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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

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 P12,460
P31,252 total
includes taxes & fees
Sep 20 - Sep 21
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, (41 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 P10,931
P12,134 total
includes taxes & fees
Oct 5 - Oct 6
Historic Tremain Cottages
Exterior

3. 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 P10,009
P52,319 total
includes taxes & fees
Sep 21 - Sep 22
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
Interior

4. 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 P9,204
P21,488 total
includes taxes & fees
Sep 9 - Sep 10
Pond Access & Grill! Group Escape, 19 Mi to WDW
Exterior

5. Th60 - 3BR House Near Disney With Pool Access

Th60 - 3BR House Near Disney With Pool Access
3.0 star property
Orlando
The price is P14,166
P29,253 total
includes taxes & fees
Sep 24 - Sep 25
Th60 - 3BR House Near Disney With Pool Access
Interior

6. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is P4,759
P15,990 total
includes taxes & fees
Sep 29 - Sep 30
Upstay: Bright Family-friendly Retreat With Patio
Interior

7. ~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
Indian Ridge
The price is P9,016
P29,794 total
includes taxes & fees
Sep 9 - Sep 10
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
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

Walt Disney World Dolphin

Walt Disney World Dolphin

10/10 Excellent
"Perfect location. Staff were amazing. Food was excellent"
JENNIFER 3-night trip
Posted less than an hour ago
Walt Disney World Dolphin

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
41
Accommodation
2275 Cottages
Lowest Price
P12,134
Highest Price
P52,319

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between P12,134 and P52,319 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.

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