Top Cottages in 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

Rp8.933.749 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

Rp9.974.317 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

Rp4.341.174 total

includes taxes & fees

14 Oct - 15 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

Rp5.830.231 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

Rp5.873.736 total

includes taxes & fees

21 Oct - 22 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

Rp7.114.620 total

includes taxes & fees

14 Oct - 15 Oct

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

7. Mount Dora Cottages

Mount Dora

PATRICIA

Rp4.237.767 total

includes taxes & fees

26 Oct - 27 Oct

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

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

Kissimmee

Rp8.745.686 total

includes taxes & fees

27 Oct - 28 Oct

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Top Winter Garden Hotel Reviews

Rosen Inn Lake Buena Vista

10/10 Excellent

"Me gustaria que en el futuro incluyera desayunos."

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

"We will most definitely be staying at this hotel again. The room was the perfect size, super clean, and having a fridge and microwave in the room made things so much easier for us since we were traveling with our infant. Also, I specifically chose this hotel due to it's location and the fact that it included daily breakfast, but were pleasantly surprised when we found out that they also included daily dinner and 3 free drinks for each adult! This allowed us to save a lot more money, and made our stay even more stress-free since we had everything we needed at the same location. The staff was great and super helpful and I highly recommend!"

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8/10 Good

"We would definitely stay here again the sprawling grounds were great for a morning or evening walk. The marketplace, pools, and recreational activities were easy to find and close in proximity. We had issues with our unit’s electricity and staff were quick to respond to remedy the matter. Newly renovated, well kept accommodations. I would have given all fives if bell services were more immediately available. We waited for over 10 minutes for someone just to appear at the desk once we arrived and then when our room was assigned. Even though staff were friendly and efficient having no electricity prevented me from charging my devices when needed, which was an issue for preparing for a long day the parks. All in all, this resort is on my resort list to stay in the future for location, the grounds, and the spacious comfortable rooms! Thanks!"

Homewood Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent

"We stayed at Homewood Suites by Hilton Orlando at Flamingo Crossings Town Center August 1–4 to celebrate my boyfriend's birthday, and it was an awesome experience! Our suite was spacious, clean and comfortable, with a full kitchen that made it feel like home. The bed was extremely comfortable, and the complimentary hot breakfast was absolutely wonderful! The gentleman at the front desk was friendly and welcoming. We felt safe and relaxed throughout our stay. What really makes this location special is the convenience! Flamingo Crossings is a beautiful, resort-style development with numerous restaurants, a Target offering groceries and everyday essentials, and even an urgent care-type medical facility nearby. Everything is practically right there, within walking distance! You can grab a meal, shop or pick up necessities without having to drive anywhere. The hotel is also conveniently located near Walt Disney World and offers a lovely resort-style pool. My only minor criticism is parking. After approximately 8 p.m., finding a space near the main entrance can be challenging. Garage parking is available, but sometimes you simply want to park outside and walk directly into the hotel. Overall, we had a fantastic birthday getaway! The comfortable accommodations, excellent breakfast, friendly service, safe surroundings and walkable conveniences made our stay memorable. We would absolutely return and highly recommend this hotel to couples and families visiting Orlando!"

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews	214
Accommodation	2264 Cottages
Lowest Price	Rp4.237.767
Highest Price	Rp9.974.317

Frequently asked questions

How much do cottages in Winter Garden cost?

Cottages in Winter Garden range between Rp4.237.767 and Rp9.974.317 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

Be picky

Check prices for these dates

Our top choices for Winter Garden cottages

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