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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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 CA $135
CA $349 total
includes taxes & fees
Oct 27 - Oct 28
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, (22 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 CA $134
CA $348 total
includes taxes & fees
Nov 2 - Nov 3
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A house with a red door, a front porch, and a pathway leading to the entrance.

3. 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 CA $108
CA $269 total
includes taxes & fees
Oct 25 - Oct 26
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 CA $226
CA $471 total
includes taxes & fees
Nov 4 - Nov 5
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 CA $113
CA $284 total
includes taxes & fees
Oct 26 - Oct 27
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A serene landscape with a pond, trees with Spanish moss, and a palm tree.

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 CA $158
CA $470 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $281
CA $706 total
includes taxes & fees
Oct 20 - Oct 21
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.

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

Th10 - 3BR House Near Disney and Universal Studios
3.0 star property
Orlando
The price is CA $348
CA $693 total
includes taxes & fees
Oct 28 - Oct 29
Th10 - 3BR House Near Disney and Universal Studios
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 CA $154
CA $330 total
includes taxes & fees
Oct 25 - Oct 26
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. Th20 - 3BR House With Resort Access Near Parks

Th20 - 3BR House With Resort Access Near Parks
3.0 star property
Orlando
The price is CA $343
CA $687 total
includes taxes & fees
Oct 28 - Oct 29
Th20 - 3BR House With Resort Access Near Parks
A pink building with a garage, a street lamp, and a fire hydrant.

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

Th60 - 3BR House Near Disney With Pool Access
3.0 star property
Orlando
The price is CA $375
CA $724 total
includes taxes & fees
Nov 9 - Nov 10
Th60 - 3BR House Near Disney With Pool Access
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. 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.
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Top Winter Springs Hotel Reviews

Avanti International Resort

Avanti International Resort

10/10 Excellent
"Great stay and close to everything! Staff was great to."
Herbie 4-night trip
Posted 1 hour ago
Avanti International Resort

Find out more about Winter Springs

Winter Springs Cottages information

Number of reviews
123
Accommodation
147 Cottages
Lowest Price
CA $269
Highest Price
CA $724

Frequently asked questions

How much do cottages in Winter Springs cost?
You'll pay between CA $269 and CA $724 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 vacation 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.

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