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 210 properties available
The home will sleep up to 12 and has a wonderful cabin feel as it is located on a secluded, wooded acre with great views of the continental divide, deer, elk, and even moose are often seen browsing through the neighborhood and only five miles from the base of Winter Park Ski Resort, two miles from downtown Winter Park and on the free town shuttle r
Hot HOT 20
61 Jabberwocky
Private Vacation Home - Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 4.5 9
Sumptuous couches will engulf you when enjoying a game or movie on the tv and enjoy the gas fireplace in the wonderful 2 bedroom condo. The open floor plan also includes access to the private deck with a of the Winter Park Ski Resort from the second floor of the building; and dining area that will comfortably seat up to 8 persons.A deluxe kitchen
Beaver Village Unit #0322
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 1
This condo is located on Vasquez Creek, on the free town shuttle route, a close walk to downtown and steps from National Forest access and hiking, biking, snowshoeing and cross-country trails. A two story, top floor condo is great for a year-round getaway to Winter Park. An ideal blend of a serene mountain setting with access to the best that Win
Creekside Unit 403
Condo -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 7 guests
Rating 4.9 17
A wonderfully decorated and spacious unit with 2 bedrooms plus loft and 3 bathroom - 3 story unit that is located on the 6th floor of the building. This great family rental will sleep 8 persons in beds and has other items in the unit to help make your stay comfortable included Pack-n-play crib, game table for cards or board games and a sound bar i
Hot HOT 10
Crestview Place Unit 607
Condo -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.7 7
The condo has a comfortable interior with updated floors and new furniture throughout the main living area for an enjoyable and perfect spot for your next Winter Park mountain getaway in this cozy 3 bedroom, 3 bath condo. The main open floor plan includes living room with gas fireplace, 55” flat screen TV, access to private patio with BBQ grill; di
Silverado I Building C Unit 101
Condo -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 9
The condo has recently gotten a remodeled kitchen with new wood cabinets, tiled flooring, counter tops and stainless steel appliances. In the dining area there is a cozy spot for up to 6 persons and is encompassed within the open floor plan to be engaged with all of the activities. The living room has comfortable seating, a sofa sleeper if there
Beaver Village Unit #1812
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 6
This spacious unit has wonderfully modern furnishings in the living room with a gas fireplace, small deck with mountain views, free Wi-Fi access and TV with VCR player. The open floor concept includes the dining and kitchen area as well. The full kitchen has newer cabinets, appliances, counter tops and tiled flooring and overlooks the dining area
Hot HOT 18
Winterstar Building G #3
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.3 6
Luxurious, new construction this 3 bedroom unit is in the heart of downtown Winter Park. This Timber Fox has a wonderful view from the private patio of the Winter Park Ski Resort and surrounding forested area – perfect spot to relax, enjoy morning coffee and the BBQ grill.The main open floor plan has hardwood flooring and large expansive windows a
Hot HOT 10
Timber Fox Building B Unit 2102
Condo -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 2
Comfortably furnishing are in the living room, accented in a mountain theme with a gas fireplace, flat screen TV, DVD, Blue Ray disk player, telephone, free Wi-Fi access and a queen sofa sleeper. No air conditioning.Lots of window surround the dining area with seating for 8 persons. In the kitchen, recent renovations include solid wood cabinets,
Lion's Gate Pines Unit 117
Condo
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
This non smoking and no pets allowed unit is on the second floor and offers a 1 car garage for parking and private deck with stunning mountain views and a total of 1,200 square feet of living space.In the open living room, a gas fireplace has a cedar panel accent, comfortable furnishings, TV with VCR, queen sofa sleeper, free Wi-Fi access and no a
Timber Run Dogwood Unit 204
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
The main floor of the unit has high vaulted ceilings in the living room area with a modern furnished decor, gas fireplace, flat screen TV, free in unit Wi-Fi access, and access to the private 5th floor balcony will allow you overlooks downtown Winter Park and mountain views.Adjacent to the main living area, the dining room is on an elevated level w
Hot HOT 13
Crestview Place Unit 507
Condo -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.5 22
From the comfy living room couch enjoy the gas fireplace, flat screen TV which includes Blu-Ray, cable TV or the view from the sliding glass doors out to the private balcony. Step outside to use the gas grill and take in the secluded woods, with glimpses of wildlife and distant mountain views make this a choice location from the second floor of the
Hot HOT 13
Beaver Village Unit #0723
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 2

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