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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Winter Garden cottages

Interior

Cottage in Windward Cay

4716-4-ww-blend of Relaxation and Convenience
2.0 star property
4716-4-ww-blend of Relaxation and Convenience
Exterior

Cottage in Lake Mary

The Little Lake Mary Guest House • Warm, Cozy & Inviting
9.8 out of 10, Exceptional, (46 reviews)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
The price is AU$402
includes taxes & fees
27 Jan - 28 Jan
The Little Lake Mary Guest House • Warm, Cozy & Inviting
Beach

Cottage in Longwood

Tiny Hidden Cottage
9.2 out of 10, Wonderful, (62 reviews)
"It was a good area to stay "
United States
Christanah O.
The price is AU$264
includes taxes & fees
1 Feb - 2 Feb
Tiny Hidden Cottage
Exterior

Cottage in Altamonte Springs

Incredible Private Lakefront Cottage Retreat
10.0 out of 10, Exceptional, (31 reviews)
"One of our best stays. "
United States
matthew m.
The price is AU$531
includes taxes & fees
14 Feb - 15 Feb
Incredible Private Lakefront Cottage Retreat
House (5 Bedrooms) | Front of property

Cottage in Kissimmee

Family-friendly Villa w Pool, Hot Tub & Games Room
3.0 star property
Family-friendly Villa w Pool, Hot Tub & Games Room
Interior

Cottage in Colonialtown North

Downtown Cottage
8.6 out of 10, Excellent, (8 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is AU$248
includes taxes & fees
25 Jan - 26 Jan
Downtown Cottage
Exterior

Cottage in College Park

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
10.0 out of 10, Exceptional, (30 reviews)
"Absolutely beautiful place, fully equipped and close to everything. We very much enjoyed our stay."
United States
Sara R.
The price is AU$542
includes taxes & fees
25 Jan - 26 Jan
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Microwave, stovetop

Cottage in Kissimmee

Tiny house close to Disney KISSIMMEE
2.0 star property
8.6 out of 10, Excellent, (4 reviews)
"Just needed a place to stay close to Disney for the night and the place was clean and easy to check in and out. "
United States
Jena B.
The price is AU$277
includes taxes & fees
13 Feb - 14 Feb
Tiny house close to Disney KISSIMMEE
The Garden, Pet Friendly | Terrace/patio

Cottage in Mount Dora

Historic Tremain Cottages
3.0 star property
8.6 out of 10, Excellent, (34 reviews)
"Easy check in. Nice, cozy and clean room. Walking distance to all local attractions. Would definitely stay here again. "
United States
Robert
Historic Tremain Cottages
Dining

Cottage in Kissimmee

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
The price is AU$327
includes taxes & fees
23 Jan - 24 Jan
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Front of property

Cottage in Lake Berkley

1061 Lake Berkley 4 Bed With Pool
2.5 star property
The price is AU$4,362
includes taxes & fees
4 Feb - 5 Feb
1061 Lake Berkley 4 Bed With Pool
Interior

Cottage in Kissimmee

Encore Swanky
3.0 star property
The price is AU$949
includes taxes & fees
1 Feb - 2 Feb
Encore Swanky
House (4 Bedrooms) | Interior

Cottage in Indian Ridge

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
The price is AU$701
includes taxes & fees
22 Jan - 23 Jan
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Smart TV, books

Cottage in Kissimmee

Family-Friendly Cottage Near Orlando’s Top Attractions
10.0 out of 10, Exceptional, (1 review)
"Perfect location to enjoy Universal Epic and Islands of Adventure with only a 15 minute ride. The beds were very comfortable and the place is clean. We were welcomed with a cute sign, bottled water and cookies. Will definitely stay here again!"
United States
Joyce R.
The price is AU$302
includes taxes & fees
22 Jan - 23 Jan
Family-Friendly Cottage Near Orlando’s Top Attractions
Exterior

Cottage in Kissimmee

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

Cottage in Reunion

Wellerden at Reunion Resort!by Shine Villas
3.5 star property
Wellerden at Reunion Resort!by Shine Villas
Property grounds

Cottage in Mount Dora

Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
10.0 out of 10, Exceptional, (6 reviews)
"The cottage was conveniently located near d'town. Comfortable, clean and well-stocked. "
United States
Jayne K.
The price is AU$404
includes taxes & fees
4 Feb - 5 Feb
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Terrace/patio

Cottage in Mount Dora

Beautiful Historic Cottage, Nantucket
9.8 out of 10, Exceptional, (7 reviews)
"It suited our needs perfectly"
United States
Lorraine O.
Beautiful Historic Cottage, Nantucket
Exterior

Cottage in Kissimmee

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
9.8 out of 10, Exceptional, (7 reviews)
"Wonderful place to stay overnight. Nice furnishings. Good room layout for family. Convenience of washer and dryer. Host was quick and responsive. Thank you for a terrific stay."
United States
George L.
The price is AU$427
includes taxes & fees
28 Jan - 29 Jan
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Property grounds

Cottage in Clermont

Cozy Lake Front Cottage
10.0 out of 10, Exceptional, (19 reviews)
"Will definitely be staying again"
United States
Tom W.
The price is AU$374
includes taxes & fees
22 Jan - 23 Jan
Cozy Lake Front Cottage
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

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

10/10 Excellent
"A nice room for the value. Very safe, and very quiet."
Mark 3-night trip
Posted 2 days ago
Rosen Inn at Pointe Orlando

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
227
Accommodation
1981 Cottages
Lowest Price
AU$264
Highest Price
AU$949

Frequently asked questions

How much do cottages in Winter Garden cost?
Rates for cottages in Winter Garden range between AU$264 and AU$949 per night. No matter your budget, you're sure to find a perfect place to reconnect with nature. This price was 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.
What is there to do in Winter Garden near my cottage?
No matter your tastes or interests, Winter Garden has tons to keep you on the move. The Wizarding World of Harry Potter™, Winter Garden Heritage Museum and Garden Theatre are on many travellers' agendas. Don't miss Museum of the Apopkans, The Woods Laser Tag and Carter Family Bowl either. With Expedia's Winter Garden hotel deals, you can discover more fantastic attractions like these with the cash you save.