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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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 ₩267,187
₩670,143 total
includes taxes & fees
Oct 18 - Oct 19
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 ₩293,011
₩325,243 total
includes taxes & fees
Nov 3 - Nov 4
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 ₩194,445
₩436,462 total
includes taxes & fees
Nov 6 - Nov 7
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 ₩139,636
₩440,606 total
includes taxes & fees
Oct 18 - Oct 19
Family Resort Home w Pool, BBQ & Game Room
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 ₩286,035
₩317,495 total
includes taxes & fees
Oct 18 - Oct 19
Mount Dora Cottages
A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

7. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is ₩122,299
₩530,177 total
includes taxes & fees
Oct 19 - Oct 20
Serenity - Family & Pet Friendly, Amazing Location
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
The price is ₩303,401
₩654,717 total
includes taxes & fees
Oct 27 - Oct 28
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
The price is ₩102,041
₩342,878 total
includes taxes & fees
Oct 19 - Oct 20
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

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"Good location. Clean room. Great breakfast buffet. Friendly staff."
Carla M Garayua 3-night trip
Posted 2 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
214
Accommodation
2264 Cottages
Lowest Price
₩317,495
Highest Price
₩670,143

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between ₩317,495 and ₩670,143 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 vacation 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 accommodations 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 travelers' 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.