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
10 July - 12 July
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Winter Garden cottages

House (2 Bedrooms) | Interior

Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is AU$792
includes taxes & fees
1 July - 2 July
Fire Pit & Yard: Updated Winter Garden Home!
The Garden, Pet Friendly | Terrace/patio

Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (37 reviews)
"Very clean room, quaint, close to the downtown area. "
United States
Raymond
The price is AU$230
includes taxes & fees
29 June - 30 June
Historic Tremain Cottages
Exterior

Poolside Weekday Retreat – Just 119 Night!

Poolside Weekday Retreat – Just 119 Night!
Lake Mary
9.8 out of 10, Exceptional, (59 reviews)
"Everything was wonderful! We loved the location and the house was cozy and comfortable. "
United States
Mike B.
The price is AU$377
includes taxes & fees
7 July - 8 July
Poolside Weekday Retreat – Just 119 Night!
Interior

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 AU$271
includes taxes & fees
28 June - 29 June
Downtown Cottage
Exterior

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 AU$328
includes taxes & fees
27 July - 28 July
Charming Historic Cottage with Cozy Porch and Garden Retreat
Terrace/patio

Last-Minute July 4th Getaway! Charming Cottage • Early Check-In

Last-Minute July 4th Getaway! Charming Cottage • Early Check-In
Lake Mary
10.0 out of 10, Exceptional, (19 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is AU$346
includes taxes & fees
28 June - 29 June
Last-Minute July 4th Getaway! Charming Cottage • Early Check-In
Property grounds

Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (23 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 AU$422
includes taxes & fees
28 June - 29 June
Cozy Lake Front Cottage
House (3 Bedrooms) | Interior

Golf, Dine & Unwind Poolside! Haines City Getaway

Golf, Dine & Unwind Poolside! Haines City Getaway
3.0 star property
Haines City
The price is AU$659
includes taxes & fees
27 June - 28 June
Golf, Dine & Unwind Poolside! Haines City Getaway
Property grounds

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, (19 reviews)
"This was a nice charming home my weekend visit to Mount Dora - home was clean, close to downtown and host was a great communicator. "
United States
Rena C.
The price is AU$361
includes taxes & fees
7 July - 8 July
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Property grounds

Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
The price is AU$544
includes taxes & fees
27 June - 28 June
Shore Steps Cottage - Walking Distance To The Town Of Windermere
Interior

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 AU$297
includes taxes & fees
29 June - 30 June
Beautiful Historic Cottage, Rendezvous
Exterior

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 AU$243
includes taxes & fees
27 June - 28 June
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
House (4 Bedrooms) | Interior

Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is AU$507
includes taxes & fees
21 July - 22 July
Family Resort Home w Pool, BBQ & Game Room
Exterior

Newly Remodeled Tiny Home 20 minutes from Disney!~

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is AU$305
includes taxes & fees
27 June - 28 June
Newly Remodeled Tiny Home 20 minutes from Disney!~
Exterior

Fenced in Backyard! Close to DT Mount Dora! King Bed + Golf Cart Rental!

Fenced in Backyard! Close to DT Mount Dora! King Bed + Golf Cart Rental!
Mount Dora
9.6 out of 10, Exceptional, (4 reviews)
"Perfect location for walking anywhere around downtown. The furnishings, the amenities and the backyard were all that we could have asked for. Would definitely return."
United States
Louis M.
The price is AU$483
includes taxes & fees
28 June - 29 June
Fenced in Backyard! Close to DT Mount Dora! King Bed + Golf Cart Rental!
Exterior

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
College Park
9.8 out of 10, Exceptional, (40 reviews)
"Our hosts were incredibly accommodating and welcoming. This was the perfect place for us to stay while in town for a wedding in Winter Park. Thank you! "
United States
Danielle S.
The price is AU$491
includes taxes & fees
13 July - 14 July
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Property grounds

Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is AU$330
includes taxes & fees
28 June - 29 June
Romantic Lakefront Getaway with Balcony near Downtown Orlando
House (3 Bedrooms) | Interior

Davenport Basecamp! 3BR Family Home w/ Patio

Davenport Basecamp! 3BR Family Home w/ Patio
3.0 star property
Davenport
The price is AU$531
includes taxes & fees
8 July - 9 July
Davenport Basecamp! 3BR Family Home w/ Patio
Front of property

Mount Dora Cottages

Mount Dora Cottages
3.0 star property
Mount Dora
9.4 out of 10, Exceptional, (211 reviews)
"Perfect spot"
United States
PATRICIA
The price is AU$343
includes taxes & fees
28 June - 29 June
Mount Dora Cottages
Terrace/patio

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 AU$315
includes taxes & fees
30 June - 1 July
Beautiful Historic Cottage, The Garden
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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

8/10 Good
"The rooms were huge and the setup was great. The hallways were not cleaned well or maintained well. The water park was nice but more for smaller kids. There are two slides and a really nice kids area. The main restaurant was not very clean and the food was okay and not great. The food from the pool restaurant was also underwhelming. The pools were nice and I was very happy that they served Starbucks in the main store."
alexis 6-night trip
Posted less than an hour ago
The Grove Resort & Water Park Orlando

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
425
Accommodation
2357 Cottages
Lowest Price
AU$230
Highest Price
AU$792

Frequently asked questions

How much do cottages in Winter Garden cost?
Rates for cottages in Winter Garden range between AU$230 and AU$792 per night. No matter your budget, you're sure to find a perfect place to reconnect with nature. This price was 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?
No matter your tastes or interests, Winter Garden has tons to keep you on the move. The Wizarding World of Harry Potter™, Winter Garden Heritage Museum and Garden Theatre are on many travellers' agendas. Don't miss Museum of the Apopkans, The Woods Laser Tag and Carter Family Bowl either. With Expedia's Winter Garden hotel deals, you can discover more fantastic attractions like these with the cash you save.