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
10 Sep - 11 Sep
Tomorrow
11 Sep - 12 Sep
This weekend
11 Sep - 13 Sep
Next weekend
18 Sep - 20 Sep

Our top choices for Winter Park historic hotels

Outdoor pool, a heated pool
Outdoor dining
Exterior
Property grounds

1. Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
United States
rick s.
AED 412
AED 1,114 total
includes taxes & fees
11 Sep - 12 Sep
Mills Cottage by the Little Lake
Outdoor pool, a heated pool
Outdoor dining
Property grounds
Exterior

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 397
AED 909 total
includes taxes & fees
13 Sep - 14 Sep
Large, beautiful, very comfortable one bedroom on small lake
Exterior detail
Property grounds
Bar (on property)
Fitness facility

3. Lake House Pets allowed

Lake House Pets allowed
Lake Weldona
United States
Jason M.
AED 611
AED 1,457 total
includes taxes & fees
14 Sep - 15 Sep
Lake House Pets allowed
Coffee/tea maker, fridge, microwave, oven
Property grounds
Dining
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 918
AED 1,232 total
includes taxes & fees
11 Oct - 12 Oct
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 312
AED 967 total
includes taxes & fees
14 Sep - 15 Sep
Eastpark. Pet friendly! Lake Nona
Exterior
Smart TV, Netflix, DVD player, toys
4 bedrooms, desk, iron/ironing board, WiFi
Dining

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 579
AED 1,537 total
includes taxes & fees
13 Sep - 14 Sep
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
Interior
Interior
Interior
Terrace/patio

7. Bella Breeze

Bella Breeze
Downtown Sanford
United States
Carolyn R.
AED 312
AED 644 total
includes taxes & fees
12 Sep - 13 Sep
Bella Breeze
Property grounds
Lobby
Dining
Coffee/tea maker, fridge, microwave, oven

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 3,089 total
includes taxes & fees
11 Sep - 12 Sep
Luxurious 5*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning
Coffee/tea maker, fridge, microwave, oven
Smart TV, foosball, books, video library
Property grounds
3 bedrooms, in-room safe, desk, iron/ironing board

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 1,618 total
includes taxes & fees
11 Sep - 12 Sep
Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!
Interior
2 bedrooms, desk, iron/ironing board, travel crib
Interior
Coffee/tea maker, fridge, microwave, oven

10. 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 841
AED 1,514 total
includes taxes & fees
7 Oct - 8 Oct
House with large deck, walking distance to Historic Downtown Winter Garden
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
"We had a great experience! Please never change. We hope to come back and stay here again."
Nadine 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
"Rooms are very clean, great customer service."
Betty 3-night trip
Posted 4 hours ago
Caribe Royale Orlando, WorldHotels Elite
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Clean and pet friendly!"
Sydney 2-night trip
Posted 10 hours ago
Rosen Inn Lake Buena Vista
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent
"A mis hijos le encantó la estancia en este lugar, el parque de agua divertido para los niños, la actividad al medio día con la participación de los niños, definitivamente regresaremos en octubre."
yara 2-night trip
Posted 1 day ago
Holiday Inn Resort Orlando Suites - Waterpark by IHG

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.