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

149 properties available

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

HOT 12

Beaver Village Unit #0322

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This condo rental is perfectly suited for two couples or singles seeking the comfort of private sleeping quarters, featuring queen beds equipped with new mattresses and a vanity sink in each bedroom. The unit has been updated to feature a flat screen HDTV positioned adjacent to the wood-burning fireplace, along with a VCR and DVD player, all compl

HOT 21

Hi Country Haus Unit 0705

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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 13

Beaver Village Unit #1932

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Enter a beautifully updated and contemporary three bedroom unit! Situated on the ground floor of the building, this residence offers convenient access, featuring hardwood flooring throughout the primary living space.Upon entering the unit, one is greeted by a stunningly remodeled kitchen featuring modern appliances, granite countertops, wooden cab

HOT 12

Hi Country Haus Unit 1801

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A renovated one-bedroom vacation rental provides ample space and is situated in a tranquil setting on the third and highest floor of the building.The unit features hardwood flooring that enhances the contemporary decor and mountain lifestyle. In the living room, guests will appreciate the comfortable furnishings, a gas fireplace, a flat screen HDT

HOT 20

Hi Country Haus Unit 2506

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Discover the vibrant downtown Winter Park from this completely refurbished three bedroom condominium with stunning views, additional amenities and ample space, it serves as an ideal retreat for enjoyment throughout the year.This corner unit located on the third floor features a private entrance and is adorned with numerous windows and a skylight, a

HOT 23

Hi Country Haus Unit 2115

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Consider renting our charming two bedroom residence, which boasts excellent amenities, a generous floor plan and a wonderful neighborhood. It is conveniently located near the vibrant downtown area of Winter Park or offers easy access to the resort and various outdoor activities via a short shuttle ride.The residence’s ground floor features a spaci

HOT 18

45 Idlewild

Private Vacation Home -

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This exquisitely renovated two bedroom residence serves as an ideal destination for a mountain retreat. It is characterized by its bright and welcoming atmosphere, offering breathtaking mountain views from three private decks. Conveniently situated just minutes from downtown Winter Park and roughly three miles from the Winter Park Resort, the pro

HOT 17

Silverado I Building B Unit 204

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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 16

12 Yukon Lane Townhome

Private Vacation Home -

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This one bedroom condominium offers everything necessary for a delightful vacation. The master bedroom is equipped with a queen-sized bed, a flat screen TV and full en-suite bathroom. A fully equipped kitchen features modern cookware, updated appliances, cabinets and countertops. A compact island accommodates seating for 2 and seamlessly connects

HOT 21

Beaver Village Unit #1633R

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A 3 bedroom unit with 1, 292 square feet on the first floor of the complex and has two interior levels.The entry level offers an open floor plan encompassing the living, dining and kitchen areas. In the living room comfortable furnishings surrounding the gas fireplace, flat screen TV with DVD and Blue Ray disk player; and queen sofa sleeper. A bonu

Lion's Gate Pines Unit 103

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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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