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 140 properties available
This condominium is situated along Vasquez Creek, conveniently positioned on the free town shuttle route, within a short walking distance to downtown and mere steps from access to the National Forest, as well as hiking, biking, snowshoeing and cross-country skiing trails. The two story, top floor unit serves as an excellent year-round retreat in Wi
Hot HOT 12
Creekside Unit 403
Condo -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 7 guests
Rating 4.9 50
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 14
Trailhead Lodges 821
Condo - Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 70
Luxurious sofas will envelop you as you relax with a game or movie on the television, while also taking pleasure in the gas fireplace within the delightful two bedroom condominium. The spacious layout also provides entry to the private balcony showcasing a view of the Winter Park Ski Resort from the building’s second floor; as well as a dining spa
Beaver Village Unit #0322
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 2
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 18
Beaver Village Unit #0931R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 9
The living room features a vaulted ceiling that enhances the influx of delightful Colorado sunlight, creating a serene environment perfect for enjoying the wood burning fireplace or the flat screen television. The dining area accommodates up to six guests comfortably and is conveniently situated adjacent to the fully equipped kitchen, which includ
Beaver Village Unit #1934R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 7
Situated on the third floor for enhanced tranquility, this charming two bedroom unit features vaulted ceilings that provide ample natural light in the living space. It is furnished for comfort, making it an ideal setting for enjoying games, movies or your preferred TV programs on the flat screen TV, complemented by the warmth of the gas fireplace.
Hot HOT 10
Beaver Village Unit #1932
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 14
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 11
Beaver Village Unit #1113R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.6 5
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
A perfect two bedroom condominium rental in the downtown area is an excellent choice for families seeking a mountain retreat, offering a spacious and renovated living space along with access to clubhouse amenities.The entire unit has undergone a complete renovation, transforming it into a charming modern condominium featuring a contemporary color p
Snowblaze Condos Building C unit 22
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.7 19
This remarkable ground floor two bedroom unit provides a picturesque view of the Fraser River, which can be appreciated from the private deck.The primary living space features a flat screen TV accompanied by a DVD player, elegantly housed in a wooden cabinet adjacent to the wood burning fireplace. It offers complimentary Wi-Fi access and an abunda
Hi Country Haus Unit 1903
Condo -
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 43
The dining room enhances the open floor plan and features a spacious solid maple dining table, perfect for meals. It is conveniently located next to the kitchen, which is equipped with all the essential appliances, including a full refrigerator, stove, dishwasher, microwave. Additionally all necessary flatware, dishes and cookware are provided, m
Beaver Village Unit #1123R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 1
Reserve your upcoming visit to Winter Park in this opulent two bedroom unit at Pine Tree Plaza. Situated on Main street in the heart of downtown, you will have convenient access to dining, shopping, nightlife, summer festivals and the complimentary town shuttle - our condominium is perfect for families or small groups looking to experience the are
Hot HOT 10
303 Pinetree
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 5

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