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Compare Cottages in Winter Garden with updated reviews, rates, and availability.

High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood
10.0 out of 10, Exceptional, (108)
"Only a 20 minute walk to downtown area and the walk is thru nice residential areas. Also very close to a cement walking path around a lake you can see from the residence. Mount Dora's shops and restaurants made the trip to town worthwhile!"
High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood
Cozy Cottage 3 blocks from town
10.0 out of 10, Exceptional, (6)
"Host Debbie was very welcoming. And she was there for any quesrions or concern. Happy to say that there was none. "
Cozy Cottage 3 blocks from town
Location Location !The Hidden Gem Cottage 4 miles from Disney 4 Star RV Resort !
10.0 out of 10, Exceptional, (10)
"Near all the attractions and anything that you want or need."
Location Location !The Hidden Gem Cottage 4 miles from Disney 4 Star RV Resort !
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"THE WOW COTTAGE" - Historic District - Mount Dora's Biggest "WOW!"
10.0 out of 10, Exceptional, (98)
"Lovely cottage beyond expectations."
"THE WOW COTTAGE" - Historic District - Mount Dora's Biggest "WOW!"
Private Pool/spa, Free Waterpark, Lazy River!
4.0 star property
10.0 out of 10, Exceptional, (1)
"Great home! Clean! Had every item in the home for comfortable living! Although I didn’t pay for pool heating I wanted to jump in on a cold day it was so clean and beautiful ! "
Private Pool/spa, Free Waterpark, Lazy River!
vanessa cottage
10.0 out of 10, Exceptional, (1)
"Was very nice, needs bigger trash cans. Would be nice to have a few cleaning supplies such as dishsoap . Overall it was a good place to stay."
vanessa cottage
"Peachy Keen" 3BD Pool & Spa Cottage Near Disney
10.0 out of 10, Exceptional, (2)
"Great Area, close to parks and Orange County Convention Center. House was exactly as described."
"Peachy Keen" 3BD Pool & Spa Cottage Near Disney
Kissimmee Home w/ Private Pool - 8 Mi to Disney!
3.0 star property
10.0 out of 10, Exceptional, (1)
"This is a great option if you’re not staying on property. It’s a spacious townhouse with a private pool which is such a plus on those hot summer days. The rooms were nice and clean and so were the bathrooms. I was happy that they had plenty of pots and plates which made it easy for us to cook and eat before heading out to the parks. The only thing I would say is I wish they had a few more essential like Paper towels, a sponge for washing dishes and a couple extra garage bags to help make sure...
Kissimmee Home w/ Private Pool - 8 Mi to Disney!
Up to Scale at Margaritaville
5.0 star property
10.0 out of 10, Exceptional, (1)
"Otima experiência. Localização excelente. Facil acesso aos parques da Disney. Proxima a supermercados, restaurantes, e lojas. A casa é muito congortavel e o Check in e check out muito faceis de realizar. Retornaremos com certeza."
Up to Scale at Margaritaville
"THE FISHERMAN'S COTTAGE" - Historic District - Mount Dora DESTINATION Cottage!
10.0 out of 10, Exceptional, (87)
"We both absolutely loved cottage! We will definitely book again. It was beautifully renovated, and very comfortable with everything we needed and more."
"THE FISHERMAN'S COTTAGE" - Historic District - Mount Dora DESTINATION Cottage!
Downtown Winter Garden Home ~ 12 Mi to Disney!
10.0 out of 10, Exceptional, (3)
"My family and I had a great stay. The host was super communicative and the property was lovely. Being a local who has since left i loved that I was walking to some of my favorite restaurants and stores."
Downtown Winter Garden Home ~ 12 Mi to Disney!
Easy walk 5 blocks to downtown dining & shopping. 2 BR, 2 Bath, POOL
10.0 out of 10, Exceptional, (10)
"We arrived here long after dark to find welcoming lights on in and through-out the residence, to guide us to the correct place and around the inside our temporary home away from home. No fumbling around in the dark looking for door knobs or light switches. Very thoughtful, it made a great first impression on us after a long day of traveling. Located in a quiet residential area, yet close to the center of town, the house was spic and span clean both inside and out, it was very comfortably...
Easy walk 5 blocks to downtown dining & shopping. 2 BR, 2 Bath, POOL
Cozy Lake Front Cottage
10.0 out of 10, Exceptional, (6)
"When you need a quiet and peaceful getaway, this little cottage can give you a shelter from life’s chaos. Spotlessly clean, a view of a private lake teaming with wildlife. Peace and quiet from the overwhelming noise of our growing dense population. The owners are a sweet couple who will invite you to a fire to watch a sunset with them. We only stayed two nights but that was all we needed to catch our breath and reset. The little barnyard full of chickens, turkeys and geese was a special treat....
The price is $175
$314 total
includes taxes & fees
May 13 - May 14
Cozy Lake Front Cottage
Margaritaville Home + Hot Tub, 3 Mi to Disney
3.0 star property
10.0 out of 10, Exceptional, (1)
"This place is great on all concerts, clean, right location, at lots of things to do around the property very practical for family get together ❤️ "
Margaritaville Home + Hot Tub, 3 Mi to Disney
NEW Margaritaville Resort 2 Bed Pool Cottage - King Bed on First Floor
10.0 out of 10, Exceptional, (1)
"We truly enjoyed our stay at Four Corners. The location was perfect for my husband to attend a work conference at the Margaritaville Resort, while I headed to Disney with family. The cottage is well equipped, nicely decorated and the private pool was a treat to have! Best is the location so close to the Disney Parks and any food or shopping you need. Daniel responded quickly to all our questions. Will be back!"
NEW Margaritaville Resort 2 Bed Pool Cottage - King Bed on First Floor
Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly
10.0 out of 10, Exceptional, (1)
"Our family enjoyed staying in this property since it was clean, quiet, and close to many stores (like Target) and restaurants. Most attractions are within 15 to 25 minutes drive from the property. Check-in was convenient. We are pleased with our stay."
Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly
Quiet 1 bedroom Guest House with pool & WiFi Lake May, Florida
9.8 out of 10, Exceptional, (16)
"Great communication from the beginning. The house was more than we expected and was super cute! We fell in love with the area and felt very safe and was able to relax. We are in our late 40's and early 50's and this was perfect for us. I adored the bed! It was the highlight of our trip (I am not kidding)! Everything was super clean, very nice and current decor and appliances, and the pool area is gorgeous. We only was able to use it once but that is because we had so many things planned. I would...
The price is $125
$278 total
includes taxes & fees
May 20 - May 21
Quiet 1 bedroom Guest House with pool & WiFi Lake May, Florida
Gorgeous Cottage w/Private Pool + Balcony, Near Disney!
9.8 out of 10, Exceptional, (42)
"Property was very clean and exactly as advertised. The pool was great and the location was great for walking, with many shops and restaurants close by."
Gorgeous Cottage w/Private Pool + Balcony, Near Disney!
Downtown Winter Garden Cottage ~ 12 Mi to Disney!
9.8 out of 10, Exceptional, (39)
"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!
Beautiful, Modern Home W/private Pool! Near WDW
4.0 star property
9.6 out of 10, Exceptional, (7)
"Well appointed but some amenities are damaged, needs to have overhaul to repair some areas zz"
Beautiful, Modern Home W/private Pool! Near WDW
Don't see what you're looking for?
See all available properties in Winter Garden
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.

Other property types in Winter Garden

Outdoor pool, pool umbrellas, sun loungers
Avanti International Resort
3.0 star property
7.6 out of 10, Good, (2042)
"I love this hotel!"
The price is $81
per night
May 23 - May 24
Avanti International Resort
2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas
Lake Buena Vista Resort Village & Spa
4.0 star property
8.4 out of 10, Very Good, (7168)
"This was a very nice place to stay with my family. "
The price is $144
per night
May 19 - May 20
Lake Buena Vista Resort Village & Spa
Meeting facility
Hyatt Regency Orlando International Airport
4.0 star property
9.4 out of 10, Exceptional, (4801)
"Loved it from beginning to end. I cant wait to stay again"
The price is $199
per night
May 29 - May 30
Hyatt Regency Orlando International Airport
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 Winter Garden cost?
Rates for cottages in Winter Garden range between and per night. No matter your budget, you’re sure to find a perfect place to reconnect with nature. This price was 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 Winter Garden with Expedia?
Expedia has some wonderful cottages in Winter Garden, so get set for a memorable vacation on nature’s doorstep. If you have a fixed budget, choose how much you’d like to spend and the preferred star rating of your property. Or, use our handy filters to search for cottages with free WiFi or a kitchen. We’ll help you find a suitable place whatever your plans or bank balance.
How can I find cheap cottages in Winter Garden?
Expedia is here to help you locate cheap cottages in Winter Garden. To book your dream stay in a couple of quick clicks, simply use the filter tool to tailor your search results by budget, star rating and amenities.
What is there to do in Winter Garden near my cottage?
No matter your tastes or interests, Winter Garden has tons to keep you on the move. The Wizarding World of Harry Potter™, Winter Garden Heritage Museum and Garden Theatre are on many travelers’ agendas. Don’t miss Museum of the Apopkans, The Woods Laser Tag and Carter Family Bowl either. With Expedia’s Winter Garden hotel deals, you can discover more fantastic attractions like these with the cash you save.