Winter Park Vacation Packages

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Top Holiday Package Deals in Winter Park

Price found within the past 48 hours. Click for updated prices.
Empire Inn

Empire Inn

2.5 out of 5
Orange Show
Price was CA $808, price is now CA $666 per person
CA $666
per person
Apr 13 - Apr 17
found 19 hours ago
Roundtrip flight included
Calgary (YYC) to Ontario (ONT)
7.8/10 Good! (1,001 reviews)
Clean, safe and the workers are awesome :) we drove all the way for a concert and had a great stay :)

Reviewed on Nov 24, 2025

Yaamava’ Resort & Casino at San Manuel

Yaamava’ Resort & Casino at San Manuel

5 out of 5
Price was CA $1,704, price is now CA $1,251 per person
CA $1,251
per person
Apr 27 - Apr 30
found 21 hours ago
Roundtrip flight included
Calgary (YYC) to Ontario (ONT)
9.6/10 Exceptional! (93 reviews)
Majority of staff very friendly. It is pricey, borderline ridiculous especially the cafe and buffet. Was told that they have no local competition so can charge as much as patrons willing to pay.

Reviewed on Mar 5, 2026

Best Western Plus Heritage Inn Ontario Rancho Cucamonga

Best Western Plus Heritage Inn Ontario Rancho Cucamonga

2.5 out of 5
Price was CA $1,110, price is now CA $891 per person
CA $891
per person
May 2 - May 8
found 23 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Ontario (ONT)
8.8/10 Excellent! (1,005 reviews)
Convenient location Plenty of parking Online check in Room ready when I showed up

Reviewed on Mar 9, 2026

DoubleTree by Hilton Ontario Airport

DoubleTree by Hilton Ontario Airport

4 out of 5
Racimo
Price was CA $1,350, price is now CA $1,109 per person
CA $1,109
per person
Apr 23 - Apr 27
found 8 hours ago
Roundtrip flight included
Edmonton (YEG) to Ontario (ONT)
8.4/10 Very Good! (1,000 reviews)
Good as I expected waiting on my $200 dollar deposit overall great thank you for everything

Reviewed on Mar 9, 2026

Fireside Lodge

Fireside Lodge

2.5 out of 5
Big Bear Central
Price was CA $1,871, price is now CA $1,540 per person
CA $1,540
per person
Apr 13 - Apr 17
found 19 hours ago
Roundtrip flight included
Calgary (YYC) to Ontario (ONT)
7.6/10 Good! (1,000 reviews)
Great amenities and view, friendly staff. Safe and quiet place. I will be back again!

Reviewed on Mar 1, 2026

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
Mountain lake and sky view in Big Bear California

Moonridge

Skiing and mountain views are notable features of Moonridge. You might consider a stop by Big Bear Mountain Resort while you're exploring the neighborhood.

Find hotels in Moonridge

Winter Park Hotel Deals

Chateau Big Bear Boutique Hotel, BW Signature Collection

Chateau Big Bear Boutique Hotel, BW Signature Collection

3.5 out of 5
42200 Moon Ridge Rd Big Bear Lake CA
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from Mar 29 to Mar 30
CA $141
CA $159 total
Mar 29 - Mar 30
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
Great hot breakfast with a lot of variety. The jacuzzi is nice. Staff was responsive to all our needs - more clean towels, etc.

Reviewed on Mar 7, 2026

Chateau Big Bear Boutique Hotel, BW Signature Collection
Lagonita Lodge

Lagonita Lodge

3 out of 5
183 Lagonita Ln Big Bear Lake CA
The price is CA $121 per night from Mar 15 to Mar 16
CA $121
CA $137 total
Mar 15 - Mar 16
includes taxes & fees
9/10 Wonderful! (4,128 reviews)
The pictures don’t do justice

Reviewed on Mar 8, 2026

Lagonita Lodge
Lake Arrowhead Resort and Spa

Lake Arrowhead Resort and Spa

3.5 out of 5
27984 Highway 189 Lake Arrowhead CA
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from Mar 15 to Mar 16
CA $166
CA $230 total
Mar 15 - Mar 16
includes taxes & fees
8.8/10 Excellent! (1,221 reviews)
We had a beautiful view of the lake--very peaceful. Walking along the pathway to the dock was a highlight. The staff was very friendly and helpful.

Reviewed on Mar 9, 2026

Lake Arrowhead Resort and Spa
See all 5,450 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.
All Inclusive Vacations
All Inclusive Vacations
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Frequently asked questions

How much does a Winter Park vacation package cost?
Custom build your Winter Park vacation package from a low CA $666. 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

Big Bear Visitor Center

After visiting Big Bear Visitor Center, make a plan to see the other sights and activities in Big Bear Lake. Stroll along the lakeside in this quaint area, or seek out the ski slopes.

Big Bear Visitor Center

Bear Mountain Golf Course

Play a round of golf in Big Bear Lake at Bear Mountain Golf Course, and enjoy other activities such as skiing. Stroll along the lakeside or discover the mountain views in this quaint area.

Bear Mountain Golf Course

Things to do

Family-Friendly Nature Hike around the Big Bear Valley

Family-Friendly Nature Hike around the Big Bear Valley

CA $51
per adult
100% of travellers recommend
Family-Friendly Nature Hike around the Big Bear Valley
Ziplining!

Zipline Tour - 9 high-speed ziplines & fun suspension bridge

CA $244
per adult
100% of travellers recommend
Zipline Tour - 9 high-speed ziplines & fun suspension bridge
See all activities in Big Bear Lake
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.