
Shelter Island House
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 RM573
RM655 total
includes taxes & fees
25 May - 26 May
Ocean Resort Inn
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 RM332
RM382 total
includes taxes & fees
19 May - 20 May
Clinton Motel
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, (473 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodation.
The price is RM318
RM366 total
includes taxes & fees
25 May - 26 May
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.0 out of 10, Wonderful, (15 reviews)
The price is RM1,175
RM1,342 total
includes taxes & fees
1 Jun - 2 Jun
North Fork Resort
View from property

Breakers Montauk

Breakers Montauk
3.0 star property
Montauk
8.6 out of 10, Excellent, (188 reviews)
  • cleanliness
    Seaside poolside escape with sun loungers and umbrellas creates a summer sanctuary.
The price is RM380
RM563 total
includes taxes & fees
19 May - 20 May
Breakers Montauk
Seasonal outdoor pool, pool umbrellas, pool loungers

Marram

Marram
4.0 star property
Montauk
8.8 out of 10, Excellent, (253 reviews)
  • cleanliness
    Cool ocean-adjacent pool getaway with loungers, umbrellas, and beach perks for the perfect summer splash.
The price is RM810
RM1,716 total
includes taxes & fees
21 May - 22 May
Marram
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 RM494
RM565 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

Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"The room was extremely clean and staff was very helpful in keeping our 4 rooms together."
Michele 2-night trip
Posted 3 hours ago
Beachcomber Resort at Montauk

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.

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