Find Hotels with a Pool in Shelter Island, NY

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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 13 - Nov 14
Total with taxes and fees
Work and Play Special! Extended Stay Discount
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 18 - Nov 19
Total with taxes and fees
Econo Lodge Inn & Suites Old Saybrook Westbrook
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, (530)
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.
$174 nightly
The price is $198
Nov 30 - Dec 1
Total with taxes and fees
The Harbor Front Inn
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, (289)
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 12 - Nov 13
Total with taxes and fees
Clinton Motel
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, (874)
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.
$120 nightly
The price is $138
Nov 25 - Nov 26
Total with taxes and fees
Kenny's Tipperary Inn
Exterior
Montauk Manor

Montauk Manor

3.5 star property
Montauk
  • Indoor pool
  • Near the beach
  • Hot tub
9.2 out of 10, Wonderful, (1261)
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 1 - Dec 2
Total with taxes and fees
Montauk Manor
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, (3)
$195 nightly
The price is $223
Nov 12 - Nov 13
Total with taxes and fees
North Fork Cottages & RV Resort
Front of property
A Wave Inn

A Wave Inn

2.5 star property
Downtown Montauk
  • Outdoor pool
7.4 out of 10, Good, (133)
Lounge and swim in luxury at the serene outdoor pool, open from May through October. Conveniently located within walking distance to beaches, shops, and restaurants, this hotel offers the perfect base for exploring The Hamptons.
$167 nightly
The price is $191
Nov 12 - Nov 13
Total with taxes and fees
A Wave 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, (375)
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.
$118 nightly
The price is $135
Dec 3 - Dec 4
Total with taxes and fees
The Bentley Hotel Southampton
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

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Well worth upgrading room. Amenities were amazing "
Jonathan 2-night trip
Posted 4 days ago
Gurney's Montauk Resort & Seawater Spa

Frequently asked questions

What are some accommodations 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. Pier Blue Inn Old Saybrook - Essex: Hotel, 1-minute walk from The Hamptons Beaches. 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: Features 2 outdoor pools, an indoor pool, and a full-service spa. Saybrook Point Resort & Marina: Offers 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking.
What is there to see and do in Shelter Island?
Surround yourself with nature at Sunset Beach and Crescent Beach. Discover sights such as Gardiner's Bay Country Club, Shelter Island Historical Society, and Havens House 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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