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 158 properties available
This two bedroom unit at Trailhead Lodge is ideal for a winter or summer retreat in the Colorado Rocky Mountains.  Gather your family and furry friend for a luxurious yet approachable escape.The unit located on the second floor can be reached by elevator and features a tastefully decorated living room with expansive windows that provide scenic
Hot HOT 11
Trailhead Lodges 422
Condos -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (27)
This townhome in Fraser boasts a spacious backyard, perfect for pets, and is ideal for families looking for a rental property.  It offers ample space, hardwood flooring throughout the unit and excellent amenities. Situated conveniently close to downtown Fraser, with its restaurants, breweries and summer hiking and biking trails, residents can
Hot HOT 18
524 Sun River #8
Townhome - Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (6)
This Winter Park family getaway offers a spacious and wonderful 2-bedroom accommodation.  Situated on the ground floor of building 2, it provides convenient access to the free town shuttle and main clubhouse.This unit has undergone an amazing renovation, featuring hardwood flooring throughout the main open floor plan that perfectly complements
Beaver Village Unit #0211
Downtown Winter Park -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (3)
Perfect for families looking for a homey feel in their vacation rental in this two bedroom two bathroom condo with a mountain theme with a personal touch.The solid hardwood flooring in dining room which will seat 4 to 6 people comfortably, for additional seating try using the kitchen counter that doubles as an extra eating place.  The kitchen
Hot HOT 14
Beaver Village Unit #0521
Downtown Winter Park -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (2)
Situated within the Trailhead Lodges complex and conveniently positioned along the shuttle route, this property serves as the ideal ski getaway for couples, small families or two individuals in search of cozy accommodations.  This delightful one bedroom unit is also in close proximity to the Rendezvous Event Center, which features a sledding h
Hot HOT 15
Trailhead Lodges 731
Condos -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 (46)
This spacious ground floor condominium boasts three bedrooms and three bathrooms, making it a perfect choice for your mountain retreat, and has been modernized for improved comfort.  Additionally, this particular unit is situated at the end of the building, providing extra privacy.The living room features an expansive design complemented by ne
Hot HOT 12
Silverado I Building B Unit 101
Condos -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (1)
Enjoy the night relaxing by the gas fireplace, while watching TV in the living room. Conveniently step out onto the private patio through the sliding glass for a memorable view from the first floor unit.Enhance your mountain getaway with a cozy condominium featuring a renovated kitchen complete with fresh cabinets, countertops, flooring and paint.
Hot HOT 18
Beaver Village Unit #0612R
Condos -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.7 (11)
This first floor unit is situated in a building near the clubhouse and the complimentary town shuttle stop, providing all the amenities  you need for your Colorado getaway. It boasts a spacious kitchen, open floor plan with a living room and separate dining area. The updated kitchen showcases hardwood floors, granite countertops, stainles
Hot HOT 11
Beaver Village Unit #0412
Condos -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (4)
This expansive and recently updated unit provides an excellent location for a mountain retreat at the foot of the slopes at Granby Ranch.  The primary living area features vaulted ceilings, inviting sofas perfect for relaxation, a gas fireplace, flat screen television and stunning mountain vistas through the large windows from this second floo
Hot HOT 19
Mountainside Unit B-20
Condos -
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (6)
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
Hot HOT 11
Trailhead Lodges 821
Condos -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 (17)
The condominium features a cozy interior, complete with modern flooring and new furnishings throughout the primary living space, making it an ideal location for your upcoming Winter Park mountain retreat in this charming three bedroom, three bathroom unit. The primary open floor plan features a living room equipped with a gas fireplace and a 5
Hot HOT 12
Silverado I Building C Unit 101
Condos -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (12)
This fully furnished unit, located next to the owner's lift at Granby Ranch, presents an ideal choice for family rentals and is pet friendly.  It offers the convenience of ski-in/ski-out access and features two bedrooms and a loft with two bathrooms, situated within Building 1 of Summit at Silvercreek, Granby.This condominium on the third
Hot HOT 13
Summit Unit 1303
Condos
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests

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