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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

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 CA $339
CA $767 total
includes taxes & fees
Aug 5 - Aug 6
Fire Pit & Yard: Updated Winter Garden Home!
The Garden, Pet Friendly | Terrace/patio

2. 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 CA $211
CA $234 total
includes taxes & fees
Aug 6 - Aug 7
Historic Tremain Cottages
Property grounds

3. Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (24 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 CA $188
CA $412 total
includes taxes & fees
Aug 3 - Aug 4
Cozy Lake Front Cottage
Property grounds

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

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
The price is CA $200
CA $515 total
includes taxes & fees
Aug 2 - Aug 3
Shore Steps Cottage - Walking Distance To The Town Of Windermere
Exterior detail

5. Downtown Cottage

Downtown Cottage
Colonialtown North
8.2 out of 10, Very good, (11 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is CA $89
CA $247 total
includes taxes & fees
Aug 5 - Aug 6
Downtown 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 CA $158
CA $374 total
includes taxes & fees
Aug 6 - Aug 7
Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone
Exterior

7. Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (37 reviews)
"Beautiful property in a fantastic location! We've booking this stay twice and will be back again."
United States
Lisa
The price is CA $210
CA $531 total
includes taxes & fees
Aug 4 - Aug 5
Incredible Private Lakefront Cottage Retreat
Exterior

8. 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, (43 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 CA $227
CA $470 total
includes taxes & fees
Aug 4 - Aug 5
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Terrace/patio

9. Early Check In Lake Mary Last-Minute Deal! Crystal Springs Adventure Awaits

Early Check In Lake Mary Last-Minute Deal! Crystal Springs Adventure Awaits
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 CA $126
CA $332 total
includes taxes & fees
Aug 6 - Aug 7
Early Check In Lake Mary Last-Minute Deal! Crystal Springs Adventure Awaits
Property grounds

10. 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)
"Wonderful eclectic cottage loaded with charm. The house was super clean and the beds extremely comfortable. Great outdoor space and a nice location convenient to everything."
United States
Nora S.
The price is CA $192
CA $354 total
includes taxes & fees
Aug 5 - Aug 6
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Interior

11. 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 CA $229
CA $285 total
includes taxes & fees
Aug 6 - Aug 7
Beautiful Historic Cottage, Rendezvous
Front of property

12. 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 CA $299
CA $332 total
includes taxes & fees
Aug 3 - Aug 4
Mount Dora Cottages
Property grounds

13. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is CA $125
CA $295 total
includes taxes & fees
Aug 2 - Aug 3
Romantic Lakefront Getaway with Balcony near Downtown Orlando
Exterior

14. 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, (3 reviews)
"Clean comfort all ok"
United States
Donald P.
The price is CA $107
CA $283 total
includes taxes & fees
Aug 3 - Aug 4
Charming Historic Cottage with Cozy Porch and Garden Retreat
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 CA $244
CA $303 total
includes taxes & fees
Aug 18 - Aug 19
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 CA $146
CA $460 total
includes taxes & fees
Aug 3 - Aug 4
Family Resort Home w Pool, BBQ & Game Room
Exterior

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

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Davenport
5.0 out of 10, (2 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 $218 total
includes taxes & fees
Aug 3 - Aug 4
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Exterior

18. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is CA $113
CA $271 total
includes taxes & fees
Aug 4 - Aug 5
Perfect Place for a Perfect Vacation
Microwave, stovetop

19. 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 CA $98
CA $243 total
includes taxes & fees
Aug 8 - Aug 9
Tiny house close to Disney KISSIMMEE
Exterior

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

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is CA $119
CA $296 total
includes taxes & fees
Aug 4 - Aug 5
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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Had the best time with my family. Can’t wait to return soon"
Yocelin 3-night trip
Posted less than an hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Find out more about Winter Garden

Winter Garden Cottages information

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 Cottages
Lowest Price
Highest Price

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between and 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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