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

Compare 199 Cottages in Winter Park with updated reviews, rates, and availability.

Orlando Lakefront Tiny House Community
Exterior

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (234)
"Over all, our stay was wonderful. Lake views are amazing. We would definitely stay again."
The price is AED 311
AED 610 total
includes taxes & fees
23 Dec - 24 Dec
Orlando Lakefront Tiny House Community
Orlando Holiday Special! Guest House with Private pool & WiFi
Pool for your enjoyment.

Orlando Holiday Special! Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (26)
"I had surgery and stayed here for my recovery, nice quiet area, easily accessible to stores and very comfortable bed. I felt very comfortable while recuperating. Washer and dryer big plus and the pool was beautiful and well kept. I didn't get to use the pool but I sure would have loved to. I will be back when I have to go for my checkups "
The price is AED 569
AED 1,157 total
includes taxes & fees
29 Dec - 30 Dec
Orlando Holiday Special! Guest House with Private pool & WiFi
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Orlando oasis ☀️

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

9.8 out of 10, Exceptional, (8)
"It's a lovely, well-appointed, well-located place. The cottage is within easy walking distance of multiple restaurants. The communication was excellent. I hope to stay at the cottage again soon!"
The price is AED 643
AED 1,276 total
includes taxes & fees
12 Jan - 13 January 2025
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Stunning Lakeview Townhome w/ Private Pool!
Pool

Stunning Lakeview Townhome w/ Private Pool!

4.0 star property
8.4 out of 10, Very Good, (9)
"Perfect location house was just what is described "
Stunning Lakeview Townhome w/ Private Pool!
Downtown Winter Garden Cottage ~ 12 Mi to Disney!
Winter Garden Vacation Rental | 2BR | 1BA | 3 Steps Required for Entry

Downtown Winter Garden Cottage ~ 12 Mi to Disney!

9.8 out of 10, Exceptional, (42)
"We wanted something special on a short trip to Winter Garden. We were combining the trip with a visit to our new grand-daughter and spending time in a lovely area of the city."
Downtown Winter Garden Cottage ~ 12 Mi to Disney!
Tiny Hidden Cottage
Room

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (24)
"The house was perfect for my weekend stay and I hope to stay again on my next trip"
The price is AED 290
AED 563 total
includes taxes & fees
20 Dec - 21 Dec
Tiny Hidden Cottage
Downtown Winter Garden Home ~ 12 Mi to Disney!
Winter Garden Vacation Rental | 3BR | 2BA | 1,200 Sq Ft | 3 Steps to Enter

Downtown Winter Garden Home ~ 12 Mi to Disney!

9.6 out of 10, Exceptional, (5)
"We evacuated from Helene. Because we were unable to return to our home, we ended up having to rent multiple vacation rentals. This is the first home that actually looked like it did online--really lovely. (I agree, yard can use some TLC) I liked the retro touches throughout. Comfortable furniture and beds. Luxury towels and linens. Really nice! Walk west and cross over Dillard two block then three blocks north to Plant street and you'll find many wonderful restaurants and shops. Saturday...
Downtown Winter Garden Home ~ 12 Mi to Disney!
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Pool

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

3.0 star property
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Orlando December Special! Cottage with queen bed & fire pit.
Family Room

Orlando December Special! Cottage with queen bed & fire pit.

10.0 out of 10, Exceptional, (8)
"Nice and clean, and small"
The price is AED 386
AED 929 total
includes taxes & fees
19 Dec - 20 Dec
Orlando December Special! Cottage with queen bed & fire pit.
Modern Winter Garden Cottage: 16 Mi to Disney
Living area

Modern Winter Garden Cottage: 16 Mi to Disney

3.0 star property
10.0 out of 10, Exceptional, (1)
"This house is adorable! It was perfect for us as a couple. Very sweetly decorated and homey. The neighborhood is very quiet and off the beaten path, as they say, yet very close to stores and beautiful downtown Winter Garden. We would SO stay again! Would love to do a seasonal stay. "
Modern Winter Garden Cottage: 16 Mi to Disney
Orlando Home w/ Lake View, Pool & Game Room!
Exterior

Orlando Home w/ Lake View, Pool & Game Room!

3.0 star property
Orlando Home w/ Lake View, Pool & Game Room!
Caribbean Dreamin
Living area

Caribbean Dreamin

3.0 star property
10.0 out of 10, Exceptional, (1)
"This Caribbean Dreamin property is awesome! It is clean, spacious, and very well kept. Contrary to the contract, the house includes all the amenities for all bathrooms as well as dishwashing detergent. Nice touch! The community is very pretty and well kept. Shopping nearby. Unfortunately, we were here for a couple nights during Hurricane Milton so didn't go out at all. But being in a nice home away from home made a difference during the stressful time. I would highly recommend this...
Caribbean Dreamin
Luxurious Home W/private Pool, Near Disney!
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!
5003 Windermere Avenue
Pool

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
Luxe Orlando Home w/ Grill & Fenced Yard!
Living area

Luxe Orlando Home w/ Grill & Fenced Yard!

3.0 star property
Luxe Orlando Home w/ Grill & Fenced Yard!
The Sanford Foodie Guest House
Terrace/patio

The Sanford Foodie Guest House

9.6 out of 10, Exceptional, (4)
"My son and I stayed in Sanford for one night to see a show at Theater West End and I chose this little guest house based mainly on proximity. It was exactly as described in the listing and was perfect to meet our needs. Super cute and convenient. The owner was very professional and communicative. I will definitely stay here again. "
The price is AED 275
AED 691 total
includes taxes & fees
19 Dec - 20 Dec
The Sanford Foodie Guest House
Storey Lake Resort Vacation Home
Pool

Storey Lake Resort Vacation Home

2.5 star property
Storey Lake Resort Vacation Home
THE HIDEAWAY AT COLLEGE PARK
Property grounds

THE HIDEAWAY AT COLLEGE PARK

8.0 out of 10, Very Good, (1)
"Overall, this was a great stay for my needs. The location was close to where I needed to be. I ABSOLUTELY loved the decor. I had three concerns. We did not know how to use the security code and had to YouTube directions. The second bedroom did not have a "bed" and there is not a curtain so my guest slept in the living room. bedro a bedroom and was very small"
THE HIDEAWAY AT COLLEGE PARK
Beautiful, Modern Home W/private Pool! Near WDW
Living area

Beautiful, Modern Home W/private Pool! Near WDW

4.0 star property
8.4 out of 10, Very Good, (12)
"It was a nice place ."
Beautiful, Modern Home W/private Pool! Near WDW
Lake View! Experience the Sunsets Here!
Pool

Lake View! Experience the Sunsets Here!

Lake View! Experience the Sunsets Here!
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
Outdoor pool

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very Good, (8202)
"Our room flood due to pipe breaking next door had to wait 6 hrs for them to move us and they didn’t even say sorry wasted the whole day waiting to have move 4 people to a whole different building not even a sorry "
The price is AED 579
AED 731 total
includes taxes & fees
19 Dec - 20 Dec
Lake Buena Vista Resort Village & Spa
The View Studio Suites and Event Venue
Front of property

The View Studio Suites and Event Venue

3.5 star property
8.4 out of 10, Very Good, (635)
"Awesome property,friendly staff and very clean.."
The price is AED 281
AED 316 total
includes taxes & fees
5 Jan - 6 January 2025
The View Studio Suites and Event Venue
Floridays Resort Orlando
Outdoor pool

Floridays Resort Orlando

3.5 star property
8.6 out of 10, Excellent, (11112)
"Great place to stay! We had one issue with a broken microwave that we discovered the morning after our first night, and the staff was very apologetic and quickly moved us to a different room. My only other minor complaint was the shower head could have been a bit more powerful to be able to rinse off faster! Other than that, we had a nice stay. Very clean and comfortable. Great location. We would definitely stay there again!"
The price is AED 592
AED 774 total
includes taxes & fees
19 Dec - 20 Dec
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?
Prices for cottages in Winter Park range between AED 275 and AED 643 per night. No matter your budget, you’re sure to find an ideal place to immerse yourself in nature. 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 great cottages in Winter Park, so get set for a memorable stay close to nature. If you have a fixed budget, choose how much you’d like to spend and your preferred property star rating. Or, make your way to the filters to search for cottages with a pool or a hot tub. We’ll help you find the perfect pad whatever your style of travel or plans.
How can I find cheap cottages in Winter Park?
With Expedia’s user-friendly filter tool, sourcing cheap cottages in Winter Park couldn’t be simpler. To view accommodations that’ll make your wallet happy, narrow your search results by star rating, budget and amenities.