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!

Search Other Popular Vacation Rental Categories:

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

149 properties available

This ground floor condo has updated throughout and is located in building 1 which is close to the shuttle stop on Highway 40 and an easy walk to the clubhouse. There is hardwood flooring throughout main living area with a large comfortable sectional sofa for you to enjoy watching the flat screen tv and gas fireplace and an extra set of windows to b

Beaver Village Unit #0111

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The presence of vaulted ceilings in the primary living space enhances the sense of spaciousness, while the picturesque views of Winter Park Resort contribute a charming aspect to this vacation rental. The expansive dining room offers ample space for mealtime gatherings, and the main living area of the condominium features a gas fireplace that culti

HOT 13

Beaver Village Unit #2032R

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This Winter Park family getaway offers a spacious and wonderful 2-bedroom accommodation. Situated on the ground floor of building 2, it provides convenient access to the free town shuttle and main clubhouse.This unit has undergone an amazing renovation, featuring hardwood flooring throughout the main open floor plan that perfectly complements the

HOT 14

Beaver Village Unit #0211

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This townhome, set against a charming forested backdrop, offers three bedrooms distributed over three levels. The main floor features an open-concept design, highlighted by a living room with vaulted wood-paneled ceilings, a fireplace, complimentary Wi-Fi, a flat screen TV and new carpeting throughout, with the exception of the kitchen area. The k

HOT 13

Timber Ridge Building 2, Unit B

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This Bear Crossing town home has a very spacious interior, high-end finishes throughout and multi-level floor plan. The 2,000 square feet offers more than enough space for a group of eight to spread out and take advantage of the great outdoor activities nearby.A wonderful 3 bedroom 4 bathroom town home provides guests a feeling of seclusion but st

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A spacious 3 bedroom unit with 2 interior levels has 1,212 square feet of living space.The living room has a mountain themed decor with gas fireplace, flat screen TV, DVD, Blue Ray disk player, telephone, free in unit Wi-Fi access and queen sofa sleeper. No air conditioning.In an alcove area adjacent to the living room, is the dining area with sol

Lion's Gate Pines Unit 105

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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

HOT 10

Beaver Village Unit #1934

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A 3 bedroom 2 bathroom unit has 1,128 square feet of living space on two levels.Upon entering the unit, an open living area has a gas fireplace, flat screen TV, DVD, Blue Ray disk player; all surrounded by comfortable furnishings. A queen sofa sleeper is available in the main living area and free in unit Wi-Fi access No air conditioning.Overlooking

Lion's Gate Pines Unit 111

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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

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A well-appointed condominium will enhance your experience in the mountains. The modernized kitchen features new cabinetry, countertops, flooring and a fresh coat of paint. You will have the opportunity to engage with guests in the adjoining dining area, which accommodates six individuals, with extra seating at the breakfast bar.Enjoy your evening

HOT 13

Beaver Village Unit #0612

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This exceptional vacation rental offers a true home-away-from-home experience, characterized by its unique lodge ambiance, featuring rich wooden elements and comfortable furnishings in the main living space. Guests can unwind while enjoying the flat screen TV and the warmth of the gas fireplace, creating an ideal setting for a snug evening. Addit

HOT 11

Beaver Village Unit #1123

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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

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