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
22 Aug - 23 Aug
Tomorrow
23 Aug - 24 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
4 Sep - 6 Sep

Our top choices for Winter Park historic hotels

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

1. Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
United States
rick s.
AED 611
AED 1,382 total
includes taxes & fees
23 Aug - 24 Aug
Mills Cottage by the Little Lake
Exterior detail
Outdoor pool, a heated pool
Fitness facility
Bar (on property)

2. Lake House Pets allowed

Lake House Pets allowed
Lake Weldona
United States
Jason M.
AED 541
AED 1,350 total
includes taxes & fees
24 Aug - 25 Aug
Lake House Pets allowed
Outdoor pool, a heated pool
Exterior
Property grounds
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 446
AED 1,008 total
includes taxes & fees
24 Aug - 25 Aug
Large, beautiful, very comfortable one bedroom on small lake
Coffee/tea maker, fridge, microwave, oven
3 bedrooms, iron/ironing board, WiFi, bed sheets
Property grounds
Smart TV

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
24 Aug - 25 Aug
Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.
Exterior
Interior
Dining
Property grounds

5. Eastpark. Pet friendly! Lake Nona

Eastpark. Pet friendly! Lake Nona
East Park
United States
Dania B.
AED 364
AED 1,043 total
includes taxes & fees
24 Aug - 25 Aug
Eastpark. Pet friendly! Lake Nona
Interior
Interior
Terrace/patio
Exterior

6. Bella Breeze

Bella Breeze
Downtown Sanford
United States
Carolyn R.
AED 312
AED 647 total
includes taxes & fees
20 Sep - 21 Sep
Bella Breeze
Exterior
Smart TV, Netflix, DVD player, toys
Coffee/tea maker, fridge, microwave, oven
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
24 Aug - 25 Aug
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
3 bedrooms, desk, iron/ironing board, WiFi (free)
Coffee/tea maker, fridge, microwave, oven
Interior
Smart TV, video games, DVD player, foosball

8. 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
23 Aug - 24 Aug
Orlando Vista Cay Dream Vacation Luxurious/Exquisite 3Bed/2Bath Condo Sleeps 8
Coffee/tea maker, fridge, microwave, oven
Coffee/tea maker, fridge, microwave, oven
3 bedrooms, in-room safe, desk, iron/ironing board
Property grounds

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
31 Aug - 1 Sep
Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!
Property grounds
A heated pool
Lobby
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
14 Sep - 15 Sep
Luxurious 5*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning
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
"Included breakfast and dinner were great."
David 7-night trip
Posted 8 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

10/10 Excellent
"The property was just beautiful, and the staff was most accommodating!"
TINA T 2-night trip
Posted 14 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 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 Winter Park History Museum. 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.