Winter Park Vacations
Pack those stellar shades. We have Winter Park vacation deals for you!
If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Winter Park – great memories and a tall tale or two.
Hotwire can help you find your travel bliss with Winter Park vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!
Pack everything you want – then take half of it out
We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.Bring comfortable walking shoes on your trip to Winter Park
No one should have to endure walking tours in dress shoes or high heels. No one.Bring photocopies of your passport or license
You flew home from a great Winter Park vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.Don’t underestimate the power of earplugs
Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.Always carry some cash
You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.Explore like a local
Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Winter Park well.Winter Park Flight + Hotel Packages
Fri, Nov 27 - Tue, Dec 1
Hopkins Intl. - Orlando Intl.
$1,600
The price now is $747 per personFlight + Hotel
Fri, Jan 15 - Tue, Jan 19
LaGuardia - Orlando Intl.
$797
The price now is $456 per personFlight + Hotel
Fri, Dec 11 - Mon, Dec 14
Hopkins Intl. - Orlando Intl.
$381
The price now is $237 per personFlight + Hotel
Fri, Dec 18 - Mon, Dec 21
Hopkins Intl. - Orlando Intl.
$369
The price now is $240 per personFlight + Hotel
Mon, Jan 4 - Tue, Jan 12
Hopkins Intl. - Orlando Intl.
$1,033
The price now is $717 per personFlight + Hotel
Thu, Dec 17 - Sun, Dec 20
Philadelphia Intl. - Orlando Executive
$308
The price now is $214 per personFlight + Hotel
Sat, Dec 26 - Wed, Dec 30
Minneapolis - St. Paul Intl. - Orlando Intl.
$584
The price now is $416 per personFlight + Hotel
Mon, Jan 4 - Tue, Jan 12
Hopkins Intl. - Orlando Intl.
$633
The price now is $464 per personFlight + Hotel
Wed, Dec 30 - Sat, Jan 2
Hopkins Intl. - Orlando Intl.
$1,770
The price now is $1,334 per personFlight + Hotel
Fri, Dec 18 - Mon, Dec 21
Hopkins Intl. - Orlando Intl.
$433
The price now is $332 per personFlight + Hotel
Wed, Dec 30 - Sun, Jan 3
Hopkins Intl. - Orlando Intl.
$1,289
The price now is $998 per personFlight + Hotel
Fri, Dec 18 - Mon, Dec 21
Hopkins Intl. - Orlando Intl.
$314
The price now is $245 per personFlight + Hotel
Winter Park Vacation Packages 3-4 Night Stays
Fri, Nov 27 - Tue, Dec 1
Hopkins Intl. - Orlando Intl.
$1,600
The price now is $747 per personFlight + Hotel
Fri, Jan 15 - Tue, Jan 19
LaGuardia - Orlando Intl.
$797
The price now is $456 per personFlight + Hotel
Fri, Dec 11 - Mon, Dec 14
Hopkins Intl. - Orlando Intl.
$381
The price now is $237 per personFlight + Hotel
Fri, Dec 18 - Mon, Dec 21
Hopkins Intl. - Orlando Intl.
$369
The price now is $240 per personFlight + Hotel
Thu, Dec 17 - Sun, Dec 20
Philadelphia Intl. - Orlando Executive
$308
The price now is $214 per personFlight + Hotel
Wed, Jan 6 - Sun, Jan 10
LaGuardia - Orlando Intl.
$510
The price now is $357 per personFlight + Hotel
Sat, Dec 26 - Wed, Dec 30
Minneapolis - St. Paul Intl. - Orlando Intl.
$584
The price now is $416 per personFlight + Hotel
Wed, Dec 30 - Sat, Jan 2
Hopkins Intl. - Orlando Intl.
$1,770
The price now is $1,334 per personFlight + Hotel
Fri, Dec 18 - Mon, Dec 21
Hopkins Intl. - Orlando Intl.
$433
The price now is $332 per personFlight + Hotel
Wed, Dec 30 - Sun, Jan 3
Hopkins Intl. - Orlando Intl.
$1,289
The price now is $998 per personFlight + Hotel
Wed, Dec 23 - Sun, Dec 27
O'Hare Intl. - Orlando Intl.
$3,366
The price now is $2,611 per personFlight + Hotel
Fri, Dec 18 - Mon, Dec 21
Hopkins Intl. - Orlando Intl.
$314
The price now is $245 per personFlight + Hotel
Winter Park Vacation Packages 5-7 Night Stays
Sun, Jan 10 - Sun, Jan 17
Minneapolis - St. Paul Intl. - Orlando Intl.
$637
The price now is $374 per personFlight + Hotel
Thu, Dec 24 - Thu, Dec 31
O'Hare Intl. - Orlando Intl.
$866
The price now is $547 per personFlight + Hotel
Wed, Nov 25 - Mon, Nov 30
LaGuardia - Orlando Intl.
$873
The price now is $570 per personFlight + Hotel
Mon, Jan 11 - Sat, Jan 16
O'Hare Intl. - Orlando Intl.
$565
The price now is $381 per personFlight + Hotel
Mon, Dec 7 - Sun, Dec 13
Minneapolis - St. Paul Intl. - Orlando Executive
$616
The price now is $440 per personFlight + Hotel
Wed, Nov 25 - Mon, Nov 30
Hopkins Intl. - Orlando Intl.
$745
The price now is $538 per personFlight + Hotel
Sun, Jan 10 - Fri, Jan 15
Philadelphia Intl. - Orlando Intl.
$658
The price now is $479 per personFlight + Hotel
Thu, Dec 24 - Thu, Dec 31
O'Hare Intl. - Orlando Intl.
$986
The price now is $730 per personFlight + Hotel
Wed, Nov 25 - Mon, Nov 30
Hopkins Intl. - Orlando Intl.
$1,817
The price now is $1,347 per personFlight + Hotel
Thu, Dec 24 - Thu, Dec 31
O'Hare Intl. - Orlando Intl.
$1,409
The price now is $1,049 per personFlight + Hotel
Wed, Nov 25 - Mon, Nov 30
Hopkins Intl. - Orlando Intl.
$563
The price now is $421 per personFlight + Hotel
Wed, Nov 25 - Mon, Nov 30
Hopkins Intl. - Orlando Intl.
$1,152
The price now is $876 per personFlight + Hotel
Last Minute Hotel Deals
Estimated price for 1 night/2 adults
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Frequently Asked Questions About Winter Park
When is the best time of the year to find Winter Park vacation package deals?
is the best time to find cheap Winter Park vacation deals.
When are the high and low seasons for Winter Park vacations?
are the busiest months for Winter Park vacations, but have the smallest crowds.
Where can I find the best last minute vacation deals for Winter Park?
Only on Hotwire can you find last minute vacations from over 11327 Winter Park destinations.
What if I have to cancel my trip to Winter Park?
The fastest path to canceling your booking is through one of our self-serve tools found at https://vacation.hotwire.com/lp/coronavirus-travel
Book your Winter Park Vacation
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Hotels in Neighborhoods Near Winter Park
Hotels Near Points of Interest in Winter Park
- Hotels near Full Sail University
- Hotels near Rollins College
- Hotels near Winter Park Village
- Hotels near Kraft Azalea Gardens
- Hotels near Casa Feliz Historic Home Museum
- Hotels near Mead Garden
- Hotels near Lee Road Shopping Center
- Hotels near Morse Museum of American Art
- Hotels near Lake Virginia
- Hotels near Albin Polasek Museum and Sculpture Gardens
- Hotels near Crealde School of Art
- Hotels near All Fired Up
- Hotels near Winter Park Playhouse
- Hotels near Alfond Swimming Pool
- Hotels near Winter Park Country Club
- Hotels near Winter Park Corner Shopping Center
- Hotels near The Center of Winter Park Shopping Center
- Hotels near Virginia S. Nelson Rose Garden
- Hotels near Winter Pines Golf Club
- Hotels near Winter Park History Museum