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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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 ₩285,075
₩694,348 total
includes taxes & fees
Oct 26 - Oct 27
Fire Pit & Yard: Updated Winter Garden Home!
A covered porch with wicker chairs and a ceiling fan.

2. 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 ₩237,371
₩263,482 total
includes taxes & fees
Oct 5 - Oct 6
Historic Tremain Cottages
A residential house with a front yard, a palm tree, and a garage.

3. 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
The price is ₩248,423
₩755,884 total
includes taxes & fees
Oct 15 - Oct 16
Chic Orlando Family Getaway w/ Fenced Yard!
A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

4. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is ₩124,000
₩537,550 total
includes taxes & fees
Oct 3 - Oct 4
Serenity - Family & Pet Friendly, Amazing Location
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 ₩141,404
₩446,184 total
includes taxes & fees
Oct 4 - Oct 5
Family Resort Home w Pool, BBQ & Game Room
A resort with a central swimming pool, sun loungers, and palm trees.

6. Mvy7632 - 4BR House Near Disney

Mvy7632 - 4BR House Near Disney
3.0 star property
Kissimmee
The price is ₩266,409
₩646,146 total
includes taxes & fees
Oct 6 - Oct 7
Mvy7632 - 4BR House Near Disney
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 ₩289,555
₩321,402 total
includes taxes & fees
Oct 5 - Oct 6
Mount Dora Cottages
A single-story house with a covered patio area, a lawn, and a clear sky.

8. Pond Access & Grill! Group Escape, 19 Mi to WDW

Pond Access & Grill! Group Escape, 19 Mi to WDW
3.0 star property
Kissimmee
The price is ₩199,553
₩273,605 total
includes taxes & fees
Oct 4 - Oct 5
Pond Access & Grill! Group Escape, 19 Mi to WDW
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

Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent
"Great place to stay! Second time and would do a 3rd!"
Patricia 3-night trip
Posted less than an hour ago
Universal's Endless Summer Resort - Dockside Inn and Suites

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
214
Accommodation
2264 Cottages
Lowest Price
₩263,482
Highest Price
₩755,884

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between ₩263,482 and ₩755,884 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.