Search Cottages in Winter Park

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Compare 201 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, (221)
"The location was beautiful. Loved the outside bed and being able to use the kayaks free of charge. Would be nice to have a few more in case our whole group wanted to go out. (6 of us) I did not ask as there may have been more if we asked. Overall, it was very nice and I would definitely stay again. Communication was great. Never had to wait for anything. However, the dryer did not work, and the one bedroom door did not close properly or lock. (not the king bedroom) Also, it would have been...
The price is SAR 301
SAR 604 total
includes taxes & fees
1 Dec - 2 Dec
Orlando Lakefront Tiny House Community
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, (41)
"Very comfortable beds. Kitchen well equipped. Nice front porch to sit on. Walking distance to shops & restaurants in downtown Winter Garden. Would definitely recommend."
Downtown Winter Garden Cottage ~ 12 Mi to Disney!
Tiny Hidden Cottage
Room

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (23)
"COZY & CLEAN. GREAT PLACE FOR A COUPLE TO GET AWAY FOR A WEEKEND. CLEAN& COMFORTABLE."
The price is SAR 345
SAR 630 total
includes taxes & fees
25 Nov - 26 Nov
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!
Modern Winter Garden Cottage: 16 Mi to Disney
Winter Garden Cottage | 1BR | 1BA | 527 Sq Ft | Single-Story Cottage

Modern Winter Garden Cottage: 16 Mi to Disney

9.8 out of 10, Exceptional, (10)
"Had a couple of reasons to contact manager. He was not as responsive as I would have liked. I also was not pleased with the final pricing. Otherwise location is good and convenient."
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!
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!
Storey Lake Resort Vacation Home
Pool

Storey Lake Resort Vacation Home

2.5 star property
Storey Lake Resort Vacation Home
4801 Tidecrest Avenue #166
Living area

4801 Tidecrest Avenue #166

3.0 star property
The price is SAR 1,825
SAR 3,025 total
includes taxes & fees
25 Dec - 26 Dec
4801 Tidecrest Avenue #166
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
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!
Weekday special! Guest House with Private pool & WiFi
Pool

Weekday 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 SAR 469
SAR 1,045 total
includes taxes & fees
16 Dec - 17 Dec
Weekday special! Guest House with Private pool & WiFi
Lake View! Experience the Sunsets Here!
Pool

Lake View! Experience the Sunsets Here!

Lake View! Experience the Sunsets Here!
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, (6)
"Our family of 4 (myself, my husband and my parents) along with our little pup enjoyed our stay. The property was clean and the availability of snacks and a stocked bar was an added bonus. I wish we could've stayed longer. Highly recommend!"
The price is SAR 488
SAR 1,092 total
includes taxes & fees
9 Dec - 10 Dec
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Cozy Tiny Home Near Disney World & Orlando Parks!
Welcome home...

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!
Resort Townhome: Perfect Orlando Vacation Spot!!
Living area

Resort Townhome: Perfect Orlando Vacation Spot!!

4.0 star property
8.0 out of 10, Very Good, (1)
Resort Townhome: Perfect Orlando Vacation Spot!!
Orlando Golden Girls Retreat: Prime Location!
Living area

Orlando Golden Girls Retreat: Prime Location!

3.0 star property
Orlando Golden Girls Retreat: Prime Location!
Chic Orlando Family Getaway w/ Fenced Yard!
Living area

Chic Orlando Family Getaway w/ Fenced Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
Chic Orlando Family Getaway w/ Fenced Yard!
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!
Sunny Kissimmee Home w/ Pool ~ 12 Mi to Disney!
Pool

Sunny Kissimmee Home w/ Pool ~ 12 Mi to Disney!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This house was amazing for family vacation. It spacious and clean . Definitely recommend "
Sunny Kissimmee Home w/ Pool ~ 12 Mi to Disney!
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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Other property types in Winter Park

The View Studio Suites and Event Venue
Front of property

The View Studio Suites and Event Venue

3.5 star property
8.6 out of 10, Excellent, (565)
"They are remodeling the building but is nice and for the price..and the breakfast is a plus"
The price is SAR 310
SAR 339 total
includes taxes & fees
25 Nov - 26 Nov
The View Studio Suites and Event Venue
The Point Hotel & Suites
Exterior

The Point Hotel & Suites

3.5 star property
8.0 out of 10, Very Good, (3097)
"The people next to us were not pleasant..breakfast was quite a joke for what was paid and the lady running it was really rude. "
The price is SAR 344
SAR 421 total
includes taxes & fees
10 Dec - 11 Dec
The Point Hotel & Suites
WorldQuest Orlando Resort
Exterior

WorldQuest Orlando Resort

4.0 star property
8.4 out of 10, Very Good, (3868)
"Everything was perfect "
The price is SAR 471
SAR 893 total
includes taxes & fees
27 Nov - 28 Nov
WorldQuest Orlando Resort
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 SAR 301 and SAR 1,825 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.