Search Cottages in Winter Park

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Winter Park cottages

Interior

Cottage in Colonialtown North

Downtown Cottage
8.6 out of 10, Excellent, (8 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is AED 215
AED 625 total
includes taxes & fees
1 Feb - 2 Feb
Downtown Cottage
Exterior

Cottage in Lake Mary

The Little Lake Mary Guest House • Warm, Cozy & Inviting
9.8 out of 10, Exceptional, (46 reviews)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
The Little Lake Mary Guest House • Warm, Cozy & Inviting
House (2 Bedrooms) | Interior

Cottage in Deltona Lakes

Deltona Lake House, Day Trip to Disney & Universal
3.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"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 AED 500
AED 1,244 total
includes taxes & fees
26 Jan - 27 Jan
Deltona Lake House, Day Trip to Disney & Universal
Exterior

Cottage in Altamonte Springs

Incredible Private Lakefront Cottage Retreat
10.0 out of 10, Exceptional, (31 reviews)
"One of our best stays. "
United States
matthew m.
The price is AED 522
AED 1,306 total
includes taxes & fees
14 Feb - 15 Feb
Incredible Private Lakefront Cottage Retreat
Property grounds

Cottage in Longwood

Tiny Hidden Cottage
9.2 out of 10, Wonderful, (62 reviews)
"It was a good area to stay "
United States
Christanah O.
The price is AED 261
AED 531 total
includes taxes & fees
29 Jan - 30 Jan
Tiny Hidden Cottage
Exterior

Cottage in College Park

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
10.0 out of 10, Exceptional, (30 reviews)
"Absolutely beautiful place, fully equipped and close to everything. We very much enjoyed our stay."
United States
Sara R.
The price is AED 694
AED 1,312 total
includes taxes & fees
26 Jan - 27 Jan
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Iron/ironing board, internet, bed sheets

Cottage in Orlando

Quiet Lakefront Retreat near Downtown with Private Patio
The price is AED 250
AED 685 total
includes taxes & fees
26 Jan - 27 Jan
Quiet Lakefront Retreat near Downtown with Private Patio
Exterior

Cottage in Orlando

The Blue Loft-Cozy Style Guest House · Close to UCF, Downtown & Theme Parks
6.0 out of 10, (1 review)
"This is a comfortable and convenient place. It is in a back yard with little privacy, and quite small. The host communication was poor, basically non existent. The water heater must be small and turned way down; it never actually gets hot and runs out quick. the shower head pressure is not great and has no options or settings, Overall not bad, clean and cozy. "
United States
Shannon T.
The price is AED 327
AED 628 total
includes taxes & fees
29 Jan - 30 Jan
The Blue Loft-Cozy Style Guest House · Close to UCF, Downtown & Theme Parks
Exterior

Cottage in Kissimmee

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
The price is AED 784
AED 3,293 total
includes taxes & fees
25 Feb - 26 Feb
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Park Hotel Reviews

Avanti International Resort

Avanti International Resort

10/10 Excellent
"Great service"
Andrea 6-night trip
Posted 1 day ago
Avanti International Resort

Frequently asked questions

How much do cottages in Winter Park cost?
Cottages in Winter Park range between AED 531 and AED 3,293 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.