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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

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 NZ$903
includes taxes & fees
15 Nov - 16 Nov
Fire Pit & Yard: Updated Winter Garden Home!
A covered patio area with a wooden table and chairs, a wicker sofa with floral cushions, and a potted plant.

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 NZ$377
includes taxes & fees
22 Nov - 23 Nov
Vacation Village Resort a "Hilltop Haven" Cozy 2-bedroom cottage in Clermont
A bench in a park with a lake and trees in the background.

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 NZ$572
includes taxes & fees
16 Nov - 17 Nov
Shore Steps Cottage - Walking Distance To The Town Of Windermere
A residential building with a brick facade, a front porch, and a well-maintained lawn.

4. 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, (7 reviews)
"Clean comfort all ok"
United States
Donald P.
The price is NZ$365
includes taxes & fees
23 Nov - 24 Nov
Charming Historic Cottage with Cozy Porch and Garden Retreat
A room with a bed, a TV on a stand, a bookshelf, and a window with blinds.

5. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (18 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is NZ$303
includes taxes & fees
17 Nov - 18 Nov
Downtown Cottage
A deck with a table and chairs, an umbrella, and a view of a lake with trees.

6. 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$674
includes taxes & fees
29 Nov - 30 Nov
Incredible Private Lakefront Cottage 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 NZ$592
includes taxes & fees
19 Nov - 20 Nov
Family Resort Home w Pool, BBQ & Game Room
A single-story building with the number 297, a red door, and a bench outside.

8. Disney Pool Days & Hammock Naps Book Your Escape NOW!

Disney Pool Days & Hammock Naps Book Your Escape NOW!
Lake Mary
9.8 out of 10, Exceptional, (71 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 NZ$448
includes taxes & fees
1 Dec - 2 Dec
Disney Pool Days & Hammock Naps Book Your Escape NOW!
A covered porch with wicker chairs and a ceiling fan.

9. 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 NZ$433
includes taxes & fees
19 Nov - 20 Nov
Historic Tremain Cottages
A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

10. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is NZ$702
includes taxes & fees
15 Nov - 16 Nov
Serenity - Family & Pet Friendly, Amazing Location
A two-story residential building with a garage, a small tree, and a well-maintained lawn.

11. Golf, Dine & Unwind Poolside! Haines City Getaway

Golf, Dine & Unwind Poolside! Haines City Getaway
3.0 star property
Haines City
The price is NZ$756
includes taxes & fees
17 Nov - 18 Nov
Golf, Dine & Unwind Poolside! Haines City Getaway
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.
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A well-maintained artificial green lawn with a flagstick, surrounded by a stone pathway and a large planter with flowers.

13. Cozy 1-bedroom tiny home minutes from Disney, SeaWorld, and Universal!

Cozy 1-bedroom tiny home minutes from Disney, SeaWorld, and Universal!
Kissimmee
The price is NZ$262
includes taxes & fees
9 Dec - 10 Dec
Cozy 1-bedroom tiny home minutes from Disney, SeaWorld, and Universal!
A white building with large windows and a brick pathway leading to it.

14. 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 NZ$606
includes taxes & fees
7 Dec - 8 Dec
The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!
A landscaped backyard with a wooden fence, gravel ground, and outdoor lighting.

15. Orlando Getaway? 🌴 Private Lanai & Cozy Cottage

Orlando 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 NZ$467
includes taxes & fees
17 Nov - 18 Nov
Orlando Getaway? 🌴 Private Lanai & Cozy Cottage
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 NZ$266
includes taxes & fees
16 Nov - 17 Nov
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to 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
Upstay: Bright Family-friendly Retreat With Patio
A well-lit garden area with a gravel pathway, decorative lights, and various plants.

18. 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 NZ$444
includes taxes & fees
15 Nov - 16 Nov
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
A hammock tied between two wooden posts, a wooden deck, and a view of a lake with trees and a clear sky.

19. 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 NZ$567
includes taxes & fees
13 Dec - 14 Dec
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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Learn more about Winter Garden

Stroll the charming brick-lined streets of historic city centre 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 NZ$262 and NZ$909 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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