Winter Park Vacations from $279

Book a Hotel + Flight or Car together to unlock savings

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.
WorldMark Big Bear Lake

WorldMark Big Bear Lake

3 out of 5
Save 100% on your flight
Price was $395, price is now $279 per person
$279
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Ontario (ONT)
9.4/10 Exceptional! (243 reviews)
All around was good

Reviewed on Oct 9, 2025

7767 Sweet Rnch Cir

7767 Sweet Rnch Cir

2 out of 5
Highgrove
Save 100% on your flight
Price was $15,612, price is now $10,224 per person
$10,224
per person
Dec 22 - Dec 28
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Ontario (ONT)
No reviews
Bluegreen Vacations Big Bear Village, an Ascend Collection Resort

Bluegreen Vacations Big Bear Village, an Ascend Collection Resort

4 out of 5
Big Bear Central
Save 100% on your flight
Price was $626, price is now $416 per person
$416
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Ontario (ONT)
9.6/10 Exceptional! (647 reviews)
The suite was great and the price was amazing. The kitchen is well-equipped. The shower had fantastic water pressure and the bed was very comfortable. The only negative I have is that the kitchen knives were incredibly dull so next time I stay I will bring my own. I plan to stay again!

Reviewed on Oct 10, 2025

Dynasty Suites Redlands

Dynasty Suites Redlands

3 out of 5
Save 100% on your flight
Price was $448, price is now $307 per person
$307
per person
Dec 31 - Jan 3
found 14 hours ago
Roundtrip flight included
San Francisco (SFO) to Ontario (ONT)
9.2/10 Wonderful! (1,007 reviews)
Fix the plumbing in the shower.

Reviewed on Oct 12, 2025

N+P Boutique Lodge

N+P Boutique Lodge

4 out of 5
Save 100% on your flight
Price was $929, price is now $637 per person
$637
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Ontario (ONT)
9.8/10 Exceptional! (185 reviews)
What a unique and well

Reviewed on Oct 2, 2025

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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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
$112 nightly
The price is $127 total per night from Oct 28 to Oct 29
$127 total
Oct 28 - Oct 29
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"Very nice place to stay for small group"

Reviewed on Oct 6, 2025

Chateau Big Bear Boutique Hotel, BW Signature Collection
Lagonita Lodge

Lagonita Lodge

3 out of 5
183 Lagonita Ln, Big Bear Lake, CA
$105 nightly
The price is $119 total per night from Oct 15 to Oct 16
$119 total
Oct 15 - Oct 16
Total with taxes and fees
9/10 Wonderful! (3,896 reviews)
"The lake view from the 2nd floor was beautiful. We enjoyed sitting on the balcony looking out at the lake too. The other amenities were wonderful: pontoon boat ride, ice cream social, etc. The staff were all wonderful!!!!"

Reviewed on Oct 8, 2025

Lagonita Lodge
Black Forest Lodge And Cabins

Black Forest Lodge And Cabins

2.5 out of 5
41121 Big Bear Blvd, Big Bear Lake, CA
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $109 total per night from Oct 21 to Oct 22
$109 total
Oct 21 - Oct 22
Total with taxes and fees
8/10 Very Good! (1,013 reviews)
"The room we booked was given away to another group (I looked photos online and booked that room for my particular request) They said we got upgrade to private cabin which is old, lower ceiling (hardly breathable) - worst in many ways. We declined it right away, ending up the room we didn't book but ..."

Reviewed on Oct 12, 2025

Black Forest Lodge And Cabins
See all 5,271 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
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Winter Park

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
IMHO the most epic view for a modest hike in all of SoCal. 30 minutes of hard work and you get the most amazing panoramic view of Big Bear above all the surrounding tree tops. Tip - this is a really popular hike so to avoid the crowds go on a weekday or early morning before most people have gotten up. #AdventurePacked #TroverTips

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

The Village

You can search for that perfect souvenir at The Village during your visit to Big Bear Lake.

The Village

Things to do

Family-Friendly Nature Hike around the Big Bear Valley

Family-Friendly Nature Hike around the Big Bear Valley

$37
per adult
100% of travellers recommend
Family-Friendly Nature Hike around the Big Bear Valley
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.