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

Why You’ll Love this Colorado Escape• Walk across the street to Downtown Winter Park dining and shopping at Cooper Creek Square• Private balcony with views of Winter Park Ski Resort and the Continental Divide• Sleeps 8 guest across two bedrooms and a loft with three full bathrooms• Family accommodations include a provided Pack and Play, a game tabl

Special

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.

Crestview Place Unit 607

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This two bedroom unit at Trailhead Lodge is ideal for a winter or summer retreat in the Colorado Rocky Mountains. Gather your family and furry friend for a luxurious yet approachable escape.The unit located on the second floor can be reached by elevator and features a tastefully decorated living room with expansive windows that provide scenic view

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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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The well-lit condo with two bedrooms is situated on the ground floor of the building, providing convenient access and a brief stroll to the primary clubhouse and complimentary town shuttle stop.The recently completed kitchen is fully stocked with supplies, making it effortless to prepare meals or snacks. It features modern appliances, cabinets and

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Beaver Village Unit #0711

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Welcome to our condo at Beaver Village Unit 613.A beautifully renovated 1 bedroom welcomes you to your next Winter Park getaway. This unit offers hardwood flooring, a private deck with forest views, washer and dryer in an ultra-chic interior design.The open floor plan encompasses the main living room, dining and kitchen spaces. The living room ha

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Beaver Village Unit #0613

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A western themed two bedroom unit, located on the third floor of the building, offers an excellent retreat while being conveniently situated near Main Street in downtown Winter Park. Additionally, as an end unit, it ensures enhanced tranquility and seclusion.The primary living space features tiled flooring and is adorned with log themed lamps. It

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Hi Country Haus Unit 1515

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This cheerful and inviting studio condominium situated in Winter Park is ideally positioned along the local free shuttle route and is merely minutes away from Winter Park Resort. Nestled in the vibrant downtown area, this studio condominium at Snowblaze Condos and Athletic Club ensures that you will have access to all the premier activities the tow

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Snowblaze Condos Building E unit 310

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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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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

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Beaver Village Unit #1934

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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 inviting, renovated condominium offers picturesque views of the Fraser River, making it an ideal rental for visitors seeking relaxation and enjoyment in Winter Park. It is situated on the building’s first floor. The unit features stunning hardwood flooring that enhances the contemporary design and new furnishings. In the living room, there i

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Hi Country Haus Unit 1503

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