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Check Prices on Hotels in Winter Park

Tonight Jul 17 - Jul 18
This weekend Jul 19 - Jul 21
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Featured Winter Park Hotels with Air Conditioning

See all 5,159 Properties in Winter Park

Estimated price for 1 night/2 adults

Park Plaza Hotel
Park Plaza Hotel
3.0 out of 5.0 307 South Park Avenue , Winter Park, FL
Free Cancellation
4.0/5 (334 reviews)
$161/ night for 2 guests

Great historic hotel. Love the staff and location.

Reviewed on Jun 15, 2019
A Rare Jewel - Steps to Park Ave, Shops, Restaurants, Rollins College, Farmers m
A Rare Jewel - Steps to Park Ave, Shops, Restaurants, Rollins College, Farmers m
Winter Park, Florida
5.0/5 (4 reviews)

For US this property was ideal! It probably could be best described as being 'eclectic' but its location in this charming community cannot be beat. There certainly was very adequate space for us and it did not lack in any amenities necessary for comfortable longer term living. And the owner was certainly ...

Reviewed on Mar 4, 2019
The Alfond Inn
The Alfond Inn
4.0 out of 5.0 300 East New England Avenue, Winter Park, FL
4.7/5 (670 reviews)
$199/ night for 2 guests

The art is incredible, beautiful room, amazing location

Reviewed on Jul 8, 2019
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Recently Booked Hotels with Air Conditioning in Winter Park

Park Plaza Hotel
3.0 out of 5.0
Last booking: 11 hours ago
The Alfond Inn
4.0 out of 5.0
Last booking: 19 hours ago

Pocket Guide: Hotels with Air Conditioning in Winter Park

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