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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 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, (48 reviews)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
The price is HK$977
HK$2,126 total
includes taxes & fees
23 Mar - 24 Mar
The Little Lake Mary Guest House • Warm, Cozy & Inviting
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 HK$633
HK$1,215 total
includes taxes & fees
22 Mar - 23 Mar
Tiny Hidden Cottage
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 HK$710
HK$1,858 total
includes taxes & fees
24 Feb - 25 Feb
Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai
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 HK$492
HK$1,370 total
includes taxes & fees
24 Feb - 25 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 HK$1,149
HK$2,868 total
includes taxes & fees
9 Mar - 10 Mar
Incredible Private Lakefront Cottage Retreat
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, (33 reviews)
"Absolutely beautiful place, fully equipped and close to everything. We very much enjoyed our stay."
United States
Sara R.
The price is HK$1,582
HK$2,870 total
includes taxes & fees
23 Feb - 24 Feb
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 HK$809
HK$1,785 total
includes taxes & fees
25 Feb - 26 Feb
Romantic Lakefront Getaway with Balcony near Downtown Orlando
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 HK$1,102
HK$2,841 total
includes taxes & fees
22 Feb - 23 Feb
Orlando Theme Park Basecamp: Family Home w/ Patio
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, (10 reviews)
"The cottage was conveniently located near d'town. Comfortable, clean and well-stocked. "
United States
Jayne K.
The price is HK$1,289
HK$2,245 total
includes taxes & fees
23 Feb - 24 Feb
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 HK$1,094
HK$2,862 total
includes taxes & fees
27 Feb - 28 Feb
Shore Steps Cottage - Walking Distance To The Town Of Windermere
Interior

Terra Verde Swanky

Terra Verde Swanky
3.0 star property
Kissimmee
Terra Verde Swanky
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 HK$1,083
HK$2,335 total
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
8.4 out of 10, Very good, (5 reviews)
"The location was great. We really just needed somewhere to sleep because we spent the day at the Disney Parks. The place had enough beds and was a great price."
United States
Christine M.
The price is HK$750
HK$1,584 total
includes taxes & fees
16 Mar - 17 Mar
Tiny house close to Disney KISSIMMEE
Exterior

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
Kissimmee
The price is HK$2,434
HK$7,875 total
includes taxes & fees
17 Mar - 18 Mar
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
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 HK$1,539
HK$1,895 total
includes taxes & fees
9 Mar - 10 Mar
Beautiful Historic Cottage, Nantucket
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 HK$958
HK$2,407 total
includes taxes & fees
4 Mar - 5 Mar
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
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 HK$806
HK$1,798 total
includes taxes & fees
1 Mar - 2 Mar
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
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 HK$906
HK$3,685 total
includes taxes & fees
8 Mar - 9 Mar
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Exterior

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
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 HK$485
HK$1,138 total
includes taxes & fees
22 Feb - 23 Feb
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
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

Sonesta Essential Orlando Airport

Sonesta Essential Orlando Airport

10/10 Excellent
"yes"
DEAN 1-night trip
Posted 1 day ago
Sonesta Essential Orlando Airport

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
226
Accommodation
1982 Cottages
Lowest Price
HK$1,138
Highest Price
HK$3,685

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between HK$1,138 and HK$3,685 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.

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