Search Winter Park Cottages

Compare Cottages in Winter Park with updated reviews, rates, and availability.

Other property types in Winter Park

Outdoor pool, pool umbrellas, sun loungers

"Everything good, excellent location."

$107 total

includes taxes & fees

Jun 11 - Jun 12

2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas

"Spacious room"

$224 total

includes taxes & fees

Jun 9 - Jun 10

"We received from the bellboy the wrong information about the shuttle time and the logistic on how to get to our terminal. We had to wait almos 45 minutes for a shuttle. Nobody helped us with our luggage. Also he told us that someone was going to call us early to wake us up but nobody did it. Our flight was very early. Please make sure all the employees have the right information for guests. Thanks "

$235 total

includes taxes & fees

Jun 30 - Jul 1

Winter Park Cottages information

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Frequently asked questions

How much do cottages in Winter Park cost?

Cottages in Winter Park range between and per night. These stays offer a chance to reconnect with nature — at a price you can afford. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Why book your cottage in Winter Park with Expedia?

We think that traveling should be a piece of cake, so if you’re searching for cottages in Winter Park at the perfect price, Expedia has got you covered. Keep costs down and select a wallet-friendly option far away from the downtown buzz, or book a 5-star cottage to pamper your favorite people.

How can I find cheap cottages in Winter Park?

Expedia is here to help you easily source cheap cottages in Winter Park. To reserve a terrific stay in a matter of clicks, simply use the filter tool to refine your search by star rating, budget and amenities.

What is there to do in Winter Park near my cottage?

Winter Park has enough sights and activities to keep you entertained for weeks (or months!), starting with Orlando Science Center. Orlando Museum of Art, Church Street Station and Boardwalk Bowl Entertainment Center are other renowned attractions. If you’re hanging around a while, Orange County Regional History Center and The Plaza Theatre will cap off your itinerary nicely.