Winter Park Chalets

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jul 18 - Jul 20
In two weeks
Jul 25 - Jul 27
In one month
Aug 8 - Aug 10
In two months
Sep 5 - Sep 7

Chalets in Winter Park

We don't have any properties that match your exact search

Recommended hotels in Winter Park

The Alfond Inn
Stunning hotel entrance with a central tower and beautifully landscaped surroundings.

The Alfond Inn

4.0 star property
9.4 out of 10, Exceptional, (1004)
"The hotel staff, restaurants and accommodations are very nice."
$294 nightly
The price is $331
Jul 17 - Jul 18
Total includes taxes and fees
The Alfond Inn
1-bedroom vacation home just 12 minutes from University of Central Florida
Relax by the pool, surrounded by a paved walkway.

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

$154 nightly
The price is $171
Jul 13 - Jul 14
Total includes taxes and fees
1-bedroom vacation home just 12 minutes from University of Central Florida
Park Plaza Hotel
Experience the vibrant atmosphere of this bustling commercial district, where unique storefronts like Jewels, Kohl, and Original showcase a variety of items.

Park Plaza Hotel

3.0 star property
8.6 out of 10, Excellent, (999)
"There is something magical about this place."
$168 nightly
The price is $188
Jul 22 - Jul 23
Total includes taxes and fees
Park Plaza Hotel
Hilton Garden Inn Winter Park
Reception area with a counter and seating, display shelves, and refrigerated section.

Hilton Garden Inn Winter Park

3.0 star property
9.2 out of 10, Wonderful, (546)
"It is an excellent hotel, reasonable rates, great location with shopping and every type of restaurant you could want. "
$162 nightly
The price is $183
Jul 20 - Jul 21
Total includes taxes and fees
Hilton Garden Inn Winter Park
Magic Studio
Relax by the pool surrounded by lush greenery and comfortable outdoor seating.

Magic Studio

10.0 out of 10, Exceptional, (2)
"Clean, roomy for two, comfortable bed, Met all our needs. Plan to stay there again."
$154 nightly
The price is $171
Jul 28 - Jul 29
Total includes taxes and fees
Magic Studio
SpringHill Suites by Marriott Winter Park
Welcome to Springhill Suites, featuring a modern architectural design with a flat roof and glass facade.

SpringHill Suites by Marriott Winter Park

2.5 star property
9.0 out of 10, Wonderful, (287)
"Staff were super friendly and accommodating. Overall excellent experience!"
$181 nightly
The price is $203
Jul 16 - Jul 17
Total includes taxes and fees
SpringHill Suites by Marriott Winter Park
Stylish Boutique Guest house in Winter Park
Relax in a serene outdoor setting with a pergola, bar, and seating area amidst lush greenery.

Stylish Boutique Guest house in Winter Park

10.0 out of 10, Exceptional, (87)
"We loved the location cleanliness accessibility "
$293 nightly
The price is $326
Jul 13 - Jul 14
Total includes taxes and fees
Stylish Boutique Guest house in Winter Park
Mills House @WP. Sleeps 11 Renovated. Queen beds
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, oven, and tiled surfaces.

Mills House @WP. Sleeps 11 Renovated. Queen beds

10.0 out of 10, Exceptional, (1)
"This was a quaint little place with plenty of sleeping. The fenced in back yard with a canopy cover and chairs was a nice bonus. The kitchen was sufficiently stocked and newly remodeled. There were new smart TV ‘s in each room. There was a Publix right up the road as well as lots of great restaurants. We also enjoyed an antique mall (in the Publix plaza). We would highly recommend this place to others ."
$293 nightly
The price is $326
Aug 3 - Aug 4
Total includes taxes and fees
Mills House @WP. Sleeps 11 Renovated. Queen beds
Charming 3-bedroom house with WiFi, AC in welcoming Winter Park
Enjoy cooking in this well-equipped kitchen with a large island, stainless steel appliances, and a spacious backsplash.

Charming 3-bedroom house with WiFi, AC in welcoming Winter Park

$387 nightly
The price is $428
Jul 14 - Jul 15
Total includes taxes and fees
Charming 3-bedroom house with WiFi, AC in welcoming Winter Park
La Quinta Inn & Suites by Wyndham Orlando UCF
Welcome to our reception area, featuring a stunning mural and comfortable seating.

La Quinta Inn & Suites by Wyndham Orlando UCF

3.0 star property
8.6 out of 10, Excellent, (2542)
"Best hotel in Orlando "
$94 nightly
The price is $106
Jul 20 - Jul 21
Total includes taxes and fees
La Quinta Inn & Suites by Wyndham Orlando UCF
Hampton Inn Orlando Southeast Nona
Relax in a cozy outdoor space with sofas, chairs, and a central fire feature, surrounded by lush greenery.

Hampton Inn Orlando Southeast Nona

2.5 star property
9.2 out of 10, Wonderful, (488)
"Perfect location for our family trip. Clean rooms and breakfast included. "
$94 nightly
The price is $105
Jul 21 - Jul 22
Total includes taxes and fees
Hampton Inn Orlando Southeast Nona
Lake Nona Wave Hotel
Relax by the pool surrounded by colorful umbrellas and lounge chairs.

Lake Nona Wave Hotel

4.0 star property
9.6 out of 10, Exceptional, (1010)
"It was a good location and a fun looking hotel with some cool features."
$232 nightly
The price is $261
Aug 10 - Aug 11
Total includes taxes and fees
Lake Nona Wave Hotel
Hyatt Regency Orlando International Airport
Relax by the pool surrounded by palm trees and lounge chairs.

Hyatt Regency Orlando International Airport

4.0 star property
9.4 out of 10, Exceptional, (3369)
"Great location and stay "
$195 nightly
The price is $219
Jul 16 - Jul 17
Total includes taxes and fees
Hyatt Regency Orlando International Airport
Fairfield Inn By Marriott Orlando Airport
Waffles and breakfast essentials are served at this buffet.

Fairfield Inn By Marriott Orlando Airport

3.5 star property
9.2 out of 10, Wonderful, (2174)
"Would stay there again. "
$84 nightly
The price is $95
Aug 12 - Aug 13
Total includes taxes and fees
Fairfield Inn By Marriott Orlando Airport
Ramada by Wyndham Suites Orlando Airport
Relax in a cozy space with a neatly made bed, flat-screen TV, and workspace area.

Ramada by Wyndham Suites Orlando Airport

3.0 star property
8.2 out of 10, Very Good, (4605)
"Excellent location, service and rooms!!"
$77 nightly
The price is $86
Jul 13 - Jul 14
Total includes taxes and fees
Ramada by Wyndham Suites Orlando Airport
Hampton Inn Orlando-International Airport
Relax by the rectangular pool surrounded by lounge chairs and umbrellas.

Hampton Inn Orlando-International Airport

2.5 star property
9.0 out of 10, Wonderful, (1398)
"Good place, if you need to stay close to the airport."
$93 nightly
The price is $104
Jul 20 - Jul 21
Total includes taxes and fees
Hampton Inn Orlando-International Airport
Wingate by Wyndham - Orlando International Airport
Two single beds with white linens and a central nightstand.

Wingate by Wyndham - Orlando International Airport

3.0 star property
8.8 out of 10, Excellent, (3523)
"excellent hotel "
$73 nightly
The price is $82
Jul 13 - Jul 14
Total includes taxes and fees
Wingate by Wyndham - Orlando International Airport
Best Western Plus Sanford Airport/Lake Mary Hotel
Enjoy a delicious breakfast at our breakfast area, featuring a self-service food station with a variety of baked goods and fresh fruit.

Best Western Plus Sanford Airport/Lake Mary Hotel

2.5 star property
7.2 out of 10, Good, (1387)
"close to airport"
$77 nightly
The price is $87
Jul 15 - Jul 16
Total includes taxes and fees
Best Western Plus Sanford Airport/Lake Mary Hotel
Hyatt House Orlando Airport
Relax in style with a comfortable sofa and matching armchairs around a central table.

Hyatt House Orlando Airport

2.0 star property
9.6 out of 10, Exceptional, (2312)
"Great stay"
$119 nightly
The price is $134
Jul 13 - Jul 14
Total includes taxes and fees
Hyatt House Orlando Airport
Hyatt Place Orlando Airport
Enjoy cooking in this well-equipped kitchen with an oven, microwave, and ample storage.

Hyatt Place Orlando Airport

3.0 star property
8.8 out of 10, Excellent, (1200)
"The staff was very helpful and shuttle service made this a super convenient stay!"
$110 nightly
The price is $123
Aug 4 - Aug 5
Total includes taxes and fees
Hyatt Place Orlando Airport
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free