Downtown Winter Park Rentals

Vacation Rentals in Downtown Winter Park CO

Downtown Winter Park boasts a vibrant array of restaurants, shops and year-round activities for guests staying in a Winter Park vacation rental. Whether you choose to stay on Main Street or within a block, you'll have convenient access to all that the excitement in Downtown Winter Park! 

Stay Winter Park offers a diverse selection of rentals from condos to luxury townhomes. In the summer, guests can enjoy music festivals at Rendezvous Event Center, art festivals, outdoor dining with live music and easy access to hiking and mountain biking trails. During the winter months, visitors can still savor local dining, visit the sledding hill and utilize the free town shuttle for transportation to the ski resort or the town of Fraser.

Excited to plan your getaway? Explore our inventory of downtown Winter Park vacation rentals below and easily book online using our reservation system. For inquiries or special requests, please reach out to our sales team for assistance in creating an unforgettable vacation experience!


Properties Available 144 properties available
Situated in the upper cul de sac of Beaver Village, this unit adjoins the forest, providing stunning views of the Winter Park Resort from the private balcony. The second floor is bathed in natural light, enhancing its appeal. As an end unit, it offers a tranquil and secluded atmosphere. The renovated kitchen is equipped to facilitate both a swift
Beaver Village Unit #1624
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 30
A generously sized and newly updated two bedroom condominium provides an excellent location for families to appreciate outdoor activities and discover the attractions of downtown Winter Park.The spacious living room features hardwood flooring, access to a private deck with forest and river views, a gas fireplace, modern furnishings, a flat screen T
Hot HOT 17
Hi Country Haus Unit 2110
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 11
This luxurious three bedroom unit is situated on the second floor and features a private deck that provides a scenic view of the Fraser River. Positioned to the right of the unit’s entrance, the kitchen features modern appliances that harmonize with the wooden cabinetry and contemporary countertops. Next to the kitchen, the dining room is furnished
Hi Country Haus Unit 1805
Condo -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 4.9 68
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 72
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 newly l
Silverado I Building B Unit 101
Condo -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 9
This remodeled two-bedroom strikes an ideal balance between mountain charm and contemporary comfort, featuring an extensively renovated ground-floor corner unit situated. Located within the established Hi Country Haus community, it is just moments away from Main Street and clubhouse amenities, providing the best of both summer and winter living rig
Hot HOT 11
Hi Country Haus Unit 0701
Condo
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
The bedroom in this one bathroom condo features a Queen bed and a flat screen TV, along with an attached bathroom that has been recently renovated with a new dual vanity and tub/shower combination. An additional sleeping area is available in the main living room on the sofa sleeper. Please note that there is no air conditioning in this unit.The k
Beaver Village Unit #0221R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 1
The kitchen is aesthetically pleasing and well-lit, featuring modern cabinetry, pendant lighting, new countertops, and stainless steel appliances, fully equipped for meal preparations. The adjoining dining area accommodates up to six individuals, with extra bench seating and spaces at the breakfast bar, allowing for a total of ten place settings.T
Beaver Village Unit #0833
Condo -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 9 guests
Rating 4.8 29
This expansive ground floor condominium features three bedrooms and three bathrooms, making it an ideal location for your mountain getaway, and has been updated for enhanced comfort. The living room boasts an open layout with newly installed hardwood flooring, a wood burning fireplace and a 50 inch flat screen HDTV, all of which can be appreciated
Silverado I Building A Unit 101
Condo -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 19
This inviting two-story townhome rental features a spacious open floor plan in the living room, which is equipped with a TV, VCR, and a wood burning fireplace. Additionally, it includes a queen sofa sleeper and provides access to a small private patio. The dining area, which accommodates six individuals with its table and chairs, is located next
Hideaway Village Alpine 4
Townhome -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 35
This condominium features one bedroom, one bathroom and is equipped with all the necessary amenities. It is located on the second floor and includes a private deck with views of the Winter Park Resort. The kitchen is fully stocked with utensils, dishes, pots, pans, a coffee maker, microwave and has seating for two at the breakfast bar.The dining a
Beaver Village Unit #0623R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 23
If you are in search of a newly renovated condominium that offers tranquility during your next holiday, this unit is ideal for you. Situated on the top floor and positioned as an end unit, this location within the building ensures a greater degree of privacy from other neighboring residents.The property underwent a comprehensive renovation in the
Beaver Village Unit #1934
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 42

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