Photo by Stephanie Moraca

Search Winter Springs Cottages

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Cottages in Winter Springs

Our top choices for Winter Springs cottages

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (328)
"We enjoyed our stay."
$147 nightly
The price is $165
Aug 25 - Aug 26
Total with taxes and fees
Orlando Lakefront Tiny House Community

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (49)
"Great location, quiet area & friendly hosts. Could use some updated kitchenware and pans, toaster didnt seem to work. Otherwise was a nice place."
$131 nightly
The price is $144
Aug 25 - Aug 26
Total with taxes and fees
Tiny Hidden Cottage

Downtown Cottage

9.6 out of 10, Exceptional, (4)
"Thank you for a wonderful stay. This gem of a guest house is in a perfect location in the Mills50 area of downtown Orlando. A perfectly cozy little home with comfortable beds and a welcoming environment. We look forward to staying again next time we are in Orlando!"
$145 nightly
The price is $160
Aug 25 - Aug 26
Total with taxes and fees
Downtown Cottage

The Sanford Foodie Guest House

8.6 out of 10, Excellent, (12)
"Cozy little place to stay"
$229 nightly
The price is $252
Sep 1 - Sep 2
Total with taxes and fees
The Sanford Foodie Guest House

Incredible Private Lakefront Cottage Retreat

10.0 out of 10, Exceptional, (27)
"One of our best stays. "
$290 nightly
The price is $321
Sep 1 - Sep 2
Total with taxes and fees
Incredible Private Lakefront Cottage Retreat

Back to School Special! Cozy Cottage with queen bed & nearby pickleball courts

10.0 out of 10, Exceptional, (15)
"Great place, will stay again"
$224 nightly
The price is $248
Sep 18 - Sep 19
Total with taxes and fees
Back to School Special! Cozy Cottage with queen bed & nearby pickleball courts

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

10.0 out of 10, Exceptional, (26)
"Easy and convenient in a nice place "
$319 nightly
The price is $354
Sep 1 - Sep 2
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winter Springs Hotel Reviews