Title: The Best Winter Park, FL Chalets from $109 | Expedia.com

[Winter Park Travel Guide](https://expedia.com/Winter-Park.dx7902)[Hotels in Winter Park](https://expedia.com/Winter-Park-Hotels.d7902.Travel-Guide-Hotels)[Vacation Rentals in Winter Park](https://expedia.com/Winter-Park-Vacation-Rentals.d7902.Travel-Guide-VacationRentals)[Flights to Winter Park](https://expedia.com/Cheap-Flights-To-Winter-Park.d7902.Travel-Guide-Flights)[Things to do in Winter Park](https://expedia.com/Things-To-Do-In-Winter-Park.d7902.Travel-Guide-Activities)[Car Rentals in Winter Park](https://expedia.com/Car-Rentals-In-Winter-Park.d7902.Car-Rental-Guide)[Winter Park Vacation Packages](https://expedia.com/Winter-Park.d7902.Destination-Travel-Guides)

![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 prices for these dates

In two weeks

[Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

No exact matches found, but these alternatives could be just right

## Recommended hotels in Winter Park

![Exterior detail](https://images.trvl-media.com/lodging/79000000/78010000/78004700/78004694/64430b2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78010000/78004700/78004694/c94baf8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78010000/78004700/78004694/4a4f7206.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/79000000/78010000/78004700/78004694/4c2b0b79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Winter Park

[](https://www.expedia.com/Orlando-Hotels-Newly-Built-Stylish-Guest-House-With-Free-Parking.h78004694.Hotel-Information)

10/10

Exceptional

(104 reviews)

"We really enjoyed our stay. The place was clean, comfortable and well provisioned. The neighborhood was quiet and the hosts were very welcoming. Definitely one of our best VRBO experiences ever! "

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

Holly N.

$298 nightly

$332 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Newly-Built-Stylish-Guest-House-With-Free-Parking.h78004694.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/124000000/123400000/123398800/123398794/w1350h895x0y5-04b0130a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/124000000/123400000/123398800/123398794/9bd56f27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123400000/123398800/123398794/f1476d84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123400000/123398800/123398794/6de8c24e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mobile Home in Fairview Shores

[](https://www.expedia.com/Orlando-Hotels-Comfy-Tiny-Home-WP-Large-Private-DeckQueen-Bed.h123398794.Hotel-Information)

$184 nightly

$204 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Comfy-Tiny-Home-WP-Large-Private-DeckQueen-Bed.h123398794.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/92000000/91100000/91093700/91093651/a4a236a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91100000/91093700/91093651/55f38262.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/92000000/91100000/91093700/91093651/3ef41108.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/92000000/91100000/91093700/91093651/22001730.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Orlando

[](https://www.expedia.com/Orlando-Hotels-1-Bedroom-Vacation-Room-Just-12-Minutes-From-University-Of-Central-Florida.h91093651.Hotel-Information)

9.4/10

Exceptional

(3 reviews)

"Fantastic Host"

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

Marek K.

$171 nightly

$189 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-1-Bedroom-Vacation-Room-Just-12-Minutes-From-University-Of-Central-Florida.h91093651.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/121000000/120650000/120648600/120648509/081e1921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120650000/120648600/120648509/180-b531af67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120650000/120648600/120648509/4d10ef55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/121000000/120650000/120648600/120648509/57a8906a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Orlando

[](https://www.expedia.com/Orlando-Hotels-Quiet-And-Safe-Neighborhood-Come-To-This-Great-Place-With-Lots-Of-Room-For-Relax.h120648509.Hotel-Information)

10/10

Exceptional

(2 reviews)

"Pool is very inviting"

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

Geri Lamborn M.

[](https://www.expedia.com/Orlando-Hotels-Quiet-And-Safe-Neighborhood-Come-To-This-Great-Place-With-Lots-Of-Room-For-Relax.h120648509.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/122000000/121860000/121857300/121857215/d9e95202.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, computer monitors](https://images.trvl-media.com/lodging/122000000/121860000/121857300/121857215/a9d269d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/122000000/121860000/121857300/121857215/7061403d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121860000/121857300/121857215/8914dae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Fairview Shores

[](https://www.expedia.com/Orlando-Hotels-Cozy-Home-5min-To-Park-Ave-And-Downtown-Orlando.h121857215.Hotel-Information)

$239 nightly

$266 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Cozy-Home-5min-To-Park-Ave-And-Downtown-Orlando.h121857215.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121830000/121826500/121826401/4e7b5cb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121830000/121826500/121826401/fb43e8b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121830000/121826500/121826401/e47ef39a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121830000/121826500/121826401/ad8a3de4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Fairview Shores

[](https://www.expedia.com/Orlando-Hotels-Sleek.h121826401.Hotel-Information)

10/10

Exceptional

(1 review)

"Great location in Winter Park! So many quality restaurants and things to do close by. The home is easily accessible with plenty of space. The host, Wendy was very hospitable. We left a toiletry bag and she was kind enough to let us know so we could come back. We enjoyed our one night stay!"

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

Adam A.

$196 nightly

$218 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Sleek.h121826401.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118780000/118778200/118778200/d7886791.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118780000/118778200/118778200/3736e6a2.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/119000000/118780000/118778200/118778200/64b5a908.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/119000000/118780000/118778200/118778200/1bba5733.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in College Park

[](https://www.expedia.com/Orlando-Hotels-Winter-Park-Gem.h118778200.Hotel-Information)

8.0/10

Very Good

(2 reviews)

"We had a wonderful stay — the house was spotless, comfortable, and offered plenty of space. The peaceful neighborhood and convenient location made it easy to explore the area."

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

Danielle H.

$235 nightly

$261 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Winter-Park-Gem.h118778200.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/121000000/120190000/120187300/120187220/957cda3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120190000/120187300/120187220/7253cdd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120190000/120187300/120187220/312f2783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120190000/120187300/120187220/b34af36d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Fairview Shores

[](https://www.expedia.com/Orlando-Hotels-Charming-Home-Wp-Patio-Gazebo-Close-To-Highwys.h120187220.Hotel-Information)

10/10

Exceptional

(1 review)

"Very clean and location was great"

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

Vicki V.

$218 nightly

$243 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Charming-Home-Wp-Patio-Gazebo-Close-To-Highwys.h120187220.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/124000000/123150000/123148000/123147976/w1350h895x0y5-06f55f02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123150000/123148000/123147976/aeff95b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123150000/123148000/123147976/c29ed280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123150000/123148000/123147976/36f4f2db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Fairview Shores

[](https://www.expedia.com/Orlando-Hotels-Funky-Remodeled-Otown-Bungalow-Sleeps-8.h123147976.Hotel-Information)

$243 nightly

$271 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Funky-Remodeled-Otown-Bungalow-Sleeps-8.h123147976.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/122000000/121560000/121551600/121551588/9a1d28f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121560000/121551600/121551588/eacfcee6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121560000/121551600/121551588/c1954c59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121560000/121551600/121551588/bf1a7baa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Fairview Shores

[](https://www.expedia.com/Orlando-Hotels-Money-Saving-Clean-Small-11-Private-Apartment-On-The-Orlando-Border.h121551588.Hotel-Information)

$99 nightly

$109 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Money-Saving-Clean-Small-11-Private-Apartment-On-The-Orlando-Border.h121551588.Hotel-Information)

![Front Side Balcony Suite, 1 King | Balcony view](https://images.trvl-media.com/lodging/2000000/1790000/1784900/1784873/eb5c76ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business center](https://images.trvl-media.com/lodging/2000000/1790000/1784900/1784873/450d6e5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1790000/1784900/1784873/52e0ae75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1790000/1784900/1784873/82e772bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel in Park Avenue District

[](https://www.expedia.com/Orlando-Hotels-Park-Plaza-Hotel.h1784873.Hotel-Information)

8.6/10

Excellent

(1,004 reviews)

"Friendly staff, clean and beautiful atmosphere."

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

Kristin

$183 nightly

$206 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Park-Plaza-Hotel.h1784873.Hotel-Information)

![Smart TV, video games](https://images.trvl-media.com/lodging/92000000/91700000/91693700/91693626/4737a68c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91700000/91693700/91693626/c4b6e35a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91700000/91693700/91693626/c75613db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/92000000/91700000/91693700/91693626/777ceefa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Goldenrod

[](https://www.expedia.com/Orlando-Hotels-Serene-Mid-Century-32-WBonus-Room-And-Huge-Shaded-Yard-WFence.h91693626.Hotel-Information)

$384 nightly

$427 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Serene-Mid-Century-32-WBonus-Room-And-Huge-Shaded-Yard-WFence.h91693626.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/46000000/45490000/45488100/45488005/a0ec7203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/46000000/45490000/45488100/45488005/443aa4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/46000000/45490000/45488100/45488005/fbeb2b17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/46000000/45490000/45488100/45488005/95677878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel in Winter Park

[](https://www.expedia.com/Orlando-Hotels-Hilton-Garden-Inn-Winter-Park.h45488005.Hotel-Information)

9.2/10

Wonderful

(656 reviews)

"Very clean, nice staff, well located"

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

KRISTIAN

$170 nightly

$191 total

Mar 29 - Mar 30

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Hilton-Garden-Inn-Winter-Park.h45488005.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/122000000/121020000/121017300/121017283/7f29b0af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121020000/121017300/121017283/9e87b9ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/122000000/121020000/121017300/121017283/170acb69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121020000/121017300/121017283/18ad5479.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winter Park

[](https://www.expedia.com/Orlando-Hotels-Spacious-5-Bedroom-House-In-Gorgeous-Winter-Park.h121017283.Hotel-Information)

$319 nightly

$354 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Spacious-5-Bedroom-House-In-Gorgeous-Winter-Park.h121017283.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/959a6964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/93bcae58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 outdoor pools, open 10:00 AM to 5:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/w720h947x0y0-b237fd72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/20000/19800/19791/fcdf7880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel in Winter Park

[](https://www.expedia.com/Orlando-Hotels-The-Alfond-Inn.h19791.Hotel-Information)

9.6/10

Exceptional

(1,006 reviews)

"Location was great, friendly staff, beautiful hotel."

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

Jessica

$394 nightly

$443 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-The-Alfond-Inn.h19791.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/120000000/119720000/119712500/119712429/120179c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/120000000/119720000/119712500/119712429/5d356775.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119720000/119712500/119712429/d0827223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/120000000/119720000/119712500/119712429/b29eebc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Fairview Shores

[](https://www.expedia.com/Orlando-Hotels-Mills-House-WP-Sleeps-11-Renovated-Queen-Beds.h119712429.Hotel-Information)

6.0/10

(1 review)

"The air fresheners plug ins were too powerful, we had to put them outside while we stayed in the house. Not enough power outlets. Hanging lamps on master bedroom are not practical, didn’t find the switch to turn them off. Spot light outside kept me up. The motion triggered the light to go on and off constantly. "

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

Monica E.

$274 nightly

$306 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Mills-House-WP-Sleeps-11-Renovated-Queen-Beds.h119712429.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/72000000/71150000/71146400/71146342/w4000h2662x0y0-9dcdde60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/72000000/71150000/71146400/71146342/ba3d3a5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/72000000/71150000/71146400/71146342/a831619a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/72000000/71150000/71146400/71146342/3dbe35a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel in Winter Park

[](https://www.expedia.com/Orlando-Hotels-SpringHill-Suites-By-Marriott-Winter-Park.h71146342.Hotel-Information)

9.2/10

Wonderful

(352 reviews)

"Nice, clean hotel with a very friendly staff. I will book again!"

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

kelly

$197 nightly

$221 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-SpringHill-Suites-By-Marriott-Winter-Park.h71146342.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/121000000/120490000/120489000/120488903/3aa946ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/121000000/120490000/120489000/120488903/b9965092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120490000/120489000/120488903/78c9ab55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/121000000/120490000/120489000/120488903/437efd0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winter Park

[](https://www.expedia.com/Orlando-Hotels-4-Bedroom-House-In-Superb-Winter-Park.h120488903.Hotel-Information)

4.0/10

(1 review)

"We checked in late and were surprised to find half eaten food in the fridge and freezer. Both were very dirty with a noticeable odor. The dishwasher was full of dirty dishes. The oven was full of dirty pans. Most of the dishes in the cupboards had little bits in them as well. There was a fire alarm battery beeping in one of the bedrooms. There was no coffee maker or wine opener or wine glasses or hand soap. There were very few dishes in general, it would have been challenging to cook and serve...

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

Nyssa S.

$546 nightly

$605 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-4-Bedroom-House-In-Superb-Winter-Park.h120488903.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/e8db9438.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/32572eec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/fab2d3be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom (2 Queenbed & 1 Sofabed) | In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/32000000/31950000/31941500/31941472/5cf2d29a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel in International Drive District

[](https://www.expedia.com/Orlando-Hotels-Hyatt-House-Orlando-International-Drive.h31941472.Hotel-Information)

9.4/10

Exceptional

(1,576 reviews)

"Breakfast was excellent! Hotel is very clean. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Danqing

$118 nightly

$133 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-Hyatt-House-Orlando-International-Drive.h31941472.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/130000/120400/120304/0bd0541c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/130000/120400/120304/32ed0efb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/130000/120400/120304/80f72df0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/130000/120400/120304/d478031c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel in Airport North

[](https://www.expedia.com/Orlando-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Orlando-Airport-North.h120304.Hotel-Information)

7.4/10

Good

(1,394 reviews)

"It was great especially the breakfast "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Ahmad Taha

$103 nightly

$116 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Orlando-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Orlando-Airport-North.h120304.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.

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## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=APART_HOTEL)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CONDO)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=VACATION_HOME)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=VILLA)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=COTTAGE)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=APARTMENT)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CABIN)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=HOUSE_BOAT)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America&regionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CHALET)

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## Top Winter Park Hotel Reviews

![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

"spotless room and friendly service"

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

![Caribe Royale Orlando](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/033f2fa5_y.jpg)

### Caribe Royale Orlando

10/10 Excellent

"Excellent "

[](https://expedia.com/Orlando-Hotels-Caribe-Royale-Orlando.h40865.Hotel-Information)

![Sonesta Essential Orlando Airport](https://images.trvl-media.com/lodging/1000000/460000/455400/455359/fb8c35c6_y.jpg)

### Sonesta Essential Orlando Airport

10/10 Excellent

"The room was clean and comfortable. The staff was very professional, friendly and helpful. The breakfast and service were great."

[](https://expedia.com/Orlando-Hotels-Sonesta-Essential-Orlando.h455359.Hotel-Information)

![DoubleTree by Hilton Hotel Orlando at SeaWorld](https://images.trvl-media.com/lodging/1000000/20000/18900/18874/69019073_y.jpg)

### DoubleTree by Hilton Hotel Orlando at SeaWorld

10/10 Excellent

"Always a go to when I need a quick clean comfortable stay been staying with them fort 7 years… "

[](https://expedia.com/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information)

![Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](https://images.trvl-media.com/lodging/1000000/540000/539500/539487/88f9edce_y.jpg)

### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent

"The amenities were amazing and so was the staff. This resort had it all without leaving the area. We wished we would have stayed longer. We definitely would like to come back. They were not able to keep us in the Bella area, however they upgraded our one bedroom for free. I was so happy with the stay! "

[](https://expedia.com/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information)

![Rosen Inn at Pointe Orlando](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653_y.jpg)

### Rosen Inn at Pointe Orlando

10/10 Excellent

"Loved it "

[](https://expedia.com/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information)

![B&B Hotel Orlando International Drive Near Universal](https://images.trvl-media.com/lodging/1000000/30000/26800/26703/8aec2083_y.jpg)

### B&B Hotel Orlando International Drive Near Universal

10/10 Excellent

"Fiquei preucupado quando fiz a reserva,,Porem ao chegar me deparei com hotel novinho,cheiroso,qto espacoso e exc atendimento. Localizacao fantastica ,Cafe manha razoavel porem nada q comprometa,enfim tudo maravilhoso e equipe d hotel sempre pronta a servir. A atendente venezuela Pilim,fora da curva, Sempre Maravilhosa e pronta para lhe atender com.excelencia. Att julio cesar & Paula"

[](https://expedia.com/Orlando-Hotels-Floridian-Express-Extended-Stay-Hotel.h26703.Hotel-Information)

![Universal's Cabana Bay Beach Resort](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/63940f45_y.jpg)

### Universal's Cabana Bay Beach Resort

10/10 Excellent

"great pool"

[](https://expedia.com/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information)

![Hyatt Regency Orlando International Airport](https://images.trvl-media.com/lodging/1000000/10000/2800/2754/acaa1e8b_y.jpg)

### Hyatt Regency Orlando International Airport

10/10 Excellent

"Amazing room!!"

[](https://expedia.com/Orlando-Hotels-Hyatt-Regency-Orlando-International-Airport.h2754.Hotel-Information)

## Find out more about Winter Park

## Winter Park Chalets information

| Number of reviews | 6,103      |
| ----------------- | ---------- |
| Accommodation     | 17 Chalets |
| Lowest Price      | $109       |
| Highest Price     | $605       |

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- [Flights from Atlanta (ATL) to Orlando (ORL) ](https://www.expedia.com/lp/flights/atl/orl/atlanta-to-orlando)
- [Flights from New York (JFK) to Orlando (MCO) ](https://www.expedia.com/lp/flights/jfk/mco/new-york-to-orlando)
- [Flights from Boston (BOS) to Orlando (MCO) ](https://www.expedia.com/lp/flights/bos/mco/boston-to-orlando)

- [Orlando Vacations ](https://www.expedia.com/Orlando.d178294.Destination-Travel-Guides)
- [Walt Disney World® Resort ](https://www.expedia.com/Walt-Disney-World-Resort-Orlando.d6034120.Vacation-Attraction)
- [Albin Polasek Museum and Sculpture Gardens ](https://www.expedia.com/Albin-Polasek-Museum-And-Sculpture-Gardens-Orlando.d6154778.Vacation-Attraction)
- [Winter Park Country Club ](https://www.expedia.com/Winter-Park-Country-Club-Orlando.d6239878.Vacation-Attraction)
- [Kraft Azalea Gardens ](https://www.expedia.com/Kraft-Azalea-Gardens-Orlando.d553248621532654339.Vacation-Attraction)
- [Copland Tennis Stadium ](https://www.expedia.com/Copland-Tennis-Stadium-Orlando.d553248621563220224.Vacation-Attraction)
- [Rollins Museum of Art ](https://www.expedia.com/Rollins-Museum-Of-Art-Orlando.d6154782.Vacation-Attraction)
- [Morse Museum of American Art ](https://www.expedia.com/Morse-Museum-Of-American-Art-Orlando.d6154772.Vacation-Attraction)
- [Casa Feliz Historic Home Museum ](https://www.expedia.com/Casa-Feliz-Historic-Home-Museum-Orlando.d6154784.Vacation-Attraction)
- [Winter Park Corner Shopping Center ](https://www.expedia.com/Winter-Park-Corner-Shopping-Center-Orlando.d553248621532654341.Vacation-Attraction)
- [Rollins College ](https://www.expedia.com/Rollins-College-Orlando.d6154361.Vacation-Attraction)
- [Barker Stadium ](https://www.expedia.com/Barker-Stadium-Orlando.d553248621563220225.Vacation-Attraction)
- [Virginia S. Nelson Rose Garden ](https://www.expedia.com/Virginia-S-Nelson-Rose-Garden-Orlando.d6239868.Vacation-Attraction)
- [Winter Park History Museum ](https://www.expedia.com/Winter-Park-History-Museum-Orlando.d553248621532654329.Vacation-Attraction)
- [Cahall Sandspur Field ](https://www.expedia.com/Cahall-Sandspur-Field-Orlando.d6239859.Vacation-Attraction)
- [Alfond Swimming Pool ](https://www.expedia.com/Alfond-Swimming-Pool-Orlando.d553248621558036313.Vacation-Attraction)
- [All Fired Up ](https://www.expedia.com/All-Fired-Up-Orlando.d553248621532654330.Vacation-Attraction)
- [Lake Virginia ](https://www.expedia.com/Lake-Virginia-Orlando.d553248621532654331.Vacation-Attraction)
- [Crealde School of Art ](https://www.expedia.com/Crealde-School-Of-Art-Orlando.d6239848.Vacation-Attraction)
- [Hannibal Square Heritage Center ](https://www.expedia.com/Hannibal-Square-Heritage-Center-Orlando.d553248621532654328.Vacation-Attraction)
- [Winter Park Playhouse ](https://www.expedia.com/Winter-Park-Playhouse-Orlando.d553248621561885914.Vacation-Attraction)
- [Winter Park Tennis Center ](https://www.expedia.com/Winter-Park-Tennis-Center-Orlando.d636723274468732928.Vacation-Attraction)
- [Lake Rose ](https://www.expedia.com/Lake-Rose-Orlando.d6360988.Vacation-Attraction)
- [Winter Park Village ](https://www.expedia.com/Winter-Park-Village-Orlando.d6239900.Vacation-Attraction)
- [Howell Branch Preserve Pavilion ](https://www.expedia.com/Howell-Branch-Preserve-Pavilion-Orlando.d553248621532654340.Vacation-Attraction)
- [Mead Garden ](https://www.expedia.com/Mead-Garden-Orlando.d6239861.Vacation-Attraction)
- [Hollie Anna Shopping Center ](https://www.expedia.com/Hollie-Anna-Shopping-Center-Orlando.d553248621563220220.Vacation-Attraction)
- [Lake Maitland Terrace Marina ](https://www.expedia.com/Lake-Maitland-Terrace-Marina-Orlando.d553248621563220228.Vacation-Attraction)
- [Enzian Theater ](https://www.expedia.com/Enzian-Theater-Orlando.d6154880.Vacation-Attraction)
- [Winter Pines Golf Club ](https://www.expedia.com/Winter-Pines-Golf-Club-Orlando.d6239892.Vacation-Attraction)
- [Lee Road Shopping Center ](https://www.expedia.com/Lee-Road-Shopping-Center-Fairview-Shores.d553248621563220222.Vacation-Attraction)
- [Visit Orwin Manor ](https://www.expedia.com/Orlando-Orwin-Manor.dx553248635976471367)
- [Lake Lily Park ](https://www.expedia.com/Lake-Lily-Park-Orlando.d553248621532654336.Vacation-Attraction)

- [Car rental Orlando Airport (MCO) ](https://www.expedia.com/Car-Rentals-In-Orlando-Intl.d5194573.Car-Rental-Guide)
- [Car rentals near Orlando ](https://www.expedia.com/Car-Rentals-In-Orlando.d178294.Car-Rental-Guide)
- [Car rentals near Albin Polasek Museum and Sculpture Gardens ](https://www.expedia.com/Car-Rentals-In-Albin-Polasek-Museum-And-Sculpture-Gardens.d6154778.Car-Rental-Guide)
- [Car rentals near Winter Park Corner Shopping Center ](https://www.expedia.com/Car-Rentals-In-Winter-Park-Corner-Shopping-Center.d553248621532654341.Car-Rental-Guide)
- [Car rentals near Rollins College ](https://www.expedia.com/Car-Rentals-In-Rollins-College.d6154361.Car-Rental-Guide)
- [Compact Car Rentals near Rollins College ](https://www.expedia.com/Compact-Car-Rentals-In-Rollins-College.d6154361-tCompact.Car-Rental-Guide-Class)
- [Car rentals near Aloma ](https://www.expedia.com/Car-Rentals-In-Aloma.d553248635975863638.Car-Rental-Guide)

- [Things to do in Orlando ](https://www.expedia.com/Things-To-Do-In-Orlando.d178294.Travel-Guide-Activities)