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Check prices for these dates

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Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

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 CA $278
CA $697 total
includes taxes & fees
Nov 9 - Nov 10
Fire Pit & Yard: Updated Winter Garden Home!
A room with a television on a wooden cabinet, a table, and two chairs. There is a sofa and a window with curtains.

2. Vacation Village Resort a "Hilltop Haven" Cozy 2-bedroom cottage in Clermont

Vacation Village Resort a "Hilltop Haven" Cozy 2-bedroom cottage in Clermont
Vacation Village
10.0 out of 10, Exceptional, (1 review)
"I loved the home: the views, the sunsets, the lake, the pool, the peace and tranquility, and so much more. Clermont is truly the "Gem of the Hills". And the nearby shops: Publix, Keyfood, the small Brazilian market, Shantee's Caribbean market, etc.; there is such a variety of foods. And Salt Shack overlooking Lake Minneola is another gem. I will be coming again and again to this home and this location."
United States
Anonymous traveller
The price is CA $113
CA $286 total
includes taxes & fees
Nov 18 - Nov 19
Vacation Village Resort a "Hilltop Haven" Cozy 2-bedroom cottage in Clermont
A laundry room with two front-loading washing machines, a drying rack, and a window with blinds.

3. 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 CA $150
CA $435 total
includes taxes & fees
Dec 1 - Dec 2
Shore Steps Cottage - Walking Distance To The Town Of Windermere
A modern kitchen with red walls, a dining area with a brown leather couch, and a bar stool.

4. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (17 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is CA $101
CA $250 total
includes taxes & fees
Nov 9 - Nov 10
Downtown Cottage
A covered porch with wicker chairs and a ceiling fan.

5. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (44 reviews)
"Lovely stay in Mount Dora, perfect location, clean and quiet. Would definitely stay again."
United States
Charlotte
The price is CA $293
CA $325 total
includes taxes & fees
Nov 9 - Nov 10
Historic Tremain Cottages
A single-story house with a stone retaining wall, a front porch, and a small garden.

6. Charming Historic Cottage with Cozy Porch and Garden Retreat

Charming Historic Cottage with Cozy Porch and Garden Retreat
Polk City
10.0 out of 10, Exceptional, (6 reviews)
"Clean comfort all ok"
United States
Donald P.
The price is CA $119
CA $287 total
includes taxes & fees
Nov 23 - Nov 24
Charming Historic Cottage with Cozy Porch and Garden Retreat
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

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

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is CA $146
CA $460 total
includes taxes & fees
Nov 29 - Nov 30
Family Resort Home w Pool, BBQ & Game Room
A single-story building with the number 297, a red door, and a bench outside.

8. 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, (69 reviews)
"The Property was very clean ! Super convenient location and the perfect size for a family with 2 younger children ! Suzy was super nice !"
United States
Gary
The price is CA $163
CA $365 total
includes taxes & fees
Nov 16 - Nov 17
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A row of yellow buildings with numbered doors, a sidewalk, and greenery.

9. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is CA $145
CA $573 total
includes taxes & fees
Nov 9 - Nov 10
Serenity - Family & Pet Friendly, Amazing Location
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, (56 reviews)
"Great location, well stocked and beds were very comfortable."
United States
Raegan S.
The price is CA $224
CA $444 total
includes taxes & fees
Nov 9 - Nov 10
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, (27 reviews)
"Very nice cottage, beautiful view"
United States
rachel c.
The price is CA $208
CA $416 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Lake Front Cottage
A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

12. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
10.0 out of 10, Exceptional, (1 review)
"Cozy and nice place. It was very clean. Comunication with host was easy. Great view and sitting area from balcony to the lake. Very relaxing!"
United States
jacqueline M.
The price is CA $128
CA $278 total
includes taxes & fees
Nov 30 - Dec 1
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A patio with outdoor furniture, a wooden deck, and a basketball hoop.

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

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (23 reviews)
"We had an amazing stay! The place was beautiful, cozy, and incredibly comfortable. Even though we had to leave earlier than planned, we truly enjoyed our time here. The host was kind, responsive, and made everything easy from start to finish. We would definitely stay here again and look forward to returning in the future. Highly recommend!"
United States
Chiann M.
The price is CA $147
CA $346 total
includes taxes & fees
Dec 6 - Dec 7
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A single-story house with a white exterior, a front door, and a garage.

14. 9 Mi to Walt Disney World: Family Home w/ Pool!

9 Mi to Walt Disney World: Family Home w/ Pool!
3.0 star property
Clear Creek
The price is CA $183
CA $516 total
includes taxes & fees
Nov 27 - Nov 28
9 Mi to Walt Disney World: Family Home w/ Pool!
A small cabin with a porch and a garage, surrounded by trees and a clear sky.

15. 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 CA $100
CA $207 total
includes taxes & fees
Nov 7 - Nov 8
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
A single-story mobile home with a front porch and a small deck.

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

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is CA $119
CA $281 total
includes taxes & fees
Nov 7 - Nov 8
Newly Remodeled Tiny Home 20 minutes from Disney!~
A residential area with houses featuring sloped roofs and solar panels.

17. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is CA $101
CA $352 total
includes taxes & fees
Nov 30 - Dec 1
Upstay: Bright Family-friendly Retreat With Patio
A poolside area with lounge chairs and palm trees, a clear blue sky, and a building with a modern design.

18. Mvy7664 - 3BR House Near Disney With Hot Tub

Mvy7664 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
The price is CA $270
CA $629 total
includes taxes & fees
Nov 11 - Nov 12
Mvy7664 - 3BR House Near Disney With Hot Tub
A well-lit garden area with a gravel pathway, decorative lights, and various plants.

19. 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, (26 reviews)
"Great stay! Very welcoming home and very comfortable beds. Would rent again."
United States
Thomas K.
The price is CA $200
CA $348 total
includes taxes & fees
Nov 9 - Nov 10
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
A modern living room with a sofa, a large wall clock, and a mirror.

20. Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions
Kissimmee
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 CA $136
CA $274 total
includes taxes & fees
Nov 17 - Nov 18
Family-Friendly Cottage Near Orlando’s Top Attractions
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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Learn more about Winter Garden

Stroll the charming brick-lined streets of historic downtown where the Plant Street Market buzzes with local food vendors and craft beer. Pedal along the West Orange Trail that cuts through town, stopping at the Heritage Museum or to catch a show at the Garden Theatre.

See all hotels in Winter Garden
A brick building with a clock tower and a sign that reads "Winter Garden."

Frequently Asked Questions

How much do cottages in Winter Garden cost?

Cottages in Winter Garden range between CA $99 and CA $293 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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