Winter Holidays in Winter Park CO

Spend the Holiday's in Winter Park Colorado

Visit Winter Park for the winter holidays and enjoy this charming town during the best time of the year!

Family gatherings needing a large home to watch the football games or something smaller for an intimate gathering. Book a large house for a Winter Break and holidays in a snow covered dream getaway!


  Search All Holiday Rentals Below

Find the perfect Holiday Accommodation in Winter Park Colorado! Our vacation rental lodging options have something for every member of your Holiday Crew! Sit around the warm fireplace while watching the snow from the window or choose a  ski in ski out option to hit the slopes with ease this winter. Enjoy a holiday weekend in Winter Park to start off the New Year. Plenty of great activities, restaurant specials and the ideal spot to say good-bye to 2023 and welcome 2024!


Winter Break - MLK
There is no better place to enjoy a snowy white MLK weekend with us in Winter Park Colorado. Enjoy winter activities like sledding or snowshoeing! Winter Park is bursting with local events that bring the winter season alive!

Search Winter Break Rentals


New Years Eve

Ring in the new year in a place you love with a price you and your partner will ABSOLUTELY LOVE!

Search NYE 2023 Rentals


Spring Break Trips

Experience a great spring break experience!  Enjoy the spring mountain sunshine and fresh powder.  Explore our diverse range of rentals, catering to every budget and taste for groups large and small.

Spring Break Trips 2024

There is never a bad time to visit Winter Park

Winter or Summer, all you have to do is give us a call! We are local reservationist are here to help you plan your trip to Winter Park Colorado. 


Properties Available 217 properties available
A 3 bedroom 2 bathroom unit has 1,128 square feet of living space on two levels.Upon entering the unit, an open living area has a gas fireplace, flat screen TV, DVD, Blue Ray disk player; all surrounded by comfortable furnishings. A queen sofa sleeper is available in the main living area and free in unit Wi-Fi access No air conditioning.Overlooking
Lion's Gate Pines Unit 111
Condo
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Hugh expansive windows provide the unforgettable view of the ski resort and the vaulted ceilings make the overall space feel even bigger. Enjoy the comfy sofas to relax, watch TV or warm the toes in front of the gas fireplace. Next to this area, the dining area and kitchen are great for the cook to interact with the rest of the group while prepar
Arrow at Winter Park Unit 248
Townhome -
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.8 12
A first floor unit with 1,200 square feet of living space that offer 2 bedrooms and 2 bathrooms. The open living room with a wood paneled accent wall to compliment the lovely furnishings, gas fireplace, TV, VCR, queen sofa sleeper and no air conditioning.In the center of the main room, the dining area overlooks the private balcony and will seat 6
Timber Run Dogwood Unit 7
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 1
The living zone is an immaculate space with in floor radiant heat, 10' ceilings, custom lighting, smart TV and gas fireplace and panoramic mountain views from the cushy leather furniture. Plenty of large, picturesque windows will offer more than one view of the mountains and surrounding mountain beauty from this main room. Outside is a large wrap
Elk Creek Condos B103
Condo -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 12 guests
Rating 4.9 13
A spacious 3 bedroom unit with 2 interior levels has 1,212 square feet of living space.The living room has a mountain themed decor with gas fireplace, flat screen TV, DVD, Blue Ray disk player, telephone, free in unit Wi-Fi access and queen sofa sleeper. No air conditioning.In an alcove area adjacent to the living room, is the dining area with sol
Lion's Gate Pines Unit 105
Condo
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Guests will enjoy the focal point of this beautiful townhome on the main floor living room offering huge expansive windows provide the unforgettable view of the ski resort and the vaulted ceilings make the overall space feel even bigger. Enjoy the comfy sofas to relax, watch TV or warm the toes in front of the gas fireplace. Next to this area, th
Hot HOT 14
Antlers At Lakota 406
Townhome -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 5 3
This Winter Park condo fits all the requirements on your vacation rental list – contemporary furnishings, decor and accessories take you back to the 60's and 70's but with a modern touch from today. Located on the ground floor, easy access to and from the main parking lot when you arrive on your vacation to the open floor plan of the unit. This ar
Hot HOT 17
Beaver Village Unit #1112
Condo -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 3
This is a first floor unit has two levels with 1,212 square feet of living space to accommodate the 3 bedrooms and 2 bathrooms.In the living room, guests will enjoy the gas fireplace, flat screen TV, DVD, Blue Ray disk player, free Wi-Fi access and extra sleeping area on the queen sofa sleeper. No air conditioning.The dining area has an open view o
Lion's Gate Pines Unit 122
Condo
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Wonderful, spacious 2-bedroom family getaway in Winter Park. This ground floor unit is in building 2 providing easy access the free town shuttle and main clubhouse.Incredible remodel in this unit with hardwood flooring throughout main open floor plan to compliment the large sectional sofa (can also be used for additional sleeping with the sofa sle
Beaver Village Unit #0211
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 2
This is unit has 1,200 square feet of living space and is on the first floor of the building. The rental is also non smoking and has a no pet 2 bedroom 2 bathroom rental.The living room has a gas fireplace, TV with VCR, queen sofa sleeper and a wood paneled accent wall and free in unit Wi-Fi access. No air conditioning.The dining area is adjacent
Timber Run Evergreen Unit 107
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Newly renovated counter tops, wood cabinets, updated appliances, new tiled flooring and wood paneled ceiling found in the dining area continues into the kitchen. In the common hallway near the kitchen is one full bathroom. The unit offers 1,101 square feet with a tri-level floor plan and the private deck off the main living room is located on the
Meadow Ridge Court 28 Unit 6
Condo -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 6
A spacious 1,200 square feet, this unit is on the first floor and has a living room decorated in with a southwestern decor, gas fireplace, TV, VCR, a queen sofa sleeper, free Wi-Fi access and no air conditioning.Next to the living room is the dining area with large table and chair setting for 6 people. Guests can also access the private deck with m
Timber Run Dogwood Unit 2
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests

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