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

168 properties available

Explore our brand new exquisite 2-bedroom, 2-bathroom condominium located in the center of downtown Winter Park! This flawless residence showcases top-notch contemporary aesthetics and comes fully furnished, perfect for your own use or as a vacation rental. Conveniently located near the main street, this unit provides easy access to Winter Park's d

Arrow at Winter Park Unit 202

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An open floor plan includes the living room with flat screen TV, DVD, Blue Ray disk player, gas fireplace, free Wi-Fi access and a queen sofa sleeper. No air conditioning.The large table in the dining area can accommodate 8 persons for meals. In the renovated kitchen, guests will enjoy the new appliances, granite counter tops and solid wood cabin

Lion's Gate Pines Unit 116

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Organize your escape to this splendid pet friendly vacation residence in Winter Park Colorado. This expansive home provides all the comforts and amenities essential for an ideal family holiday, featuring three bedrooms and 2,790 square feet of living space spread across three levels, all just minutes from Winter Park Resort. The primary level feat

HOT 23

12 Yukon Lane Townhome

Private Vacation Home -

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This property offers an excellent setting for a small family or a couple seeking to experience downtown Winter Park, along with convenient access to local attractions. The updated one bedroom unit is located on the second floor, featuring a shuttle stop directly outside and a recreation building adjacent to the unit. The kitchenette is equipped wit

Hi Country Haus Unit 0309

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Visitors can catch sight of a moose or a fox strolling outside through the patio sliding doors or the dining room window of this lovely and updated one-bedroom condo. Positioned on the ground floor (also an end unit for increased peace and quiet).The primary living space features tiled in-floor heating, a cozy sofa with a queen-sized sofa sleeper.

HOT 13

Beaver Village Unit #0414R

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This 3 bedroom 2 bathroom unit offers 1, 212 square feet of interior living space on the first floor of the building.The main living room has an open floor plan with gas fireplace, flat screen TV with DVD player with Blue Ray disk player, free in unit Wi-Fi access and queen sofa sleeper. No air conditioning.In the adjacent dining room, guests will

Lion's Gate Pines Unit 102

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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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Experience breathtaking river vistas and the convenience of being mere steps away from Vasquez Creek in this meticulously remodeled multi-level townhome, which perfectly combines a tranquil mountain environment with proximity to the finest attractions that Winter Park provides. The complimentary town shuttle route and is conveniently located within

HOT 18

Townhome on Vasquez Creek #8

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A first floor unit with 1,212 square feet and two levels, guests have an open floor plan encompassing the gas fireplace, flat screen TV with DVD and Blue Ray disk player, free Wi-Fi access and queen sofa sleeper in the main living room. No air conditioning.In the dining area that is adjacent to the living room, there is a comfortable table and chai

Lion's Gate Pines Unit 123

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Reserve your upcoming Winter Park getaway in this recently renovated one bedroom unit at Beaver Village Condos, conveniently located near the clubhouse facilities, a short walk from town and the complimentary shuttle service.The updated kitchen appliances and lighting enhance the evening ambiance for cooking your preferred dish. The dining area off

Beaver Village Unit #0332

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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

HOT 31

Hi Country Haus Unit 1805

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This beautifully renovated two bedroom condominium enhances your Winter Park getaway significantly. Situated on the third floor, this unit features vaulted ceilings in the spacious open-concept main area. The hardwood flooring throughout perfectly complements the stunning kitchen, which boasts new wood cabinetry, stainless steel appliances and co

Beaver Village Unit #1734

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