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Check prices for these dates

Compare 1527 Cottages in Windermere with updated reviews, rates, and availability.

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (257)
"The views are absolutely incredible. Every time I go to Orlando, I stay here"
The price is SAR 270
SAR 578 total
includes taxes & fees
23 Feb - 24 Feb
Orlando Lakefront Tiny House Community

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

9.8 out of 10, Exceptional, (9)
"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 SAR 743
SAR 1,400 total
includes taxes & fees
4 Feb - 5 Feb
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (29)
"Cute tiny house. Very clean. Private. I was not happy with the AC window unit in the bedroom as it woke me up whenever it turned on. There is a chicken coop next to it with a rooster that greeted me in the morning. But I love backyard chickens so that was ok. Would be nice to provide ice for drinks and cream for coffee. Thanks. "
The price is SAR 308
SAR 588 total
includes taxes & fees
20 Feb - 21 Feb
Tiny Hidden Cottage

Large Villa W/private Pool & Game Room! Waterpark

3.5 star property
9.6 out of 10, Exceptional, (10)
"Great property! Was perfect for our family and made down time from the parks really nice."
Large Villa W/private Pool & Game Room! Waterpark

Townhome W/private Pool & Themed Rooms, Near Wdw!

4.0 star property
9.6 out of 10, Exceptional, (5)
"Great home and great resort! Loved having a private pool at the house and then all amenities included with the resort. Family had a great time. "
Townhome W/private Pool & Themed Rooms, Near Wdw!

Gorgeous Cottage near Lake Louisa & mins 2 Disney.

9.6 out of 10, Exceptional, (38)
"We enjoyed our stay at Vacation Village, and this Cottage. There are good instructions for most things. The cottage is stocked well with dishes & appliances. Refrigerator even had food for us to use - like condiments. That was nice, but we didn't expect that-it was confusing to us. Beds are very comfortable. It is very quiet there. A few things could be cleaned better: ovens, ceiling & other vents. TV is great in living room. Guest room TV didn't work - or remote didn't work. Blinds could be...
Gorgeous Cottage near Lake Louisa & mins 2 Disney.

~ 10 Mi to Animal Kingdom: Davenport Family Home

3.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect two day stay for us … close to everything we n ended it to be. "
~ 10 Mi to Animal Kingdom: Davenport Family Home

Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

3.0 star property
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

Parkside Serenity by Avantstay Private Pool!

3.0 star property
Parkside Serenity by Avantstay Private Pool!

Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621

3.0 star property
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621

1 bedroom, private laundry in resort near Disney!!

9.2 out of 10, Wonderful, (126)
"I will start by saying that this place is great. It is located in a gated RV/small home park with plenty of open spaces and amenities, near the Old Town area. It is economical and quite a bang for the buck. There were a couple of issues (the most notable one being a rather noisy washing machine, although Shawna said it was new and she'd look into it). It was a bit small for us, but the location was great, and we liked the large dog run for our doodles.I do have to say the neighborhood may...
1 bedroom, private laundry in resort near Disney!!

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!

4 miles from Disney 5 Star RV Resort! Location Location !The Hidden Gem Cottage!

9.8 out of 10, Exceptional, (24)
"Everything was super clean and great service "
4 miles from Disney 5 Star RV Resort! Location Location !The Hidden Gem Cottage!

Downtown Cottage

10.0 out of 10, Exceptional, (3)
"Thank you for a wonderful stay. This gem of a guest house is in a perfect location in the Mills50 area of downtown Orlando. A perfectly cozy little home with comfortable beds and a welcoming environment. We look forward to staying again next time we are in Orlando!"
The price is SAR 375
SAR 817 total
includes taxes & fees
4 Feb - 5 Feb
Downtown Cottage

Dtwn 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...
Dtwn Winter Garden Home: 12 Mi to Disney!

Townhome Splash Pool BBQ Free Water Park!

3.5 star property
9.6 out of 10, Exceptional, (9)
"Nice and relaxing quiet neighborhood "
Townhome Splash Pool BBQ Free Water Park!

Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly

10.0 out of 10, Exceptional, (4)
"It was a short but fun birthday weekend.I had asked for an early check in from the start and then ask to ask again on Friday and denied.Basically when we where getting in a couple left next to us and we had no neighbors."
Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly

Cozy Lake Front Cottage

10.0 out of 10, Exceptional, (11)
"Easy check-in. Loved the sandhill cranes outside my window and the peacefulness of this location. Thank you!"
The price is SAR 671
SAR 1,181 total
includes taxes & fees
4 Feb - 5 Feb
Cozy Lake Front Cottage

6 Br / 4,5 Bath + Pool/Spa + Game Room / Less than 4 miles from Disney

9.6 out of 10, Exceptional, (9)
"Great location in a quiet gated community near Disney as well as grocery stores etc. House was big and spacious, with all appliances needed, and lots of beds & bathrooms. Only downside was that the cold weather made for very little pool time!"
6 Br / 4,5 Bath + Pool/Spa + Game Room / Less than 4 miles from Disney

Once Upon a Lime – Margaritaville 3 BDR Sleeps 9! Incredible Amenities

2.0 star property
Once Upon a Lime – Margaritaville 3 BDR Sleeps 9! Incredible Amenities
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 Windermere

The View Studio Suites and Event Venue

3.5 star property
8.4 out of 10, Very Good, (794)
"Large rooms"
The price is SAR 304
SAR 342 total
includes taxes & fees
4 Feb - 5 Feb
The View Studio Suites and Event Venue

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1183)
"Need full length mirror i. Villa…and although it was clean it was not sparkling clean, saw lot of dust on the floors and stairs. Caulking needs to be redone in the showers. Very nice place to stay, i would recommend. Thank you"
Margaritaville Resort Orlando Cottages by Rentyl

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very Good, (8341)
"Great property to stay at and fantastic staff!! "
Lake Buena Vista Resort Village & Spa
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 Windermere cost?
You can expect to pay between SAR 270 and SAR 743 per night for cottages in Windermere. Whatever your budget, an epic stay is a click away on Expedia. 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 Windermere with Expedia?
Booking a cottage in Windermere is as easy as clicking on your travel dates and selecting your ideal place for a vacation in the outdoors. From luxurious retreats to low-cost stays and cottages that offer perks like a hot tub, Expedia has something for all tastes. As for the best deals around? We’ve have them as well!
How can I find cheap cottages in Windermere?
With Expedia’s convenient filter tool, comparing cheap cottages in Windermere couldn’t be easier. To view accommodations that’ll make your bank balance smile, narrow down your search by star rating, budget and amenities.