Downtown Winter Park Rentals

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, Colorado Cabins, Pet Friendly Rentals, Winter Park Base Village , Ski-In, Ski-Out Condo Rentals, Condo Complexes, Luxury Vacation Rentals, Fraser, Tabernash, Granby, Grand Lake

145 properties available

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

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Stay Longer in Winter Park, Save Bigger

Sink into vacation mode in the Fraser Valley and Winter Park area and enjoy 20% off 7–21 night stays with promo code LTR26. Travel between April 14 and December 18, 2026, and book by December 10, 2026, to lock in your savings.*

Looking for something beyond a three-week stay? We'll help you plan a longer stay that works for you, contact us at (800) 215-6535 or [email protected] to inquire about flexible options and best pricing.

*Offer is valid on new online bookings when you book by December 10, 2026, for length of stays between 7 and 21 days between April 14 and December 18, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Hi Country Haus Unit 1801

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This traditional two bedroom condominium in Winter Park offers everything necessary for your vacation and is situated on the third floor of the building. A fully equipped kitchen features modern cookware, updated appliances, cabinets and countertops. A compact island provides seating for two and opens into the dining area, which accommodates an a

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Beaver Village Unit #1633

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This four bedroom unit features an exceptional remodel! Guests will appreciate the newly installed flooring, modern furnishings and the generous space of this condo, which comfortably accommodates up to 10 individuals. Situated on the third floor of the building, the open floor plan features a vaulted ceiling that incorporates additional windows, a

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Beaver Village Unit #1134

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Why You’ll Love this Colorado Escape• 2.0 miles to Winter Park Resort and situated on the complimentary shuttle route• 0.1 miles to Downtown Winter Park and Main Street• Access to communal amenities Including an indoor heated pool, hot tubs and an outdoor firepit• Fully renovated interior featuring a gas fireplace and a private deck with mountain v

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Snowblaze Condos Building C unit 22

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This condominium features two bedrooms and two bathrooms, encompassing a total area of 950 square feet. It boasts an open floor plan, enhanced by newer carpeting throughout and a modern kitchen equipped with stainless steel appliances. Located on the third floor, this unit does not have elevator access; the elevator services only the parking level

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Silverado II Unit 334

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This expansive ground floor condominium features three bedrooms and three bathrooms, making it an ideal location for your mountain getaway, and has been updated for enhanced comfort. The living room boasts an open layout with newly installed hardwood flooring, a wood burning fireplace and a 50 inch flat screen HDTV, all of which can be appreciated

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Silverado I Building A Unit 101

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The living room features a vaulted ceiling that enhances the influx of delightful Colorado sunlight, creating a serene environment perfect for enjoying the wood burning fireplace or the flat screen television. The dining area accommodates up to six guests comfortably and is conveniently situated adjacent to the fully equipped kitchen, which includ

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Beaver Village Unit #1934R

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This remodeled two-bedroom strikes an ideal balance between mountain charm and contemporary comfort, featuring an extensively renovated ground-floor corner unit situated. Located within the established Hi Country Haus community, it is just moments away from Main Street and clubhouse amenities, providing the best of both summer and winter living rig

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New Featured Properties

Browse our selection of new properties to our program and save 15% off 2 nights or more on your stay with promo code NEWUNIT.

*Offer is valid on new online bookings for 2+ night stays. Cannot be combined with other offers. Other exclusions and restrictions may apply to select properties.

Stay Longer in Winter Park, Save Bigger

Hi Country Haus Unit 0701

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Situated in the upper cul de sac of Beaver Village, this unit adjoins the forest, providing stunning views of the Winter Park Resort from the private balcony. The second floor is bathed in natural light, enhancing its appeal. As an end unit, it offers a tranquil and secluded atmosphere. The renovated kitchen is equipped to facilitate both a swift

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Beaver Village Unit #1624

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This residence is ideally suited for several families or small groups seeking both privacy and a convenient location for their skiing or summer holiday. Notable features of this Winter Park home include stunning mountain views of the Continental Divide and Byers Peak, along with the added benefit of three master suites for enhanced privacy. We bel

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Leland Creek Home

Private Vacation Home -

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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

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Beaver Village Unit #1123

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A gas fireplace provides a warm and welcoming atmosphere during chilly winter days and nights, as well as on the rare cool summer evenings. The living room is furnished with comfortable seating, allowing for an enjoyable experience while watching flat screen TV and it offers convenient access to the private patio from this ground floor unit. Addi

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Beaver Village Unit #0712R

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