Best Cottages Winter Garden in 2026

A child riding a bicycle on a wooden boardwalk with a body of water and trees in the background.

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Our top choices for Winter Garden cottages

A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

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

Winter Garden

₹47,807 total

includes taxes & fees

18 Oct - 19 Oct

A residential house with a front yard, a palm tree, and a garage.

2. Chic Orlando Family Getaway w/ Fenced Yard!

Rosemont

Jennifer

₹53,334 total

includes taxes & fees

15 Oct - 16 Oct

A covered porch with wicker chairs and a ceiling fan.

3. Historic Tremain Cottages

Mount Dora

Betty

₹20,675 total

includes taxes & fees

19 Oct - 20 Oct

A residential area with a well-maintained lawn, a street with parked cars, and a green dumpster.

4. Ei8555 - 3BR House Near Disney

Kissimmee

₹31,175 total

includes taxes & fees

6 Nov - 7 Nov

A two-story house with a garage, surrounded by well-maintained lawns and palm trees.

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

Solana

₹31,432 total

includes taxes & fees

18 Oct - 19 Oct

A multi-story building with a 'STUDIO MOVIE GRILL' sign, parking lot, and surrounding greenery.

6. Serenity - Family & Pet Friendly, Amazing Location

Crestwynd Bay

₹38,043 total

includes taxes & fees

15 Oct - 16 Oct

A small, single-story house with a gabled roof and a front porch.

7. Mount Dora Cottages

Mount Dora

PATRICIA

₹22,559 total

includes taxes & fees

27 Oct - 28 Oct

A modern hotel with a curved driveway, large windows, and palm trees.

8. Mvv7482 - 3BR House Near Disney at Magic Village

Kissimmee

₹44,762 total

includes taxes & fees

27 Oct - 28 Oct

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Top Winter Garden Hotel Reviews

Homewood Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent

"Staff are very friendly and always helpful. Suites are spacious and kitchen facilities very good"

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent

"This was our first time at Westgate Lakes Resort, and we will definitely come back! We had an amazing and HUGE 2 bedroom unit that overlooked a lake, and it was also very convenient to one of the pools. Also close to the shops, restaurants and main building. We unfortunately had some bad weather and couldn't enjoy the water park, but I went to the fitness center and it was outstanding! All of the staff was helpful, the beds were super comfortable and I even got to enjoy a bubble bath in the huge jacuzzi tub in the master bedroom. There were ample towels, hand towels, toilet paper, paper towels etc. I highly recommend this resort, we were 15 minutes from Universal Theme Parks, as well as only a few minutes from International Drive and other restaurants and the Kia Center. We'll definitely come back, as we visit Orlando often! The only slight negative at all was the check in Friday night was very busy and took a little bit, and also our key stopped working before our check out time but we were able to text the front desk and they set up for us to reactivate our key from the building. Very efficient and nice staff though, Jennica at the front was wonderful and the assistance we got with our bags was so appreciated from the person who also led us to our building. Looking forward to our next trip to hopefully be able to stay at Westgate again!"

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

"I absolutely LOVED my stay at Drury. I traveled with my teenager and we stayed for 11 days and could not have been more happier. Manager (AM) at the front desk is nothing short of amazing. The staff and shuttle drivers are absolutely incredible and definitely go above and beyond. The breakfast was delicious and had many options, from cereal, to eggs, potatoes, Mickey waffles, fruit, biscuits, and gravy and so much more. They’re 530. Dinner was absolutely delicious as well and adults. Get free drinks during this time. Our room had a balcony overlooking the pool and was able to see the fireworks every night. Our stay was nothing short of magical."

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews	214
Accommodation	2266 Cottages
Lowest Price	₹20,675
Highest Price	₹53,334

Frequently asked questions

How much do cottages in Winter Garden cost?

Cottages in Winter Garden range between ₹20,675 and ₹53,334 per night. These stays offer a chance to get reacquainted with nature — at a price you can afford. 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 Winter Garden with Expedia?

Expedia has some great cottages in Winter Garden, so get ready for a memorable holiday on nature's doorstep. If you're sticking to a budget, select how much you'd like to spend and the preferred star rating of your property. Or, use our filters to search for cottages with free WiFi or a kitchen. We'll help you find the right fit whatever your bank balance or plans.

How can I find cheap cottages in Winter Garden?

With Expedia's convenient filter tool, scoring cheap cottages in Winter Garden has never been simpler. To discover accommodation that'll make your wallet happy, fine-tune your search results by budget, star rating and amenities.

What is there to do in Winter Garden near my cottage?

Whatever you're into, Winter Garden has plenty of things to keep you on the go. Orange County National Golf Club, Resurrection Catholic Church and West Orange Trail are on many travellers' agendas. Don't forget to explore Winter Garden Art Association, Winter Garden Heritage Museum and Oakland Nature Preserve either. With Expedia's Winter Garden hotel deals, you'll be able to see more renowned attractions like these with the cash you save.

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Change your mind

Treat yourself

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Check prices for these dates

Our top choices for Winter Garden cottages

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