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Check prices for these dates

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

Our top choices for Winter Park cottages

A modern kitchen with red walls, a dining area with a brown leather couch, and a bar stool.

1. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (18 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is CA $96
CA $236 total
includes taxes & fees
Nov 19 - Nov 20
Downtown Cottage
A white building with large windows and a brick pathway leading to it.

2. The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!

The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!
College Park
10.0 out of 10, Exceptional, (56 reviews)
"Great location, well stocked and beds were very comfortable."
United States
Raegan S.
The price is CA $251
CA $479 total
includes taxes & fees
Nov 16 - Nov 17
The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!
A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

3. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
10.0 out of 10, Exceptional, (1 review)
"Cozy and nice place. It was very clean. Comunication with host was easy. Great view and sitting area from balcony to the lake. Very relaxing!"
United States
jacqueline M.
The price is CA $127
CA $288 total
includes taxes & fees
Dec 7 - Dec 8
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A backyard with a wooden fence, two wicker lounge chairs with floral cushions, and a large beige umbrella.

4. Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Lake Mary
9.8 out of 10, Exceptional, (71 reviews)
"The Property was very clean ! Super convenient location and the perfect size for a family with 2 younger children ! Suzy was super nice !"
United States
Gary
The price is CA $154
CA $356 total
includes taxes & fees
Dec 1 - Dec 2
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A patio with outdoor furniture, a wooden deck, and a basketball hoop.

5. Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (23 reviews)
"We had an amazing stay! The place was beautiful, cozy, and incredibly comfortable. Even though we had to leave earlier than planned, we truly enjoyed our time here. The host was kind, responsive, and made everything easy from start to finish. We would definitely stay here again and look forward to returning in the future. Highly recommend!"
United States
Chiann M.
The price is CA $148
CA $348 total
includes taxes & fees
Dec 6 - Dec 7
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A laundry room with two front-loading washing machines, a drying rack, and a window with blinds.

6. Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
10.0 out of 10, Exceptional, (1 review)
The price is CA $151
CA $439 total
includes taxes & fees
Nov 18 - Nov 19
Shore Steps Cottage - Walking Distance To The Town Of Windermere
A single-story mobile home with a front porch and a small deck.

7. Newly Remodeled Tiny Home 20 minutes from Disney!~

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is CA $120
CA $284 total
includes taxes & fees
Nov 12 - Nov 13
Newly Remodeled Tiny Home 20 minutes from Disney!~
A lakeside patio with wooden rocking chairs and a table, overlooking a calm lake and a forested area.

8. Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Orlando
The price is CA $154
CA $323 total
includes taxes & fees
Nov 18 - Nov 19
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
A resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.

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

Th20 - 3BR House With Resort Access Near Parks
3.0 star property
Orlando
The price is CA $326
CA $669 total
includes taxes & fees
Nov 28 - Nov 29
Th20 - 3BR House With Resort Access Near Parks
A dining area with a wooden table set for four, surrounded by chairs with cushioned seats. A chandelier hangs above the table, and a large mirror with a wooden frame is on the wall.

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

Th89 - 3BR House Near Disney With Resort Access
3.0 star property
Orlando
The price is CA $330
CA $672 total
includes taxes & fees
Dec 5 - Dec 6
Th89 - 3BR House Near Disney With Resort Access
A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is CA $282
CA $708 total
includes taxes & fees
Nov 12 - Nov 13
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 CA $96 and CA $330 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 vacation 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.

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