A clear lake surrounded by trees and a concrete walkway.

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Winter Springs cottages

A patio with outdoor furniture, a wooden deck, and a basketball hoop.

1. Labor Day Weekend! Orlando Last-Minute Deal! Book Today!

Labor Day Weekend! Orlando Last-Minute Deal! Book Today!
Lake Mary
10.0 out of 10, Exceptional, (21 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is £168
includes taxes & fees
14 Sept - 15 Sept
Labor Day Weekend! Orlando Last-Minute Deal! Book Today!
A single-story building with the number 297, a red door, and a bench outside.

2. 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)
"A great, cozy home that checked all of our boxes. We have stayed a few times with this host and find them consistently good. Very comfy and clean!! Already have them booked twice more!"
United States
Lisa M.
The price is £177
includes taxes & fees
8 Sept - 9 Sept
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A house with a porch, surrounded by a grassy area and a pond with lily pads.

3. Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (38 reviews)
"Beautiful property in a fantastic location! We've booking this stay twice and will be back again."
United States
Lisa
The price is £267
includes taxes & fees
4 Sept - 5 Sept
Incredible Private Lakefront Cottage Retreat
A house with a red door, a front porch, and a pathway leading to the entrance.

4. 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 £134
includes taxes & fees
6 Sept - 7 Sept
Downtown Cottage
A white building with large windows and a brick pathway leading to it.

5. 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, (50 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
The price is £243
includes taxes & fees
29 Sept - 30 Sept
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.

6. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is £168
includes taxes & fees
7 Sept - 8 Sept
Romantic Lakefront Getaway with Balcony near Downtown Orlando
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
The price is £177
includes taxes & fees
6 Sept - 7 Sept
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)
The price is £279
includes taxes & fees
12 Sept - 13 Sept
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
The price is £378
includes taxes & fees
21 Sept - 22 Sept
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
The price is £346
includes taxes & fees
17 Sept - 18 Sept
Th20 - 3BR House With Resort Access Near Parks
A resort with multiple buildings, a large swimming pool, and a lake in the background.

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

Th89 - 3BR House Near Disney With Resort Access
3.0 star property
Orlando
The price is £346
includes taxes & fees
6 Sept - 7 Sept
Th89 - 3BR House Near Disney With Resort Access
A pink building with a garage, a street lamp, and a fire hydrant.

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

Th60 - 3BR House Near Disney With Pool Access
3.0 star property
Orlando
The price is £337
includes taxes & fees
8 Sept - 9 Sept
Th60 - 3BR House Near Disney With Pool Access
A multi-story residential building with balconies, a lawn, and outdoor seating.

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

Th10 - 3BR House Near Disney and Universal Studios
3.0 star property
Orlando
The price is £347
includes taxes & fees
14 Sept - 15 Sept
Th10 - 3BR House Near Disney and Universal Studios
A row of yellow buildings with red-tiled roofs, a paved driveway, and a well-maintained lawn with palm trees.

14. Th14 - 3BR House With Pool Access Near Disney

Th14 - 3BR House With Pool Access Near Disney
3.0 star property
Orlando
The price is £376
includes taxes & fees
4 Sept - 5 Sept
Th14 - 3BR House With Pool Access Near Disney
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 Springs Hotel Reviews

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Great stay"
Nathaniel 2-night trip
Posted less than an hour ago
DoubleTree by Hilton at the Entrance to Universal Orlando

Find out more about Winter Springs

Winter Springs Cottages information

Number of reviews
125
Accommodation
147 Cottages
Lowest Price
£134
Highest Price
£378

Frequently asked questions

How much do cottages in Winter Springs cost?
You'll pay between £134 and £378 per night for cottages in Winter Springs. Whatever your budget, an ideal stay is only a few clicks away on Expedia. 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 Springs with Expedia?
Expedia has some terrific cottages in Winter Springs, so start packing your bags for a memorable holiday on nature's doorstep. If you're sticking to a budget, select how much you want to spend and the star rating of your property. Or take advantage of our filters to search for cottages with a hot tub or a kitchen. We'll help you find the perfect pad whatever your trip looks like.
How can I find cheap cottages in Winter Springs?
A good way to find cheap cottages in Winter Springs is with Expedia's useful filter tool. Tailor your search results by star rating, amenities and budget to access unbeatable rates with only a few clicks.
What is there to do in Winter Springs near my cottage?
After you've unpacked your things and settled in, head out and discover the cool things Winter Springs has to offer. Tuscawilla Golf Course is a popular attraction to add to your itinerary.