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Find Hotels with a Pool in Shelter Island Heights, NY

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Check availability on Shelter Island Heights Hotels with a Pool

Tonight
Nov 23 - Nov 24
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Nov 24 - Nov 25
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Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7

Top Shelter Island Heights Hotels with a Pool

BBQ/picnic area
Offshore Montauk

Offshore Montauk

2.0 star property
Montauk
  • Outdoor pool
  • Near the beach
9.4 out of 10, Exceptional, (70)
The price is NT$2,554
NT$4,713 total
includes taxes & fees
Dec 7 - Dec 8
Offshore Montauk
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Best Western Niantic - New London/Mystic Area

Best Western Niantic - New London/Mystic Area

2.5 star property
Niantic
  • Pool loungers
  • Near the beach
9.0 out of 10, Wonderful, (437)
Sparkling clear waters beckon guests to the seasonal outdoor pool, where sun loungers and umbrellas create a peaceful retreat. The recently renovated hotel complements pool time with a 24-hour fitness center and immaculate, spacious rooms.
The price is NT$2,903
NT$3,339 total
includes taxes & fees
Nov 25 - Nov 26
Best Western Niantic - New London/Mystic Area
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers
The Harbor Front Inn

The Harbor Front Inn

3.5 star property
Greenport
  • Pool loungers
  • Near the beach
8.8 out of 10, Excellent, (535)
Sunlight dances across the seasonal outdoor pool where comfortable loungers invite leisurely afternoons. After swimming, guests appreciate the 24-hour health club, designer bathroom amenities, and continental breakfast before exploring nearby shops and restaurants.
The price is NT$3,277
NT$5,282 total
includes taxes & fees
Dec 21 - Dec 22
The Harbor Front Inn
Exterior
Montauk Manor

Montauk Manor

3.5 star property
Montauk
  • Indoor pool
  • Near the beach
  • Hot tub
9.2 out of 10, Wonderful, (1262)
Swimming options abound at this tudor-style retreat where an indoor pool welcomes year-round while a seasonal outdoor pool showcases breathtaking scenic vistas. Guests appreciate the relaxing hot tub, tennis courts, and 24-hour fitness center.
The price is NT$4,355
NT$5,591 total
includes taxes & fees
Dec 1 - Dec 2
Montauk Manor
Seasonal outdoor pool, pool umbrellas, sun loungers
Kenny's Tipperary Inn

Kenny's Tipperary Inn

2.0 star property
Culloden Shores
  • Pool loungers
  • Near the beach
8.4 out of 10, Very Good, (877)
Surrounded by lush gardens, the seasonal summer pool creates a peaceful retreat for guests seeking sunshine and relaxation. This immaculate motel provides spacious, individually furnished rooms with private decks and premium bedding for complete comfort.
Kenny's Tipperary Inn
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2.0 star property
Southampton
  • Pool loungers
  • Near private beach
9.6 out of 10, Exceptional, (383)
Swimming awaits at the immaculately clean seasonal outdoor pool where plush loungers invite leisurely afternoons under shady umbrellas. Recently renovated spaces, private beach access just 2 miles away, and proximity to renowned golf courses complete this Southampton retreat.
The price is NT$3,243
NT$3,736 total
includes taxes & fees
Nov 25 - Nov 26
The Bentley Hotel Southampton
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

2.0 star property
Southampton
  • Pool loungers
  • Near private beach
8.6 out of 10, Excellent, (438)
Refreshing dips await at the seasonal outdoor pool, complete with sun loungers for afternoon relaxation. Nearby water adventures include kayaking, sailing, and surfing, while the private beach provides a peaceful coastal sanctuary.
The price is NT$2,489
NT$3,217 total
includes taxes & fees
Nov 25 - Nov 26
Hamlet Inn
Indoor pool, a heated pool
Sleep Inn & Suites Niantic North

Sleep Inn & Suites Niantic North

2.5 star property
Niantic
  • Indoor pool
8.4 out of 10, Very Good, (1011)
Swimming enthusiasts delight at this hotel's indoor heated pool, open until 10:00 PM daily for extended aquatic enjoyment. Families appreciate the beach-adjacent location, clean facilities, and complimentary breakfast buffet that complete a refreshing coastal getaway.
The price is NT$2,457
NT$2,826 total
includes taxes & fees
Dec 7 - Dec 8
Sleep Inn & Suites Niantic North
Property map
North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3.0 star property
Greenport
  • Pool
  • Kitchen
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
9.4 out of 10, Exceptional, (6)
The price is NT$5,515
NT$6,301 total
includes taxes & fees
Nov 24 - Nov 25
North Fork Cottages & RV Resort
Seasonal outdoor pool, pool umbrellas, sun loungers
Sound View Greenport

Sound View Greenport

4.0 star property
Greenport
  • Poolside bar
  • Pool loungers
  • On private beach
8.6 out of 10, Excellent, (593)
Panoramic oceanfront vistas captivate from the seasonal pool area, complete with loungers, umbrellas, and a lively poolside bar. After swimming, guests savor fresh seafood at The Halyard restaurant while watching magnificent sunsets paint the sky.
The price is NT$5,037
NT$7,293 total
includes taxes & fees
Nov 24 - Nov 25
Sound View Greenport
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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Top Shelter Island Heights Hotel Reviews

Sleep Inn & Suites Niantic North

Sleep Inn & Suites Niantic North

10/10 Excellent
"The staff was excellent. Very nice and helpful. The room was comfortable and clean."
Ellen 2-night trip
Posted 3 days ago
Sleep Inn & Suites Niantic North

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Frequently asked questions

What's it like visiting Shelter Island Heights?
If lounging by a pool is your idea of a great vacation, you may want to check out Shelter Island Heights, which has 10 places to stay with pools. While you're visiting, you can explore sights such as Sunset Beach and Crescent Beach, and then kick back and relax poolside at one of the accommodations in Shelter Island Heights that guests like for their pools.
What are some accommodations with pools in Shelter Island Heights?
The Pridwin Hotel: Features a private beach, a seasonal outdoor pool, and a full-service spa. The Chequit: Provides a snack bar/deli, a seasonal outdoor pool, and daily. Shelter Island House: Features a seasonal outdoor pool, an indoor pool, and a private beach. Gurney's Montauk Resort & Seawater Spa: Features sun loungers, an indoor pool, and complimentary wireless internet access. Pier Blue Inn Old Saybrook - Essex: 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 with an outdoor swimming pool if you will be visiting Shelter Island Heights in the warmest months of August, July, or September when the average temp is 70°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or March when the average temp is 38°F.