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Check prices for these dates

Next weekend
14 Rab. I - 16 Rab. I
In two weeks
21 Rab. I - 23 Rab. I
In one month
4 Rab. II - 6 Rab. II
In two months
2 Jum. I - 4 Jum. I

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

Orlando Lakefront Tiny House Community
The Club House | Individually decorated, individually furnished, laptop workspace

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (274)
"The property was in great shape, safe and clean. Highly recommended. "
The price is SAR 280
SAR 589 total
includes taxes & fees
10 Mar - 11 Mar
Orlando Lakefront Tiny House Community
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
2 bedrooms, in-room safe, desk, iron/ironing board

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 SAR 656
SAR 1,243 total
includes taxes & fees
11 Mar - 12 Mar
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Tiny Hidden Cottage
Fridge, microwave, stovetop, coffee/tea maker

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (32)
"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 SAR 296
SAR 575 total
includes taxes & fees
6 Mar - 7 Mar
Tiny Hidden Cottage
The Sanford Foodie Guest House
1 bedroom, desk, WiFi, bed sheets

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 SAR 300
SAR 846 total
includes taxes & fees
9 Mar - 10 Mar
The Sanford Foodie Guest House
Florida Guest House with Private pool & WiFi
Property grounds

Florida 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 SAR 596
SAR 1,202 total
includes taxes & fees
22 Mar - 23 Mar
Florida Guest House with Private pool & WiFi
Stunning Lakeview Townhome w/ Private Pool!
Outdoor pool

Stunning Lakeview Townhome w/ Private Pool!

4.0 star property
8.4 out of 10, Very Good, (10)
"Perfect location house was just what is described "
Stunning Lakeview Townhome w/ Private Pool!
Downtown Cottage
Desk, iron/ironing board, free WiFi, bed sheets

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 SAR 375
SAR 813 total
includes taxes & fees
11 Mar - 12 Mar
Downtown Cottage
Dtwn Winter Garden Home: 12 Mi to Disney!
Fridge, microwave, stovetop, dishwasher

Dtwn Winter Garden Home: 12 Mi to Disney!

9.8 out of 10, Exceptional, (7)
"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!
Cottage with queen bed & fire pit.
Terrace/patio

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 SAR 394
SAR 915 total
includes taxes & fees
10 Mar - 11 Mar
Cottage with queen bed & fire pit.
The Pink Door Cottage-Historic Sanford
Outdoor dining

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
Miscellaneous

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 . "
5003 Windermere Avenue
16 Mi to Disney: Cottage w/ Deck in Winter Garden
Cottage (1 Bedroom) | Interior

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
Interior

Screened Lanai + Fenced Yard: Luxe Orlando Home

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

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
Cottage, Multiple Beds, Patio, Garden View | 3 bedrooms, free WiFi, bed sheets

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!
House (4 Bedrooms) | Interior

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!
House (3 Bedrooms) | Private kitchen | Paper towels

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!
Outdoor 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
Miscellaneous

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
House (3 Bedrooms) | Interior

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
2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very Good, (8399)
"Very convenient. Close to the parks. Good parking. Kids loved the pool. Friendly staff. "
Lake Buena Vista Resort Village & Spa
Florida Hotel & Conference Center in the Florida Mall
Reception

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.2 out of 10, Wonderful, (1784)
"Saprina was great "
The price is SAR 652
SAR 831 total
includes taxes & fees
16 Mar - 17 Mar
Florida Hotel & Conference Center in the Florida Mall
The View Studio Suites and Event Venue
Exterior

The View Studio Suites and Event Venue

3.5 star property
8.4 out of 10, Very Good, (903)
"Nice property Personel are friendly Not a good breakfast time for early travellers"
The price is SAR 385
SAR 433 total
includes taxes & fees
9 Mar - 10 Mar
The View Studio Suites and Event Venue
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?
Cottages in Winter Park range between and per night. These stays offer a chance to touch base 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 Park with Expedia?
Expedia has some terrific cottages in Winter Park, so start packing for a memorable vacation close to nature. If you have a fixed budget, choose how much you’d like to spend and the preferred star rating of your property. Or, make use of our filters to search for cottages with a pool or a kitchen. We’ll help you find the perfect fit whatever your plans or bank balance.
How can I find cheap cottages in Winter Park?
Expedia is here to help you easily track down cheap cottages in Winter Park. To discover your dream stay in a couple of quick clicks, simply use our handy filter tool to tailor your search results by amenities, star rating and budget.