Winter Park Vacations

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to $580 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Winter Park Vacation

Discover the unique personality of Winter Park with a customized Winter Park vacation package. From its hiking to its skiing, this neighborhood offers lots of opportunities for relaxation and fun. When it's time to get out and explore, you'll find plenty of popular attractions nearby including Snow Summit, Bear Mountain and Alpine Slide at Magic Mountain. Visit one, two or all during your trip to Winter Park. Whatever your ideal Winter Park vacation looks like, you can make it a reality with Expedia.

The Latest Winter Park Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Ontario

Baymont by Wyndham Ontario

2.5 out of 5
per person
Sep 19 - Sep 22
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Ontario (ONT)
6.4/10 (924 reviews)
The staff here are excellent. The area is starting to look better than it did three years ago. Great service.

Reviewed on Apr 22, 2024

Ontario Airport Inn

Ontario Airport Inn

2.5 out of 5
per person
Jul 31 - Aug 3
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Ontario (ONT)
8.2/10 Very Good! (1,070 reviews)
Love using this hotel when flying out of Ontario airport. They are very friendly, reasonably priced, you can park your car there while out of town, and they shuttle you to and from the airport.

Reviewed on Jun 23, 2024

Hotel Seville

Hotel Seville

2 out of 5
per person
Aug 15 - Aug 18
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Ontario (ONT)
8.6/10 Excellent! (1,000 reviews)
Easy access to freeway. Rooms are clean and quiet. Friendly staff.

Reviewed on Jun 15, 2024

Economy Inn - Ontario Airport/Chino

Economy Inn - Ontario Airport/Chino

2 out of 5
per person
Aug 15 - Aug 18
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Ontario (ONT)
6.8/10 (217 reviews)
bed was ok, the common area was dirty and all the people smoking right outside their rooms/ stairs/ parking lot. why have a smoke free room when all the smoking its done in the property

Reviewed on Jun 20, 2024

Hampton Inn & Suites Ontario

Hampton Inn & Suites Ontario

2.5 out of 5
per person
Aug 15 - Aug 18
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Ontario (ONT)
8.6/10 Excellent! (1,001 reviews)
The lady at the front desk when first checking in was very sweet, wish I remembered her name. then the lady I seen the next two days didn’t really have a good customer service attitude. She always seemed bothered or something. Never welcoming. If I asked her anything she never knew the answer she walked to the back to ask whoever was back there. Breakfast was amazing and the housekeepers were very friendly and helpful! Also, there’s a little sign in the bathroom that says if you forgot to pack something ask the desk, they have it complementary, but when I did they said they didn’t have any of what I was asking for (toothbrush, etc.)

Reviewed on Jun 13, 2024

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
Default Image

Boulder Bay

5/5(1 area review)

If you're spending some time in Boulder Bay, Boulder Bay Park and Metcalf Bay are top sights worth seeing.

Find hotel + flight trips in Boulder Bay

Winter Park Hotel Deals

Best Western Big Bear Chateau
Best Western Big Bear Chateau
3.5 out of 5
42200 Moon Ridge Rd, Big Bear Lake, CA
Fully refundableReserve now, pay when you stay
The price is $130 per night from Jul 1 to Jul 2
$130
$146 total
includes taxes & fees
Jul 1 - Jul 2
8.4/10 Very Good! (1,004 reviews)
Cozy Hotel
"Cozy hotel with great staff"

Reviewed on Jun 21, 2024

Best Western Big Bear Chateau
Lake Arrowhead Resort and Spa
Lake Arrowhead Resort and Spa
3.5 out of 5
27984 Highway 189, Lake Arrowhead, CA
The price is $161 per night from Jun 26 to Jun 27
$161
$208 total
includes taxes & fees
Jun 26 - Jun 27
8/10 Very Good! (1,005 reviews)
"Really Beautiful property.Great staff. The Food is supper yummy......Bartender was really nice, and just had a great time. I will be back!"

Reviewed on Jun 21, 2024

Lake Arrowhead Resort and Spa
Lagonita Lodge
Lagonita Lodge
3 out of 5
183 Lagonita Ln, Big Bear Lake, CA
The price is $115 per night from Jun 26 to Jun 27
$115
$129 total
includes taxes & fees
Jun 26 - Jun 27
9/10 Wonderful! (3,299 reviews)
"Great place"

Reviewed on Jun 22, 2024

Lagonita Lodge
See all 5,596 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Winter Park vacation package cost?
Custom build your Winter Park vacation package from a low $319. Pick from any combination of rental cars, flights and hotels to build the trip you’ve been dreaming about. Be sure to add on a few activities!
How do I get a cheap travel package to Winter Park?
You’ll save piles of cash if you bundle your hotels, car rentals and flights into a Winter Park travel package. Sometimes cheap means fewer options. But that’s not the case with Expedia. We offer over 550 airlines and 1,000,000 hotels throughout the world, so you’ll always have plenty of options to choose from. Like to save even more? Add some exciting activities to your package deal and unlock even bigger discounts! After all, travel is about more than just getting to your destination.
Where should I stay in Winter Park?
If you want to be in the middle of the action, stay near Snow Summit. Many happy campers book a hotel around this renowned attraction.
What are the top hotels in Winter Park?
If it’s your very first time in Winter Park, lock in a room at Best Western Big Bear Chateau or Moose Manor - Hot Tub | Pool Table. Both offer friendly service and are favorites with many savvy travelers.
How far in advance should I book my Winter Park vacation?
Be rewarded with the widest variety and the lowest prices by booking your adventure to Winter Park early. Airlines typically sell tickets anywhere up to a year in advance, so secure your spot as soon as possible. Having said that, Expedia is dedicated to giving you the best bargains around, so there’s never a bad time to book your dream vacation!
What does an Expedia Winter Park travel package include?
It all depends on what type of escape you’re thinking about. Winter Park vacation deals can include flights, car rentals and hotels. You can mix and match to find the travel package that suits your style and budget. You can also add on activities and experiences after you’ve booked to pick up even bigger discounts.
What should I know before booking a Winter Park travel package?
Get ready to save with an Expedia travel package. Combine your flights, rental cars and hotels and score fantastic discounts. You’re not restricted to hotels, however. We’ve got oceanfront condos, creek-side mountain cabins and even treehouses and ranches!
Can I choose my airline with a Winter Park Expedia vacation package?
Most definitely. Expedia has access to more than 550 partner airlines throughout the world, so you can design your Winter Park getaway according to your budget and needs.
If I'm not able to travel, can I cancel my Winter Park vacation package?
Your situation can change unexpectedly, so yes. You may be able to cancel or change your Winter Park vacation package for free if you’ve booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel or make changes, but your hotel, car rental company or airline may charge additional fees. Want more information? Check out our Customer Service Portal. We’ll help make sure your trip goes off without a hitch.

Discover the most popular places to visit in Winter Park

Image for Snow Summit

Snow Summit

4.5/5(761 reviews)

Hit the slopes in Big Bear Lake with a visit to Snow Summit. Stroll along the lakeside or discover the mountain views in this quaint area.

Snow Summit
Image for Castle Rock Trail

Castle Rock Trail

4/5(16 reviews)

Enjoy a trip to Castle Rock Trail and popular activities like skiing in Big Bear Lake. Stroll along the lakeside or discover the mountain views in this quaint area.

Castle Rock Trail
Image for Big Bear Alpine Zoo

Big Bear Alpine Zoo

4.5/5(18 reviews)

Why not meet the animals who call Big Bear Alpine Zoo home during your trip to Big Bear Lake? Amble around this quaint area's lakeside, or seek out the ski slopes.

Big Bear Alpine Zoo

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.