Search Cottages in Windermere

  • 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 1507 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, (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 AED 295
AED 591 total
includes taxes & fees
1 Dec - 2 Dec
Orlando Lakefront Tiny House Community
Gorgeous Cottage near Lake Louisa & mins 2 Disney.
Private kitchen

Gorgeous Cottage near Lake Louisa & mins 2 Disney.

9.6 out of 10, Exceptional, (34)
"The place had everything you need for a great stay. All the basics are there. I enjoyed my stay and would stay here again."
Gorgeous Cottage near Lake Louisa & mins 2 Disney.
Margarita Porch Paradise
Outdoor dining

Margarita Porch Paradise

5.0 star property
10.0 out of 10, Exceptional, (1)
"The house was beautiful and comfortable for our family, we would have stayed longer! The resort is fun, plenty of stores and good restaurants. We will definitely come back. "
Margarita Porch Paradise
1-bedroom cottage just a 13-minute walk to Old Town
Exterior of cottage

1-bedroom cottage just a 13-minute walk to Old Town

9.2 out of 10, Wonderful, (120)
"This is a super cute little cottage. It is easily accessible on the property. I saw deer and other wildlife on the property. It was very peaceful and perfect lovation for our trip. "
1-bedroom cottage just a 13-minute walk to Old Town
Davenport Family Home ~ 10 Mi to Animal Kingdom
Living area

Davenport Family Home ~ 10 Mi to Animal Kingdom

3.0 star property
Davenport Family Home ~ 10 Mi to Animal Kingdom
Contemporary Home w/ Hot Tub: 4 Mi to Disney Magic
Kissimmee Vacation Rental | 4BR | 3BA | 2 Stories | 1,500 Sq Ft

Contemporary Home w/ Hot Tub: 4 Mi to Disney Magic

9.6 out of 10, Exceptional, (27)
"Great place to stay. "
Contemporary Home w/ Hot Tub: 4 Mi to Disney Magic
Private Pool/spa, Free Waterpark, Lazy River!
Living area

Private Pool/spa, Free Waterpark, Lazy River!

4.0 star property
10.0 out of 10, Exceptional, (4)
"Very comfortable "
Private Pool/spa, Free Waterpark, Lazy River!
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!
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
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
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 AED 338
AED 616 total
includes taxes & fees
25 Nov - 26 Nov
Tiny Hidden Cottage
Jedi cottage 4 miles from Disney! Mins from universal!
Interior

Jedi cottage 4 miles from Disney! Mins from universal!

10.0 out of 10, Exceptional, (17)
"Extended our stay at Disney and decided to stay off property the one day! Kathryn was a great host!"
The price is AED 312
AED 824 total
includes taxes & fees
25 Nov - 26 Nov
Jedi cottage 4 miles from Disney! Mins from universal!
Enchanted Cottage with Pool and Mini-Golf Near Disney
Enchanted Cottage - 1 bedroom, 1 bathroom near Disney

Enchanted Cottage with Pool and Mini-Golf Near Disney

9.6 out of 10, Exceptional, (14)
"This location was perfect for me and my two dogs. "
Enchanted Cottage with Pool and Mini-Golf Near Disney
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
Sunlit Davenport Family Home w/ Lanai & Gas Grill!
Pool

Sunlit Davenport Family Home w/ Lanai & Gas Grill!

3.0 star property
8.0 out of 10, Very Good, (1)
"House nicely kept, lots of room and beds for large gatherings. Clean, convenient washer and dryer in unit, great location, close to shops and restaurants. Overall, really nice place to stay. "
Sunlit Davenport Family Home w/ Lanai & Gas Grill!
3000 Latitude Lane
Outdoor spa tub

3000 Latitude Lane

3.0 star property
10.0 out of 10, Exceptional, (2)
"Great stay!"
3000 Latitude Lane
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!
Davenport Home w/ Game Room, Home Theater, Pool
Pool

Davenport Home w/ Game Room, Home Theater, Pool

3.0 star property
10.0 out of 10, Exceptional, (1)
"What an amazing home! Clean and everything you need for a staycation or trip to Disney! The pictures online do not do this Gargage justice. It’s an arcade in the home. So much fun! I would recommend this home for all. "
Davenport Home w/ Game Room, Home Theater, Pool
Kissimmee Vacation Home: Heated Pool, Near Disney!
Pool

Kissimmee Vacation Home: Heated Pool, Near Disney!

3.0 star property
Kissimmee Vacation Home: Heated Pool, Near 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.
Don't see what you're looking for?
See all available properties in Windermere
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 Windermere

Seralago Hotel & Suites Main Gate East
Exterior

Seralago Hotel & Suites Main Gate East

3.0 star property
5.2 out of 10, (5565)
"I had to wait 20 minutes for the front counter lady to come in from smoking. The security guard was sitting in the lobby playing on his phone and he just kept saying she will be back soon.. Then she told me I had booked a double bed room and I said no I booked a family suite.. So I had to show her my email and she said well I don't know why they put you in another room, let me make sure I have a clean one.. After standing in the lobby for a total of 40 minutes (including her smoke break time), I...
The price is AED 144
AED 238 total
includes taxes & fees
25 Nov - 26 Nov
Seralago Hotel & Suites Main Gate East
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 AED 303
AED 331 total
includes taxes & fees
25 Nov - 26 Nov
The View Studio Suites and Event Venue
Summer Bay Orlando by Exploria Resorts
Property amenity

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very Good, (5025)
"Our unit was clean but in definite need of an update. The carpet was threadbare and torn in some areas. We still had a great stay and appreciated the prompt attention from security when we needed access to our unit."
The price is AED 479
AED 654 total
includes taxes & fees
8 Dec - 9 Dec
Summer Bay Orlando by Exploria Resorts
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 295 and AED 338 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.