Downtown Winter Park

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!

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Private Homes, Winter Park Cabins, Base Village & Ski in Ski Out Vacation Rentals, Condo Complexes in Winter Park, Luxury Properties

168 properties available

This beautifully appointed and expansive unit features two bedrooms, a loft and three bathrooms, situated on the sixth floor of the building. Ideal for families, this rental accommodates up to eight guests in beds and includes various amenities to enhance your comfort, such as a Pack-n-play crib, a game table suitable for cards or board games and a

HOT 17

Crestview Place Unit 607

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The optimal placement for this unit is within building number 2, near the main clubhouse and free town shuttle stop. Additionally, this unit has undergone recent renovations to ensure utmost comfort.The kitchen has been renovated with modern countertops, cabinets and new flooring, bringing a fresh look to the area. The open layout enhances the sen

HOT 12

Beaver Village Unit #0221

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This completely renovated one bedroom unit located on the first floor offers an excellent opportunity to enhance your upcoming Winter Park retreat.This condominium is an end unit featuring an additional window in the main living area. It includes a comfortable sofa, which also serves as a sofa sleeper for those requiring extra sleeping accommodati

HOT 12

Hi Country Haus Unit 0406

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Presenting a picturesque wooded scenery, this townhome features a 3 bedrooms townhome spread across 3 levels. The main level boasts an open floor plan with living room showcasing wood paneled vaulted ceilings, a fireplace, free Wi-Fi, a flat screen TV and new carpeting throughout except for the kitchen area. The kitchen is equipped with new counte

HOT 12

Timber Ridge Building 3, Unit B

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This three bedroom townhome at Vasquez Creek, conveniently located on a bus route, offers beautiful river views, a gas fireplace, and is pet friendly, accommodating up to 11 guests. For your next mountain getaway, this well-appointed townhome is an ideal choice, featuring stunning vistas of Vasquez Creek and a prime location within walking distance

HOT 13

Townhome on Vasquez Creek #5

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Dogwood 203 is 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 a

Timber Run Dogwood Unit 3

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Experience this renovated condominium featuring granite countertops in the kitchen, complemented by modern appliances, hardwood flooring and cabinetry. A compact island provides a convenient space for two individuals to enjoy a quick meal. The primary dining area is equipped with a spacious table that accommodates six guests.The living room exude

HOT 14

Beaver Village Unit #1612

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The condominium is well-maintained boasting a modern kitchen equipped with new appliances, cabinets and countertops. The dining space features an elegant wooden table complemented by comfortable cushioned chairs, accommodating up to six individuals. An added perk of the dining area is the extra side window, allowing ample natural light to filter

HOT 13

Beaver Village Unit #0724

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The main living area radiates a warm and inviting ambiance, offering seating for four at the kitchen bar, complemented by a more intimate arrangement for two. Additional ottomans can be utilized to accommodate up to four guests at the table, making it an ideal setting for celebrating the daily accomplishments in the great outdoors. From the welcomi

HOT 17

Beaver Village Unit #1531R

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This unit offers a split level interior and the second floor of the building with 806 square feet of living space designated within the 2 bedrooms and 1 bathroom.From the main entrance, a renovated kitchen has solid wood cabinets, new counter tops, updated appliances and seating at the breakfast bar. A dining table and chairs are adjacent to the k

Lion's Gate Pines Unit 114

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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

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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

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