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

Find Historic Hotels in Winter Garden, FL

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Our top choices for Winter Garden historic hotels

A bedroom with a bed, a bedside table with a lamp, and a wall decorated with woven baskets.

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

Fire Pit & Yard: Updated Winter Garden Home!
Winter Garden
9.6 out of 10, Exceptional, (12 reviews)
$452 nightly
The price is $502
Oct 18 - Oct 19
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
A two-story house with a swimming pool, outdoor seating, and a covered patio area.

2. Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
9.6 out of 10, Exceptional, (68 reviews)
"Great stay. "
United States
rick s.
$291 nightly
The price is $324
Oct 14 - Oct 15
Total with taxes and fees
Mills Cottage by the Little Lake
A greenhouse with a sign reading "L'ORANGERIE," surrounded by bamboo plants and stone walls.

3. Lake House Pets allowed

Lake House Pets allowed
Lake Weldona
9.8 out of 10, Exceptional, (64 reviews)
"Very convenient to downtown! The Host, Jerome was very accommodating! "
United States
Jason M.
$320 nightly
The price is $355
Oct 14 - Oct 15
Total with taxes and fees
Lake House Pets allowed
A two-story house with a swimming pool, outdoor seating, and a covered patio area.

4. Large, beautiful, very comfortable one bedroom on small lake

Large, beautiful, very comfortable one bedroom on small lake
Lake Weldona
9.8 out of 10, Exceptional, (71 reviews)
"Love the location. "
United States
Jolyn W.
$326 nightly
The price is $362
Oct 21 - Oct 22
Total with taxes and fees
Large, beautiful, very comfortable one bedroom on small lake
A swimming pool with a clear blue water, surrounded by palm trees and lounge chairs.

5. Incredible Renovated home located near all !!

Incredible Renovated home located near all !!
Champions Gate
6.0 out of 10, (8 reviews)
"We really enjoyed Melissa’s condo Deja Blue. Quite pretty inside and quiet surroundings. Beds are comfortable, plenty of towels available, most things you need for a stay are provided. A few things in the condo could be updated but overall we had a great month in this unit and love the Champions Gate area for walking and dining."
United States
Susan K.
$232 nightly
The price is $257
Nov 1 - Nov 2
Total with taxes and fees
Incredible Renovated home located near all !!
An aerial view of a resort with multiple swimming pools, palm trees, and a parking area.

6. Luxury 8BR Villa Private Pool, Game Room ,Near Disney , Windsor Island Resort

Luxury 8BR Villa Private Pool, Game Room ,Near Disney , Windsor Island Resort
Davenport
9.4 out of 10, Exceptional, (124 reviews)
"We enjoyed our stay!"
United States
Lyndsay D.
$689 nightly
The price is $761
Oct 17 - Oct 18
Total with taxes and fees
Luxury 8BR Villa Private Pool, Game Room ,Near Disney , Windsor Island Resort
A bedroom with two beds, a dresser, and a television.

7. Orlando Vista Cay Dream Vacation Luxurious/Exquisite 3Bed/2Bath Condo Sleeps 8

Orlando Vista Cay Dream Vacation Luxurious/Exquisite 3Bed/2Bath Condo Sleeps 8
Orlando
9.8 out of 10, Exceptional, (178 reviews)
"Fantastic place and host!"
United States
Brandon D.
$355 nightly
The price is $394
Oct 17 - Oct 18
Total with taxes and fees
Orlando Vista Cay Dream Vacation Luxurious/Exquisite 3Bed/2Bath Condo Sleeps 8
A modern kitchen with a central island, grey cabinets, and a black accent wall.

8. Apartment next to International Dr and Universal

Apartment next to International Dr and Universal
International Drive District
8.6 out of 10, Excellent, (17 reviews)
"Our family had a wonderful stay! The apartment is conveniently located near Universal, shopping, and restaurants. The apartment was very clean, the beds were comfortable, and everyone was extremely helpful and nice! I would definitely stay here again! "
United States
Anonymous traveler
$260 nightly
The price is $289
Nov 4 - Nov 5
Total with taxes and fees
Apartment next to International Dr and Universal
An aerial view of a resort with a large swimming pool, a dock, and a parking area.

9. Serene Oasis Lakefront Penthouse Facing Disney

Serene Oasis Lakefront Penthouse Facing Disney
Orlando
10.0 out of 10, Exceptional, (10 reviews)
"Great place to stay for WDW! Host is great! Location is great!"
United States
Kay R.
$401 nightly
The price is $445
Oct 17 - Oct 18
Total with taxes and fees
Serene Oasis Lakefront Penthouse Facing Disney
A bedroom with a large bed, two bedside tables, a chandelier, and a view of the outdoors.

10. ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!

ON SALE! 4BD 3BTH 1.5 MILES TO DISNEY!
Kissimmee
9.6 out of 10, Exceptional, (136 reviews)
"We liked everything"
United States
Jacklyn
$348 nightly
The price is $389
Oct 26 - Oct 27
Total with taxes and fees
ON SALE! 4BD 3BTH 1.5 MILES 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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Top Winter Garden Hotel Reviews

Drury Plaza Hotel Orlando - Disney Springs Area

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."
Stacy 1-night trip
Posted 1 hour ago
Drury Plaza Hotel Orlando - Disney Springs Area
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"I enjoyed my stay"
Amishaa 9-night trip
Posted 3 hours ago
Rosen Inn Lake Buena Vista

Frequently asked questions

What should a history buff expect from a stay in Winter Garden?
The historical sites in Winter Garden are probably a big part of your travel plans. While you're here, you might want to visit the fun-filled theme parks and array of shops. And also relish a stop at the top-notch restaurants in this relaxing area.
How many historical hotels are there in Winter Garden?
In Winter Garden, there are 371 hotels and other lodging options bookable on Expedia but not many designated as historic hotels.
What are the most important historical places and other sights to visit in Winter Garden?
Landmarks like Garden Theatre and Central Florida Railroad Museum in Winter Garden might be worth a visit. Families come for the theme park and water parks, specifically attractions such as Surfari Water Park. Additionally, in the area you'll find Universal Studios Florida and Universal Orlando Resort.
What is a historic hotel like in Winter Garden?
By choosing a historic hotel, you can enjoy a vacation in a place that has an officially recognized national historic designation. A palace, castle, grand home or even an old police station, pub, lodge, or skyscraper can be transformed into a historic hotel as long as it's of special interest. Traditional architecture and period features are typically found in the communal spaces and guestrooms of historic hotels in Winter Garden, giving a real sense of character.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is a term often used in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. but overall the terms are quite similar. The architecture and building of historic hotels are generally what's most significant. For a heritage hotel, mainly, it's cultural value and how it influenced the community.
Do historic hotels in Winter Garden have modern facilities?
Hotel interiors feature the modern conveniences and safety features you might expect, though efforts have been made to preserve the historic aspects and traditions. Private rooms with updated bathroom facilities, free WiFi, and the amenities found in any hotel will also be available in a historic hotel. When you book a historic hotel in Winter Garden, don't worry that you'll be staying at a place that's uncomfortable for guests or simply rundown.

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