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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Winter Garden cottages

House (2 Bedrooms) | Interior

Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is ￥39,647
￥89,695 total
includes taxes & fees
Jul 26 - Jul 27
Fire Pit & Yard: Updated Winter Garden Home!
Property grounds

Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
The price is ￥23,444
￥60,904 total
includes taxes & fees
Jul 31 - Aug 1
Shore Steps Cottage - Walking Distance To The Town Of Windermere
House (2 Bedrooms) | Interior

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 ￥29,981
￥91,224 total
includes taxes & fees
Jul 29 - Jul 30
Chic Orlando Family Getaway w/ Fenced Yard!
Exterior

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
College Park
10.0 out of 10, Exceptional, (43 reviews)
"The place was great overall, had everything needed. Rooms and bathrooms were spacious. Hosts left goodies for the stay, communicated what was needed, and made the check-in/check-out process very easy. Would stay again. It was perfect distance from Kia Center (5 min drive) "
United States
M L.
The price is ￥27,855
￥56,529 total
includes taxes & fees
Aug 2 - Aug 3
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Property grounds

Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (24 reviews)
"The setting was very nice and in a quiet area, but conveniently located to travel around Florida. Cottage was clean and very comfortable. Would definitely stay again."
United States
Brenda P.
The price is ￥24,411
￥51,179 total
includes taxes & fees
Jul 31 - Aug 1
Cozy Lake Front Cottage
Exterior detail

Downtown Cottage

Downtown Cottage
Colonialtown North
8.2 out of 10, Very Good, (11 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is ￥10,444
￥28,850 total
includes taxes & fees
Jul 29 - Jul 30
Downtown Cottage
Exterior

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (37 reviews)
"Beautiful property in a fantastic location! We've booking this stay twice and will be back again."
United States
Lisa
The price is ￥21,298
￥57,930 total
includes taxes & fees
Aug 3 - Aug 4
Incredible Private Lakefront Cottage Retreat
The Garden, Pet Friendly | Terrace/patio

Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (39 reviews)
"Very clean room, quaint, close to the downtown area. "
United States
Raymond
The price is ￥24,659
￥27,372 total
includes taxes & fees
Jul 27 - Jul 28
Historic Tremain Cottages
House (5 Bedrooms) | Interior

Upstay Disney 5BR Movie Mansionwindsor Cay Resort

Upstay Disney 5BR Movie Mansionwindsor Cay Resort
3.0 star property
Clermont
The price is ￥35,551
￥81,105 total
includes taxes & fees
Jul 26 - Jul 27
Upstay Disney 5BR Movie Mansionwindsor Cay Resort
Interior

Beautiful Historic Cottage, Rendezvous

Beautiful Historic Cottage, Rendezvous
Mount Dora
9.4 out of 10, Exceptional, (16 reviews)
"This property is the perfect location for walking downtown shops and dining! "
United States
Julie
The price is ￥26,830
￥33,057 total
includes taxes & fees
Jul 27 - Jul 28
Beautiful Historic Cottage, Rendezvous
Front of property

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 ￥34,945
￥38,788 total
includes taxes & fees
Jul 26 - Jul 27
Mount Dora Cottages
Terrace/patio

Beautiful Historic Cottage, The Garden

Beautiful Historic Cottage, The Garden
Mount Dora
10.0 out of 10, Exceptional, (15 reviews)
"It was a perfect house for our short stay. Great location."
United States
Connie D.
The price is ￥28,518
￥35,094 total
includes taxes & fees
Jul 27 - Jul 28
Beautiful Historic Cottage, The Garden
Property grounds

Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Mount Dora
10.0 out of 10, Exceptional, (21 reviews)
"Wonderful eclectic cottage loaded with charm. The house was super clean and the beds extremely comfortable. Great outdoor space and a nice location convenient to everything."
United States
Nora S.
The price is ￥22,412
￥41,449 total
includes taxes & fees
Aug 5 - Aug 6
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Outdoor dining

Comfy Cottage with Hot Tub near Disney with Margaritaville Resort & Island H2O.

Comfy Cottage with Hot Tub near Disney with Margaritaville Resort & Island H2O.
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is ￥37,189
￥88,600 total
includes taxes & fees
Aug 23 - Aug 24
Comfy Cottage with Hot Tub near Disney with Margaritaville Resort & Island H2O.
Exterior

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.4 out of 10, Exceptional, (11 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is ￥19,496
￥49,521 total
includes taxes & fees
Aug 9 - Aug 10
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Microwave, stovetop

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very Good, (8 reviews)
"Nice, Cute little place"
United States
Brenda N.
The price is ￥12,451
￥29,496 total
includes taxes & fees
Aug 24 - Aug 25
Tiny house close to Disney KISSIMMEE
Terrace/patio

Beautiful Historic Cottage, Nantucket

Beautiful Historic Cottage, Nantucket
Mount Dora
9.8 out of 10, Exceptional, (7 reviews)
"Great location. Very clean "
United States
University Sports M.
The price is ￥25,143
￥31,185 total
includes taxes & fees
Jul 27 - Jul 28
Beautiful Historic Cottage, Nantucket
Exterior

Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is ￥13,270
￥31,355 total
includes taxes & fees
Aug 5 - Aug 6
Perfect Place for a Perfect Vacation
Exterior

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
The price is ￥15,408
￥50,600 total
includes taxes & fees
Aug 3 - Aug 4
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Exterior

Bright Cottage near Disney with Margaritaville Resort & Island H2O Access -.

Bright Cottage near Disney with Margaritaville Resort & Island H2O Access -.
Kissimmee
8.0 out of 10, Very Good, (1 review)
"Beware the check in process. VRBO lets you select the cottage location and make the booking. On arrival, they tried to move the location to one way around the block, far from the hotel. I assume in order to spread the rental pool money around, or else to save the locations near the main hotel for friends/family, but confirm addresses before arrival to the hotel. Hotel is nice, pool is nice, lots to do, service otherwise fine. "
Canada
Coach Bob H.
The price is ￥37,189
￥88,600 total
includes taxes & fees
Aug 23 - Aug 24
Bright Cottage near Disney with Margaritaville Resort & Island H2O Access -.
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

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent
"The rooms are larger than an average hotel room. Easily fits are family of 4-6 when we travel to the Orlando area. The rooms are always clean. The breakfast is good, however get there early as the seating can fill up quickly. We will continue to stay here for future stays."
Daniel 1-night trip
Posted less than an hour ago
Home2 Suites by Hilton Orlando at Flamingo Crossings

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
378
Accommodation
2317 Cottages
Lowest Price
￥27,372
Highest Price
￥91,224

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between ￥27,372 and ￥91,224 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.