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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 NZ$531
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 NZ$404
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 NZ$259
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 NZ$282
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 NZ$578
includes taxes & fees
9 Mar - 10 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 NZ$626
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 NZ$1,048
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 NZ$602
includes taxes & fees
16 Feb - 17 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 NZ$370
includes taxes & fees
4 Mar - 5 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 NZ$452
includes taxes & fees
16 Feb - 17 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 NZ$597
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 NZ$492
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 NZ$334
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 NZ$474
includes taxes & fees
16 Feb - 17 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 NZ$400
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 NZ$428
includes taxes & fees
4 Mar - 5 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 NZ$442
includes taxes & fees
26 Feb - 27 Feb
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 NZ$781
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 NZ$433
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

Sonesta Essential Orlando Airport

Sonesta Essential Orlando Airport

10/10 Excellent
"Muito bom!"
robison 1-night trip
Posted 16 hours ago
Sonesta Essential Orlando Airport

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
304
Accommodation
1982 Cottages
Lowest Price
NZ$259
Highest Price
NZ$1,048

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between NZ$259 and NZ$1,048 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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