Christmas Holiday rentals in Winter Park

Book Your Christmas Vacation in Winter Park, Colorado

Secure your Christmas holiday getaway in the Colorado Rockies with StayWinterPark.

We cater to families of all sizes, groups and offer intimate cabins for couples.  Leave the hustle and bustle of the city behind and immerse yourself in the picturesque snowy landscapes, festive atmosphere, seasonal activities and private hot tubs to soothe your muscles after a day filled with outdoor adventures.

Moreover, we provide flexible booking dates if you have yet to discover your perfect rental.  

Choose from a variety of popular vacation accommodations including Winter Park Cabins, Downtown Winter Park, Pet Friendly Vacation Homes, Base Village of Winter Park Resort, Ski-in/Ski-out condos and Granby Ranch.  






Properties Available 171 properties available
Welcome to our cabin at 1585 Moose Run! Savor a tranquil escape enhanced by stunning views of the night sky filled with countless stars and the surrounding forest. This welcoming cabin can comfortably accommodate up to 5 guests (including pets!) and is located on a generous plot of land, just a 15-minute drive from downtown Winter Park. The cabin i
Hot HOT 12
1585 Moose Run
Cabin - Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 5 guests
Rating 5 30
This well-appointed and recently renovated one bedroom one bathroom unit is conveniently situated near the town of Winter Park and is accessible via the complimentary town shuttle to Winter Park Resort. The rental is equipped with all essential amenities for a pleasant vacation, including a fully equipped kitchen complete with dishware and cookwar
Beaver Village Unit #0931R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 26
Welcome to our condo at Waterside West Unit A303! Adventure awaits! We are thrilled to offer our cozy mountain retreat to you. Our condo is ideally situated just a short 10-minute drive or shuttle ride away from winter skiing and surrounded by summer outdoor activities. Winter Park is a mere 6 miles away and easily accessible via the complimentary
Waterside West A303
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 171
Discover this exceptional one-bedroom condominium, fully equipped for a remarkable retreat. In the evenings, gather around the gas fireplace after a day in the snow to warm up and indulge in your favorite shows on the Smart TV, which offers both streaming and cable options in the charming living room. The space also features a sofa sleeper for addi
Hot HOT 12
Fraser Crossing 3417
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 1
The warm mountain ambiance created by the rich wooden furniture and decorations beautifully contrasts with the bright, airy wall colors and high vaulted ceiling in this three bedroom unit on the third floor. Guests will find convenient access to the main clubhouse, located in the adjacent building as well as the free town shuttle stop nearby.The ki
Beaver Village Unit #0131
Condo -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.8 22
Why You’ll Love this Colorado Escape• Located at the base of Granby Ranch Resort for incredible access to mountain activities • Private hot tub and outdoor propane fire pit for evening relaxation• Lower level game area featuring a large sectional and foosball table• Dedicated workspace in the primary suite with a desk and monitor• Professionally M
Hot HOT 15
308 Valley Ranch Lodge
Private Vacation Home
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Welcome to our townhome at Hideaway Village Lenado 4.Renovated unit with private patio and 2 private decks, forest and river views. This unit has tri-level interior and will sleep up to 6, on the free town shuttle and is located in a quiet Winter Park neighborhood and close to many outdoor hiking, biking, snowshoe and cross country trails. Ideal m
Hideaway Village Lenado 4
Townhome -
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 5 34
A gas fireplace provides a warm and welcoming atmosphere during chilly winter days and nights, as well as on the rare cool summer evenings. The living room is furnished with comfortable seating, allowing for an enjoyable experience while watching flat screen TV and it offers convenient access to the private patio from this ground floor unit. Addi
Beaver Village Unit #0712R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 48
This fully furnished 2 bedroom condo is pet friendly, situated adjacent to the owner's lift at Granby Ranch for ski-in/ski-out access, private deck with views, and a gas fireplace.is an excellent option for family rentals and is also pet-friendly. It provides the advantage of and includes two bedrooms along with a loft and two bathrooms, This condo
Hot HOT 15
Summit Unit 1303
Condo - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 52
The interior of this vacation rental is adorned with a calming color palette, complemented by contemporary mountain-style furnishings and decor throughout the renovated space. The kitchen is equipped with modern appliances, elegant countertops and light wood cabinetry, seamlessly connecting to the dining area, which boasts a spacious table with ben
Beaver Village Unit #1824
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 27
Welcome to our condo at WinterStar Unit A6! This delightful and spacious Pet Friendly townhome in Fraser offers breathtaking mountain views from its private deck and patio, complemented by two interior levels that foster a tranquil rental experience. It is perfectly situated close to a range of outdoor activities accessible throughout the year. Ne
Winterstar Building A #6
Condo - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 6
Experience a genuine Grand Lake cabin retreat in the Rocky Mountains with this 3-bedroom property featuring a private outdoor hot tub, a spacious interior layout, and situated in a tranquil neighborhood, yet just a short drive from downtown Grand Lake and directly across from Shadow Mountain Lake, perfect for thrilling summer water sports.The cabin
279 Shorewood Dr
Cabin -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 56

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