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Check prices for these dates

Next weekend
5 Sept - 7 Sept
In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct

Our top choices for Winter Garden cottages

Orlando Lakefront Tiny House Community
2 bedrooms, individually decorated, individually furnished

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (328)
"We enjoyed our stay."
The price is HK$675
HK$1,329 total
includes taxes & fees
1 Sept - 2 Sept
Orlando Lakefront Tiny House Community
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 HK$385
HK$1,246 total
includes taxes & fees
31 Aug - 1 Sept
Downtown Cottage
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 HK$554
HK$1,126 total
includes taxes & fees
29 Aug - 30 Aug
Tiny Hidden Cottage
Back to School Special! Cozy Cottage with queen bed & nearby pickleball courts
Property grounds

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

10.0 out of 10, Exceptional, (15)
"Great place, will stay again"
The price is HK$818
HK$1,962 total
includes taxes & fees
18 Sept - 19 Sept
Back to School Special! Cozy Cottage with queen bed & nearby pickleball courts
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Fridge, microwave, oven, stovetop

Charming 2-bedroom Country Cottage in Kissimmee with private parking

10.0 out of 10, Exceptional, (2)
"The house was exactly as shown. It was very clean and really nice. Great space for parking my large trailer. The neighborhood was nice and very quiet. We would definitely stay again."
The price is HK$818
HK$1,084 total
includes taxes & fees
9 Sept - 10 Sept
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Incredible Private Lakefront Cottage Retreat
Property grounds

Incredible Private Lakefront Cottage Retreat

10.0 out of 10, Exceptional, (27)
"One of our best stays. "
The price is HK$904
HK$2,601 total
includes taxes & fees
3 Sept - 4 Sept
Incredible Private Lakefront Cottage Retreat
Historic Tremain Cottages
Front of property

Historic Tremain Cottages

3.0 star property
8.4 out of 10, Very good, (31)
"Great location!"
Historic Tremain Cottages
Jedi cottage 4 miles from Disney! Mins from universal!
Fridge, microwave, oven, stovetop

Jedi cottage 4 miles from Disney! Mins from universal!

9.4 out of 10, Exceptional, (21)
"We loved staying here! "
The price is HK$506
HK$1,570 total
includes taxes & fees
29 Aug - 30 Aug
Jedi cottage 4 miles from Disney! Mins from universal!
Hidden Lake View Cottage 5 miles from Disney!
Property grounds

Hidden Lake View Cottage 5 miles from Disney!

9.0 out of 10, Wonderful, (2)
"Awesome"
The price is HK$623
HK$1,734 total
includes taxes & fees
1 Sept - 2 Sept
Hidden Lake View Cottage 5 miles from Disney!
Romantic 1BR/1BA Cottage overlooking Lake Alfred!
Exterior

Romantic 1BR/1BA Cottage overlooking Lake Alfred!

10.0 out of 10, Exceptional, (19)
"Beautiful and clean place. Very quiet which gives you the opportunity to hear nature right outside. I can’t wait to stay here again!"
The price is HK$1,783
HK$3,469 total
includes taxes & fees
31 Aug - 1 Sept
Romantic 1BR/1BA Cottage overlooking Lake Alfred!
Disney, Universal and Legoland Getaway
A heated pool

Disney, Universal and Legoland Getaway

9.2 out of 10, Wonderful, (9)
The price is HK$584
HK$1,674 total
includes taxes & fees
29 Aug - 30 Aug
Disney, Universal and Legoland Getaway
Mount Dora Cottages
Terrace/patio

Mount Dora Cottages

3.0 star property
9.4 out of 10, Exceptional, (208)
"Our family loved this place and the neighborhood is perfect for a quiet afternoon. "
The price is HK$1,451
HK$1,610 total
includes taxes & fees
2 Sept - 3 Sept
Mount Dora Cottages
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Smart TV

Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

10.0 out of 10, Exceptional, (4)
"The cottage was conveniently located near d'town. Comfortable, clean and well-stocked. "
The price is HK$874
HK$1,704 total
includes taxes & fees
29 Aug - 30 Aug
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Relaxing Getaway on the Lake at Adams Estate
Exterior

Relaxing Getaway on the Lake at Adams Estate

10.0 out of 10, Exceptional, (2)
"Gorgeous setting, very nice, clean accommodation. Quiet location, but great location for going to Orlando or the Lakeland area, in addition to Lake Alfred and Winter Haven."
The price is HK$1,176
HK$2,117 total
includes taxes & fees
31 Aug - 1 Sept
Relaxing Getaway on the Lake at Adams Estate
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Property grounds

Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,

8.4 out of 10, Very good, (15)
"This was a cute place in a nice neighborhood "
The price is HK$1,090
HK$2,599 total
includes taxes & fees
4 Sept - 5 Sept
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Charming 2-bedroom cottage in Kissimmee
Children’s area

Charming 2-bedroom cottage in Kissimmee

2.0 star property
10.0 out of 10, Exceptional, (1)
"Kudos to the hosts. A seamless experience. My first ever vacation rental and I was very impressed. The cottage was super clean and was equipped with everything and then some. "
The price is HK$680
HK$1,806 total
includes taxes & fees
2 Sept - 3 Sept
Charming 2-bedroom cottage in Kissimmee
Waterfront Lake Dora Escape w/ Private Dock & Slip
Interior

Waterfront Lake Dora Escape w/ Private Dock & Slip

3.0 star property
Waterfront Lake Dora Escape w/ Private Dock & Slip
Cozy Lake Front Cottage
Property grounds

Cozy Lake Front Cottage

10.0 out of 10, Exceptional, (17)
"The cottage is exactly as described. It is a beautiful place with beautiful views and relaxing setting."
The price is HK$1,254
HK$2,305 total
includes taxes & fees
4 Sept - 5 Sept
Cozy Lake Front Cottage
Beautiful Historic Cottage, Rendezvous
Fridge, microwave, oven, stovetop

Beautiful Historic Cottage, Rendezvous

9.2 out of 10, Wonderful, (14)
"Can’t beat this place for proximity to all Mount Dora offers, but in a quiet location with parking. Wish it had two comfortable chairs rather than a lumpy chaise, but otherwise great."
The price is HK$1,191
HK$1,493 total
includes taxes & fees
1 Sept - 2 Sept
Beautiful Historic Cottage, Rendezvous
Relaxing Stay in Duplex at Adams Estate
Exterior

Relaxing Stay in Duplex at Adams Estate

10.0 out of 10, Exceptional, (6)
"Great place!"
The price is HK$1,300
HK$2,522 total
includes taxes & fees
31 Aug - 1 Sept
Relaxing Stay in Duplex at Adams Estate
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 Garden Hotel Reviews

Find out more about Winter Garden

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
168
Accommodation
2018 Cottages
Lowest Price
HK$554
Highest Price
HK$874

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between HK$554 and HK$874 per night. These stays offer a chance to get reacquainted with nature — at a price you can afford. 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 Garden with Expedia?
Expedia has some great cottages in Winter Garden, so get ready for a memorable holiday on nature's doorstep. If you're sticking to a budget, select how much you'd like to spend and the preferred star rating of your property. Or, use our filters to search for cottages with free WiFi or a kitchen. We'll help you find the right fit whatever your bank balance or plans.
How can I find cheap cottages in Winter Garden?
With Expedia's convenient filter tool, scoring cheap cottages in Winter Garden has never been simpler. To discover accommodation that'll make your wallet happy, fine-tune your search results by budget, star rating and amenities.