Search Chalets in Winter Park

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
Feb 14 - Feb 16
In two weeks
Feb 21 - Feb 23
In one month
Mar 7 - Mar 9
In two months
Apr 4 - Apr 6

Browse Select Winter Park Chalets

Beautiful Resort like Chalet - North Of Orlando In Longwood, Florida
Exterior

Beautiful Resort like Chalet - North Of Orlando In Longwood, Florida

9.6 out of 10, Exceptional, (14)
"Came to Sanford for softball tournament. Place was great.We felt like we were at home. Pari was wonderful. Would answer call or text right away. Didn’t have any problems or issues. Plan on staying here again if my team goes back to same tournament."
Beautiful Resort like Chalet - North Of Orlando In Longwood, Florida
Hidden Gem Jiminy Cricket
Resort view

Hidden Gem Jiminy Cricket

3.0 star property
Hidden Gem Jiminy Cricket
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.
Don't see what you're looking for?
See all available properties in Winter Park
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winter Park

The View Studio Suites and Event Venue
Property entrance

The View Studio Suites and Event Venue

3.5 star property
8.4 out of 10, Very good, (802)
"Pleasant stay"
The price is CA $128
CA $144 total
includes taxes & fees
Feb 20 - Feb 21
The View Studio Suites and Event Venue
Lake Buena Vista Resort Village & Spa
2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very good, (8341)
"Great property to stay at and fantastic staff!! "
Lake Buena Vista Resort Village & Spa
Florida Hotel & Conference Center in the Florida Mall
Reception

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.0 out of 10, Wonderful, (1733)
"The stay was great, hospitality was great."
The price is CA $285
CA $357 total
includes taxes & fees
Feb 13 - Feb 14
Florida Hotel & Conference Center in the Florida Mall
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.