Find Hotels with a Pool in Shelter Island, NY

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Check availability on Shelter Island Hotels with a Pool

Top Shelter Island Hotels with a Pool

Outdoor pool, a heated pool
Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount

Shelter Island
  • Outdoor pool
  • Near the beach
10.0 out of 10, Exceptional, (52)
$1,165 nightly
The price is $1,331
Nov 21 - Nov 22
Total with taxes and fees
Work and Play Special! Extended Stay Discount
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, (382)
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.
$135 nightly
The price is $154
Nov 20 - Nov 21
Total with taxes and fees
The Bentley Hotel Southampton
BBQ/picnic area
Offshore Montauk

Offshore Montauk

2.0 star property
Montauk
  • Outdoor pool
  • Near the beach
9.4 out of 10, Exceptional, (69)
$131 nightly
The price is $150
Dec 3 - Dec 4
Total with taxes and fees
Offshore Montauk
Seasonal outdoor pool
Clinton Motel

Clinton Motel

2.5 star property
Clinton
  • Pool
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • 24/7 front desk
8.6 out of 10, Excellent, (292)
Seasonal swimming beckons from July through September in the outdoor pool, complementing days spent exploring nearby beaches. Garden grounds feature barbecue areas and picnic spots, creating a laid-back summer escape just minutes from local cafes.
$78 nightly
The price is $90
Nov 20 - Nov 21
Total with taxes and fees
Clinton Motel
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.
$156 nightly
The price is $178
Dec 3 - Dec 4
Total with taxes and fees
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, (876)
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.
$131 nightly
The price is $150
Dec 3 - Dec 4
Total with taxes and fees
Kenny's Tipperary Inn
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)
$195 nightly
The price is $223
Nov 20 - Nov 21
Total with taxes and fees
North Fork Cottages & RV Resort
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.
$154 nightly
The price is $176
Nov 20 - Nov 21
Total with taxes and fees
The Harbor Front Inn
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
Old Saybrook
  • Near the beach
7.2 out of 10, Good, (459)
Cooling waters welcome afternoon swimmers to the serene outdoor pool surrounded by lush gardens and a spacious terrace. Individually furnished rooms with modern updates create a comfortable retreat after days spent exploring the Old Saybrook city center.
$72 nightly
The price is $82
Nov 25 - Nov 26
Total with taxes and fees
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
  • Pool loungers
  • Near private beach
8.6 out of 10, Excellent, (437)
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.
$131 nightly
The price is $147
Nov 20 - Nov 21
Total with taxes and fees
Hamlet Inn
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 Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"amenities clean room with turndown service "
michael 2-night trip
Posted 4 days ago
Saybrook Point Resort & Marina

Frequently asked questions

What are some accommodations with pools in Shelter Island?
Gurney's Montauk Resort & Seawater Spa: Features a seasonal outdoor pool, an indoor pool, and a private beach. Pier Blue Inn Old Saybrook - Essex: Provides sun loungers, an indoor pool, and complimentary wireless internet access. Montauk Blue Hotel: Features buffet, an indoor pool, and free self parking. Quality Inn Old Saybrook - Westbrook: Offers a private beach, a seasonal outdoor pool, and 2 bars. Sound View Greenport: Features 2 outdoor pools, an indoor pool, and a full-service spa.
What is there to see and do in Shelter Island?
Surround yourself with nature at Sunset Beach and Crescent Beach. Discover sights such as Shelter Island Historical Society, Shelter Island Whale's Tail, and Mashomack Preserve during your stay.
When is the best time to book a hotel with a pool in Shelter Island?
You may want to think about an accommodation that has an outdoor pool if you will be visiting Shelter Island in the hottest months of August, July, or September when the average temp is 70°F. Lodging 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 38°F.

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