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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Winter Garden cottages

Exterior

The Little Lake Mary Guest House • Warm, Cozy & Inviting

The Little Lake Mary Guest House • Warm, Cozy & Inviting
Lake Mary
9.8 out of 10, Exceptional, (47 reviews)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
The price is £233
includes taxes & fees
14 Mar - 15 Mar
The Little Lake Mary Guest House • Warm, Cozy & Inviting
Property grounds

Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai

Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai
Lake Mary
10.0 out of 10, Exceptional, (18 reviews)
"An excellent location for stays in Lake Mary. It has everything a single or a couple needs to feel at home."
United States
Kanzeda C.
The price is £182
includes taxes & fees
17 Feb - 18 Feb
Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai
Property grounds

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.2 out of 10, Wonderful, (62 reviews)
"Great little cottage, it was easy to locate and access the property. Nice quiet area and we really enjoyed our stay."
United States
Anna M.
The price is £118
includes taxes & fees
15 Mar - 16 Mar
Tiny Hidden Cottage
Interior

Downtown Cottage

Downtown Cottage
Colonialtown North
8.6 out of 10, Excellent, (8 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is £128
includes taxes & fees
18 Feb - 19 Feb
Downtown Cottage
Exterior

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (31 reviews)
"One of our best stays. "
United States
matthew m.
The price is £246
includes taxes & fees
15 Mar - 16 Mar
Incredible Private Lakefront Cottage Retreat
The Garden, Pet Friendly | Terrace/patio

Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (36 reviews)
"Easy check in. Nice, cozy and clean room. Walking distance to all local attractions. Would definitely stay here again. "
United States
Robert
Historic Tremain Cottages
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, (32 reviews)
"Absolutely beautiful place, fully equipped and close to everything. We very much enjoyed our stay."
United States
Sara R.
The price is £284
includes taxes & fees
19 Feb - 20 Feb
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Interior

Encore Swanky

Encore Swanky
3.0 star property
Kissimmee
The price is £464
includes taxes & fees
26 Feb - 27 Feb
Encore Swanky
Interior

Orlando Theme Park Basecamp: Family Home w/ Patio

Orlando Theme Park Basecamp: Family Home w/ Patio
3.0 star property
Davenport
The price is £266
includes taxes & fees
17 Feb - 18 Feb
Orlando Theme Park Basecamp: Family Home w/ Patio
Property grounds

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Orlando
The price is £161
includes taxes & fees
3 Mar - 4 Mar
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Exterior

The Beauclair * 3 min walk to Downtown Mt. Dora!!

The Beauclair * 3 min walk to Downtown Mt. Dora!!
Mt Dora
10.0 out of 10, Exceptional, (50 reviews)
"Super close to Mount Dora downtown and room was very nicely appointed"
United States
Sandra
The price is £203
includes taxes & fees
17 Feb - 18 Feb
The Beauclair * 3 min walk to Downtown Mt. Dora!!
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 £271
includes taxes & fees
17 Feb - 18 Feb
Shore Steps Cottage - Walking Distance To The Town Of Windermere
Property grounds

Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (20 reviews)
"Will definitely be staying again"
United States
Tom W.
The price is £220
includes taxes & fees
27 Feb - 28 Feb
Cozy Lake Front Cottage
Microwave, stovetop

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.6 out of 10, Excellent, (4 reviews)
"Just needed a place to stay close to Disney for the night and the place was clean and easy to check in and out. "
United States
Jena B.
The price is £151
includes taxes & fees
16 Mar - 17 Mar
Tiny house close to Disney KISSIMMEE
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, (9 reviews)
"The cottage was conveniently located near d'town. Comfortable, clean and well-stocked. "
United States
Jayne K.
The price is £213
includes taxes & fees
17 Feb - 18 Feb
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Terrace/patio

Beautiful Historic Cottage, Nantucket

Beautiful Historic Cottage, Nantucket
Mount Dora
9.8 out of 10, Exceptional, (7 reviews)
"It suited our needs perfectly"
United States
Lorraine O.
The price is £179
includes taxes & fees
9 Mar - 10 Mar
Beautiful Historic Cottage, Nantucket
Property grounds

Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is £180
includes taxes & fees
3 Mar - 4 Mar
Romantic Lakefront Getaway with Balcony near Downtown Orlando
Exterior

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
The price is £234
includes taxes & fees
28 Feb - 1 Mar
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
House (4 Bedrooms) | Interior

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
Indian Ridge
The price is £345
includes taxes & fees
21 Feb - 22 Feb
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Interior

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, (1 review)
"The communication with the property owner was excellent. The cottage is attached to the owners home but is quite private and comfortable. I’ve already recommended it to family members who wish to visit that area."
United States
Tina O.
The price is £195
includes taxes & fees
15 Mar - 16 Mar
Charming Historic Cottage with Cozy Porch and Garden Retreat
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

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent
"The staff were excellent! The breakfast had lots of variety and was delicious. I loved the clean, spacious room! I would gladly stay again!"
Heather 4-night trip
Posted 1 day ago
Homewood Suites by Hilton Orlando at Flamingo Crossings

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
304
Accommodation
1982 Cottages
Lowest Price
£118
Highest Price
£464

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between £118 and £464 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.