Winter Holidays in Winter Park CO

Spend the Holiday's in Winter Park Colorado

Experience the enchantment of Winter Park during the winter holidays and immerse yourself in the beauty of this delightful town at its peak season!

Whether you require a spacious residence for family gatherings  to enjoy football games or a cozier setting for a more intimate celebration, consider reserving a large home for your MLK Winter Break in a picturesque, snow-laden escape!

Discover the ideal holiday accommodation in Winter Park Colorado! Our diverse vacation rental options cater to every member of your holiday group.  Gather around the inviting fireplace while admiring the snowfall  through the window or opt for a ski-in/ski-out property for convenient access to the slopes this winter.  Celebrate a holiday weekend in Winter Park to usher in the New Year, with an abundance of exciting activities, restaurant promotions and the perfect location to bid farewell to 2024 and embrace 2025!

            Popular Searches:  Private Homes,Luxury Vacation Rentals, Pet Friendly Rentals, Downtown Winter Park, Condo Complexes,                                Base Village at Winter Park Resort, Ski Group Rentals and Granby Ranch

  Search All Holiday Rentals Below


Thanksgiving 
Winter Park serves as an excellent location for your family's annual gathering, providing an opportunity to relish both the festive occasion and each other's presence, along with a variety of outdoor activities suitable for all age groups!

Search Thanksgiving 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 2024 Rentals

Coming for Christmas instead?  Book your holiday rentals here.


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 2025

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. 

Winter Weather Favorites

Summertime Adventures

Properties Available 216 properties available
A comfortable studio apartment situated on the ski access level, providing convenient entry to the slopes of the Winter Park Resort.The kitchen exudes a contemporary aesthetic, featuring newly installed cabinets, granite countertops, tiled flooring and modern appliances. The sightline from the kitchen to the open-concept living area creates an ide
Hot HOT 15
Iron Horse Building D Unit 5054
Iron Horse Building D Unit 5054
Condo -
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 6
This cheerful and inviting studio condominium situated in Winter Park is ideally positioned along the local free shuttle route and is merely minutes away from Winter Park Resort. Nestled in the vibrant downtown area, this studio condominium at Snowblaze Condos and Athletic Club ensures that you will have access to all the premier activities the tow
Hot HOT 28
Snowblaze Condos Building E unit 310
Snowblaze Condos Building E unit 310
Condo -
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 32
This charming studio unit is ideally situated in a prime downtown location, conveniently near various shops, restaurants, and year-round activities. The free town shuttle stops directly in front of the building, making it an excellent place to unwind after a day of outdoor enjoyment.The open floor layout features newly installed flooring across th
Hot HOT 22
Snowblaze Condos Building E Unit 102
Snowblaze Condos Building E Unit 102
Condo -
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 26
This luminous studio features vaulted ceilings that enhance the spaciousness of the condominium situated on the top floor of the Fraser Crossing building. Its exceptional location is unparalleled, being just a 150 yard stroll to the slopes and the village. This charming unit encompasses 443 square feet and features several interior enhancements, p
Hot HOT 24
Fraser Crossing 3618
Fraser Crossing 3618
Condo -
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 6
This studio unit, encompassing 443 square feet, has been thoughtfully renovated and features new flooring and furnishings. Situated on the fifth floor, it offers stunning views of the Winter Park Resort and is conveniently located just a 150-yard walk from the slopes and the village. The kitchenette is equipped with granite countertops and stainles
Hot HOT 23
Fraser Crossing 3518
Fraser Crossing 3518
Condo -
Bathrooms 1 baths
Guests 2 guests
Rating 4.7 13
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
Hot HOT 10
Trailhead Lodges 821
Trailhead Lodges 821
Condo - Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 9
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
Hot HOT 17
Beaver Village Unit #0721R
Beaver Village Unit #0721R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4 1
This recently renovated one-bedroom condominium is ideal for a small family, a couple or individuals, situated in a prime ski-in/ski-out location. The kitchen features newly installed granite countertops, tiled flooring, and modern appliances, offering an unobstructed view of the main living room. It accommodates two individuals at the counter, wit
Hot HOT 23
Iron Horse Building C Unit 1023
Iron Horse Building C Unit 1023
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.3 3
This one bedroom condo has a mountain theme accents with personal touches making for a perfect spot to rent for families or a couples.The solid hardwood flooring in the 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 offers lots of counte
Hot HOT 13
Beaver Village Unit #0521R
Beaver Village Unit #0521R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 6
This well-appointed and recently renovated one bedroom one bathroom unit is conveniently situated near the town of Winter Park and is accessible via the complimentary town shuttle to Winter Park Resort. The rental is equipped with all essential amenities for a pleasant vacation, including a fully equipped kitchen complete with dishware and cookwar
Hot HOT 26
Beaver Village Unit #0931R
Beaver Village Unit #0931R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4 1
The living area features exotic jewel tones on the walls, complemented by furnishings and accessories in similarly warm and rich hues. This ground floor unit offers the enjoyment of a gas fireplace, a flat screen TV and a private patio. This vacation rental boasts modern enhancements in the kitchen, including new cabinetry and fixtures, as well a
Hot HOT 14
Beaver Village Unit #1113R
Beaver Village Unit #1113R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 1
Adventure awaits! We are thrilled to offer our cozy mountain retreat to you. Our condo is ideally situated just a short 10-minute drive or shuttle ride away from winter skiing and surrounded by summer outdoor activities. Winter Park is a mere 6 miles away and easily accessible via the complimentary shuttle service for all your seasonal adventures.
Hot HOT 32
Waterside West A303
Waterside West A303
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 24

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