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Check prices for these dates

Next weekend
14 Feb - 16 Feb
In two weeks
21 Feb - 23 Feb
In one month
7 Mar - 9 Mar
In two months
4 Apr - 6 Apr

Compare 1517 Cottages in Windermere 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, (257)
"The property was AMAZING! Didn’t feel like I was even in the city of Orlando. Super close to Camping World Stadium, my go to for events! "
The price is AED 265
AED 566 total
includes taxes & fees
23 Feb - 24 Feb
Orlando Lakefront Tiny House Community
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, (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 AED 735
AED 1,376 total
includes taxes & fees
6 Mar - 7 Mar
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Tiny Hidden Cottage
Room

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 AED 298
AED 571 total
includes taxes & fees
10 Feb - 11 Feb
Tiny Hidden Cottage
Large Villa W/private Pool & Game Room! Waterpark
Pool

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
Home w/ Hot Tub: 4 Mi to Disney!
Kissimmee Vacation Rental | 4BR | 3BA | 2 Stories | 1,500 Sq Ft

Home w/ Hot Tub: 4 Mi to Disney!

9.4 out of 10, Exceptional, (30)
"Family friendly home. We stayed here for a multi family trip to Disney. We especially love that there were two primary rooms with king beds and on suites. The house has all the necessities in the kitchen, with coffee /keurig combo , cups and plates, and other cookie necessities. Very comfortable and specious stay and would highly recommend. "
Home w/ Hot Tub: 4 Mi to Disney!
Townhome W/private Pool & Themed Rooms, Near Wdw!
Pool

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.
Private kitchen

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
Living area

~ 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
Pool

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!
Pool

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
Living room

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!!
Exterior of cottage

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!
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!
4 miles from Disney 5 Star RV Resort! Location Location !The Hidden Gem Cottage!
Outdoor sitting area with water fountain.

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
Exterior detail

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 AED 367
AED 800 total
includes taxes & fees
9 Feb - 10 Feb
Downtown Cottage
Dtwn Winter Garden Home: 12 Mi to Disney!
Winter Garden Vacation Rental | 3BR | 2BA | 1,200 Sq Ft | 3 Steps to Enter

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!
Property grounds

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
Unwind in the private hot tub, soaking away your cares in the sunshine

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
Living area

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 AED 657
AED 1,142 total
includes taxes & fees
9 Feb - 10 Feb
Cozy Lake Front Cottage
6 Br / 4,5 Bath + Pool/Spa + Game Room / Less than 4 miles from Disney
Pool

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
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
Front of property

The View Studio Suites and Event Venue

3.5 star property
8.4 out of 10, Very Good, (804)
"Large rooms"
The price is AED 327
AED 368 total
includes taxes & fees
20 Feb - 21 Feb
The View Studio Suites and Event Venue
Margaritaville Resort Orlando Cottages by Rentyl
Front of property

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1184)
"Great place enjoyed our stay "
Margaritaville Resort Orlando Cottages by Rentyl
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, (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 AED 265 and AED 735 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.