Hotels with Swimming Pool in Dering Harbor, Shelter Island

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Check availability on Dering Harbor Hotels with Swimming Pool

Top Dering Harbor Hotels with Swimming Pool

Greenporter Hotel
Property grounds

Greenporter Hotel

2.0 star property
9.4 out of 10, Exceptional, (131)
"wonderful stay! we loved lounging by the
pool
and being such a short walk to so many amazing restaurants and cafes right in greenport!"
Alison
Greenporter Hotel
Saybrook Point Resort & Marina
Exterior

Saybrook Point Resort & Marina

3.5 star property
9.4 out of 10, Exceptional, (1005)
"Room was super clean, beautiful & spacious. Bed and pillows very comfy.
Indoor pool
was heated! Everything was great! "
Julie
The price is P20,284
P24,456 total
includes taxes & fees
Jul 14 - Jul 15
Saybrook Point Resort & Marina
Canoe Place Inn and Cottages
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Canoe Place Inn and Cottages

4.0 star property
10.0 out of 10, Exceptional, (45)
"The Canoe Place Inn and Cottages met my expectations and more. It really is a lovely treat to experience, not too far from home, but just enough to allow you to unwind and rest into their organic accommodations and thoughtful decor. I took my daughter for a mommy/daughter birthday celebration and she loved it. There was the pampering, the delicious eats [including the truffles that awaited our arrival with a handwritten note], the lovely room, heated floors, cozy bed with fluffy pillows and...
Mr. And Mrs. Karla and Mark
Canoe Place Inn and Cottages
The Bentley Hotel Southampton
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Bentley Hotel Southampton

2.0 star property
9.6 out of 10, Exceptional, (279)
"Beautiful spacious room, clean and renovated. Beautiful
pool
too"
Anonymous traveler
The price is P15,200
P18,978 total
includes taxes & fees
Jul 20 - Jul 21
The Bentley Hotel Southampton
Clinton Motel
Property grounds

Clinton Motel

2.5 star property
8.6 out of 10, Excellent, (255)
"Very nice motel stayed with the family. Comfortable and very friendly staff. Bathroom was great and the
pool
was clean!"
Leanna
The price is P5,027
P5,781 total
includes taxes & fees
Jul 28 - Jul 29
Clinton Motel
Hampton's Vacation Inn
Children's activities

Hampton's Vacation Inn

2.5 star property
9.0 out of 10, Wonderful, (288)
"Great value for the location. The property is well manicured with a lot of activities (playground, tennis, basketball, bonfire for s’mores). The heated
pool
was a highlight for my kids as well!"
Melissa
The price is P19,572
P22,362 total
includes taxes & fees
Jul 14 - Jul 15
Hampton's Vacation Inn
Water's Edge Resort & Spa
Exterior

Water's Edge Resort & Spa

3.5 star property
8.8 out of 10, Excellent, (1003)
"I love that this is (like its name) right by the water's edge, with a private beach. I appreciate having different options between the indoor and
outdoor pool
and the beach. The grounds are beautifully kept and the staff are very friendly. "
Tania
The price is P16,889
P20,397 total
includes taxes & fees
Jul 14 - Jul 15
Water's Edge Resort & Spa
Quality Inn Old Saybrook - Westbrook
Indoor pool, open 9:00 AM to 9:00 PM, sun loungers

Quality Inn Old Saybrook - Westbrook

2.5 star property
7.6 out of 10, Good, (1009)
"Ez access from I95. Ten minutes drive from Old Saybrook with excellent dining. Large room and very comfy bed. We enjoyed the
pool
and patio."
Patricia
The price is P6,242
P7,178 total
includes taxes & fees
Aug 3 - Aug 4
Quality Inn Old Saybrook - Westbrook
Southampton Inn
Aerial view

Southampton Inn

3.0 star property
8.6 out of 10, Excellent, (526)
"Such a great find! Close to Cooper’s Beach! Walking distance to shopping and restaurants. Prime location and beautiful sitting area outside. The
pool
is an added plus."
Ana
The price is P28,243
P33,802 total
includes taxes & fees
Jul 14 - Jul 15
Southampton Inn
The Pridwin Hotel
Seasonal outdoor pool, pool umbrellas, sun loungers

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (65)
"The Pridwin is amazing for a shelter island getaway. The property is gorgeous and the access to the beach and
pool
, kayaking and pickleball courts leave nothing to be desired. The staff is wonderful and so accommodating. Don’t miss the summer Wednesday bbqs!"
Amanda
The Pridwin Hotel
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.

Frequently asked questions

What are some accommodations with pools in Dering Harbor?
Quality Inn Old Saybrook - Westbrook: Features buffet, an indoor pool, and free self parking. Saybrook Point Resort & Marina: Offers 2 outdoor pools, an indoor pool, and a full-service spa. Pier Blue Inn Old Saybrook - Essex: Features 2 outdoor tennis courts, a seasonal outdoor pool, and continental. The Atlantic Hotel: Hotel, 2-minute walk from The Hamptons Beaches. Offers spa services, a seasonal outdoor pool, and a snack bar/deli. Baron's Cove: Features a private beach, a seasonal outdoor pool, and 2 bars.
What is there to see and do in Dering Harbor?
Make a point to visit attractions like Greenport Carousel and Railroad Museum of Long Island. Discover sights such as Sunset Beach, Kontokosta Winery, and Crescent 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 offers 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 70°F. Lodging offering an indoor pool may be the way to go if you visit during the coldest months of January, February, or March when the average temp is 38°F.