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
6 Sep - 7 Sep
Tomorrow
7 Sep - 8 Sep
Next weekend
11 Sep - 13 Sep
In two weeks
18 Sep - 20 Sep

Our top choices for Winter Park historic hotels

Outdoor pool, a heated pool
Bar (on property)
Property grounds
Outdoor dining

1. Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
United States
rick s.
AED 471
AED 1,188 total
includes taxes & fees
7 Sep - 8 Sep
Mills Cottage by the Little Lake
Outdoor pool, a heated pool
Outdoor dining
Exterior
Property grounds

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 413
AED 953 total
includes taxes & fees
7 Sep - 8 Sep
Large, beautiful, very comfortable one bedroom on small lake
Exterior detail
Bar (on property)
Outdoor pool, a heated pool
Fitness facility

3. Lake House Pets allowed

Lake House Pets allowed
Lake Weldona
United States
Jason M.
AED 506
AED 1,321 total
includes taxes & fees
7 Sep - 8 Sep
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 1,110 total
includes taxes & fees
7 Sep - 8 Sep
Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.
Exterior
Flat-screen TV
Property grounds
Dining

5. Eastpark. Pet friendly! Lake Nona

Eastpark. Pet friendly! Lake Nona
East Park
United States
Dania B.
AED 312
AED 967 total
includes taxes & fees
9 Sep - 10 Sep
Eastpark. Pet friendly! Lake Nona
Exterior
Dining
Coffee/tea maker, fridge, microwave, oven
Smart TV, Netflix, DVD player, toys

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

Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
Sanford
United States
Wendy K.
AED 496
AED 1,430 total
includes taxes & fees
7 Sep - 8 Sep
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
Interior
Interior
Exterior
Terrace/patio

7. Bella Breeze

Bella Breeze
Downtown Sanford
United States
Carolyn R.
Bella Breeze
Property grounds
Coffee/tea maker, fridge, microwave, oven
A heated pool
Dining

8. 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 526
AED 3,085 total
includes taxes & fees
7 Sep - 8 Sep
Luxurious 5*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning
Interior
Interior
2 bedrooms, desk, iron/ironing board, travel crib
Coffee/tea maker, fridge, microwave, oven

9. House with large deck, walking distance to Historic Downtown Winter Garden

House with large deck, walking distance to Historic Downtown Winter Garden
Winter Garden
United States
Sam M.
AED 526
AED 1,118 total
includes taxes & fees
13 Sep - 14 Sep
House with large deck, walking distance to Historic Downtown Winter Garden
2 bedrooms, WiFi, bed sheets
Coffee/tea maker, fridge, microwave, stovetop
Exterior detail
TV, fireplace, books

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

Fire Pit & Yard: Updated Winter Garden Home!
Winter Garden
United States
Patrick O.
AED 602
AED 1,892 total
includes taxes & fees
18 Sep - 19 Sep
Fire Pit & Yard: Updated Winter Garden Home!
View all properties

Top Winter Park Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"First time staying here and we loved it! We came down to Orlando to celebrate our daughter and our only regret is not staying longer. Very clean, beautiful property, staff was great!"
Vanessa 2-night trip
Posted less than an hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"The best off property place to stay."
Leslie 3-night trip
Posted 6 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area
Caribe Royale Orlando, WorldHotels Elite

Caribe Royale Orlando, WorldHotels Elite

10/10 Excellent
"Great hotel clean and with great customer service"
JENNIFER 2-night trip
Posted 13 hours 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
"Friendly, Clean, Nice Breakfast"
Airriona 3-night trip
Posted 15 hours ago
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Every thing was great"
Ruben 1-night trip
Posted 18 hours ago
Rosen Inn Lake Buena Vista

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 138 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, Rollins Museum of Art, and Morse Museum of American 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.