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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Winter Garden cottages

House (2 Bedrooms) | 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 NZ$847
includes taxes & fees
23 Aug - 24 Aug
Fire Pit & Yard: Updated Winter Garden Home!
Property grounds

2. Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
The price is NZ$614
includes taxes & fees
16 Aug - 17 Aug
Shore Steps Cottage - Walking Distance To The Town Of Windermere
The Garden, Pet Friendly | Terrace/patio

3. 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 NZ$296
includes taxes & fees
25 Aug - 26 Aug
Historic Tremain Cottages
Exterior detail

4. Downtown Cottage

Downtown Cottage
Colonialtown North
8.6 out of 10, Excellent, (13 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is NZ$291
includes taxes & fees
23 Aug - 24 Aug
Downtown Cottage
Property grounds

5. Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (25 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 NZ$494
includes taxes & fees
16 Aug - 17 Aug
Cozy Lake Front Cottage
Exterior

6. Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone

Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone
Lake Mary
9.8 out of 10, Exceptional, (63 reviews)
"Everything was great as usual!!"
United States
Christine B.
The price is NZ$451
includes taxes & fees
16 Aug - 17 Aug
Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone
Exterior

7. 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, (44 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 NZ$552
includes taxes & fees
14 Sept - 15 Sept
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Exterior

8. Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (38 reviews)
"Beautiful property in a fantastic location! We've booking this stay twice and will be back again."
United States
Lisa
The price is NZ$636
includes taxes & fees
2 Sept - 3 Sept
Incredible Private Lakefront Cottage Retreat
Property grounds

9. 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)
"Great stay! Very welcoming home and very comfortable beds. Would rent again."
United States
Thomas K.
The price is NZ$426
includes taxes & fees
16 Aug - 17 Aug
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Property grounds

10. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
Romantic Lakefront Getaway with Balcony near Downtown Orlando
Terrace/patio

11. Early Check In Lake Mary Last-Minute Deal!

Early Check In Lake Mary Last-Minute Deal!
Lake Mary
10.0 out of 10, Exceptional, (20 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is NZ$400
includes taxes & fees
17 Aug - 18 Aug
Early Check In Lake Mary Last-Minute Deal!
Interior

12. 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 NZ$342
includes taxes & fees
17 Aug - 18 Aug
Beautiful Historic Cottage, Rendezvous
Front of property

13. 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 NZ$402
includes taxes & fees
16 Aug - 17 Aug
Mount Dora Cottages
House (2 Bedrooms) | Interior

14. Mount Dora Home: Private Pool, Spa & Tropical Bar!

Mount Dora Home: Private Pool, Spa & Tropical Bar!
3.0 star property
Mount Dora
6.0 out of 10, (1 review)
The price is NZ$578
includes taxes & fees
16 Aug - 17 Aug
Mount Dora Home: Private Pool, Spa & Tropical Bar!
Terrace/patio

15. 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 NZ$364
includes taxes & fees
17 Aug - 18 Aug
Beautiful Historic Cottage, The Garden
House (4 Bedrooms) | Interior

16. Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is NZ$557
includes taxes & fees
17 Aug - 18 Aug
Family Resort Home w Pool, BBQ & Game Room
Exterior

17. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is NZ$337
includes taxes & fees
25 Aug - 26 Aug
Perfect Place for a Perfect Vacation
Property grounds

18. Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Orlando
The price is NZ$392
includes taxes & fees
16 Aug - 17 Aug
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
House (3 Bedrooms) | Interior

19. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is NZ$637
includes taxes & fees
16 Aug - 17 Aug
Serenity - Family & Pet Friendly, Amazing Location
Microwave, stovetop

20. Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very good, (9 reviews)
"Proximity to theme parks, restaurants, and shopping"
United States
NOLI
The price is NZ$286
includes taxes & fees
14 Sept - 15 Sept
Tiny house close to Disney KISSIMMEE
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
"My second time staying and it’s amazing. Staff amazing and always willing to help and answer questions. The food court staff was also amazing help! Can’t wait to come back"
Gayvell 4-night trip
Posted less than an hour ago
DoubleTree by Hilton at the Entrance to Universal Orlando

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
442
Accommodation
2317 Cottages
Lowest Price
NZ$280
Highest Price
NZ$847

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between NZ$280 and NZ$847 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.
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 travellers' 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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