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Oct 31 - Nov 2
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Feb 6 - Feb 8

Cottages in Winter Garden

Interior
Tiny Hidden Cottage
Tiny Hidden Cottage
9.2 out of 10, Wonderful, (53)
"Clean, nice, homey"
$131 nightly
The price is $144
Oct 20 - Oct 21
Total with taxes and fees
Tiny Hidden Cottage
Interior
5180 Spectacular 5bd4ba- Private Pool&spa
5180 Spectacular 5bd4ba- Private Pool&spa
3.0 star property
$346 nightly
The price is $388
Oct 22 - Oct 23
Total with taxes and fees
5180 Spectacular 5bd4ba- Private Pool&spa
House (6 Bedrooms) | Interior
411 Wanderlust Heaven 5bed/pool
411 Wanderlust Heaven 5bed/pool
3.0 star property
$489 nightly
The price is $555
Oct 21 - Oct 22
Total with taxes and fees
411 Wanderlust Heaven 5bed/pool
Front of property
Historic Tremain Cottages
Historic Tremain Cottages
3.0 star property
8.4 out of 10, Very Good, (31)
"Great location!"
$218 nightly
The price is $242
Oct 28 - Oct 29
Total with taxes and fees
Historic Tremain Cottages
Exterior
Incredible Private Lakefront Cottage Retreat
Incredible Private Lakefront Cottage Retreat
10.0 out of 10, Exceptional, (27)
"One of our best stays. "
$294 nightly
The price is $324
Oct 18 - Oct 19
Total with taxes and fees
Incredible Private Lakefront Cottage Retreat
House (4 Bedrooms) | Interior
161 - 4 bed Gem at Terraverde Resort
161 - 4 bed Gem at Terraverde Resort
3.0 star property
161 - 4 bed Gem at Terraverde Resort
House (4 Bedrooms) | Interior
Southern Dunes Family Retreat: Hot Tub & Game Room
Southern Dunes Family Retreat: Hot Tub & Game Room
3.0 star property
$328 nightly
The price is $364
Oct 29 - Oct 30
Total with taxes and fees
Southern Dunes Family Retreat: Hot Tub & Game Room
Exterior
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Charming 2-bedroom Country Cottage in Kissimmee with private parking
10.0 out of 10, Exceptional, (3)
"great experience. very clean and in a good area"
$120 nightly
The price is $133
Oct 29 - Oct 30
Total with taxes and fees
Charming 2-bedroom Country Cottage in Kissimmee with private parking
1 bedroom, desk, iron/ironing board, free WiFi
Downtown Cottage
Downtown Cottage
8.4 out of 10, Very Good, (6)
"Thank you for a wonderful stay. This gem of a guest house is in a perfect location in the Mills50 area of downtown Orlando. A perfectly cozy little home with comfortable beds and a welcoming environment. We look forward to staying again next time we are in Orlando!"
$164 nightly
The price is $181
Oct 20 - Oct 21
Total with taxes and fees
Downtown Cottage
Exterior
Jedi cottage 4 miles from Disney! Mins from universal!
Jedi cottage 4 miles from Disney! Mins from universal!
9.4 out of 10, Exceptional, (23)
"We loved staying here! "
$195 nightly
The price is $218
Oct 17 - Oct 18
Total with taxes and fees
Jedi cottage 4 miles from Disney! Mins from universal!
Microwave, oven, stovetop
Charming Historic Cottage with Cozy Porch and Garden Retreat
Charming Historic Cottage with Cozy Porch and Garden Retreat
$242 nightly
The price is $268
Oct 23 - Oct 24
Total with taxes and fees
Charming Historic Cottage with Cozy Porch and Garden Retreat
2 bedrooms, iron/ironing board, WiFi, bed sheets
Tiny house close to Disney KISSIMMEE
Tiny house close to Disney KISSIMMEE
2.0 star property
$141 nightly
The price is $157
Oct 20 - Oct 21
Total with taxes and fees
Tiny house close to 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
$376 nightly
The price is $423
Oct 17 - Oct 18
Total with taxes and fees
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
Exterior
The Ingram * 3 min walk to Downtown Mt. Dora!!
The Ingram * 3 min walk to Downtown Mt. Dora!!
9.8 out of 10, Exceptional, (46)
"Excellent, had a great time. Had everything u could need. "
$256 nightly
The price is $281
Oct 19 - Oct 20
Total with taxes and fees
The Ingram * 3 min walk to Downtown Mt. Dora!!
Property grounds
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
10.0 out of 10, Exceptional, (5)
"The cottage was conveniently located near d'town. Comfortable, clean and well-stocked. "
$228 nightly
The price is $250
Oct 19 - Oct 20
Total with taxes and fees
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Property grounds
Cozy Lake Front Cottage
Cozy Lake Front Cottage
10.0 out of 10, Exceptional, (17)
"As advertised!"
$218 nightly
The price is $239
Oct 28 - Oct 29
Total with taxes and fees
Cozy Lake Front Cottage
Interior
Family-Friendly Cottage Near Orlando’s Top Attractions
Family-Friendly Cottage Near Orlando’s Top Attractions
$183 nightly
The price is $205
Oct 20 - Oct 21
Total with taxes and fees
Family-Friendly Cottage Near Orlando’s Top Attractions
House (4 Bedrooms) | Interior
Family-friendly Home w/ Lanai ~ 6 Mi to Disney
Family-friendly Home w/ Lanai ~ 6 Mi to Disney
3.0 star property
$385 nightly
The price is $433
Oct 18 - Oct 19
Total with taxes and fees
Family-friendly Home w/ Lanai ~ 6 Mi to Disney
Fridge, microwave, oven, stovetop
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
8.6 out of 10, Excellent, (16)
"We got the place for my family to stay while they came an visited. It was spacious, clean and in a perfect central location to everything in Altamonte. Highly recommend!!!"
$281 nightly
The price is $311
Nov 10 - Nov 11
Total with taxes and fees
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Property grounds
Hidden Lake View Cottage 5 miles from Disney!
Hidden Lake View Cottage 5 miles from Disney!
9.0 out of 10, Wonderful, (2)
"Awesome"
$199 nightly
The price is $223
Oct 22 - Oct 23
Total with taxes and fees
Hidden Lake View Cottage 5 miles from Disney!
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

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

10/10 Excellent
"This is a very nice Hotel and I highly recommend it (I actually just did recommend it to a friend that will be going next month). We will definitely be back."
John 5-night trip
Posted 21 hours ago
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
220
Accommodation
1992 Cottages
Lowest Price
$133
Highest Price
$555

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between $133 and $555 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.
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 travelers' 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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