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

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

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.
$163 nightly
The price is $181
Sep 24 - Sep 25
Total with taxes and fees
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, (52 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
$292 nightly
The price is $324
Sep 21 - Sep 22
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
An outdoor seating area with a fire pit and chairs under an umbrella, overlooking a calm lake.

3. Luxury Lakefront Cottage - Private Hot Tub -Stunning Sunset Views near UCF

Luxury Lakefront Cottage - Private Hot Tub -Stunning Sunset Views near UCF
Orlando
Luxury Lakefront Cottage - Private Hot Tub -Stunning Sunset Views near UCF
A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

4. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
$181 nightly
The price is $201
Sep 20 - Sep 21
Total with taxes and fees
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A single-story building with the number 297, a red door, and a bench outside.

5. 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, (66 reviews)
"The place was beautiful, cozy and so clean!!!! loved the pool and enjoyed spending my birthday there! will visit again soon!"
United States
Sara L.
$212 nightly
The price is $234
Sep 21 - Sep 22
Total with taxes and fees
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A patio with outdoor furniture, a wooden deck, and a basketball hoop.

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

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (21 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
$202 nightly
The price is $223
Sep 21 - Sep 22
Total with taxes and fees
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A lakeside patio with wooden rocking chairs and a table, overlooking a calm lake and a forested area.

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

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Orlando
$211 nightly
The price is $234
Sep 17 - Sep 18
Total with taxes and fees
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
A serene landscape with a pond, trees with Spanish moss, and a palm tree.

8. 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)
$334 nightly
The price is $371
Sep 17 - Sep 18
Total with taxes and fees
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.

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
$444 nightly
The price is $499
Sep 20 - Sep 21
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
A resort with a swimming pool, parking, and a view of a lake.

10. 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 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
$188 nightly
The price is $210
Sep 17 - Sep 18
Total with taxes and fees
Newly Remodeled Tiny Home 20 minutes from Disney!~
An aerial view of a resort with multiple swimming pools, a dock, and a residential area with houses.

12. 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
$728 nightly
The price is $826
Sep 21 - Sep 22
Total with taxes and fees
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
A residential area with multi-story buildings, a well-maintained lawn, and trees with autumn foliage.

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

Th60 - 3BR House Near Disney With Pool Access
3.0 star property
Orlando
$416 nightly
The price is $467
Sep 24 - Sep 25
Total with taxes and fees
Th60 - 3BR House Near Disney With Pool Access
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

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Rooms were clean. Staff was very helpful. Convenient for Universal Studios park passes."
Sean 7-night trip
Posted less than an hour ago
Universal's Cabana Bay Beach Resort

Find out more about Winter Park

Winter Park Cottages information

Number of reviews
139
Accommodation
374 Cottages
Lowest Price
$181
Highest Price
$826

Frequently asked questions

How much do cottages in Winter Park cost?
Cottages in Winter Park range between $181 and $826 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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