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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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.
$167 nightly
The price is $186
Oct 11 - Oct 12
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, (54 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
$294 nightly
The price is $327
Oct 12 - Oct 13
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
A residential house with a front yard, a palm tree, and a garage.

3. Chic Orlando Family Getaway w/ Fenced Yard!

Chic Orlando Family Getaway w/ Fenced Yard!
3.0 star property
Rosemont
10.0 out of 10, Exceptional, (2 reviews)
"The house was well supplied with amenities, family friendly and it was very fun to use the pool and games. There’s a super Walmart and other shops close by."
United States
Jennifer
$495 nightly
The price is $557
Oct 15 - Oct 16
Total with taxes and fees
Chic Orlando Family Getaway w/ Fenced Yard!
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, (67 reviews)
"The property was very clean and the host was quick to respond to any questions."
United States
Colette T.
$220 nightly
The price is $244
Oct 13 - Oct 14
Total with taxes and fees
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

5. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
$182 nightly
The price is $202
Nov 3 - Nov 4
Total with taxes and fees
Romantic Lakefront Getaway with Balcony near Downtown Orlando
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, (22 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
$200 nightly
The price is $221
Oct 8 - Oct 9
Total with taxes and fees
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
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)
$295 nightly
The price is $327
Oct 13 - Oct 14
Total with taxes and fees
Shore Steps Cottage - Walking Distance To The Town Of Windermere
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
$214 nightly
The price is $238
Oct 19 - Oct 20
Total with taxes and fees
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
A resort with a large central pool, a smaller circular pool, and a fountain. There are multiple buildings with balconies and a parking lot.

9. 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
A single-story mobile home with a front porch and a small deck.

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

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
$186 nightly
The price is $208
Oct 8 - Oct 9
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.

11. 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
$724 nightly
The price is $821
Nov 2 - Nov 3
Total with taxes and fees
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
A multi-story residential building with balconies, a lawn, and outdoor seating.

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

Th10 - 3BR House Near Disney and Universal Studios
3.0 star property
Orlando
$436 nightly
The price is $490
Oct 28 - Oct 29
Total with taxes and fees
Th10 - 3BR House Near Disney and Universal Studios
A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

13. 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
Oct 18 - Oct 19
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
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. Th20 - 3BR House With Resort Access Near Parks

Th20 - 3BR House With Resort Access Near Parks
3.0 star property
Orlando
$432 nightly
The price is $486
Oct 28 - Oct 29
Total with taxes and fees
Th20 - 3BR House With Resort Access Near 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.
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Top Winter Park Hotel Reviews

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent
"La locación"
Sonia 2-night trip
Posted 11 hours ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Find out more about Winter Park

Winter Park Cottages information

Number of reviews
123
Accommodation
429 Cottages
Lowest Price
$186
Highest Price
$821

Frequently asked questions

How much do cottages in Winter Park cost?
Cottages in Winter Park range between $186 and $821 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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