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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Featured Cottages in Winter Springs

Orlando Lakefront Tiny House Community
The Club House

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (328)
"We enjoyed our stay."
The price is AU$263
includes taxes & fees
1 Sept - 2 Sept
Orlando Lakefront Tiny House Community
Tiny Hidden Cottage
Interior

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."
The price is AU$225
includes taxes & fees
28 Aug - 29 Aug
Tiny Hidden Cottage
Labor Day Getaway!! Guest House with Private pool & WiFi
Outdoor pool

Labor Day Getaway!! Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (40)
"Wonderful stay. This is my second time here and love the accommodations and location. Very quiet. "
Labor Day Getaway!! Guest House with Private pool & WiFi
~ 12 Mi to Disney: Downtown Winter Garden Cottage!
Exterior

~ 12 Mi to Disney: Downtown Winter Garden Cottage!

9.8 out of 10, Exceptional, (43)
"We LOVE staying at Flamingo House. We are a repeat customer and will be back again soon. Suzie and is wonderful to work with and the house is everything we need!"
~ 12 Mi to Disney: Downtown Winter Garden Cottage!
Private Patio: College Park Cottage in Orlando!
Outdoor dining

Private Patio: College Park Cottage in Orlando!

10.0 out of 10, Exceptional, (8)
"I stayed here for a month with my dog. It was exactly what I needed! The hosts thought of everything that you could possibly need. There is a ton of space and everything is organized and clean. Location is great being close to local shops, necessities, and major roads."
Private Patio: College Park Cottage in Orlando!
Lovely Spacious Guesthouse in Mills 50 District, Orlando
Exterior detail

Lovely Spacious Guesthouse in Mills 50 District, Orlando

9.0 out of 10, Wonderful, (2)
"Loved this space, by great locations. Can’t wait to visit again."
Lovely Spacious Guesthouse in Mills 50 District, Orlando
2BR COTTAGE IN SANFORD HISTORIC DISTRICT
Interior

2BR COTTAGE IN SANFORD HISTORIC DISTRICT

10.0 out of 10, Exceptional, (107)
"We had a great time at this charming cottage. Hosts were easy to communicate with and very accommodating. "
2BR COTTAGE IN SANFORD HISTORIC DISTRICT
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Paper towels

Orlando Home w/ Private Pool: 10 Mi to UCF Campus!

3.0 star property
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Resort Townhome: Perfect Orlando Vacation Spot!!
House (3 Bedrooms) | Property amenity

Resort Townhome: Perfect Orlando Vacation Spot!!

4.0 star property
8.0 out of 10, Very good, (1)
Resort Townhome: Perfect Orlando Vacation Spot!!
Downtown Cottage
1 bedroom, desk, iron/ironing board, free WiFi

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!"
The price is AU$242
includes taxes & fees
28 Aug - 29 Aug
Downtown Cottage
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
2 bedrooms, in-room safe, desk, iron/ironing board

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 "
The price is AU$549
includes taxes & fees
2 Sept - 3 Sept
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Orlando Golden Girls Retreat: Prime Location!
House (1 Bedroom) | Interior

Orlando Golden Girls Retreat: Prime Location!

3.0 star property
Orlando Golden Girls Retreat: Prime Location!
Chic Orlando Family Getaway w/ Fenced Yard!
House (4 Bedrooms) | Front of property

Chic Orlando Family Getaway w/ Fenced Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
Chic Orlando Family Getaway w/ Fenced Yard!
~ 9 Mi to Universal: Orlando Retreat w/ Sun Porch!
House (3 Bedrooms) | Interior

~ 9 Mi to Universal: Orlando Retreat w/ Sun Porch!

3.0 star property
~ 9 Mi to Universal: Orlando Retreat w/ Sun Porch!
Fire Pit & Yard: Updated Winter Garden Home!
House (2 Bedrooms) | Interior

Fire Pit & Yard: Updated Winter Garden Home!

3.0 star property
Fire Pit & Yard: Updated Winter Garden Home!
Screened Lanai + Fenced Yard: Luxe Orlando Home
Interior

Screened Lanai + Fenced Yard: Luxe Orlando Home

3.0 star property
Screened Lanai + Fenced Yard: Luxe Orlando Home
The Sanford Foodie Guest House
1 bedroom, desk, WiFi, bed sheets

The Sanford Foodie Guest House

8.6 out of 10, Excellent, (12)
"Cozy little place to stay"
The price is AU$390
includes taxes & fees
1 Sept - 2 Sept
The Sanford Foodie Guest House
Dtwn Winter Garden Home: 12 Mi to Disney!
Fridge, microwave, stovetop, dishwasher

Dtwn Winter Garden Home: 12 Mi to Disney!

10.0 out of 10, Exceptional, (13)
"Our family greatly enjoyed staying at this downtown Winter Garden home. Clean, well decorated, accommodating, and conveniently located for all things Winter Garden, FL. "
Dtwn Winter Garden Home: 12 Mi to Disney!
Near Kayak Launch: Riverfront Home in Sanford!
House (2 Bedrooms) | Interior

Near Kayak Launch: Riverfront Home in Sanford!

3.0 star property
Near Kayak Launch: Riverfront Home in Sanford!
Dtwn Winter Garden Home: 12 Mi to Disney!
Cottage (3 Bedrooms) | Interior

Dtwn Winter Garden Home: 12 Mi to Disney!

3.0 star property
Dtwn Winter Garden Home: 12 Mi to 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

Find out more about Winter Springs

Find out more about Winter Springs

Winter Springs Cottages information

Number of reviews
504
Accommodation
126 Cottages
Lowest Price
AU$225
Highest Price
AU$549

Frequently asked questions

How much do cottages in Winter Springs cost?
Rates for cottages in Winter Springs range between AU$225 and AU$549 per night. No matter your budget, you're sure to find the perfect place to get reacquainted with nature. This price was 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.
What is there to do in Winter Springs near my cottage?
Whatever your interests, Winter Springs has plenty of things to keep you on the hop. Central Florida Zoo & Botanical Gardens, Sanford Museum and Albin Polasek Museum and Sculpture Gardens are on most travellers' to-do lists. Don't miss Morse Museum of American Art, The Princess Theatre and Hard Knocks either. With Expedia's hotel deals in Winter Springs, you can see even more neat attractions like these with the money you save.