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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Cottages in Winter Park

Exterior
Cozy Deltona Stay Fire Pit + Orlando

Cottage in Deltona Lakes

2.0 star property
10.0 out of 10, Exceptional, (1)
"We came down to see family who just had a baby and we were able to book this rental on very short notice. The host was very responsive to all of our questions and very welcoming.The home was exactly what we needed and came at a good price. Everything was clean and the kitchen was stocked with everything we needed. The coffee station was great, as well. The backyard was definitely the centerpiece here. It was very spacious and beautiful. Our kids insisted on eating just about every meal out...
United States
Gregory C.
The price is SAR 396
SAR 1,176 total
includes taxes & fees
22 Nov - 23 Nov
Cozy Deltona Stay Fire Pit + Orlando
The Sunshine Lake Shake | 2 bedrooms, individually decorated, individually furnished
Orlando Lakefront Tiny House Community

Cottage in Orlando

3.0 star property
9.4 out of 10, Exceptional, (331)
"We enjoyed our stay."
United States
Ardeeh
The price is SAR 328
SAR 643 total
includes taxes & fees
2 Dec - 3 Dec
Orlando Lakefront Tiny House Community
Property grounds
Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai

Cottage in Lake Mary

10.0 out of 10, Exceptional, (16)
"Great place and exactly as described. "
United States
Kanzeda C.
The price is SAR 354
SAR 903 total
includes taxes & fees
22 Nov - 23 Nov
Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai
1 bedroom, desk, WiFi, bed sheets
The Sanford Foodie Guest House

Cottage in Sanford

8.8 out of 10, Excellent, (13)
"Cozy little place to stay"
United States
Ruth P.
The price is SAR 200
SAR 530 total
includes taxes & fees
30 Nov - 1 Dec
The Sanford Foodie Guest House
1 bedroom, desk, iron/ironing board, free WiFi
Downtown Cottage

Cottage in Colonialtown North

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!"
United States
Josh L.
The price is SAR 203
SAR 619 total
includes taxes & fees
1 Dec - 2 Dec
Downtown Cottage
Exterior
Charming 2-bedroom Country Cottage in Kissimmee with private parking

Cottage in Kissimmee

9.0 out of 10, Wonderful, (4)
"great experience. very clean and in a good area"
United States
Aubrey V.
The price is SAR 394
SAR 522 total
includes taxes & fees
1 Dec - 2 Dec
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Exterior
The Blue Loft-Cozy Style Guest House · Close to UCF, Downtown & Theme Parks

Cottage in Orlando

2.0 star property
The price is SAR 297
SAR 599 total
includes taxes & fees
2 Dec - 3 Dec
The Blue Loft-Cozy Style Guest House · Close to UCF, Downtown & Theme Parks
Fridge, microwave, oven, stovetop
Garden Cottage-Swim/Spa sleeps 6 Ctrl Orlando Disney Universal SeaWorld Beaches,

Cottage in Altamonte Springs

8.6 out of 10, Excellent, (17)
"Lots of room to spend time with family and friends. Great location, easy to move around Orlando from here."
United States
Rachael C.
The price is SAR 514
SAR 1,164 total
includes taxes & fees
22 Dec - 23 Dec
Garden Cottage-Swim/Spa sleeps 6 Ctrl Orlando Disney Universal SeaWorld Beaches,
Interior
Tiny Hidden Cottage

Cottage in Longwood

9.2 out of 10, Wonderful, (56)
"Check in process and house were both great. "
United States
Marc H.
The price is SAR 267
SAR 542 total
includes taxes & fees
23 Nov - 24 Nov
Tiny Hidden Cottage
Exterior
Incredible Private Lakefront Cottage Retreat

Cottage in Altamonte Springs

10.0 out of 10, Exceptional, (27)
"One of our best stays. "
United States
matthew m.
The price is SAR 435
SAR 1,224 total
includes taxes & fees
23 Nov - 24 Nov
Incredible Private Lakefront Cottage Retreat
House (2 Bedrooms) | Front of property
Deltona Lake House, Day Trip to Disney & Universal

Cottage in Deltona Lakes

3.0 star property
10.0 out of 10, Exceptional, (3)
"This house was perfect! Very spacious, clean, and felt like a very safe neighborhood for a few women traveling. The ONLY improvements I would suggest would be having more towels, and extra blankets available for guests. And I would replace the pull out couch mattress as it was very uncomfortable. Still a 10/10 overall!"
United States
Anonymous traveler
The price is SAR 645
SAR 1,295 total
includes taxes & fees
30 Nov - 1 Dec
Deltona Lake House, Day Trip to Disney & Universal
Exterior
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

Cottage in College Park

10.0 out of 10, Exceptional, (29)
"Absolutely beautiful place, fully equipped and close to everything. We very much enjoyed our stay."
United States
Sara R.
The price is SAR 759
SAR 1,408 total
includes taxes & fees
29 Nov - 30 Nov
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
House (2 Bedrooms) | Interior
Fire Pit & Yard: Updated Winter Garden Home!

Cottage in Winter Garden

3.0 star property
The price is SAR 761
SAR 1,785 total
includes taxes & fees
1 Dec - 2 Dec
Fire Pit & Yard: Updated Winter Garden Home!
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 Park Hotel Reviews

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

10/10 Excellent
"Better than expected "
Dinesha 3-night trip
Posted 2 days ago
Rosen Inn at Pointe Orlando

Frequently asked questions

How much do cottages in Winter Park cost?
Cottages in Winter Park range between SAR 522 and SAR 1,785 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.

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