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Check prices for these dates

In two weeks
12 Sep - 14 Sep
In one month
26 Sep - 28 Sep
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Cottages in Winter Park

Our top choices for Winter Park cottages

Orlando Lakefront Tiny House Community
The Club House | 2 bedrooms, individually decorated, individually furnished

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (328)
"We enjoyed our stay."
The price is SAR 325
SAR 640 total
includes taxes & fees
2 Sep - 3 Sep
Orlando Lakefront Tiny House Community
Downtown Cottage
1 bedroom, desk, iron/ironing board, free WiFi

Downtown Cottage

9.6 out of 10, Exceptional, (4)
"Thank you for a wonderful stay. This gem of a guest house is in a perfect location in the Mills50 area of downtown Orlando. A perfectly cozy little home with comfortable beds and a welcoming environment. We look forward to staying again next time we are in Orlando!"
The price is SAR 186
SAR 601 total
includes taxes & fees
31 Aug - 1 Sep
Downtown Cottage
The Sanford Foodie Guest House
1 bedroom, desk, WiFi, bed sheets

The Sanford Foodie Guest House

8.6 out of 10, Excellent, (12)
"Cozy little place to stay"
The price is SAR 186
SAR 940 total
includes taxes & fees
1 Sep - 2 Sep
The Sanford Foodie Guest House
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Fridge, microwave, oven, stovetop

Charming 2-bedroom Country Cottage in Kissimmee with private parking

10.0 out of 10, Exceptional, (2)
"The house was exactly as shown. It was very clean and really nice. Great space for parking my large trailer. The neighborhood was nice and very quiet. We would definitely stay again."
The price is SAR 394
SAR 522 total
includes taxes & fees
9 Sep - 10 Sep
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Incredible Private Lakefront Cottage Retreat
Property grounds

Incredible Private Lakefront Cottage Retreat

10.0 out of 10, Exceptional, (27)
"One of our best stays. "
The price is SAR 503
SAR 1,340 total
includes taxes & fees
1 Sep - 2 Sep
Incredible Private Lakefront Cottage Retreat
Tiny Hidden Cottage
Interior

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (49)
"Great location, quiet area & friendly hosts. Could use some updated kitchenware and pans, toaster didnt seem to work. Otherwise was a nice place."
The price is SAR 267
SAR 542 total
includes taxes & fees
2 Sep - 3 Sep
Tiny Hidden Cottage
Back to School Special! Cozy Cottage with queen bed & nearby pickleball courts
Property grounds

Back to School Special! Cozy Cottage with queen bed & nearby pickleball courts

10.0 out of 10, Exceptional, (15)
"Great place, will stay again"
The price is SAR 394
SAR 946 total
includes taxes & fees
18 Sep - 19 Sep
Back to School Special! Cozy Cottage with queen bed & nearby pickleball courts
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Property grounds

Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,

8.4 out of 10, Very Good, (15)
"This was a cute place in a nice neighborhood "
The price is SAR 525
SAR 1,252 total
includes taxes & fees
4 Sep - 5 Sep
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
2 bedrooms, in-room safe, desk, iron/ironing board

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

10.0 out of 10, Exceptional, (26)
"Easy and convenient in a nice place "
The price is SAR 672
SAR 1,313 total
includes taxes & fees
12 Sep - 13 Sep
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
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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Top Winter Park Hotel Reviews

Explore a world of travel with Expedia

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Frequently asked questions

How much do cottages in Winter Park cost?
Cottages in Winter Park range between SAR 186 and SAR 672 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.