A child riding a bicycle on a wooden boardwalk with a body of water and trees in the background.

Search Winter Garden Cottage Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Winter Garden cottages

Interior

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is S$632
includes taxes & fees
24 Sept - 25 Sept
Fire Pit & Yard: Updated Winter Garden Home!
Terrace/patio

2. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (42 reviews)
"Accommodations were comfortable, quaint space. Bed was very comfortable. Just beware the shower is very narrow and ceilings low. Not ideal for a taller or bigger person. Nice and close to the downtown area. Would stay here again."
United States
Betty
The price is S$228
includes taxes & fees
17 Sept - 18 Sept
Historic Tremain Cottages
Interior

3. Mount Dora Home: Private Pool, Spa & Tropical Bar!

Mount Dora Home: Private Pool, Spa & Tropical Bar!
3.0 star property
Mount Dora
6.0 out of 10, (1 review)
The price is S$432
includes taxes & fees
27 Sept - 28 Sept
Mount Dora Home: Private Pool, Spa & Tropical Bar!
Front of property

4. Mount Dora Cottages

Mount Dora Cottages
3.0 star property
Mount Dora
9.4 out of 10, Exceptional, (212 reviews)
"Perfect spot"
United States
PATRICIA
The price is S$300
includes taxes & fees
12 Oct - 13 Oct
Mount Dora Cottages
Exterior

5. Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
Kissimmee
The price is S$1,050
includes taxes & fees
21 Sept - 22 Sept
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
Property grounds

6. Th20 - 3BR House With Resort Access Near Parks

Th20 - 3BR House With Resort Access Near Parks
3.0 star property
Orlando
Th20 - 3BR House With Resort Access Near Parks
Interior

7. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is S$334
includes taxes & fees
22 Sept - 23 Sept
Upstay: Bright Family-friendly Retreat With Patio
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Garden Hotel Reviews

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Room was very clean and spacious. The location was convenient and right outside the entrance of universal studios and a 15 min walk to the entrance. Staff was very helpful about shuttle information and buying tickets for Halloween Horror Nights!"
Travis George 4-night trip
Posted 1 hour ago
DoubleTree by Hilton at the Entrance to Universal Orlando

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
254
Accommodation
2263 Cottages
Lowest Price
S$228
Highest Price
S$1,050

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between S$228 and S$1,050 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.
What is there to do in Winter Garden near my cottage?
Whatever you're into, Winter Garden has plenty of things to keep you on the go. Orange County National Golf Club, Resurrection Catholic Church and West Orange Trail are on many travellers' agendas. Don't forget to explore Winter Garden Art Association, Winter Garden Heritage Museum and Oakland Nature Preserve either. With Expedia's Winter Garden hotel deals, you'll be able to see more renowned attractions like these with the cash you save.

Explore a world of travel with Expedia