Search Chalets in Winter Park

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct
No exact matches found, but these alternatives could be just right

Recommended hotels in Winter Park

Exterior

Cute 5-bedroom house in peaceful Winter Park

Cute 5-bedroom house in peaceful Winter Park
Winter Park
10.0 out of 10, Exceptional, (1 review)
"This property is perfect for a family get together. Very clean and close to so many restaurants and entertainment. The communication the host was great. I would definely stay there again."
United States
Mary Ellen R.
The price is AED 918
AED 1,142 total
includes taxes & fees
23 Jun - 24 Jun
Cute 5-bedroom house in peaceful Winter Park
Exterior

Quiet and safe neighborhood come to this great place with lots of room for relax

Quiet and safe neighborhood come to this great place with lots of room for relax
Orlando
9.4 out of 10, Exceptional, (3 reviews)
"Pool is very inviting"
United States
Geri Lamborn M.
The price is AED 489
AED 1,074 total
includes taxes & fees
28 Jun - 29 Jun
Quiet and safe neighborhood come to this great place with lots of room for relax
Property grounds

1-bedroom vacation room just 12 minutes from University of Central Florida

1-bedroom vacation room just 12 minutes from University of Central Florida
Orlando
9.6 out of 10, Exceptional, (4 reviews)
"Great location close to lots of things to do. Very clean and cozy. Quiet neighborhood, very friendly owners. Will definitely go back."
United States
jamie l.
The price is AED 238
AED 651 total
includes taxes & fees
23 Jun - 24 Jun
1-bedroom vacation room just 12 minutes from University of Central Florida
Exterior detail

Charming home @wp. Patio +Gazebo. close to highwys

Charming home @wp. Patio +Gazebo. close to highwys
Fairview Shores
5.4 out of 10, (3 reviews)
"Very clean and location was great"
United States
Vicki V.
The price is AED 364
AED 821 total
includes taxes & fees
23 Jun - 24 Jun
Charming home @wp. Patio +Gazebo. close to highwys
Exterior

Funky Remodeled Otown Bungalow Sleeps 8

Funky Remodeled Otown Bungalow Sleeps 8
Fairview Shores
10.0 out of 10, Exceptional, (1 review)
"Easy booking/check-in process, great location"
United States
Julia K.
The price is AED 465
AED 935 total
includes taxes & fees
21 Jul - 22 Jul
Funky Remodeled Otown Bungalow Sleeps 8
Exterior

The Canopy on Periwinkle- A Home Away From Home

The Canopy on Periwinkle- A Home Away From Home
Goldenrod
10.0 out of 10, Exceptional, (1 review)
"Clean and tidy"
United States
Randall W.
The price is AED 732
AED 1,507 total
includes taxes & fees
23 Jun - 24 Jun
The Canopy on Periwinkle- A Home Away From Home
Exterior

Comfy Tiny Home @WP. Large Private Deck+Queen bed

Comfy Tiny Home @WP. Large Private Deck+Queen bed
Fairview Shores
The price is AED 448
AED 795 total
includes taxes & fees
1 Jul - 2 Jul
Comfy Tiny Home @WP. Large Private Deck+Queen bed
Exterior

Spacious 5-bedroom house in gorgeous Winter Park

Spacious 5-bedroom house in gorgeous Winter Park
Winter Park
10.0 out of 10, Exceptional, (2 reviews)
"Rented this property for a friend's engagement party and it worked super well. Host was super nice and great with communication"
United States
Hannah F.
The price is AED 900
AED 1,125 total
includes taxes & fees
6 Jul - 7 Jul
Spacious 5-bedroom house in gorgeous Winter Park
Smart TV, video games

Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence

Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Goldenrod
10.0 out of 10, Exceptional, (4 reviews)
"Nice and roomy!"
United States
Ashley C.
The price is AED 992
AED 1,983 total
includes taxes & fees
1 Jul - 2 Jul
Serene Mid-Century 3/2 w/Bonus Room and Huge Shaded Yard w/Fence
Interior

Cozy home 5min to Park Ave and Downtown Orlando

Cozy home 5min to Park Ave and Downtown Orlando
Fairview Shores
The price is AED 596
AED 1,098 total
includes taxes & fees
1 Jul - 2 Jul
Cozy home 5min to Park Ave and Downtown Orlando
Front Side Balcony Suite, 1 King | Balcony view

Park Plaza Hotel

Park Plaza Hotel
3.0 star property
Park Avenue District
8.6 out of 10, Excellent, (1,003 reviews)
"It was a lovely place and I’m definitely going to stay there again!"
United States
Sarah
The price is AED 645
AED 726 total
includes taxes & fees
30 Jun - 1 Jul
Park Plaza Hotel
Exterior detail

Mills House @WP. Sleeps 11 Renovated. Queen beds

Mills House @WP. Sleeps 11 Renovated. Queen beds
Fairview Shores
8.0 out of 10, Very Good, (2 reviews)
"Comfortable beds and plentiful TV screens. Nice central location to shopping and dining. Lights are bright without dimming options, and some fixtures not working. "
United States
Larry S.
The price is AED 642
AED 1,231 total
includes taxes & fees
28 Jun - 29 Jun
Mills House @WP. Sleeps 11 Renovated. Queen beds
Exterior

Hilton Garden Inn Winter Park

Hilton Garden Inn Winter Park
3.0 star property
Winter Park
9.2 out of 10, Wonderful, (707 reviews)
"Clean room, friendly staff"
United States
Dudley
The price is AED 731
AED 832 total
includes taxes & fees
28 Jun - 29 Jun
Hilton Garden Inn Winter Park
Terrace/patio

The Alfond Inn

The Alfond Inn
4.0 star property
Winter Park
9.6 out of 10, Exceptional, (1,001 reviews)
"Always the perfect stay! The Alfond Inn is consistently nice and very welcoming!"
United States
kelly
The price is AED 925
AED 1,152 total
includes taxes & fees
28 Jun - 29 Jun
The Alfond Inn
Exterior

SpringHill Suites by Marriott Winter Park

SpringHill Suites by Marriott Winter Park
2.5 star property
Winter Park
9.2 out of 10, Wonderful, (381 reviews)
"Friendly front staff, clean property, modern looking, large area for breakfast."
United States
Kara
The price is AED 621
AED 707 total
includes taxes & fees
12 Jul - 13 Jul
SpringHill Suites by Marriott Winter Park
Exterior

Cute 5-bedroom,6bed house in superb Winter Park.

Cute 5-bedroom,6bed house in superb Winter Park.
Winter Park
4.0 out of 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
Nyssa S.
The price is AED 1,102
AED 1,392 total
includes taxes & fees
1 Jul - 2 Jul
Cute 5-bedroom,6bed house in superb Winter Park.
Exterior

5/4 King bed LUX Arcade near WP/CP & DT Orlando ‼️

5/4 King bed LUX Arcade near WP/CP & DT Orlando ‼️
College Park
10.0 out of 10, Exceptional, (1 review)
"had a great time. beautiful house"
United States
katie L.
The price is AED 8,972
AED 11,547 total
includes taxes & fees
23 Jun - 24 Jun
5/4 King bed LUX Arcade near WP/CP & DT Orlando ‼️
Exterior

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
3.0 star property
International Drive District
8.6 out of 10, Excellent, (1,658 reviews)
"Breakfast was great Clean room Good location"
Canada
Tracy
The price is AED 303
AED 341 total
includes taxes & fees
13 Jul - 14 Jul
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
Exterior

Hyatt House Orlando International Drive

Hyatt House Orlando International Drive
4.0 star property
International Drive District
9.4 out of 10, Exceptional, (1,951 reviews)
"Great place to stay"
United States
Idoel
The price is AED 426
AED 480 total
includes taxes & fees
5 Jul - 6 Jul
Hyatt House Orlando International Drive
Waterslide

Holiday Inn Resort Orlando Suites - Waterpark by IHG

Holiday Inn Resort Orlando Suites - Waterpark by IHG
3.5 star property
Orlando
8.0 out of 10, Very Good, (131 reviews)
"Hotel was perfect"
United States
Unique
The price is AED 327
AED 554 total
includes taxes & fees
24 Jun - 25 Jun
Holiday Inn Resort Orlando Suites - Waterpark by IHG
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Park Hotel Reviews

Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

10/10 Excellent
"Everything was nice, beautiful, and clean villa. If I had to rate our stay, it would be an eight out of ten. Why? The king beds in the suites were very, very uncomfortable. We asked the front desk for a foam mattress topper, but they did not have one. The young lady at the desk was very helpful; she suggested using a lot of blankets to help. It wasn’t too bad. And the toilet seat was loose, but they came right away and took care of it."
Twengela 3-night trip
Posted less than an hour ago
Lake Buena Vista Resort Village & Spa