Winter Park Vacation Packages 2025/2026 from $359

Winter Park flight + hotel vacation packages

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

Empire Inn

Orange Show

Save 100% on your flight

per person

Aug 21 - Aug 26

found 9 hours ago

Roundtrip flight included

Denver (DEN) to Ontario (ONT)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. Express check-out, a computer station, and laundry facilities are also on offer.

@ Marbella Lane - Rejuvenating Single-family Home

Save 100% on your flight

per person

Sep 3 - Sep 6

found 1 day ago

Roundtrip flight included

Denver (DEN) to Ontario (ONT)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and barbecue grills are also provided.

Dynasty Suites Redlands

Save 100% on your flight

per person

Aug 21 - Aug 26

found 9 hours ago

Roundtrip flight included

Denver (DEN) to Ontario (ONT)

This hotel features an outdoor pool and a hot tub. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the sauna and free perks like buffet breakfast and free self parking.

@Marbella Lane - Serene Haven Retreat

per person

Sep 3 - Sep 6

found 1 day ago

Roundtrip flight included

Denver (DEN) to Ontario (ONT)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden is also provided.

Candlewood Suites Loma Linda San Bernardino S by IHG

per person

Aug 21 - Aug 26

found 9 hours ago

Roundtrip flight included

Denver (DEN) to Ontario (ONT)

A gym, self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.

Top Winter Park hotels deals

Chateau Big Bear Boutique Hotel, BW Signature Collection

42200 Moon Ridge Rd, Big Bear Lake, CA

Free Cancellation

Reserve now, pay when you stay

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This hotel features a hot tub, a gym, and a restaurant. There's fun for all ages with a theme park shuttle and an arcade/game room. Enjoy the seasonal outdoor pool and perks like free WiFi and a free area shuttle.

Pool

Hot Tub

Lake Arrowhead Resort and Spa

27984 Highway 189, Lake Arrowhead, CA

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A private beach, a full-service spa, and 2 hot tubs are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 14 conference rooms, along with express check-out. There's a restaurant and a bar/lounge for dining and drinks, and also an outdoor pool on site.

On private beach

Pool

Big Bear Frontier

40472 Big Bear Blvd, Big Bear Lake, CA

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A private beach and an outdoor pool are featured at this hotel. Enjoy the hot tub and perks like free self parking and free WiFi. A lobby fireplace, a picnic area, and barbecue grills are also on offer.

On private beach

Pool

Lagonita Lodge

183 Lagonita Ln, Big Bear Lake, CA

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A marina and an indoor pool are featured at this aparthotel. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.

Pool

Hot Tub

Holiday Inn Resort The Lodge At Big Bear Lake by IHG

40650 Village Drive, Big Bear Lake, CA

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A restaurant and a gym are featured at this hotel. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. Enjoy the sauna and conveniences like a 24-hour front desk and laundry facilities.

Pool

Pet friendly

Black Forest Lodge And Cabins

41121 Big Bear Blvd, Big Bear Lake, CA

Free Cancellation

Reserve now, pay when you stay

Get rates

A full-service spa and an outdoor pool are featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. Enjoy the hot tub and conveniences like a garden and barbecue grills.

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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.

Popular places to visit

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.

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.

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.

Frequently asked questions

How much are vacation packages to Winter Park?

Adventures are calling in Winter Park, with Travelocity vacation packages from as low as $359. Offering both hotels and flights, these incredible deals are an easy way to explore more of our wonderful planet.

Where can I get the best vacation package deals for Winter Park?

There are terrific Winter Park package deals to be scored with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 worldwide properties? Remember this the next time you're ready to tick another place off your bucket list.

Why should I book my Winter Park vacation package via Travelocity?

Whether you're in search of the ultimate unplugged vacation or after the fun and excitement of the big smoke, booking everything with Travelocity saves you time, hassle and money. No need to scour through countless websites to find the best deal --- our Price Match Guarantee ensures you'll always get the lowest price, and our professional customer service experts are available for you round-the-clock.

Will I save money on my Winter Park car rental if I combine it with a hotel or flight?

You certainly can --- and if you also add an activity or experience to your Winter Park vacation package, you'll pick up even greater savings. With one of our affordable packages, you can find things to do around the region that suit you. Then, jump in your rental car and work your way through the list. Disneyland® Resort is one terrific attraction to have a look at. You'll find it 65 mi from Winter Park.