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

166 properties available

Whether you’re here for skiing or to bask in the beautiful summer weather, our location is unbeatable. We are just a short walk from downtown Winter Park and approximately two miles from the Winter Park Resort. This two bedroom two bath condo on the second floor offers all the amenities you need, including a private deck with views of the Winter P

HOT 5383

Beaver Village Unit #0623

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It is essential to consider a stay at Kings Crossing 13 during your upcoming visit to Winter Park. This townhome features three bedrooms and three bathrooms and is conveniently located in downtown Winter Park, within walking distance to numerous restaurants, a movie theater with bowling alley and the Grand Park Recreation Center. Additionally, the

Kings Crossing Townhome 13

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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 7782

12 Yukon Lane Townhome

Private Vacation Home -

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This inviting two-story townhome rental features a spacious open floor plan in the living room, which is equipped with a TV, VCR, and a wood burning fireplace. Additionally, it includes a queen sofa sleeper and provides access to a small private patio. The dining area, which accommodates six individuals with its table and chairs, is located next

HOT 6685

Hideaway Village Alpine 4

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This expansive rental unit spans 1,085 square feet and features two bedrooms and two bathrooms. It includes a master suite and provides scenic views, making it an ideal choice for families or small groups. The condo is located on the second floor.The spacious living room, integrated into the open floor plan, features comfortable furnishings, a wo

HOT 6176

Hi Country Haus Unit 2111

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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

HOT 5948

Hi Country Haus Unit 1903

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In the open floor plan, the living room has a gas fireplace and flat screen TV surrounded by comfortably furnishings. Additional amenities include local telephone access, free Wi-Fi, DVD and Blue Ray disk player and queen sofa sleeper. No air conditioning.Located behind the living area is the dining room. This area has lots of windows, solid wood

Lion's Gate Pines Unit 121

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In the main living room of the unit, large comfortable furnishings compliment a wood paneled accent wall, TV, VCR/DVD, gas fireplace, free in unit Wi-Fi access, queen sofa sleeper and no air conditioning. The dining area provides guests access the private balcony with wonderful mountain views and the large table offers seating for 8 persons.A full

Timber Run Cedar Unit 3

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The main living room of this two bedroom two bathroom condo features vaulted ceilings, allowing ample natural light to filter in and creating a sense of openness. Renovated to perfection, our previous guests have consistently rated this condo as excellent. The cozy couches in the living room offer a delightful place to unwind by the gas fireplace,

HOT 452

Beaver Village Unit #0333

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A vintage one-bedroom condominium provides a cozy rental option, featuring a private balcony and situated on the ground floor of the building allowing for convenient access to parking and the complimentary town shuttle service.In the primary living area, unwind by the gas fireplace, enjoy the television equipped with a VCR, and make use of the quee

HOT 5987

Hi Country Haus Unit 2501

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The attractive furniture in the primary living space provides an excellent area to unwind, appreciate the gas fireplace, flat screen TV and entrance to the secluded patio. A modernized dining space accommodates seating for four individuals.The renovated kitchen features hardwood flooring, granite countertops, stainless steel appliances and wooden c

HOT 5607

Beaver Village Unit #0412R

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This completely renovated three bedroom apartment located on the third floor of the building, offers a tranquil retreat with stunning views, all while being conveniently close to the vibrant activities on Main Street in downtown.The living room is elegantly appointed with high-quality furnishings, featuring a wood fireplace, a flat screen TV, and a

HOT 5939

Hi Country Haus Unit 2121

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