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 224 properties available
An upgraded two bedroom townhome offers a generous 880 square feet across two levels of interior space. This rental property maintains a strict no smoking and no pets policy. The unit provides numerous vantage points overlooking the Continental Divide, as well as the surrounding valley and forest. The primary living area features an open layout,
Hideaway Village Columbine 7
Townhome -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 3.5 2
This vacation rental features a stunning, luminous and inviting interior that has been recently renovated, making it an excellent choice for families or small groups, accommodating up to 8 guests. The primary level of the unit features hardwood flooring that compliments the contemporary western decor. Alongside the breakfast bar, there is a dinin
Snowblaze Condos Building A unit 33
Condo -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 19
This property is perfectly suited for two couples or a small family gathering and it is a brief walk to access the town shuttle. The cozy 2-bedroom condominium, situated on the second floor of the building in Fraser within the Grand Park neighborhood, is conveniently located near trails, activities and events, making it an excellent place to relax
Hot HOT 15
Cozens Pointe Building G Unit 202
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 23
Experience an unforgettable mountain retreat in this newly constructed three-bedroom townhome with modern interior design, an open floor plan, private deck with mountain and golf course view with plenty of space for families, friend groups or anyone looking for luxurious but affordable lodging accommodation near the Grand Elk golf course.The main u
174 Eagle Ridge
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.7 4
The vacation rental features a newly designed kitchen equipped with pendant lighting, luminous cabinetry, stainless steel appliances and granite countertops. The open-concept layout includes a living room and dining area, furnished with a table that comfortably seats six. The living space is enhanced by a plush couch and armchair, complemented by a
Beaver Village Unit #0721R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 7
This newly constructed, luxurious three bedroom unit is situated in the vibrant center of downtown Winter Park. The Timber Fox offers a splendid view from its private patio, overlooking the Winter Park Ski Resort and the adjacent forested landscape, making it an ideal location to unwind, savor morning coffee and utilize the BBQ grill.The primary o
Hot HOT 21
Timber Fox Building B Unit 2102
Condo -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 22
The attractive furniture in the primary living space provides an excellent area to unwind, appreciate the gas fireplace, flat screen TV and entrance to the secluded patio. A modernized dining space accommodates seating for four individuals.The renovated kitchen features hardwood flooring, granite countertops, stainless steel appliances and wooden c
Hot HOT 15
Beaver Village Unit #0412R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 5
This condo rental is perfectly suited for two couples or singles seeking the comfort of private sleeping quarters, featuring queen beds equipped with new mattresses and a vanity sink in each bedroom. The unit has been updated to feature a flat screen HDTV positioned adjacent to the wood-burning fireplace, along with a VCR and DVD player, all compl
Hi Country Haus Unit 0705
Condo -
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 4.8 43
Experience the luxury of this spacious and stunning home that is pet friendly and has so much to offer! Homer’s Hideaway is a newly constructed, 3 bedroom plus loft, 3.5 bath private residence that can comfortably sleep 10 people. Located in the desirable Grand Park neighborhood, it is perfect for a large family or two families vacationing togethe
71 Alder Brook Homer’s Hideaway
Private Vacation Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 47
Cozy, downtown Winter Park 1 bedroom condo that has been renovated into an ideal mountain getaway - great for couples or small families. One block to main street, clubhouse amenities, forest views and easy access to the free town shuttle.Our 1 bedroom condo is situated on the second floor of the building and offers an open floor concept in the mai
Hi Country Haus Unit 1009
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.6 21
This exceptionally spacious and modern two-bedroom condominium, located in the Reserve at Ten Mile Creek Apartments, offers mountain views from the private patio on the ground floor and facilitates easy access to numerous outdoor activities at Granby Ranch Resort. The unit features a generous open floor plan that includes the living area and gourme
Ten Mile B-102
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 7
This magnificent custom mountain residence boasts one of the finest locations, positioned on the 8th fairway of the acclaimed Pole Creek Golf Course, offering breathtaking views of Sheep Mountain and Indian Peaks. Our home serves as a luxurious mountain sanctuary nestled on two private acres, ensuring both seclusion and stunning vistas in every dir
144 Rainbow - Fairways at Pole Creek
Private Vacation Home - Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 5 4

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