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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sep - 20 Sep
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

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 AED 889
AED 2,011 total
includes taxes & fees
25 Jul - 26 Jul
Fire Pit & Yard: Updated Winter Garden Home!
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 AED 526
AED 1,365 total
includes taxes & fees
6 Aug - 7 Aug
Shore Steps Cottage - Walking Distance To The Town Of Windermere
House (2 Bedrooms) | Interior

Chic Orlando Family Getaway w/ Fenced Yard!

Chic Orlando Family Getaway w/ Fenced Yard!
3.0 star property
Rosemont
10.0 out of 10, Exceptional, (2 reviews)
"The house was well supplied with amenities, family friendly and it was very fun to use the pool and games. There’s a super Walmart and other shops close by."
United States
Jennifer
Chic Orlando Family Getaway w/ Fenced Yard!
Exterior detail

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 AED 234
AED 647 total
includes taxes & fees
29 Jul - 30 Jul
Downtown Cottage
Property grounds

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 AED 547
AED 1,147 total
includes taxes & fees
30 Jul - 31 Jul
Cozy Lake Front Cottage
The Garden, Pet Friendly | Terrace/patio

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 AED 553
AED 614 total
includes taxes & fees
4 Aug - 5 Aug
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
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 AED 617
AED 1,248 total
includes taxes & fees
3 Aug - 4 Aug
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Exterior

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 AED 477
AED 1,295 total
includes taxes & fees
27 Jul - 28 Jul
Incredible Private Lakefront Cottage Retreat
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 AED 444
AED 926 total
includes taxes & fees
25 Jul - 26 Jul
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Exterior

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, (61 reviews)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
The price is AED 413
AED 981 total
includes taxes & fees
3 Aug - 4 Aug
Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone
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 AED 602
AED 741 total
includes taxes & fees
27 Jul - 28 Jul
Beautiful Historic Cottage, Rendezvous
Front of property

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 AED 783
AED 870 total
includes taxes & fees
4 Aug - 5 Aug
Mount Dora Cottages
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, (21 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 AED 502
AED 926 total
includes taxes & fees
22 Aug - 23 Aug
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
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 AED 639
AED 787 total
includes taxes & fees
27 Jul - 28 Jul
Beautiful Historic Cottage, The Garden
Terrace/patio

Lake Mary Last-Minute Deal! Crystal Springs Adventure Awaits

Lake Mary Last-Minute Deal! Crystal Springs Adventure Awaits
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 AED 331
AED 866 total
includes taxes & fees
28 Jul - 29 Jul
Lake Mary Last-Minute Deal! Crystal Springs Adventure Awaits
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 AED 798
AED 3,309 total
includes taxes & fees
11 Aug - 12 Aug
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
Exterior

Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is AED 345
AED 768 total
includes taxes & fees
23 Aug - 24 Aug
Perfect Place for a Perfect Vacation
House (5 Bedrooms) | Interior

Upstay Family Home w Cinema, Pool & BBQ Clermont

Upstay Family Home w Cinema, Pool & BBQ Clermont
3.0 star property
Clermont
Upstay Family Home w Cinema, Pool & BBQ Clermont
Smart TV, books

Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Perfect location to enjoy Universal Epic and Islands of Adventure with only a 15 minute ride. The beds were very comfortable and the place is clean. We were welcomed with a cute sign, bottled water and cookies. Will definitely stay here again!"
United States
Joyce R.
The price is AED 375
AED 805 total
includes taxes & fees
23 Aug - 24 Aug
Family-Friendly Cottage Near Orlando’s Top Attractions
Microwave, stovetop

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very Good, (8 reviews)
"Nice, Cute little place"
United States
Brenda N.
The price is AED 257
AED 636 total
includes taxes & fees
8 Aug - 9 Aug
Tiny house close to Disney KISSIMMEE
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

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"Room was very nice. Staff very friendly. A+"
Mona 2-night trip
Posted less than an hour ago
Kompose Boutique Resort at Theme Parks

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.