Search Cottages in Winter Park

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 247 Cottages in Winter Park with updated reviews, rates, and availability.

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (281)
"Very nice home away from home with a beautiful view"
The price is AED 256
AED 556 total
includes taxes & fees
30 Mar - 31 Mar
Orlando Lakefront Tiny House Community

Florida Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (29)
"Great place"
Florida Guest House with Private pool & WiFi

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

10.0 out of 10, Exceptional, (12)
"Very inviting and cozy cottage with all amenities to get you started. Amazing cozy home if you're traveling with furry friends, great neighborhood and sites around. Many thanks!"
The price is AED 735
AED 1,361 total
includes taxes & fees
3 Apr - 4 Apr
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (36)
"The cottage was cozy and complete, with even silverware and coffee cups. When the microwave stopped working, the owner went out and bought and set up a new microwave.She asked permission before showing up at the front door!"
The price is AED 345
AED 625 total
includes taxes & fees
28 Apr - 29 Apr
Tiny Hidden Cottage

Downtown Cottage

9.6 out of 10, Exceptional, (4)
"This place was alright. Clean & was exactly as described. Bare concrete floors are a bit of a drawback. "
The price is AED 367
AED 797 total
includes taxes & fees
27 Apr - 28 Apr
Downtown Cottage

3-br Condo BBQ & Heated Pool Near Disney&malls

3.0 star property
4.0 out of 10, (1)
"Mold on windows no screens on some windows. Faced a forest of trees no outdoor patio like I thought there would be. Communication was terrible the person I talked to on the phone knew nothing about the property never given times for the pools or that we could go to different pools within missed two days of swimming because of this showed a whirlpool tub but the spout for the tub didn’t even work "
3-br Condo BBQ & Heated Pool Near Disney&malls

Incredible Private Lakefront Cottage Retreat

10.0 out of 10, Exceptional, (25)
"My partner and I were so awestruck by the beauty of the property! The house was immaculately clean and the location was perfect. The lake it sat on was beautiful and serene. We had everything we needed to decompress from the daily grind. We enjoyed the cute and cozy fireplace after visiting nearby botanical gardens. The bed was so comfortable we had a hard time getting up and going. Absolutely one of the best places we have ever stayed, just wish we could have stayed longer! Definitely will be...
The price is AED 544
AED 1,224 total
includes taxes & fees
3 Apr - 4 Apr
Incredible Private Lakefront Cottage Retreat

Lakeview Home w/ Private Pool & Free Water Park!

3.5 star property
10.0 out of 10, Exceptional, (3)
"Love the inside heated swimming pool. Ive maker was not working."
Lakeview Home w/ Private Pool & Free Water Park!

Private Patio: College Park Cottage in Orlando!

10.0 out of 10, Exceptional, (8)
"We throughly enjoyed our stay! I would highly recommend staying at The Cottage!"
Private Patio: College Park Cottage in Orlando!

The Sanford Foodie Guest House

9.2 out of 10, Wonderful, (9)
"It was a great place to crash for a night. "
The price is AED 275
AED 797 total
includes taxes & fees
31 Mar - 1 Apr
The Sanford Foodie Guest House

Modern Townhome W/private Pool & Free Water Park!

4.0 star property
8.8 out of 10, Excellent, (5)
"This property was excellent and lived up to the expectations in the post! So close to the parks, we came back everyday to cool down by the pool and recharge our batteries."
Modern Townhome W/private Pool & Free Water Park!

2BR COTTAGE IN SANFORD HISTORIC DISTRICT

10.0 out of 10, Exceptional, (98)
"This cottage is a quaint spot, inside and out. Cozy, clean and comfortable. Love the location. Great communication."
2BR COTTAGE IN SANFORD HISTORIC DISTRICT

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

Beautiful, Modern Home W/private Pool! Near WDW

4.0 star property
8.2 out of 10, Very Good, (13)
"It was a nice place ."
Beautiful, Modern Home W/private Pool! Near WDW

The Pink Door Cottage-Historic Sanford

10.0 out of 10, Exceptional, (11)
"Fully equipped with everything one could need whilst staying here."
The Pink Door Cottage-Historic Sanford

4813 Crusoe Street

3.0 star property
4813 Crusoe Street

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!

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

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

Stunning Lakeview Townhome w/ Private Pool!

4.0 star property
8.6 out of 10, Excellent, (11)
"We loved staying at this condo! Easy and close access to all theme parks and only an hour to the ocean! The condo was beautiful and nicely furnished and had everything we needed! Nice and clean in the areas of the condo that mattered...could use some deep cleaning of baseboards, walls, and ceilings. Our family will definitely stay here again! "
Stunning Lakeview Townhome w/ Private Pool!

Cozy Tiny Home Near Disney World & Orlando Parks!

8.0 out of 10, Very Good, (9)
"I really liked the location and the size of the cottage but people should not have to pay to stay with roaches, i dont live with them and i dont want to travel a 1000 miles to stay with them"
Cozy Tiny Home Near Disney World & Orlando Parks!
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.
Don't see what you're looking for?
See all available properties in Winter Park
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Winter Park

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very Good, (8483)
"It was an overall great stay. Would have liked a little housekeeping without an extra fee. "
The price is AED 559
AED 737 total
includes taxes & fees
31 Mar - 1 Apr
Lake Buena Vista Resort Village & Spa

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.2 out of 10, Wonderful, (1844)
"After a very exhausting couple of days of my trip, it was a delight that they allowed me to have a very early check in, so I could take a nap in the middle of the day, much needed. The room was cold and crispy clean. Especially thankfull to Aliya for arraging all of that with me over the phone before leaving at the end of her shift. Definetly my place to stay when going to Orlando. "
The price is AED 615
AED 787 total
includes taxes & fees
10 Apr - 11 Apr
Florida Hotel & Conference Center in the Florida Mall

Floridays Resort Orlando

3.5 star property
8.6 out of 10, Excellent, (11287)
"The resort was very nice for the price. "
The price is AED 621
AED 843 total
includes taxes & fees
30 Mar - 31 Mar
Floridays Resort 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.

Frequently asked questions

How much do cottages in Winter Park cost?
Cottages in Winter Park range between AED 256 and AED 735 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.