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
    today icon
    Change your mind
    Book hotels with free cancellation

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (221)
"Perfect for a weekend away; whether it be business or play. Will book again!"
Orlando Lakefront Tiny House Community

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

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

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

3.0 star property
Davenport Family Home ~ 10 Mi to Animal Kingdom

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!

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!

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

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

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

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 HK$716
HK$1,306 total
includes taxes & fees
1 Dec - 2 Dec
Tiny Hidden Cottage

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 HK$662
HK$1,762 total
includes taxes & fees
24 Nov - 25 Nov
Jedi cottage 4 miles from Disney! Mins from universal!

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!

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

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!

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

3.0 star property
10.0 out of 10, Exceptional, (2)
"Great stay!"
3000 Latitude Lane

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

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!

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

Other property types in Windermere

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very good, (8138)
"Very close to everything!"
Lake Buena Vista Resort Village & Spa

Seralago Hotel & Suites Main Gate East

3.0 star property
5.2 out of 10, (5565)
"Wow! SeraLago has definitely stepped up their rooms. We stayed in the new suites and had plenty of room for 3 adults. Separated bedroom, living room and kitchen area. I would suggest coffee maker and a comfy chair but everything else was great for the price."
The price is HK$305
HK$505 total
includes taxes & fees
26 Nov - 27 Nov
Seralago Hotel & Suites Main Gate East

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 HK$642
HK$722 total
includes taxes & fees
26 Nov - 27 Nov
The View Studio Suites and Event Venue
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.

Frequently asked questions

How much do cottages in Windermere cost?
You can expect to pay between HK$662 and HK$716 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 holiday 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 accommodation that’ll make your bank balance smile, narrow down your search by star rating, budget and amenities.
What is there to do in Windermere near my cottage?
If you want to explore the sights of Windermere, don’t miss Isleworth Golf and Country Club. It’s a winner with tourists and locals alike.