Title: Book the Best HISTORIC Hotels in Winter Park in 2026 | Expedia.ca

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![Kraft Azalea Gardens showing a fountain, a park and a pond](https://images.trvl-media.com/place/553248621532654339/aef9d03a-cd86-4dcc-8e9d-049aef598da5.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/553248621532654339/aef9d03a-cd86-4dcc-8e9d-049aef598da5.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Winter Park Historic Hotels

Tonight

[Jan 16 - Jan 17](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2026-01-16&endDate=2026-01-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 17 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2026-01-17&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winter Park historic hotels

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/36000000/35740000/35738700/35738680/c76ba063.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/36000000/35740000/35738700/35738680/cc517c74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/36000000/35740000/35738700/35738680/e093ed20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/36000000/35740000/35738700/35738680/eb10fab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mills Cottage by the Little Lake

[](https://www.expedia.ca/Orlando-Hotels-Mills-Cottage-On-Small-Lake.h35738680.Hotel-Information)

Lake Weldona

10/10

Exceptional

(50 reviews)

"Beautiful property with excellent amenities. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alexis E.

CA $193

CA $474 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Orlando-Hotels-Mills-Cottage-On-Small-Lake.h35738680.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/100000000/99360000/99355200/99355180/7f8848b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99360000/99355200/99355180/82a6ad82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Mini-fridge, microwave, cookware/dishes/utensils](https://images.trvl-media.com/lodging/100000000/99360000/99355200/99355180/9d43162b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99360000/99355200/99355180/c6a2da7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bella Breeze

[](https://www.expedia.ca/Sanford-Hotels-Bella-Breeze.h99355180.Hotel-Information)

Sanford

9.6/10

Exceptional

(5 reviews)

"The place was clean, cozy, and well decorated, and the amenities were wonderful! The hosts have done a great job here."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Courteny

[](https://www.expedia.ca/Sanford-Hotels-Bella-Breeze.h99355180.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/49000000/48650000/48644000/48643933/181f625e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/49000000/48650000/48644000/48643933/c92a25e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/49000000/48650000/48644000/48643933/f2c6e82c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/49000000/48650000/48644000/48643933/dfc172b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Oak View Place.. 

[](https://www.expedia.ca/Winter-Garden-Hotels-The-Oak-View-Place.h48643933.Hotel-Information)

Oakland

9.2/10

Wonderful

(10 reviews)

"The VRBO looked brand new and I only knew it was not because of the reviews from previous years. The live oak trees on the property added to the beauty of the surroundings."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Libba F.

CA $250

CA $405 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Winter-Garden-Hotels-The-Oak-View-Place.h48643933.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/38000000/37150000/37145500/37145476/5c0c5265.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Banquet hall](https://images.trvl-media.com/lodging/38000000/37150000/37145500/37145476/f463c141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/38000000/37150000/37145500/37145476/1992b316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/38000000/37150000/37145500/37145476/2f544f47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DELUXE STUDIO AT BEAUTIFUL RESORT WITH MANY AMENITIES TO ENJOY

[](https://www.expedia.ca/Orlando-Hotels-DELUXE-STUDIO-AT-BEAUTIFUL-RESORT-WITH-MANY-AMENITIES-TO-ENJOY.h37145476.Hotel-Information)

Orlando

9.6/10

Exceptional

(55 reviews)

"Balcony over looking was the best."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tammy B.

[](https://www.expedia.ca/Orlando-Hotels-DELUXE-STUDIO-AT-BEAUTIFUL-RESORT-WITH-MANY-AMENITIES-TO-ENJOY.h37145476.Hotel-Information)

![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/91000000/90540000/90537200/90537195/fc4545a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90540000/90537200/90537195/33ba1695.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90540000/90537200/90537195/w1079h792x0y4-67e900f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90540000/90537200/90537195/0cd596f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 BD/2 BA minutes from Universal Studios & Epic Universe 

[](https://www.expedia.ca/Orlando-Hotels-Remodeled-2-BD2-BA-Minutes-From-Universal-Studios.h90537195.Hotel-Information)

International Drive District

9.6/10

Exceptional

(15 reviews)

"My mother son and i really enjoyed our night here. It was beautiful and clean and had everything we needed "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Taylor

CA $174

CA $388 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Orlando-Hotels-Remodeled-2-BD2-BA-Minutes-From-Universal-Studios.h90537195.Hotel-Information)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120090000/120088200/120088187/33f89d2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/121000000/120090000/120088200/120088187/d5b1ef62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120090000/120088200/120088187/ab8ed68f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120090000/120088200/120088187/6ba93c97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Retreat in the Heart of Orlando – Close to Theme Parks

[](https://www.expedia.ca/Orlando-Hotels-Vacation-Retreat-In-The-Heart-Of-Orlando-Close-To-Theme-Parks.h120088187.Hotel-Information)

International Drive District

CA $113

CA $274 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Orlando-Hotels-Vacation-Retreat-In-The-Heart-Of-Orlando-Close-To-Theme-Parks.h120088187.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/50000000/49260000/49256800/49256791/58f022da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/50000000/49260000/49256800/49256791/w1599h1066x1y1-086ad819.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/50000000/49260000/49256800/49256791/eb562748.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/50000000/49260000/49256800/49256791/307dafb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large, beautiful, very comfortable one bedroom on small lake

[](https://www.expedia.ca/Orlando-Hotels-Cute-One-Bedroom-On-Small-Lake.h49256791.Hotel-Information)

Lake Weldona

10/10

Exceptional

(60 reviews)

"Our 2 night stay was wonderful! A beautiful place to enjoy and relax. We will definitely being staying here again when we are in Orlando."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jolyn W.

CA $238

CA $467 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Orlando-Hotels-Cute-One-Bedroom-On-Small-Lake.h49256791.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22400000/22394600/22394594/3ab2b318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/23000000/22400000/22394600/22394594/0adc64ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22400000/22394600/22394594/04a1ee85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/23000000/22400000/22394600/22394594/w799h599x1y1-2d465cca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stunning 3BR/2BA Orlando Vista Cay - Disney/Universal/Occc!

[](https://www.expedia.ca/Orlando-Hotels-Stunning-3br2ba-Orlando-Vista-Cay-Disneyuniversaloccc.h22394594.Hotel-Information)

Orlando

9.8/10

Exceptional

(265 reviews)

"The condo was great and booking and check in very easy. Great location near Convention Center and close to the pool, which we loved. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Miranda S.

CA $285

CA $626 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Orlando-Hotels-Stunning-3br2ba-Orlando-Vista-Cay-Disneyuniversaloccc.h22394594.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/98000000/97400000/97393200/97393108/514b3100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/98000000/97400000/97393200/97393108/2421ddf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/98000000/97400000/97393200/97393108/34a46a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/98000000/97400000/97393200/97393108/1776dd03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment next to International Dr and Universal

[](https://www.expedia.ca/Orlando-Hotels-Apartment-Next-To-International-Dr-And-Universal.h97393108.Hotel-Information)

International Drive District

9.0/10

Wonderful

(13 reviews)

"Loved staying at The Enclave its very close to everything and you feel safe. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kimberly J.

CA $181

CA $476 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Orlando-Hotels-Apartment-Next-To-International-Dr-And-Universal.h97393108.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/109000000/108340000/108337200/108337146/a7939ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/109000000/108340000/108337200/108337146/ee034698.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/109000000/108340000/108337200/108337146/a21b8d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108340000/108337200/108337146/ee58a0d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Florida near Universal and Intern. Dr

[](https://www.expedia.ca/Orlando-Hotels-Apartment-In-Florida-Near-Universal-And-Intern-Dr.h108337146.Hotel-Information)

International Drive District

8.8/10

Excellent

(6 reviews)

"Great location close to key areas in Orlando.Apartment is super clean and confortable.Thanks"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Manuel G.

CA $153

CA $439 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Orlando-Hotels-Apartment-In-Florida-Near-Universal-And-Intern-Dr.h108337146.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-30&endDate=2026-01-31&regionId=7902&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true)

## Top Winter Park Hotel Reviews

![Hyatt Regency Orlando](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/1bb0a2ac_y.jpg)

### Hyatt Regency Orlando

10/10 Excellent

"Excellent"

[](https://expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.Hotel-Information)

![Lake Buena Vista Resort Village & Spa](https://images.trvl-media.com/lodging/2000000/1360000/1350900/1350864/16b6b8e7_y.jpg)

### Lake Buena Vista Resort Village & Spa

10/10 Excellent

"Clean parking is a hassle but very. Clean "

[](https://expedia.ca/Orlando-Hotels-Lake-Buena-Vista-Resort-Village-Spa.h1350864.Hotel-Information)

![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_y.jpg)

### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent

"Excellent and clean Resort, good location, spacious, easy to get around. Friendly staff. "

[](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information)

## Frequently asked questions

### What should a history enthusiast expect from a trip to Winter Park?

### How many historical hotels are there in Winter Park?

### What are the must-see historical places and other sights to visit in Winter Park?

### What is a historic hotel like in Winter Park?

### What is the difference between a historic hotel and a heritage hotel?

### Do historic hotels in Winter Park have modern facilities?

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