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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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 £378
includes taxes & fees
18 Oct - 19 Oct
Fire Pit & Yard: Updated Winter Garden Home!
A serene landscape with a pond, trees with Spanish moss, and a palm tree.

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

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
10.0 out of 10, Exceptional, (1 review)
The price is £250
includes taxes & fees
16 Oct - 17 Oct
Shore Steps Cottage - Walking Distance To The Town Of Windermere
A residential property with a well-maintained lawn, a paved driveway, and a small garden area with plants.

3. Gorgeous Cottage near Lake Louisa & mins 2 Disney.

Gorgeous Cottage near Lake Louisa & mins 2 Disney.
Vacation Village
9.4 out of 10, Exceptional, (65 reviews)
"Wonderful time at a property just right for our needs and wants. "
United States
Peter C.
The price is £122
includes taxes & fees
15 Oct - 16 Oct
Gorgeous Cottage near Lake Louisa & mins 2 Disney.
A residential house with a front yard, a palm tree, and a garage.

4. 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 £422
includes taxes & fees
15 Oct - 16 Oct
Chic Orlando Family Getaway w/ Fenced Yard!
A house with a red door, a front porch, and a pathway leading to the entrance.

5. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (15 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is £144
includes taxes & fees
14 Oct - 15 Oct
Downtown Cottage
A single-story building with the number 297, a red door, and a bench outside.

6. Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Lake Mary
9.8 out of 10, Exceptional, (67 reviews)
"The property was very clean and the host was quick to respond to any questions."
United States
Colette T.
The price is £187
includes taxes & fees
14 Oct - 15 Oct
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A covered porch with wicker chairs and a ceiling fan.

7. 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 £165
includes taxes & fees
15 Oct - 16 Oct
Historic Tremain Cottages
A residential area with a well-maintained lawn, a street with parked cars, and a green dumpster.

8. Ei8555 - 3BR House Near Disney

Ei8555 - 3BR House Near Disney
3.0 star property
Kissimmee
The price is £246
includes taxes & fees
6 Nov - 7 Nov
Ei8555 - 3BR House Near Disney
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

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

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is £249
includes taxes & fees
18 Oct - 19 Oct
Family Resort Home w Pool, BBQ & Game Room
A white building with large windows and a brick pathway leading to it.

10. 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, (54 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
The price is £247
includes taxes & fees
4 Nov - 5 Nov
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
A hammock tied between two wooden posts, a wooden deck, and a view of a lake with trees and a clear sky.

11. Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (25 reviews)
"Very nice cottage, beautiful view"
United States
rachel c.
The price is £256
includes taxes & fees
18 Oct - 19 Oct
Cozy Lake Front Cottage
A patio with outdoor furniture, a wooden deck, and a basketball hoop.

12. Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (22 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is £172
includes taxes & fees
15 Oct - 16 Oct
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

13. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is £157
includes taxes & fees
14 Oct - 15 Oct
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

14. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is £301
includes taxes & fees
14 Oct - 15 Oct
Serenity - Family & Pet Friendly, Amazing Location
A small, single-story house with a gabled roof and a front porch.

15. 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 £179
includes taxes & fees
22 Oct - 23 Oct
Mount Dora Cottages
A small cabin with a porch and a garage, surrounded by trees and a clear sky.

16. Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Davenport
6.8 out of 10, (3 reviews)
"Needs some upgrades. The bed was a full size, very small for a couple, should really think of upgrading to a king. Pans were old and could use replacing. Bugs and ants constant. Shower was small. Very small tv. Stovetop had missing nob and was difficult to operate. Definitely needs upgrading, left a day early, didn’t feel comfortable there. "
United States
Rebecca F.
The price is £121
includes taxes & fees
14 Oct - 15 Oct
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
A well-lit garden area with a gravel pathway, decorative lights, and various plants.

17. 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, (25 reviews)
"Great stay! Very welcoming home and very comfortable beds. Would rent again."
United States
Thomas K.
The price is £202
includes taxes & fees
30 Oct - 31 Oct
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
A modern hotel with a curved driveway, large windows, and palm trees.

18. Mvv7482 - 3BR House Near Disney at Magic Village

Mvv7482 - 3BR House Near Disney at Magic Village
3.0 star property
Kissimmee
The price is £370
includes taxes & fees
27 Oct - 28 Oct
Mvv7482 - 3BR House Near Disney at Magic Village
A residential area with houses featuring sloped roofs and solar panels.

19. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is £190
includes taxes & fees
19 Oct - 20 Oct
Upstay: Bright Family-friendly Retreat With Patio
A single-story mobile home with a front porch and a small deck.

20. Newly Remodeled Tiny Home 20 minutes from Disney!~

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is £160
includes taxes & fees
14 Oct - 15 Oct
Newly Remodeled Tiny Home 20 minutes from Disney!~
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

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent
"Amenities of the property as well as the design and immensities in the room absolutely awesome"
Aaleyah 4-night trip
Posted less than an hour ago
Westgate Lakes Resort & Spa Universal Studios Area

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
385
Accommodation
2644 Cottages
Lowest Price
£121
Highest Price
£422

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between £121 and £422 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 holiday 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 accommodation 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 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.