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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Winter Springs cottages

A single-story building with the number 297, a red door, and a bench outside.

1. 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 £206
includes taxes & fees
10 Nov - 11 Nov
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A patio with outdoor furniture, a wooden deck, and a basketball hoop.

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

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (23 reviews)
"We had an amazing stay! The place was beautiful, cozy, and incredibly comfortable. Even though we had to leave earlier than planned, we truly enjoyed our time here. The host was kind, responsive, and made everything easy from start to finish. We would definitely stay here again and look forward to returning in the future. Highly recommend!"
United States
Chiann M.
The price is £223
includes taxes & fees
28 Nov - 29 Nov
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A modern kitchen with red walls, a dining area with a brown leather couch, and a bar stool.

3. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (16 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is £139
includes taxes & fees
29 Oct - 30 Oct
Downtown Cottage
A white building with large windows and a brick pathway leading to it.

4. 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, (55 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
The price is £245
includes taxes & fees
2 Nov - 3 Nov
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.

5. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is £156
includes taxes & fees
1 Nov - 2 Nov
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A laundry room with two front-loading washing machines, a drying rack, and a window with blinds.

6. 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 £276
includes taxes & fees
2 Nov - 3 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.

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is £374
includes taxes & fees
5 Nov - 6 Nov
Fire Pit & Yard: Updated Winter Garden Home!
A resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.

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

Th60 - 3BR House Near Disney With Pool Access
3.0 star property
Orlando
The price is £371
includes taxes & fees
9 Nov - 10 Nov
Th60 - 3BR House Near Disney With Pool Access
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 £180
includes taxes & fees
29 Oct - 30 Oct
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
A resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.

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

Th10 - 3BR House Near Disney and Universal Studios
3.0 star property
Orlando
The price is £356
includes taxes & fees
1 Nov - 2 Nov
Th10 - 3BR House Near Disney and Universal Studios
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

Orlando Palms Hotel

Orlando Palms Hotel

8/10 Good
"Nice stay, cold water because boiler overloaded but they will turn it on if you complain. Very nice staff members. It was a good stay"
Iris 1-night trip
Posted 3 hours ago
Orlando Palms Hotel

Find out more about Winter Springs

Winter Springs Cottages information

Number of reviews
162
Accommodation
147 Cottages
Lowest Price
£139
Highest Price
£374

Frequently asked questions

How much do cottages in Winter Springs cost?
You'll pay between £139 and £374 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.