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Nov 20 - Nov 22
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Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
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Jan 8 - Jan 10

Our top choices for Windermere cottages

A serene landscape with a pond, trees with Spanish moss, and a palm tree.

1. Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
10.0 out of 10, Exceptional, (1 review)
$278 nightly
The price is $310
Nov 17 - Nov 18
Total with taxes and fees
Shore Steps Cottage - Walking Distance To The Town Of Windermere
A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

2. Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
Winter Garden
$444 nightly
The price is $499
Nov 12 - Nov 13
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
A room with a television on a wooden cabinet, a table, and two chairs. There is a sofa and a window with curtains.

3. Vacation Village Resort a "Hilltop Haven" Cozy 2-bedroom cottage in Clermont

Vacation Village Resort a "Hilltop Haven" Cozy 2-bedroom cottage in Clermont
Vacation Village
10.0 out of 10, Exceptional, (1 review)
"I loved the home: the views, the sunsets, the lake, the pool, the peace and tranquility, and so much more. Clermont is truly the "Gem of the Hills". And the nearby shops: Publix, Keyfood, the small Brazilian market, Shantee's Caribbean market, etc.; there is such a variety of foods. And Salt Shack overlooking Lake Minneola is another gem. I will be coming again and again to this home and this location."
United States
Anonymous traveler
$185 nightly
The price is $204
Nov 18 - Nov 19
Total with taxes and fees
Vacation Village Resort a "Hilltop Haven" Cozy 2-bedroom cottage in Clermont
A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

4. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
10.0 out of 10, Exceptional, (1 review)
"Cozy and nice place. It was very clean. Comunication with host was easy. Great view and sitting area from balcony to the lake. Very relaxing!"
United States
jacqueline M.
$185 nightly
The price is $206
Nov 30 - Dec 1
Total with taxes and fees
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A modern kitchen with red walls, a dining area with a brown leather couch, and a bar stool.

5. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (18 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
$155 nightly
The price is $173
Nov 17 - Nov 18
Total with taxes and fees
Downtown Cottage
A resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.

6. Th20 - 3BR House With Resort Access Near Parks

Th20 - 3BR House With Resort Access Near Parks
3.0 star property
Orlando
$420 nightly
The price is $472
Nov 28 - Nov 29
Total with taxes and fees
Th20 - 3BR House With Resort Access Near Parks
A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

7. Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
$350 nightly
The price is $389
Nov 15 - Nov 16
Total with taxes and fees
Serenity - Family & Pet Friendly, Amazing Location
A residential area with houses featuring sloped roofs and solar panels.

8. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
$215 nightly
The price is $244
Nov 12 - Nov 13
Total with taxes and fees
Upstay: Bright Family-friendly Retreat With Patio
A white building with large windows and a brick pathway leading to it.

9. The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!

The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!
College Park
10.0 out of 10, Exceptional, (56 reviews)
"Great location, well stocked and beds were very comfortable."
United States
Raegan S.
$303 nightly
The price is $338
Nov 16 - Nov 17
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!
A well-maintained artificial green lawn with a flagstick, surrounded by a stone pathway and a large planter with flowers.

10. Cozy 1-bedroom tiny home minutes from Disney, SeaWorld, and Universal!

Cozy 1-bedroom tiny home minutes from Disney, SeaWorld, and Universal!
Kissimmee
$121 nightly
The price is $135
Dec 7 - Dec 8
Total with taxes and fees
Cozy 1-bedroom tiny home minutes from Disney, SeaWorld, and Universal!
A house with a porch, surrounded by a grassy area and a pond with lily pads.

11. Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (38 reviews)
"Beautiful property in a fantastic location! We've booking this stay twice and will be back again."
United States
Lisa
$337 nightly
The price is $374
Nov 20 - Nov 21
Total with taxes and fees
Incredible Private Lakefront Cottage Retreat
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

12. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
9.0 out of 10, Wonderful, (2 reviews)
"Clean. A little confusing on the location. Gate guard was a little tough. Price a little high for a double wide."
United States
Michael R.
$165 nightly
The price is $185
Nov 12 - Nov 13
Total with taxes and fees
Perfect Place for a Perfect Vacation
A modern living room with a sofa, a large wall clock, and a mirror.

13. Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"Perfect location to enjoy Universal Epic and Islands of Adventure with only a 15 minute ride. The beds were very comfortable and the place is clean. We were welcomed with a cute sign, bottled water and cookies. Will definitely stay here again!"
United States
Joyce R.
$179 nightly
The price is $202
Nov 17 - Nov 18
Total with taxes and fees
Family-Friendly Cottage Near Orlando’s Top Attractions
A single-story mobile home with a front porch and a small deck.

14. Newly Remodeled Tiny Home 20 minutes from Disney!~

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
$178 nightly
The price is $200
Nov 12 - Nov 13
Total with taxes and fees
Newly Remodeled Tiny Home 20 minutes from Disney!~
A resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.

15. Th89 - 3BR House Near Disney With Resort Access

Th89 - 3BR House Near Disney With Resort Access
3.0 star property
Orlando
$422 nightly
The price is $474
Dec 5 - Dec 6
Total with taxes and fees
Th89 - 3BR House Near Disney With Resort Access
A compact kitchen with a built-in TV, a dining area with a bench, and a wall decorated with motivational posters.

16. Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Kissimmee
$187 nightly
The price is $210
Nov 12 - Nov 13
Total with taxes and fees
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

17. Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
$293 nightly
The price is $328
Nov 29 - Nov 30
Total with taxes and fees
Family Resort Home w Pool, BBQ & Game Room
A single-story house with a gabled roof, a front porch, and a small front yard with a large agave plant.

18. Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
$257 nightly
The price is $290
Nov 17 - Nov 18
Total with taxes and fees
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
A small cabin with a porch and a garage, surrounded by trees and a clear sky.

19. Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Davenport
6.8 out of 10, (3 reviews)
"Needs some upgrades. The bed was a full size, very small for a couple, should really think of upgrading to a king. Pans were old and could use replacing. Bugs and ants constant. Shower was small. Very small tv. Stovetop had missing nob and was difficult to operate. Definitely needs upgrading, left a day early, didn’t feel comfortable there. "
United States
Rebecca F.
$133 nightly
The price is $148
Nov 14 - Nov 15
Total with taxes and fees
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min 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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Learn more about Windermere

Nestled among pristine lakes, this charming town offers a peaceful escape with upscale golf courses and country clubs. Nature lovers can explore the Tibet-Butler Preserve's trails, while four-legged friends enjoy romping at Buena Vista Place Dog Park.

See all hotels in Windermere
A lakeside community with houses and boats.

Frequently Asked Questions

How much do cottages in Windermere cost?

Rates for cottages in Windermere range between $135 and $524 per night. Whatever your budget, you'll find an ideal place to get reacquainted with 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.

Are there any family-friendly cottages in Windermere?

If you want to slow the pace down a notch in Windermere, you can't go past Fresh And Remodeled In Vista Cay Townhome. With a 3-star rating and amenities like a barbecue grill and a picnic area, you'll find it easy to settle in at this family-friendly cottage. Windermere boasts plenty of family-friendly attractions to visit when the kids are getting restless. Walt Disney World® Resort and Universal Studios Florida guarantee a fun day out for young and old.

Why book your cottage in Windermere with Expedia?

Reserving a cottage in Windermere is as simple as working out your travel dates and selecting your ideal place for outdoor recreation and relaxation. From luxurious retreats to low-cost stays and cottages that have amenities like laundry facilities, Expedia has something for all traveler styles. As for awesome deals? We've got them as well!

How can I find cheap cottages in Windermere?

Expedia is here to help you locate cheap cottages in Windermere. To reserve your perfect stay in a couple of quick clicks, try out the filter tool to refine your search by star rating, budget and amenities.

What is there to do in Windermere near my cottage?

After you've unpacked your things and settled in, head out and discover the fantastic things Windermere has for you to experience. Isleworth Golf and Country Club is a great attraction to add to your to-do list.

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