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Compare 1626 Cottages in Winter Garden with updated reviews, rates, and availability.

Orlando Lakefront Tiny House Community
Exterior

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (235)
"Spectacularly quaint and friendly as F**K. Wish this community existed everywhere we traveled! Bravo!"
The price is AED 292
AED 597 total
includes taxes & fees
23 Dec - 24 Dec
Orlando Lakefront Tiny House Community
Tiny Hidden Cottage
Room

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (24)
"The house was perfect for my weekend stay and I hope to stay again on my next trip"
The price is AED 345
AED 625 total
includes taxes & fees
25 Dec - 26 Dec
Tiny Hidden Cottage
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Orlando oasis ☀️

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

9.8 out of 10, Exceptional, (9)
"It's a lovely, well-appointed, well-located place. The cottage is within easy walking distance of multiple restaurants. The communication was excellent. I hope to stay at the cottage again soon!"
The price is AED 643
AED 1,276 total
includes taxes & fees
12 Jan - 13 January 2025
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood
Exterior

High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood

10.0 out of 10, Exceptional, (121)
"Wonderful hosts and perfect location. We have returned many times and hope to visit again soon."
High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood
Orlando Holiday Special! Guest House with Private pool & WiFi
Pool for your enjoyment.

Orlando Holiday Special! Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (26)
"I had surgery and stayed here for my recovery, nice quiet area, easily accessible to stores and very comfortable bed. I felt very comfortable while recuperating. Washer and dryer big plus and the pool was beautiful and well kept. I didn't get to use the pool but I sure would have loved to. I will be back when I have to go for my checkups "
Orlando Holiday Special! Guest House with Private pool & WiFi
Gorgeous Cottage near Lake Louisa & mins 2 Disney.
Private kitchen

Gorgeous Cottage near Lake Louisa & mins 2 Disney.

9.6 out of 10, Exceptional, (36)
"Glad to report place is as nice as depicted in photos. House is part of a duplex in a community of homes called Vacation Village Resort. Two true bedrooms and two true baths. I don't want to give away the surprise but have a couple of quarters handy especially if traveling with kids. Small but highly functional kitchen area with full size refrigerator and a dishwasher as well. "
Gorgeous Cottage near Lake Louisa & mins 2 Disney.
Historic Tremain Cottages
Terrace/patio

Historic Tremain Cottages

3.0 star property
8.4 out of 10, Very Good, (29)
"This is an excellent quaint property. It’s in a quiet area and is walkable to town. It’s wonderful."
The price is AED 802
AED 890 total
includes taxes & fees
23 Dec - 24 Dec
Historic Tremain Cottages
Enchanted Cottage with Pool and Mini-Golf Near Disney
Enchanted Cottage - 1 bedroom, 1 bathroom near Disney

Enchanted Cottage with Pool and Mini-Golf Near Disney

9.6 out of 10, Exceptional, (14)
"This location was perfect for me and my two dogs. "
Enchanted Cottage with Pool and Mini-Golf Near Disney
Easy walk 5 blocks to downtown dining & shopping. 2 BR, 2 Bath, POOL
Covered Parking for one car. Two tandem spaces.

Easy walk 5 blocks to downtown dining & shopping. 2 BR, 2 Bath, POOL

10.0 out of 10, Exceptional, (16)
"Nice to be able to walk downtown to enjoy the Christmas activities and restaurants without having to find parking. Also close to the Christmas Parade. The home was very clean and had plenty of kitchen supplies. Highly recommend if staying in the area."
Easy walk 5 blocks to downtown dining & shopping. 2 BR, 2 Bath, POOL
Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly
Unwind in the private hot tub, soaking away your cares in the sunshine

Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly

10.0 out of 10, Exceptional, (3)
"SO nice that each couple had a queen or king sized bed and each bedroom had its own bathroom. Hot tub was a huge bonus after long days on your feet at the theme parks. Very nice house in a beautiful area convenient to the Disney parks."
Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly
Up to Scale With Margaritas
Exterior

Up to Scale With Margaritas

3.0 star property
8.4 out of 10, Very Good, (5)
"The only issue was the upstairs airconditioner was not working in terms the rooms were hot while hallway was cold. But nice for our family. "
Up to Scale With Margaritas
Cozy Cottage 3 blocks from town
Best address in town. Very quiet street only 3 blocks from town. You'll love it

Cozy Cottage 3 blocks from town

10.0 out of 10, Exceptional, (21)
"The cottage has everything you need. It has an excellent location and is clean and well maintained. Debbie, our hostess was wonderful - very attentive & accommodating. Highly recommend staying here. "
Cozy Cottage 3 blocks from town
Stunning Lakeview Townhome w/ Private Pool!
Pool

Stunning Lakeview Townhome w/ Private Pool!

4.0 star property
8.4 out of 10, Very Good, (9)
"Perfect location house was just what is described "
Stunning Lakeview Townhome w/ Private Pool!
Cozy Lake Front Cottage
Living area

Cozy Lake Front Cottage

10.0 out of 10, Exceptional, (9)
"Will definitely be staying again"
The price is AED 657
AED 1,168 total
includes taxes & fees
27 Dec - 28 Dec
Cozy Lake Front Cottage
8000 Lost Shaker Lane
Outdoor spa tub

8000 Lost Shaker Lane

3.0 star property
9.6 out of 10, Exceptional, (5)
"Lots of room , beautifully decorated. Close to everything we needed for the weekend . "
The price is AED 2,013
AED 3,316 total
includes taxes & fees
28 Dec - 29 Dec
8000 Lost Shaker Lane
Davenport Family Home ~ 10 Mi to Animal Kingdom
Living area

Davenport Family Home ~ 10 Mi to Animal Kingdom

3.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect two day stay for us … close to everything we n ended it to be. "
Davenport Family Home ~ 10 Mi to Animal Kingdom
Beautiful Historic Cottage, Nantucket, RIGHT DOWNTOWN. BIG DISCOUNTS THIS MONTH
1

Beautiful Historic Cottage, Nantucket, RIGHT DOWNTOWN. BIG DISCOUNTS THIS MONTH

9.8 out of 10, Exceptional, (6)
"My husband and I really love the place . The decor was so cute. We could walk downtown Mount Dora from where we were at we never had to get into our car. The host was very accommodating with everything will return if we come back to Mount Dora."
The price is AED 723
AED 887 total
includes taxes & fees
6 Jan - 7 January 2025
Beautiful Historic Cottage, Nantucket, RIGHT DOWNTOWN. BIG DISCOUNTS THIS MONTH
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Pool

Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

3.0 star property
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Living room

Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621

3.0 star property
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Parkside Serenity by Avantstay Private Pool!
Pool

Parkside Serenity by Avantstay Private Pool!

3.0 star property
Parkside Serenity by Avantstay Private Pool!
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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Other property types in Winter Garden

Lake Buena Vista Resort Village & Spa
Outdoor pool

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very Good, (8214)
"I really want to give 5 stars but the when you walk off the elevator to go to the apartment there is an overwhelming musty smell. Then when we were in our apartment the smell was so bad, we got there at 3:30am and I had been driving over 12 hours so at that point I just wanted to sleep and worry about it tomorrow. We bought airfresher the next day, it’s not like we planned to be in the room often, and decided to just deal with it. The couch and the dining chairs really need to be replaced. ...
The price is AED 716
AED 914 total
includes taxes & fees
23 Dec - 24 Dec
Lake Buena Vista Resort Village & Spa
The View Studio Suites and Event Venue
Front of property

The View Studio Suites and Event Venue

3.5 star property
8.4 out of 10, Very Good, (638)
"Had a pleasant stay. Customer service was top notch and the breakfast was table service and included with your stay. Very nice surprise. Spacious rooms and large bed. Very nice decor inside. Quiet and neat. Would recommend staying here and is on our list of visit again. Thank you. "
The price is AED 281
AED 316 total
includes taxes & fees
12 Jan - 13 January 2025
The View Studio Suites and Event Venue
Floridays Resort Orlando
Outdoor pool

Floridays Resort Orlando

3.5 star property
8.6 out of 10, Excellent, (11119)
"It’s always nice to stay here . Clean and close to everything "
The price is AED 691
AED 901 total
includes taxes & fees
23 Dec - 24 Dec
Floridays Resort Orlando
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.

Frequently asked questions

How much do cottages in Winter Garden cost?
Prices for cottages in Winter Garden range between AED 292 and AED 2,013 per night. Whatever your budget, you’ll find the perfect place to get reacquainted with nature. 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?
Reserving a cottage in Winter Garden is as easy as entering your travel dates and picking an ideal place for a vacation in the outdoors. From upmarket retreats to budget-friendly stays and cottages that include perks like a hot tub, Expedia has something for all tastes. As for irresistible deals? We’ve got you covered!
How can I find cheap cottages in Winter Garden?
Expedia can help you locate cheap cottages in Winter Garden. To book your dream stay in a few quick keystrokes, try out our handy filter tool to refine your search by star rating, budget and amenities.