A two-story house with a balcony, surrounded by lush greenery and trees.

Search Cottages in Winter Park

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Winter Park cottages

A house with a red door, a front porch, and a pathway leading to the entrance.

1. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (15 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is SAR 287
SAR 715 total
includes taxes & fees
26 Oct - 27 Oct
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, (54 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
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
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A single-story building with the number 297, a red door, and a bench outside.

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, (68 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 SAR 358
SAR 923 total
includes taxes & fees
18 Oct - 19 Oct
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, (22 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is SAR 394
SAR 955 total
includes taxes & fees
14 Nov - 15 Nov
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A resort with multiple buildings, a central pool area, and a lake.

6. Th60 - 3BR House Near Disney With Pool Access

Th60 - 3BR House Near Disney With Pool Access
3.0 star property
Orlando
Th60 - 3BR House Near Disney With Pool Access
A serene landscape with a pond, trees with Spanish moss, and a palm tree.

7. 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 SAR 465
SAR 1,299 total
includes taxes & fees
16 Nov - 17 Nov
Shore Steps Cottage - Walking Distance To The Town Of Windermere
A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is SAR 747
SAR 1,873 total
includes taxes & fees
18 Oct - 19 Oct
Fire Pit & Yard: Updated Winter Garden Home!
A lakeside patio with wooden rocking chairs and a table, overlooking a calm lake and a forested area.

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

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Orlando
The price is SAR 409
SAR 892 total
includes taxes & fees
19 Oct - 20 Oct
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
An aerial view of a resort with multiple swimming pools, a dock, and a residential area with houses.

10. Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
Kissimmee
The price is SAR 541
SAR 3,069 total
includes taxes & fees
2 Nov - 3 Nov
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
A single-story mobile home with a front porch and a small deck.

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

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is SAR 319
SAR 785 total
includes taxes & fees
17 Oct - 18 Oct
Newly Remodeled Tiny Home 20 minutes from Disney!~
A resort with a large central pool, a smaller circular pool, and a fountain. There are multiple buildings with balconies and a parking lot.

12. Th10 - 3BR House Near Disney and Universal Studios

Th10 - 3BR House Near Disney and Universal Studios
3.0 star property
Orlando
Th10 - 3BR House Near Disney and Universal Studios
A resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.

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

Th20 - 3BR House With Resort Access Near Parks
3.0 star property
Orlando
Th20 - 3BR House With Resort Access Near Parks
A resort with a large central pool, a smaller circular pool, and a fountain. There are multiple buildings with balconies and a parking lot.

14. Th130 - 3BR House Near Disney and Universal Parks

Th130 - 3BR House Near Disney and Universal Parks
3.0 star property
Orlando
Th130 - 3BR House Near Disney and Universal Parks
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Park Hotel Reviews

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

8/10 Good
"Convenient nice hotel"
Kirk 1-night trip
Posted less than an hour ago
Hyatt Regency Orlando International Airport

Frequently asked questions

How much do cottages in Winter Park cost?
Cottages in Winter Park range between SAR 715 and SAR 3,069 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.