A two-story house with a balcony, surrounded by lush greenery and trees.

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Check availability on Winter Park Historic Hotels

Tonight
18 Aug - 19 Aug
Tomorrow
19 Aug - 20 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

Our top choices for Winter Park historic hotels

Outdoor pool, a heated pool
Exterior
Outdoor dining
Property grounds

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

Large, beautiful, very comfortable one bedroom on small lake
Lake Weldona
United States
Jolyn W.
AED 413
AED 968 total
includes taxes & fees
19 Aug - 20 Aug
Large, beautiful, very comfortable one bedroom on small lake
Outdoor pool, a heated pool
Property grounds
Bar (on property)
Exterior

2. Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
United States
rick s.
AED 436
AED 1,160 total
includes taxes & fees
19 Aug - 20 Aug
Mills Cottage by the Little Lake
Exterior detail
Outdoor pool, a heated pool
Bar (on property)
Fitness facility

3. Lake House Pets allowed

Lake House Pets allowed
Lake Weldona
United States
Jason M.
AED 489
AED 1,320 total
includes taxes & fees
19 Aug - 20 Aug
Lake House Pets allowed
Coffee/tea maker, fridge, microwave, oven
Smart TV
3 bedrooms, iron/ironing board, WiFi, bed sheets
Dining

4. Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.

Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.
Paramore
United States
Molly A.
AED 793
AED 1,124 total
includes taxes & fees
24 Aug - 25 Aug
Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.
Exterior
Flat-screen TV
Dining
Property grounds

5. Eastpark. Pet friendly! Lake Nona

Eastpark. Pet friendly! Lake Nona
East Park
United States
Dania B.
AED 364
AED 1,043 total
includes taxes & fees
24 Aug - 25 Aug
Eastpark. Pet friendly! Lake Nona
Interior
Interior
Interior
Exterior

6. Bella Breeze

Bella Breeze
Downtown Sanford
United States
Carolyn R.
AED 312
AED 647 total
includes taxes & fees
22 Aug - 23 Aug
Bella Breeze
Exterior
4 bedrooms, desk, iron/ironing board, WiFi
Dining
Coffee/tea maker, fridge, microwave, oven

7. Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!

Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
Sanford
United States
Danielle C.
AED 529
AED 1,452 total
includes taxes & fees
20 Aug - 21 Aug
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
3 bedrooms, desk, iron/ironing board, WiFi (free)
Interior
Outdoor pool, a heated pool
Coffee/tea maker, fridge, microwave, oven

8. 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
United States
Lindsay J.
AED 584
AED 1,438 total
includes taxes & fees
19 Aug - 20 Aug
Orlando Vista Cay Dream Vacation Luxurious/Exquisite 3Bed/2Bath Condo Sleeps 8
Coffee/tea maker, fridge, microwave, oven
Smart TV, foosball, books, video library
3 bedrooms, in-room safe, desk, iron/ironing board
Property grounds

9. Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!

Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!
Orlando
United States
jeremy e.
AED 724
AED 1,617 total
includes taxes & fees
31 Aug - 1 Sep
Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!
2 bedrooms, WiFi, bed sheets
Exterior detail
TV, fireplace, books
TV, fireplace, books

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

Fire Pit & Yard: Updated Winter Garden Home!
Winter Garden
United States
John T.
AED 566
AED 1,843 total
includes taxes & fees
27 Aug - 28 Aug
Fire Pit & Yard: Updated Winter Garden Home!
View all properties

Top Winter Park Hotel Reviews

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"clean, with nice staff. i would stay here again"
Kasumi 3-night trip
Posted 1 hour ago
Drury Plaza Hotel Orlando - Disney Springs Area
Caribe Royale Orlando, WorldHotels Elite

Caribe Royale Orlando, WorldHotels Elite

10/10 Excellent
"sexond time staying really good place"
Oscar 7-night trip
Posted 1 hour ago
Caribe Royale Orlando, WorldHotels Elite
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent
"Everyday was something new to do"
Quintin 3-night trip
Posted 4 hours ago
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

10/10 Excellent
"If you are traveling with a large family. The 3/4 bedroom Suites are a homerun. There is more than enough space for everyone."
Omar 4-night trip
Posted 5 hours ago
Lake Buena Vista Resort Village & Spa
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

10/10 Excellent
"Superbe"
Sylvain 5-night trip
Posted 1 day ago
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Frequently asked questions

What should a history enthusiast expect from a trip to Winter Park?
Significant historical sites in Winter Park are probably a big part of your travel plans. During your stay, you can visit the shops and restaurants.
How many historical hotels are there in Winter Park?
In Winter Park, there are 139 hotels and other lodging options bookable on Expedia though you won't find many designated historic hotels.
What are the must-see historical places and other sights to visit in Winter Park?
Winter Park is notable for landmarks like Casa Feliz Historic Home Museum. Cultural venues include Morse Museum of American Art, Albin Polasek Museum and Sculpture Gardens, and Winter Park History Museum. Additionally, in the area you'll find Universal Studios Florida and Universal Orlando Resort.
What is a historic hotel like in Winter Park?
When you book a historic hotel, you'll stay in a place that has an officially recognized national historic designation. A castle, a palace or even a pub or an old police station can be identified as a historic hotel as long as it's a place of special interest. Traditional architecture and period features can be admired in the communal spaces and guestrooms of such hotels in Winter Park, giving a real sense of character.
What is the difference between a historic hotel and a heritage hotel?
You'll often hear the term "heritage hotel" in Asia and Europe, while "historic hotel" is a term often used in the U.S. though overall the terms are quite similar. The physical building and architecture of historic hotels are generally what's most significant. For a heritage hotel, mainly, it's cultural value as well as how it inspired the community.
Do historic hotels in Winter Park have modern facilities?
Hotel interiors feature the modern conveniences and safety features you expect to find, while every effort is made to preserve historic facades and treasured traditions. Private rooms with updated bathroom facilities, free WiFi, and the popular amenities found in any hotel should be available at a historic hotel. When you book a historic hotel in Winter Park, don't worry that you'll find yourself staying at a place that is rundown or uncomfortable.