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

Tonight
24 Aug - 25 Aug
Tomorrow
25 Aug - 26 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sep - 6 Sep

Our top choices for Winter Park historic hotels

Outdoor pool, a heated pool
Exterior
Outdoor dining
Bar (on property)

1. Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
United States
rick s.
AED 558
AED 1,316 total
includes taxes & fees
25 Aug - 26 Aug
Mills Cottage by the Little Lake
Outdoor pool, a heated pool
Property grounds
Exterior
Bar (on property)

2. 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 446
AED 1,008 total
includes taxes & fees
25 Aug - 26 Aug
Large, beautiful, very comfortable one bedroom on small lake
Exterior detail
Property grounds
Fitness facility
Bar (on property)

3. Lake House Pets allowed

Lake House Pets allowed
Lake Weldona
United States
Jason M.
AED 523
AED 1,330 total
includes taxes & fees
25 Aug - 26 Aug
Lake House Pets allowed
Coffee/tea maker, fridge, microwave, oven
Dining
Property grounds
3 bedrooms, iron/ironing board, WiFi, bed sheets

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
31 Aug - 1 Sep
Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.
Exterior
Flat-screen TV
Interior
Dining

5. Eastpark. Pet friendly! Lake Nona

Eastpark. Pet friendly! Lake Nona
East Park
United States
Dania B.
AED 312
AED 978 total
includes taxes & fees
30 Aug - 31 Aug
Eastpark. Pet friendly! Lake Nona
Interior
Interior
Exterior
Interior

6. Bella Breeze

Bella Breeze
Downtown Sanford
United States
Carolyn R.
AED 312
AED 644 total
includes taxes & fees
25 Aug - 26 Aug
Bella Breeze
Exterior
Coffee/tea maker, fridge, microwave, oven
Dining
4 bedrooms, desk, iron/ironing board, WiFi

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 579
AED 1,544 total
includes taxes & fees
25 Aug - 26 Aug
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
2 bedrooms, WiFi, bed sheets
Coffee/tea maker, fridge, microwave, stovetop
TV, fireplace, books
Exterior detail

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

Fire Pit & Yard: Updated Winter Garden Home!
Winter Garden
United States
Patrick O.
AED 602
AED 1,899 total
includes taxes & fees
14 Sep - 15 Sep
Fire Pit & Yard: Updated Winter Garden Home!
3 bedrooms, desk, iron/ironing board, WiFi (free)
Interior
Outdoor pool, a heated pool
Coffee/tea maker, fridge, microwave, oven

9. 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 621
AED 1,480 total
includes taxes & fees
6 Sep - 7 Sep
Orlando Vista Cay Dream Vacation Luxurious/Exquisite 3Bed/2Bath Condo Sleeps 8
Property grounds
Lobby
A heated pool
Dining

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

Luxurious 5*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning
orlando
United States
Darby S.
AED 584
AED 3,199 total
includes taxes & fees
1 Sep - 2 Sep
Luxurious 5*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning
View all properties

Top Winter Park Hotel Reviews

Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Todo el hotel muy bonito , y el personal muy amable, buena limpieza 😊 lo único que no me gustó , que fuimos con mi hija a comer al bar , y la mesera que nos atendió después de llevar la comida nunca regresó a preguntar si queríamos algo más . Y solo pasó platicando con otra clienta. Yo iba a pedir otro mojito , pero ella nunca regresó a la mesa y cuando yo me levanté a pedir la cuenta le pedí un vaso de agua , y solo me llevó la cuenta , eso es pésimo servicio solo porque la propina ya está incluida en la cuenta, si no ,, no le hubiera dejado nada , porque esa es la razón que no le dan importancia de dar buen servicio, porque saben que la propina ya se incluyó…"
Adriana 1-night trip
Posted less than an hour ago
Rosen Inn Lake Buena Vista
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8/10 Good
"The accomodation is spacious with great amenities."
Vanroy 6-night trip
Posted 1 hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent
"We had amazing weekend the only think was the weather raining we can have more fun but was my second time all the new slide my kids had so much fun"
Xiomara 2-night trip
Posted 1 hour ago
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

10/10 Excellent
"Las instalaciones muy buenas, la limpieza excelente En cuanto al staff, me sentí discriminada en el trato de uno de los camareros en el bar de la piscina, grosero en su trato."
Zailyt 2-night trip
Posted 10 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
"👍"
Tania 7-night trip
Posted 2 days 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 Rollins Museum of Art. 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.