Vacation to Winter Park

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Winter Park Flight and Hotel Deals

FantasyWorld Resort

FantasyWorld Resort

3.5 out of 5
Save 100% on your flightPrice was $809, price is now $495 per person
per person
Feb 11 - Feb 17
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
4.2/5 Very Good! (4,512 reviews)
Entering the unit walls and cleanliness could use some updating. Several areas with cracked molding and mildew in the tiles. Return vents haven’t been changed in months. Dishes in dishwasher were dirty. Beds are way past their prime and sink. Would have linked a bathroom in the master suite but not a deal breaker. Two story option is great. Screen in porch was missing several screens but fixed within two days. Lots to do for the kids.

Reviewed on Nov 26, 2022

Westgate Palace a Two Bedroom Condo Resort

Westgate Palace a Two Bedroom Condo Resort

4 out of 5
Florida Center
Save 100% on your flightPrice was $622, price is now $418 per person
per person
Jan 5 - Jan 8
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
4/5 Very Good! (1,002 reviews)
Need more staff at the front desk but overall everything was great

Reviewed on Nov 21, 2022

The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Save 100% on your flightPrice was $912, price is now $642 per person
per person
Jan 8 - Jan 14
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
4.1/5 Very Good! (1,342 reviews)
We loved the service, cleanliness, and comfort

Reviewed on Nov 25, 2022

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was $441, price is now $321 per person
per person
Jan 5 - Jan 8
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
3.8/5 Good! (2,796 reviews)
Everything was unique about the property. I was impress how they don’t charge about using the laundry. Some other hotels do. I loved the golf park for the kids and the affordable water park which we enjoyed, very very clean. Everything about this hotel I loved. My family and I would love to go back some day again to the same hotel.

Reviewed on Dec 2, 2022

Insight Hospitality

Insight Hospitality

4 out of 5
Four Corners
Price was $602, price is now $451 per person
per person
Jan 22 - Jan 24
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
4.4/5 Excellent! (78 reviews)
It was a beautiful home and having access to the community club house was amazing!!

Reviewed on Jul 26, 2022

Where to stay in Winter Park

Find the best Winter Park areas and neighborhoods for the activities you enjoy most. Learn more about Winter Park
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    Baldwin Park

    5/5Exceptional!(1 area review)

    Baldwin Park might not have many top sights, but East Orlando Shopping Center and Harry P. Leu Gardens are two attractions nearby that you can check out.

    Find hotel + flight trips in Baldwin Park

Winter Park Hotel Deals

Park Plaza Hotel
Park Plaza Hotel
3 out of 5
307 South Park Avenue , Winter Park, FL, 32789
Fully refundableReserve now, pay when you stay
The price is $188 per night from Dec 5 to Dec 6
$188
per night
Dec 5 - Dec 6
4.2/5 Excellent! (665 reviews)
"I haven’t been to the Plaza in twenty years, and I was excited to see that it had not changed. It’s classic style and friendly atmosphere are the things that impressed me back then and now! Carry on the tradition"

Reviewed on Nov 1, 2022

Park Plaza Hotel
The Alfond Inn
The Alfond Inn
4 out of 5
300 East New England Avenue, Winter Park, FL, 32789
Fully refundable
The price is $223 per night from Dec 19 to Dec 20
$223
per night
Dec 19 - Dec 20
4.7/5 Exceptional! (997 reviews)
"The staff was excellent and extremely friendly."

Reviewed on Nov 28, 2022

The Alfond Inn
Hilton Garden Inn Winter Park
Hilton Garden Inn Winter Park
3 out of 5
1275 Lee Road, Winter Park, FL, 32789
Fully refundableReserve now, pay when you stay
The price is $189 per night from Dec 4 to Dec 5
$189
per night
Dec 4 - Dec 5
4.5/5 Wonderful! (191 reviews)
"I found the staff to be very friendly. The room clean and quiet. I am a 68 yr old women traveling alone and felt safe at all times both in my room and around the premises. Would stay there again and recommend to friends and relatives."

Reviewed on Nov 25, 2022

Hilton Garden Inn Winter Park
See all 12454 properties in Winter Park
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.

Frequently asked questions

How much does a Winter Park vacation package cost?
Browse and book everything in one place with our Winter Park vacation packages, which start from just $321. Choose the hotels and flights that suit your travel plans. Then, add on a few tours or activities for an amazing getaway.
If I'm not able to travel, can I cancel my Winter Park vacation package?
Yes, you can. We totally understand that things don’t always go to plan, so we’re happy to help if you have to make changes to your Winter Park vacation package. You may be able to cancel or amend your itinerary for free if you’ve booked within 24 hours. Your hotel, airline or car rental company may impose a fee if you booked more than 24 hours ago. Look up our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.
How do I get a cheap travel package to Winter Park?
Think of all the thrilling things you could do in Winter Park with a spare $366. If you combine your hotel and airfare bookings into a vacation package, that’s what you could save! You have so much choice with Expedia. In fact, you can select from more than 550 airlines and 1,000,000 hotels around the world. Whether you’re taking off with the whole family or flying solo, planning a getaway to Winter Park is better with a package.
Where should I stay in Winter Park?
Make sightseeing easy by staying someplace close to Winter Park’s terrific attractions. Winter Park Village and Kraft Azalea Gardens are two of the best in the area.
What are the top hotels in Winter Park?
Get your vacation off to a great start by locking in a room at The Alfond Inn. It’s one of most popular properties in Winter Park. Another leading option is Hilton Garden Inn Winter Park.
When is the best time of year to visit Winter Park?
You’ll need to consider your priorities to find the right answer. Typically, you’ll score the best deals in , while is when prices usually rise. Winter Park is at its busiest in . If you’re in the mood for a more relaxed vacation, would be a better time to visit.
How far in advance should I book my Winter Park vacation?
Search Expedia to compare flights ASAP. You can normally purchase a seat up to 12 months prior to departure. If you can’t find your preferred carrier, or you’ve left things to the last moment, don’t despair. Low prices to Winter Park sometimes appear within weeks of the date of departure.
What does an Expedia Winter Park travel package include?
Much of that is up to you. You can choose from a variety of Winter Park packages, such as a flight, rental car and hotel. You can also book a hotel and a flight, or a flight with a rental car. Once you’ve made your booking, you can add on the fun stuff like activities and tours. Whatever your Winter Park escape looks like, you’ll save!
What should I know before booking a Winter Park travel package?
You can save big by bundling your hotels, airfares and rental cars. Once you’ve created your package, you can add on things like day tours or experiences. Your next awesome vacation is only a couple of clicks away.
Does Expedia offer Book Now, Pay Later Winter Park vacation packages?
With a vacation package, you can customize both your getaway and a payment arrangement. Expedia can help reduce financial strain to do with your travel with a Book Now, Pay Later booking, thanks to us joining forces with online lender Affirm. That way, all you have to focus on is preparing to jet off into the sunset.
Can I choose my airline with a Winter Park Expedia vacation package?
With a vacation package, you’re the one in charge. Whether you’re hoping to fly to Winter Park in economy or business class, simply pick from the available airline options. Expedia has access to more than 550 airline partners throughout the world.
Can I travel to Winter Park right now?
For all the information you need about getting to Winter Park, check out our Covid-19 Travel Advisor. Covering travel restrictions, quarantine policies and more, this guide will help make your trip planning go off without a hitch.

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