Search Cottages in Winter Park

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Find holiday rentals that suit your style

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Winter Park cottages

A resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.

1. Th20 - 3BR House With Resort Access Near Parks

Th20 - 3BR House With Resort Access Near Parks
3.0 star property
Orlando
The price is Rp4.159.550
Rp8.527.529 total
includes taxes & fees
28 Nov - 29 Nov
Th20 - 3BR House With Resort Access Near Parks
A resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.

2. Th89 - 3BR House Near Disney With Resort Access

Th89 - 3BR House Near Disney With Resort Access
3.0 star property
Orlando
The price is Rp4.250.915
Rp8.633.881 total
includes taxes & fees
5 Dec - 6 Dec
Th89 - 3BR House Near Disney With Resort Access
A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

3. Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is Rp3.599.711
Rp9.028.582 total
includes taxes & fees
11 Nov - 12 Nov
Fire Pit & Yard: Updated Winter Garden Home!
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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Learn more about Winter Park

Stroll through the Morse Museum to see the world's largest collection of Tiffany glass, then boat through the Winter Park Chain of Lakes. Charming Park Avenue offers upscale shopping and outdoor cafés where you can people-watch before catching a sunset concert in Central Park.

See all hotels in Winter Park
A clock with 'Winter Park' and 'Central Park' inscribed, surrounded by lush greenery and trees.

Frequently Asked Questions

How much do cottages in Winter Park cost?

Cottages in Winter Park range between Rp2.785.706 and Rp4.250.915 per night. These stays offer a chance to touch base with nature — at a price you can afford. These prices were 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?

Expedia has some terrific cottages in Winter Park, so start packing for a memorable holiday close to nature. If you have a fixed budget, choose how much you'd like to spend and the preferred star rating of your property. Or, make use of our filters to search for cottages with a pool or a kitchen. We'll help you find the perfect fit whatever your plans or bank balance.

How can I find cheap cottages in Winter Park?

Expedia is here to help you easily track down cheap cottages in Winter Park. To discover your dream stay in a couple of quick clicks, simply use our handy filter tool to tailor your search results by amenities, star rating and budget.

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

There are tons of superb things to sink your teeth into in Winter Park. Discover well-known attractions like Winter Park Country Club, Crealde School of Art and Winter Park Village. Casa Feliz Historic Home Museum, Albin Polasek Museum and Sculpture Gardens and Kraft Azalea Gardens are other must-see's.