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Hotels with Pool & Resorts in Shelter Island from NZ$154

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Check availability on Shelter Island Hotels with Pool

Tonight
4 Oct - 5 Oct
Tomorrow
5 Oct - 6 Oct
Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct

Best Shelter Island Hotels with Pool

Clinton Motel
Seasonal outdoor pool

Clinton Motel

2.5 star property
8.6 out of 10, Excellent, (279)
"Great staff and clean rooms"
The price is NZ$154
includes taxes & fees
6 Oct - 7 Oct
Clinton Motel
Ocean Vista Resort
Indoor pool, a waterfall pool

Ocean Vista Resort

2.5 star property
9.0 out of 10, Wonderful, (194)
"Lovely short stay! Right on the beautiful beach. Staff were so welcoming and even quickly sent me something I accidentally left behind in the room. Absolutely plan to be back!"
Ocean Vista Resort
Hampton's Vacation Inn
Children’s activities

Hampton's Vacation Inn

2.5 star property
9.0 out of 10, Wonderful, (317)
"A great Hampton location that's less than a thirty minutes drive from Coopers Beach and South Hampton main street."
The price is NZ$247
includes taxes & fees
5 Oct - 6 Oct
Hampton's Vacation Inn
Greenporter Hotel
Property grounds

Greenporter Hotel

2.0 star property
9.2 out of 10, Wonderful, (259)
"Staff was amazing and this hotel is in the perfect location "
Greenporter Hotel
Driftwood Resort
Property grounds

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (235)
"Great place to stay for small family "
The price is NZ$338
includes taxes & fees
13 Oct - 14 Oct
Driftwood Resort
New and Modern Bridgehampton Accommodations
Outdoor pool, a heated pool

New and Modern Bridgehampton Accommodations

2.0 star property
9.6 out of 10, Exceptional, (14)
"Had a great stay here with a small group. Host was very accommodating and responsive. "
The price is NZ$751
includes taxes & fees
5 Oct - 6 Oct
New and Modern Bridgehampton Accommodations
Montauk Manor
Exterior

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1252)
"Beautiful grounds, excellent staff"
The price is NZ$616
includes taxes & fees
24 Oct - 25 Oct
Montauk Manor
Ocean Surf Resort
Street view

Ocean Surf Resort

2.0 star property
8.4 out of 10, Very good, (210)
"Perfect way to relax on the beach. "
The price is NZ$240
includes taxes & fees
7 Oct - 8 Oct
Ocean Surf Resort
Quality Inn Old Saybrook - Westbrook
Indoor pool, open 9:00 AM to 9:00 PM, pool loungers

Quality Inn Old Saybrook - Westbrook

2.5 star property
7.6 out of 10, Good, (1003)
"We have stayed there before so have been pleased with it."
The price is NZ$184
includes taxes & fees
2 Nov - 3 Nov
Quality Inn Old Saybrook - Westbrook
Carole's Place B & B
Property grounds

Carole's Place B & B

3.0 star property
9.8 out of 10, Exceptional, (59)
"Small B&B with a charming old school vibe. Second time we’ve stayed there and we will return."
The price is NZ$294
includes taxes & fees
5 Oct - 6 Oct
Carole's Place B & B
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.
View all properties

Top Shelter Island Hotel Reviews

Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Beautiful room right across from the ocean and by town. Definitely go back!"
James 2-night trip
Posted 5 days ago
Beachcomber Resort at Montauk

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Frequently asked questions

What are some accommodation options with pools in Shelter Island?
Pier Blue Inn Old Saybrook - Essex: Offers a seasonal outdoor pool, an indoor pool and a private beach. Gurney's Montauk Resort & Seawater Spa: Provides buffet, an indoor pool and free self parking. Quality Inn Old Saybrook - Westbrook: Offers sunloungers, an indoor pool and complimentary wireless Internet access. New Designer-Built Home with Private Beach: Features a private beach, a seasonal outdoor pool and 2 bars. Montauk Blue Hotel: 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 Mashomack Preserve, Gardiner's Bay Country Club and Shelter Island Historical Society during your stay.
When is the best time to book a hotel with a pool in Shelter Island?
You may want to think about accommodation that has an outdoor pool if you'll be visiting Shelter Island in the hottest months of August, July or September, when the average temp is 21°C. Accommodation 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 3°C.