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 226 properties available
Visitors are guaranteed to appreciate the elegantly renovated kitchen, which features stainless steel appliances, granite countertops, newly installed hardwood flooring, and cabinetry, It is fully equipped with cookware, dishes and utensils. allowing for the preparation of delightful meals throughout their stay.The presence of vaulted ceilings enh
Hot HOT 14
Beaver Village Unit #2032
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 37
The living room provides a wonderful spot for relaxation, featuring a gas fireplace, a 50” flat screen TV and private deck overlooking the Winter Park Ski Resort in this 1 bedroom condo.The kitchen is aesthetically pleasing and well-lit, featuring modern cabinetry, pendant lighting, new countertops, and stainless steel appliances, fully equipped fo
Beaver Village Unit #0833R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 4
The living room features a fireplace that is ideal for chilly evenings in both summer and winter. Take a look at the collection of books in the owner’s library, neatly arranged along the wall, perfect for days when you feel like staying indoors and reading a book or watching a movie on the flat screen TV. Guests also have access to the private pat
Beaver Village Unit #0711R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 36
This charming and expansive pet friendly three bedroom unit is located in the very center of downtown Winter Park. The Trailhead Lodge unit offers a stunning view from the back deck overlooking the Winter Park Ski Resort and downtown area. It serves as an excellent location for enjoying morning coffee, featuring an outdoor dining area and provide
Hot HOT 10
Trailhead Lodges 131
Condo - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 9 guests
Rating 5 235
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
Hot HOT 11
Beaver Village Unit #0712R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 27
Beaver Village Condominiums represent the ideal blend of comfort and convenience, situated a mere 1.5 miles from the Ski Area, and only a five minute walk from the vibrant downtown shopping and dining district of Cooper Creek Square. In the summer, a bike path provides direct access from the property to the extensive mountain biking trail system i
Hot HOT 11
Beaver Village Unit #1821
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.6 16
Experience a getaway in the ideal mountain retreat for your upcoming mountain holiday. This stunning location is situated on 40 acres, just a brief 10 minute drive from downtown Winter Park. It is pet friendly, constructed off the grid in 1998, boasting 3,884 square feet of space, and can comfortably house up to 11 guests.The spacious layout of the
Hot HOT 20
Miles Behind Log Cabin
Cabin - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 10 guests
Rating 4.9 88
A cozy, pet friendly studio apartment located on the second floor, offering easy access and a delightful view of the mountains and surrounding landscape and lots of on-site amenities.The kitchenette is fully equipped with modern cabinetry, countertops, and hardwood flooring throughout the unit, complemented by contemporary appliances and includes a
564 Silvercreek Inn
Condo - Pet Friendly
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 31
Welcome to Apex Peak! This luxurious 2-bedroom, 2-bath condo is situated on the top floor of the Founder's Pointe building, featuring soaring ceilings and breathtaking mountain views. You will appreciate the expansive vistas from your adirondack chairs on the private balcony! This spacious unit comfortably accommodates up to 6 adults, providing all
Founders Pointe 4649
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.9 28
True ski in ski out condo within Base Camp One at Granby Ranch with a great view from the private deck, in unit washer and dryer and elevator access to the unit on the third floor.This 3 bedroom unit offers plenty of space for your and your family to stretch out and enjoy! The open floor plan features hardwood flooring throughout the living and ki
Hot HOT 15
Base Camp Cir #305
Condo -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 9
Trailhead 821 is an excellent destination for families and is pet friendly, offering a sledding hill suitable for all ages, as well as fire pits for warming up at the Rendezvous Event Center. In the summer, visitors can enjoy the skate park and outdoor gymnasium. The property is conveniently accessible via the free town shuttle, making it an idea
Trailhead Lodges 821
Condo - Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 79
This traditional two bedroom condominium in Winter Park offers everything necessary for your vacation and is situated on the third floor of the building. A fully equipped kitchen features modern cookware, updated appliances, cabinets and countertops. A compact island provides seating for two and opens into the dining area, which accommodates an a
Hot HOT 10
Beaver Village Unit #1633
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 7

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