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

Find Historic Hotels in Winter Park, FL

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winter Park Historic Hotels

Our top choices for Winter Park historic hotels

Exterior

Eastpark. Pet friendly! Lake Nona

Eastpark. Pet friendly! Lake Nona
East Park
9.2 out of 10, Wonderful, (100 reviews)
"Very nice accommodations. Great stay!!"
United States
John G.
The price is AED 364
AED 1,039 total
includes taxes & fees
27 Jul - 28 Jul
Eastpark. Pet friendly! Lake Nona
Interior

Bella Breeze

Bella Breeze
Downtown Sanford
8.4 out of 10, Very Good, (6 reviews)
"Enjoyable stay. "
United States
Carolyn R.
The price is AED 312
AED 644 total
includes taxes & fees
22 Jul - 23 Jul
Bella Breeze
Exterior

Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!

Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
Sanford
10.0 out of 10, Exceptional, (25 reviews)
"Great host "
United States
jordan l.
The price is AED 579
AED 1,537 total
includes taxes & fees
22 Jul - 23 Jul
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
Outdoor pool, a heated pool

Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
9.6 out of 10, Exceptional, (66 reviews)
"Great stay. "
United States
rick s.
The price is AED 694
AED 1,469 total
includes taxes & fees
18 Jul - 19 Jul
Mills Cottage by the Little Lake
Outdoor pool, a heated pool

Large, beautiful, very comfortable one bedroom on small lake

Large, beautiful, very comfortable one bedroom on small lake
Lake Weldona
10.0 out of 10, Exceptional, (67 reviews)
"Love the location. "
United States
Jolyn W.
The price is AED 579
AED 1,165 total
includes taxes & fees
18 Jul - 19 Jul
Large, beautiful, very comfortable one bedroom on small lake
Exterior detail

Lake House Pets allowed

Lake House Pets allowed
Lake Weldona
9.8 out of 10, Exceptional, (57 reviews)
"Cozy dog friendly stay for 3 a dog"
United States
David S.
The price is AED 576
AED 1,411 total
includes taxes & fees
18 Jul - 19 Jul
Lake House Pets allowed
Fridge, microwave, oven, stovetop

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

Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.
Paramore
9.2 out of 10, Wonderful, (18 reviews)
"Was a really nice stay we enjoyed ourselves and slept like a baby"
United States
Molly A.
Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.
Coffee/tea maker, fridge, microwave, oven

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

Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!
Orlando
9.8 out of 10, Exceptional, (272 reviews)
"Jim was just amazing to work with! The condo was perfect and in an ideal location to shops, restaurants and of course Universal and Disney. We just loved it!"
United States
Michelle A.
The price is AED 724
AED 1,618 total
includes taxes & fees
1 Aug - 2 Aug
Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!
Property grounds

Luxurious 5*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning

Luxurious 5*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning
orlando
9.8 out of 10, Exceptional, (194 reviews)
"Great place, Irina was very accommodating. Couldn’t be happier with my stay!"
United States
Darby S.
The price is AED 657
AED 3,285 total
includes taxes & fees
12 Aug - 13 Aug
Luxurious 5*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning
3 bedrooms, desk, iron/ironing board, free WiFi

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
10.0 out of 10, Exceptional, (172 reviews)
"Fantastic place and host!"
United States
Brandon D.
The price is AED 555
AED 1,387 total
includes taxes & fees
14 Aug - 15 Aug
Orlando Vista Cay Dream Vacation Luxurious/Exquisite 3Bed/2Bath Condo Sleeps 8
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.
View all properties

Top Winter Park Hotel Reviews

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

10/10 Excellent
"Went for a long weekend getaway with my 8 and 10 year old. Absolutely no complaints!! The grounds are very clean, the restaurants are great, you really don’t have to leave the property. Housekeeping accidentally took one of our towels on our last night. At checkout the front desk promised to look for it and mail it if it came up. The day after I arrived back home management called me and gave me a credit. Very nice gesture more importantly highlighting their exceptional customer service. Highly recommend!!"
Nishal 3-night trip
Posted 5 hours ago
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Explore a world of travel with Expedia

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 134 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 Albin Polasek Museum and Sculpture Gardens, Morse Museum of American Art, and Winter Park History Museum. Additionally, in the area you'll find Kia Center and Universal Studios Florida.
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.