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
8 Aug - 9 Aug
Tomorrow
9 Aug - 10 Aug
Next weekend
14 Aug - 16 Aug
In two weeks
21 Aug - 23 Aug

Our top choices for Winter Park historic hotels

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

1. Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
United States
rick s.
AED 719
AED 1,518 total
includes taxes & fees
10 Aug - 11 Aug
Mills Cottage by the Little Lake
Exterior detail
Bar (on property)
Outdoor pool, a heated pool
Fitness facility

2. Lake House Pets allowed

Lake House Pets allowed
Lake Weldona
United States
Jason M.
AED 845
AED 1,769 total
includes taxes & fees
17 Aug - 18 Aug
Lake House Pets allowed
Outdoor pool, a heated pool
Property grounds
Outdoor dining
Bar (on property)

3. 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 579
AED 1,165 total
includes taxes & fees
9 Aug - 10 Aug
Large, beautiful, very comfortable one bedroom on small lake
Coffee/tea maker, fridge, microwave, oven
3 bedrooms, iron/ironing board, WiFi, bed sheets
Dining
Property grounds

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 882
AED 1,220 total
includes taxes & fees
7 Sep - 8 Sep
Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.
Interior
Private kitchen
TV
Dining

5. Apartment next to International Dr and Universal

Apartment next to International Dr and Universal
International Drive District
United States
Anonymous traveler
AED 477
AED 1,244 total
includes taxes & fees
7 Sep - 8 Sep
Apartment next to International Dr and Universal
Property grounds
Lobby
Dining
A heated pool

6. 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
3 bedrooms, desk, iron/ironing board, WiFi (free)
Coffee/tea maker, fridge, microwave, oven
Outdoor pool, a heated pool
Smart TV, video games, DVD player, foosball

7. 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
11 Aug - 12 Aug
Orlando Vista Cay Dream Vacation Luxurious/Exquisite 3Bed/2Bath Condo Sleeps 8
Pool
Property grounds
Property grounds
Bar (on property)

8. Kings Palace at Vista Cay Resort

Kings Palace at Vista Cay Resort
Orlando
United States
Rachelle S.
AED 401
AED 1,498 total
includes taxes & fees
9 Aug - 10 Aug
Kings Palace at Vista Cay Resort
Coffee/tea maker, fridge, microwave, oven
Smart TV, foosball, books, video library
Property grounds
Coffee/tea maker, fridge, microwave, oven

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
9 Aug - 10 Aug
Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!
Exterior
Coffee/tea maker, fridge, microwave, oven
Dining
Smart TV, Netflix, DVD player, toys

10. 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 1,463 total
includes taxes & fees
9 Aug - 10 Aug
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
View all properties

Top Winter Park Hotel Reviews

Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

8/10 Good
"Great Services"
FELICIA 3-night trip
Posted 5 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
"Out stay was short and sweet , we will will be back"
Gillian 2-night trip
Posted 9 hours ago
Lake Buena Vista Resort Village & Spa
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Loved it!"
Denise 2-night trip
Posted 10 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

8/10 Good
"The service is 11 out of 10. The best of the whole experience was the service."
maria J. 1-night trip
Posted 20 hours 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 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 Orlando International Premium Outlets.
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.