A two-story house with a balcony, surrounded by lush greenery and trees.

Find Historic Hotels in Winter Park, FL from CA $242

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Check availability on Winter Park Historic Hotels

Tonight
Oct 3 - Oct 4
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Oct 4 - Oct 5
Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

Our top choices for Winter Park historic hotels

A two-story house with a swimming pool, outdoor seating, and a covered patio area.
A patio with a brick floor, a wooden table and chairs, a glass greenhouse, and bamboo plants.
A small, rustic building with a metal roof and a red door, surrounded by lush greenery and a pond.
A rustic bar with wooden shelves stocked with bottles, a coffee machine, and bar stools.

1. Mills Cottage by the Little Lake

Mills Cottage by the Little Lake
Lake Weldona
United States
rick s.
CA $237
CA $532 total
includes taxes & fees
Oct 4 - Oct 5
Mills Cottage by the Little Lake
A two-story house with a swimming pool, outdoor seating, and a covered patio area.
A patio with a brick floor, a wooden table and chairs, a glass greenhouse, and bamboo plants.
A rustic bar with wooden shelves stocked with bottles, a coffee machine, and bar stools.
A stone staircase leading to a pond surrounded by lush greenery and stone railings.

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.
CA $230
CA $464 total
includes taxes & fees
Oct 5 - Oct 6
Large, beautiful, very comfortable one bedroom on small lake
A greenhouse with a sign reading "L'ORANGERIE," surrounded by bamboo plants and stone walls.
A gym with various exercise equipment, mirrors, and a bench.
A two-story house with a swimming pool, outdoor seating, and a covered patio area.
A rustic bar with wooden shelves stocked with bottles, a coffee machine, and bar stools.

3. Lake House Pets allowed

Lake House Pets allowed
Lake Weldona
United States
Jason M.
CA $264
CA $602 total
includes taxes & fees
Oct 4 - Oct 5
Lake House Pets allowed
A compact kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a dishwasher.
A dining area with a dark table, chairs, a vase with flowers, a chandelier, and a wall with abstract art and a shelf with items.
A house with a blue door, a white porch, and a garden with plants.
A bedroom with a bed, bedside tables, a desk, and a ceiling fan.

4. Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.

Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.
Paramore
United States
Molly A.
CA $308
CA $432 total
includes taxes & fees
Oct 12 - Oct 13
Downtown Orlando Creative Oasis- Hand Painted Murals & Free Parking.
A residential area with houses, a lake, and a fountain.
A living room with a brown leather sofa, patterned armchair, and a coffee table. There's a chandelier, a desk with a computer, and a TV.
A fenced outdoor area with a palm tree, a sign, and a body of water.
A dining area with a round table, wooden chairs, a chandelier, and a window with curtains.

5. Eastpark. Pet friendly! Lake Nona

Eastpark. Pet friendly! Lake Nona
East Park
United States
Dania B.
CA $141
CA $402 total
includes taxes & fees
Oct 12 - Oct 13
Eastpark. Pet friendly! Lake Nona
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6. Bella Breeze

Bella Breeze
Downtown Sanford
United States
Carolyn R.
CA $114
CA $242 total
includes taxes & fees
Oct 4 - Oct 5
Bella Breeze
A modern kitchen with a central island, grey cabinets, and a black accent wall.
A bedroom with two beds, wooden headboards, a window with curtains, a flat-screen TV, and a nightstand with a lamp.
A modern kitchen with grey cabinets, stainless steel appliances, and a white island.
A dining area with a wooden table, chairs, and a flat-screen TV.

7. Apartment next to International Dr and Universal

Apartment next to International Dr and Universal
International Drive District
United States
Anonymous traveller
CA $128
CA $413 total
includes taxes & fees
Oct 26 - Oct 27
Apartment next to International Dr and Universal
A bedroom with a bed, a bedside table with a lamp, and a wall decorated with woven baskets.
A living room with a sectional sofa, a wooden coffee table, and a ceiling fan.
A living room with a sofa, coffee table, and a lamp. There are two paintings on the wall and a plant on the coffee table.
A porch with a white railing, a blue door, and a potted plant.

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

Fire Pit & Yard: Updated Winter Garden Home!
Winter Garden
United States
Patrick O.
CA $234
CA $737 total
includes taxes & fees
Oct 18 - Oct 19
Fire Pit & Yard: Updated Winter Garden Home!
A spacious living area with a dining table, chairs, a sofa, and a kitchen in the background.
A modern kitchen with white cabinets, a stainless steel range, and a yellow door.
A dining area with a wooden table and chairs, a hanging light fixture, and a world map on the wall.
A narrow hallway with a patterned rug, a white door at the end, and a wooden shelf with a picture frame and a box on the right.

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.
House with large deck, walking distance to Historic Downtown Winter Garden
A pathway leading to a building with a central archway, flanked by palm trees.
A pool area with a circular design, surrounded by a tiled walkway and shaded by pergolas.
A modern kitchen with stainless steel appliances, wooden cabinets, and a dining area with a glass table and metal chairs.
A spacious living room with a large chandelier, comfortable seating, and a fireplace.

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.
CA $230
CA $1,230 total
includes taxes & fees
Oct 4 - Oct 5
Luxurious 5*Executive 3Br Villa Vista Cay/Pool | Enhanced Cleaning
View all properties

Top Winter Park Hotel Reviews

Buena Vista Suites Orlando

Buena Vista Suites Orlando

10/10 Excellent
"Loved the clean rooms and the wonderful breakfast in the morning. Would absolutely recommend staying here again."
Jana 1-night trip
Posted 2 hours ago
Buena Vista Suites Orlando
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Excellent staff. Excellent communication. Very friendl"
Adam 1-night trip
Posted 4 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Rosen Inn Lake Buena Vista

Rosen Inn Lake Buena Vista

10/10 Excellent
"Bathroom could have been better maintained."
Shelley 3-night trip
Posted 5 hours ago
Rosen Inn Lake Buena Vista
Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

10/10 Excellent
"The electric power outlets are not working well"
Jin Jun 3-night trip
Posted 1 day ago
Fairfield Inn & Suites Lake Buena Vista in Marriott Village

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, Morse Museum of American Art, 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.

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