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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 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 Rp3.561.901
Rp8.933.749 total
includes taxes & fees
18 Oct - 19 Oct
Fire Pit & Yard: Updated Winter Garden Home!
A residential house with a front yard, a palm tree, and a garage.

2. Chic Orlando Family Getaway w/ Fenced Yard!

Chic Orlando Family Getaway w/ Fenced Yard!
3.0 star property
Rosemont
10.0 out of 10, Exceptional, (2 reviews)
"The house was well supplied with amenities, family friendly and it was very fun to use the pool and games. There’s a super Walmart and other shops close by."
United States
Jennifer
Chic Orlando Family Getaway w/ Fenced Yard!
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, (43 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 Rp3.910.967
Rp4.341.174 total
includes taxes & fees
14 Oct - 15 Oct
Historic Tremain Cottages
A residential area with a well-maintained lawn, a street with parked cars, and a green dumpster.

4. Ei8555 - 3BR House Near Disney

Ei8555 - 3BR House Near Disney
3.0 star property
Kissimmee
The price is Rp2.595.355
Rp5.825.677 total
includes taxes & fees
6 Nov - 7 Nov
Ei8555 - 3BR House Near Disney
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

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

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is Rp1.861.496
Rp5.873.736 total
includes taxes & fees
18 Oct - 19 Oct
Family Resort Home w Pool, BBQ & Game Room
A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

6. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
Serenity - Family & Pet Friendly, Amazing Location
A small, single-story house with a gabled roof and a front porch.

7. 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 Rp3.817.857
Rp4.237.767 total
includes taxes & fees
18 Oct - 19 Oct
Mount Dora Cottages
A modern hotel with a curved driveway, large windows, and palm trees.

8. Mvv7482 - 3BR House Near Disney at Magic Village

Mvv7482 - 3BR House Near Disney at Magic Village
3.0 star property
Kissimmee
Mvv7482 - 3BR House Near Disney at Magic Village
A residential area with houses featuring sloped roofs and solar panels.

9. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
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.
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Top Winter Garden Hotel Reviews

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"Love the pool and the bar"
karen 3-night trip
Posted less than an hour ago
Westgate Lakes Resort & Spa Universal Studios Area

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
214
Accommodation
2264 Cottages
Lowest Price
Rp4.237.767
Highest Price
Rp8.933.749

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between Rp4.237.767 and Rp8.933.749 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.