Dering Harbor Hotel Guide - Hotels with Pool in Dering Harbor, Shelter Island

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Check availability on Dering Harbor Hotels with Pool

Our top choices for Dering Harbor hotels with a pool

Indoor pool, open 9:00 AM to 9:00 PM, pool loungers

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,001 reviews)
"The very friendly staff made this stay enjoyable from The beginning. The hotel was very clean and comfy. "
United States
Virginia
The price is €88
includes taxes & fees
15 Feb - 16 Feb
Quality Inn 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
8.6 out of 10, Excellent, (448 reviews)
"Room was in good condition however I found the shower to be extremely small despite having great water pressure and extremely nice temperature."
United States
gail
The price is €96
includes taxes & fees
22 Jan - 23 Jan
Hamlet Inn
Seasonal outdoor pool, pool umbrellas, pool loungers

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (606 reviews)
"Nice place"
United States
Mateusz
The price is €157
includes taxes & fees
21 Jan - 22 Jan
Sound View Greenport
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (300 reviews)
"Is good"
United States
Miguel
The price is €77
includes taxes & fees
24 Jan - 25 Jan
Clinton Motel
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool loungers

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (562 reviews)
"Everything was Great Immaculate hotel very good location sraff was great"
United States
latoya
The price is €141
includes taxes & fees
19 Jan - 20 Jan
The Harbor Front Inn
Exterior

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
Southampton
8.6 out of 10, Excellent, (206 reviews)
"Staff was amazing. The room was very clean. I've stayed here numerous times, even on the night before my wedding as I was married in the Hamptons and I highly recommend! "
United States
Martine
The price is €108
includes taxes & fees
19 Jan - 20 Jan
Southampton Long Island Hotel
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
9.6 out of 10, Exceptional, (425 reviews)
"Adorable boutique hotel with charming unique touches. "
United States
Mary
The price is €120
includes taxes & fees
29 Jan - 30 Jan
The Bentley Hotel Southampton
Sports court

The Atlantic Hotel

The Atlantic Hotel
2.5 star property
Southampton
7.2 out of 10, Good, (978 reviews)
"Good place to stay in this area"
United States
Brenda
The Atlantic Hotel
Exterior

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Water Mill
10.0 out of 10, Exceptional, (6 reviews)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is €6,333
includes taxes & fees
19 Jan - 20 Jan
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
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, (466 reviews)
"All good it met our expectations as a budget hotel. Large clean room bed was comfortable although the pillows were past it. "
United States
Hilary
The price is €66
includes taxes & fees
26 Jan - 27 Jan
Econo Lodge Inn & Suites Old Saybrook Westbrook
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 Dering Harbor Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Great room and staff"
Joanne 1-night trip
Posted 4 days ago
Water's Edge Resort & Spa

Frequently asked questions

What are some accommodation options with pools in Dering Harbor?
Water's Edge Resort & Spa: Features a seasonal outdoor pool, an indoor pool and a private beach. Pier Blue Inn Old Saybrook - Essex: Provides free self parking, a seasonal outdoor pool and complimentary wireless Internet access. The Bentley Hotel Southampton: Hotel, 3-minute walk from The Hamptons Beaches. Features complimentary wireless Internet access, an outdoor pool and kitchens. Sea Crest Resort: Offers a private beach, a seasonal outdoor pool and complimentary cabanas. Bayview Resort: Features 2 outdoor tennis courts, a seasonal outdoor pool and free self parking.
What is there to see and do in Dering Harbor?
Make a point to visit attractions such as Greenport Carousel and Railroad Museum of Long Island. Discover sights such as Sunset Beach, Kontokosta Winery and 67 Steps Beach during your stay.
When is the best time to book a hotel with a pool in Dering Harbor?
You may want to think about a place to stay that has an outdoor pool if you're planning to visit Dering Harbor in the warmest months of August, July or September, when the average temperature 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.