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

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Winter Garden cottages

A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is 5.140.966 ₫
12.894.266 ₫ total
includes taxes & fees
3 Nov - 4 Nov
Fire Pit & Yard: Updated Winter Garden Home!
A residential street with houses, a parking lot, and a car.

2. Ei8555 - 3BR House Near Disney

Ei8555 - 3BR House Near Disney
3.0 star property
Kissimmee
The price is 3.745.930 ₫
8.408.321 ₫ total
includes taxes & fees
6 Nov - 7 Nov
Ei8555 - 3BR House Near Disney
A covered porch with wicker chairs and a ceiling fan.

3. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (44 reviews)
"Lovely stay in Mount Dora, perfect location, clean and quiet. Would definitely stay again."
United States
Charlotte
The price is 5.644.781 ₫
6.265.707 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Historic Tremain Cottages
A residential area with houses featuring sloped roofs and solar panels.

4. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is 1.937.550 ₫
6.568.036 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Upstay: Bright Family-friendly Retreat With Patio
A row of yellow buildings with numbered doors, a sidewalk, and greenery.

5. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is 2.397.395 ₫
10.260.652 ₫ total
includes taxes & fees
30 Oct - 31 Oct
Serenity - Family & Pet Friendly, Amazing Location
A small, single-story house with a gabled roof and a front porch.

6. 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 5.513.592 ₫
6.120.010 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Mount Dora Cottages
A poolside area with lounge chairs and palm trees, a clear blue sky, and a building with a modern design.

7. Mvy7632 - 4BR House Near Disney

Mvy7632 - 4BR House Near Disney
3.0 star property
Kissimmee
Mvy7632 - 4BR House Near Disney
A single-story house with a white exterior, a front door, and a garage.

8. 9 Mi to Walt Disney World: Family Home w/ Pool!

9 Mi to Walt Disney World: Family Home w/ Pool!
3.0 star property
Clear Creek
9 Mi to Walt Disney World: Family Home w/ Pool!
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

9. Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is 3.229.250 ₫
9.085.300 ₫ total
includes taxes & fees
5 Nov - 6 Nov
Family Resort Home w Pool, BBQ & Game Room
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

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"."
Alexandra 2-night trip
Posted 2 hours ago
Kompose Boutique Resort at Theme Parks

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
256
Accommodation
2509 Cottages
Lowest Price
6.120.010 ₫
Highest Price
12.894.266 ₫

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between 6.120.010 ₫ and 12.894.266 ₫ 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.