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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

Compare 247 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, (284)
"We spent 8 nights staying in the Breeze and had an absolutely fabulous experience. The accommodation had everything we needed and we loved how cute and quirky it is. There is a supermarket 5 minutes drive away. We loved sitting on the decking looking out over the lake and watching the variety of birds diving and wading, it was so relaxing. We also kayaked round the lake a couple of of times - that was a first for us but was really easy to pick up. There are life jackets and kayaks readily...
The price is SAR 290
SAR 601 total
includes taxes & fees
8 Apr - 9 Apr
Orlando Lakefront Tiny House Community
Florida Guest House with Private pool & WiFi
Outdoor pool

Florida Guest House with Private pool & WiFi

10.0 out of 10, Exceptional, (31)
"Very clean and private "
The price is SAR 582
SAR 1,167 total
includes taxes & fees
18 Apr - 19 Apr
Florida Guest House with Private pool & WiFi
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!

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 SAR 750
SAR 1,412 total
includes taxes & fees
16 Apr - 17 Apr
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, (37)
"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 SAR 296
SAR 575 total
includes taxes & fees
7 Apr - 8 Apr
Tiny Hidden Cottage
Downtown Cottage
1 bedroom, desk, iron/ironing board, free WiFi

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 SAR 375
SAR 814 total
includes taxes & fees
17 Apr - 18 Apr
Downtown Cottage
3-br Condo BBQ & Heated Pool Near Disney&malls
Outdoor pool

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
Aerial view

Incredible Private Lakefront Cottage Retreat

10.0 out of 10, Exceptional, (26)
"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 SAR 559
SAR 1,255 total
includes taxes & fees
7 Apr - 8 Apr
Incredible Private Lakefront Cottage Retreat
Lakeview Home w/ Private Pool & Free Water Park!
Miscellaneous

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!
Outdoor dining

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
1 bedroom, desk, WiFi, bed sheets

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 SAR 221
SAR 739 total
includes taxes & fees
17 Apr - 18 Apr
The Sanford Foodie Guest House
Modern Townhome W/private Pool & Free Water Park!
Miscellaneous

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
Exterior

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
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
Beautiful, Modern Home W/private Pool! Near WDW
Miscellaneous

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
Outdoor dining

The Pink Door Cottage-Historic Sanford

10.0 out of 10, Exceptional, (13)
"This property was nice and met our needs very well. It is on a street that is decent, but the house backs up to a beautiful historic district with great areas to walk and explore. Felt very safe and enjoyed the area tremendously. "
The Pink Door Cottage-Historic Sanford
4813 Crusoe Street
Miscellaneous

4813 Crusoe Street

3.0 star property
4813 Crusoe Street
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!
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!
Stunning Lakeview Townhome w/ Private Pool!
Outdoor pool

Stunning Lakeview Townhome w/ Private Pool!

4.0 star property
8.8 out of 10, Excellent, (12)
"Great for kids and close to attractions!"
Stunning Lakeview Townhome w/ Private Pool!
Cozy Tiny Home Near Disney World & Orlando Parks!
Fridge, microwave, oven, stovetop

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
Sign in
Sign up, it's free

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, (8528)
"Overall nice place "
The price is SAR 503
SAR 677 total
includes taxes & fees
6 Apr - 7 Apr
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, (1859)
"Very nice and welcoming. The staff is very friendly and go out of their way to help with anything. "
The price is SAR 652
SAR 831 total
includes taxes & fees
16 Apr - 17 Apr
Florida Hotel & Conference Center in the Florida Mall
The View Studio Suites and Event Venue
Exterior

The View Studio Suites and Event Venue

3.0 star property
8.4 out of 10, Very Good, (998)
"Amazing value with free breakfast "
The price is SAR 298
SAR 336 total
includes taxes & fees
6 May - 7 May
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 SAR 221 and SAR 750 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.