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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 204 Cottages in Winter Park 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, (270)
"Nice quiet place. Perfect for our mini getaway. Loved it at night and was able to do a bonfire."
The price is AED 295
AED 600 total
includes taxes & fees
4 Mar - 5 Mar
Orlando Lakefront Tiny House Community
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, (10)
"Great place in beautiful quiet neighborhood. The extra touch of snacks and breakfast was a nice surprise "
The price is AED 643
AED 1,232 total
includes taxes & fees
11 Mar - 12 Mar
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Tiny Hidden Cottage
Room

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (30)
"We loved staying here! It exceeded our expectations! Is small, but super cozy, and has everything you need to be comfortable. Loved the TV right above the foot of the bed, the firepit, waking up to the cute sounds of chickens softly clucking… was just so relaxing being there, and we are already talking about coming back sometime!Thank-you for a wonderful stay!"
The price is AED 290
AED 563 total
includes taxes & fees
5 Mar - 6 Mar
Tiny Hidden Cottage
The Sanford Foodie Guest House
Terrace/patio

The Sanford Foodie Guest House

9.0 out of 10, Wonderful, (7)
"Great spot if you are visiting the area. The host was nice and helpful!"
The price is AED 294
AED 810 total
includes taxes & fees
2 Mar - 3 Mar
The Sanford Foodie Guest House
Florida Valentine’s Day Guest House with Private pool & WiFi
Miscellaneous

Florida Valentine’s Day Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (28)
"This house is absolutely adorable. Care and attention to detail made staying here the best part of my trip. Suzy is far and away the most thoughtful host I’ve ever had. "
The price is AED 533
AED 1,086 total
includes taxes & fees
2 Mar - 3 Mar
Florida Valentine’s Day Guest House with Private pool & WiFi
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!
Downtown Cottage
Exterior detail

Downtown Cottage

10.0 out of 10, Exceptional, (3)
"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!"
The price is AED 367
AED 811 total
includes taxes & fees
4 Mar - 5 Mar
Downtown Cottage
Dtwn Winter Garden Home: 12 Mi to Disney!
Winter Garden Vacation Rental | 3BR | 2BA | 1,200 Sq Ft | 3 Steps to Enter

Dtwn Winter Garden Home: 12 Mi to Disney!

9.6 out of 10, Exceptional, (5)
"We were in for a work trip and this location was central and perfect for our needs. Beds are great, towels are soft, and furniture and decor were charming.. highly recommend!!"
Dtwn Winter Garden Home: 12 Mi to Disney!
Valentine’s Day Cottage with queen bed & fire pit.
Room

Valentine’s Day Cottage with queen bed & fire pit.

10.0 out of 10, Exceptional, (11)
"Suite was super comfy and attention to detail in furnishings was great"
The price is AED 386
AED 911 total
includes taxes & fees
10 Mar - 11 Mar
Valentine’s Day Cottage with queen bed & fire pit.
The Pink Door Cottage-Historic Sanford
Exterior detail

The Pink Door Cottage-Historic Sanford

10.0 out of 10, Exceptional, (11)
"Super clean, comfortable home within walking distance to Sanford downtown. You’re right smack in the middle of the historic district if you stay on this charming home. We walked everywhere and really enjoyed the location. The house as well had everything you’d need. "
The Pink Door Cottage-Historic Sanford
5003 Windermere Avenue
Pool

5003 Windermere Avenue

3.0 star property
10.0 out of 10, Exceptional, (1)
"very nice house , with 4 Rooms , 1 of them in the 1st floor so very convenient to my mom . kitchen is awesome , new and good quality appliances we take the kids to the club , there is a lazy river and the sliders are fun . No additional charges . "
The price is AED 1,064
AED 2,331 total
includes taxes & fees
25 Feb - 26 Feb
5003 Windermere Avenue
16 Mi to Disney: Cottage w/ Deck in Winter Garden
Living area

16 Mi to Disney: Cottage w/ Deck in Winter Garden

3.0 star property
10.0 out of 10, Exceptional, (1)
"This house is adorable! It was perfect for us as a couple. Very sweetly decorated and homey. The neighborhood is very quiet and off the beaten path, as they say, yet very close to stores and beautiful downtown Winter Garden. We would SO stay again! Would love to do a seasonal stay. "
16 Mi to Disney: Cottage w/ Deck in Winter Garden
Screened Lanai + Fenced Yard: Luxe Orlando Home
Living area

Screened Lanai + Fenced Yard: Luxe Orlando Home

3.0 star property
Screened Lanai + Fenced Yard: Luxe Orlando Home
THE HIDEAWAY AT COLLEGE PARK
Property grounds

THE HIDEAWAY AT COLLEGE PARK

8.0 out of 10, Very Good, (1)
"Overall, this was a great stay for my needs. The location was close to where I needed to be. I ABSOLUTELY loved the decor. I had three concerns. We did not know how to use the security code and had to YouTube directions. The second bedroom did not have a "bed" and there is not a curtain so my guest slept in the living room. bedro a bedroom and was very small"
THE HIDEAWAY AT COLLEGE PARK
Caribbean Dreamin
Living area

Caribbean Dreamin

3.0 star property
10.0 out of 10, Exceptional, (1)
"This Caribbean Dreamin property is awesome! It is clean, spacious, and very well kept. Contrary to the contract, the house includes all the amenities for all bathrooms as well as dishwashing detergent. Nice touch! The community is very pretty and well kept. Shopping nearby. Unfortunately, we were here for a couple nights during Hurricane Milton so didn't go out at all. But being in a nice home away from home made a difference during the stressful time. I would highly recommend this...
Caribbean Dreamin
Lake-view Home w/ Game Room in Orlando!
Exterior

Lake-view Home w/ Game Room in Orlando!

3.0 star property
Lake-view Home w/ Game Room in Orlando!
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Pool

Orlando Home w/ Private Pool: 10 Mi to UCF Campus!

3.0 star property
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Luxurious Home W/private Pool, Near Disney!
Pool

Luxurious Home W/private Pool, Near Disney!

4.0 star property
8.0 out of 10, Very Good, (3)
"House was great, however chose to pay for the early check-in so we could use the pool. To use the heater for the pool it’s an up charge. Understand. However they charged me $25 per day for the entire stay but the pool wasn’t warm until the morning we checked out."
Luxurious Home W/private Pool, Near Disney!
Beautiful, Modern Home W/private Pool! Near WDW
Living area

Beautiful, Modern Home W/private Pool! Near WDW

4.0 star property
8.4 out of 10, Very Good, (12)
"It was a nice place ."
Beautiful, Modern Home W/private Pool! Near WDW
Close to Attraction: Home in Orlando
Living area

Close to Attraction: Home in Orlando

3.0 star property
Close to Attraction: Home in 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.
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Other property types in Winter Park

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, (8366)
"Convenient store onsite. Nice staff"
The price is AED 640
AED 828 total
includes taxes & fees
24 Feb - 25 Feb
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, (863)
"Room was clean and nice. Staff was friendly. Good price. Breakfast was fantastic and waiters pleasant. Sit down breakfast with nice amount of breakfast items to choose from. I had a ham and cheese omlet, bacon, fresh fruit, and a large orage juice. I did not like that the water and ice machine was broken on every floor except for 5th floor. The matress was not the most comfortable. The air-conditioner was extremely loud. I would stay here again."
The price is AED 377
AED 424 total
includes taxes & fees
24 Feb - 25 Feb
The View Studio Suites and Event Venue
Florida Hotel & Conference Center in the Florida Mall
Exterior

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.0 out of 10, Wonderful, (1757)
"Great place to stay while in Orlando."
The price is AED 730
AED 916 total
includes taxes & fees
25 Feb - 26 Feb
Florida Hotel & Conference Center in the Florida Mall
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 Park cost?
Prices for cottages in Winter Park range between AED 290 and AED 1,064 per night. No matter your budget, you’re sure to find an ideal place to immerse yourself in 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 Park with Expedia?
Expedia has some great cottages in Winter Park, so get set for a memorable stay close to nature. If you have a fixed budget, choose how much you’d like to spend and your preferred property star rating. Or, make your way to the filters to search for cottages with a pool or a hot tub. We’ll help you find the perfect pad whatever your style of travel or plans.
How can I find cheap cottages in Winter Park?
With Expedia’s user-friendly filter tool, sourcing cheap cottages in Winter Park couldn’t be simpler. To view accommodations that’ll make your wallet happy, narrow your search results by star rating, budget and amenities.