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
27 Aug - 28 Aug
Tomorrow
28 Aug - 29 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
Bar (on property)
Outdoor dining

1. 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 473
AED 1,042 total
includes taxes & fees
30 Aug - 31 Aug
Large, beautiful, very comfortable one bedroom on small lake
Exterior detail
Property grounds
Fitness facility
Outdoor pool, a heated pool

2. Lake House Pets allowed

Lake House Pets allowed
Lake Weldona
United States
Jason M.
AED 471
AED 1,242 total
includes taxes & fees
28 Aug - 29 Aug
Lake House Pets allowed
Outdoor pool, a heated pool
Property grounds
Outdoor dining
Bar (on property)

3. Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
United States
rick s.
AED 534
AED 1,285 total
includes taxes & fees
30 Aug - 31 Aug
Mills Cottage by the Little Lake
Coffee/tea maker, fridge, microwave, oven
Property grounds
Smart TV
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 1,258 total
includes taxes & fees
27 Sep - 28 Sep
Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.
Exterior
Dining
Property grounds
Interior

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
Terrace/patio
Exterior

6. Bella Breeze

Bella Breeze
Downtown Sanford
United States
Carolyn R.
Bella Breeze
Exterior
4 bedrooms, desk, iron/ironing board, WiFi
Coffee/tea maker, fridge, microwave, oven
Smart TV, Netflix, DVD player, toys

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 645
AED 1,618 total
includes taxes & fees
28 Aug - 29 Aug
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
Coffee/tea maker, fridge, microwave, oven
Coffee/tea maker, fridge, microwave, oven
3 bedrooms, in-room safe, desk, iron/ironing board
Smart TV, foosball, books, video library

8. 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
28 Aug - 29 Aug
Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!
2 bedrooms, WiFi, bed sheets
Coffee/tea maker, fridge, microwave, stovetop
TV, fireplace, books
Exterior detail

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

Fire Pit & Yard: Updated Winter Garden Home!
Winter Garden
United States
Patrick O.
AED 566
AED 1,843 total
includes taxes & fees
6 Sep - 7 Sep
Fire Pit & Yard: Updated Winter Garden Home!
Property grounds
A heated pool
Lobby
Coffee/tea maker, fridge, microwave, oven

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 3,195 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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"We love our stays here. Always clean and comfortable. Love all the amenities and convenient location."
Kristie 1-night trip
Posted 5 hours 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
"Excellent location with easy walking access to Disney Springs. The bus service was frequent, reliable, and very convenient. The hotel was modern, very clean, and well maintained. We especially enjoyed the great breakfast and afternoon snack selection. The staff were friendly, welcoming, and very helpful. Overall, a fantastic stay!"
Sian 15-night trip
Posted 8 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent
"We loved it, it was our second time… we will be back!!!"
John Ramon 4-night trip
Posted 10 hours ago
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

10/10 Excellent
"Five star hotel on Disney property - in a league by itself"
John 1-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 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 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.