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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Cottages in Winter Park

Interior
Tiny Hidden Cottage
Tiny Hidden Cottage
9.2 out of 10, Wonderful, (54)
"Clean, nice, homey"
United States
Alan H.
The price is AED 261
AED 531 total
includes taxes & fees
25 Oct - 26 Oct
Tiny Hidden Cottage
1 bedroom, desk, WiFi, bed sheets
The Sanford Foodie Guest House
The Sanford Foodie Guest House
8.8 out of 10, Excellent, (13)
"Cozy little place to stay"
United States
Ruth P.
The price is AED 182
AED 503 total
includes taxes & fees
25 Oct - 26 Oct
The Sanford Foodie Guest House
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"
United States
Aubrey V.
The price is AED 386
AED 511 total
includes taxes & fees
3 Nov - 4 Nov
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Property grounds
Cozy Cottage Retreat – Queen Bed, Fire Pit & Private Lanai
Cozy Cottage Retreat – Queen Bed, Fire Pit & Private Lanai
10.0 out of 10, Exceptional, (16)
"Great place and exactly as described. "
United States
Kanzeda C.
The price is AED 386
AED 939 total
includes taxes & fees
22 Nov - 23 Nov
Cozy Cottage Retreat – Queen Bed, Fire Pit & Private Lanai
Exterior
Incredible Private Lakefront Cottage Retreat
Incredible Private Lakefront Cottage Retreat
10.0 out of 10, Exceptional, (27)
"One of our best stays. "
United States
matthew m.
The price is AED 459
AED 1,228 total
includes taxes & fees
17 Nov - 18 Nov
Incredible Private Lakefront Cottage Retreat
Outdoor spa tub
LAKEFRONT - kayak, fish, paddleboard, canoe, HOT TUB, golf -near Orlando
LAKEFRONT - kayak, fish, paddleboard, canoe, HOT TUB, golf -near Orlando
10.0 out of 10, Exceptional, (181)
"Absolutely amazing property!! We had an amazing time "
United States
Hillary R.
The price is AED 545
AED 1,375 total
includes taxes & fees
1 Nov - 2 Nov
LAKEFRONT - kayak, fish, paddleboard, canoe, HOT TUB, golf -near Orlando
Outdoor dining
Cozy Deltona Stay Fire Pit + Orlando
Cozy Deltona Stay Fire Pit + Orlando
2.0 star property
The price is AED 388
AED 1,181 total
includes taxes & fees
26 Oct - 27 Oct
Cozy Deltona Stay Fire Pit + Orlando
Exterior
Guesthouse Retreat – Private Pool & King Suite
Guesthouse Retreat – Private Pool & King Suite
9.8 out of 10, Exceptional, (42)
"Wonderful stay. This is my second time here and love the accommodations and location. Very quiet. "
United States
Christine B.
The price is AED 422
AED 987 total
includes taxes & fees
17 Nov - 18 Nov
Guesthouse Retreat – Private Pool & King Suite
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)
"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 AED 503
AED 1,151 total
includes taxes & fees
10 Nov - 11 Nov
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
House (2 Bedrooms) | Interior
Fire Pit & Yard: Updated Winter Garden Home!
Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Fire Pit & Yard: Updated Winter Garden Home!
Exterior
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
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 AED 661
AED 1,293 total
includes taxes & fees
27 Oct - 28 Oct
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
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

Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent
"Clean room, excellent staff"
Mary 2-night trip
Posted 9 hours ago
Universal's Endless Summer Resort - Dockside Inn and Suites

Frequently asked questions

How much do cottages in Winter Park cost?
Cottages in Winter Park range between AED 503 and AED 1,748 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.