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

141 properties available

Rated five stars, the fully renovated two bedroom condominium is sure to impress guests. The vacation rental features a modern kitchen equipped with pendant lighting, bright cabinetry, stainless steel appliances and granite countertops. The open-concept design includes a living room and dining area, with a table that comfortably seats six. The li

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.

Beaver Village Unit #0721

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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

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Arrow at Winter Park Unit 202

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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

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Beaver Village Unit #0111

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Reserve your upcoming visit to Winter Park in this opulent two bedroom unit at Pine Tree Plaza. Situated on Main street in the heart of downtown, you will have convenient access to dining, shopping, nightlife, summer festivals and the complimentary town shuttle - our condominium is perfect for families or small groups looking to experience the are

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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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Why You’ll Love this Colorado Escape• Walkable valley location 0.2 miles from Downtown Winter Park • Extensive complex amenities including an indoor pool, three hot tubs, and a fitness center • Completely renovated first floor end unit with a custom stainless steel kitchenette • Steps away from the complimentary town shuttle stop to Winter P

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Hi Country Haus Unit 0406

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Welcome to Arrow 213, a stunning new condo nestled in the heart of Downtown Winter Park, Colorado. This modern retreat offers a perfect blend of comfort and style, making it an ideal getaway for families or groups of friends seeking adventure and relaxation in the mountains.This spacious 1-bedroom, 2-bathroom unit comfortably accommodates up to 6 g

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Arrow At Winter Park Unit 213

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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

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Hi Country Haus Unit 2115

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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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Welcome to our condo at Timber Fox Unit C3308! This newly constructed, luxurious three bedroom unit is situated in the vibrant center of downtown Winter Park. Our unit offers a splendid view from its private patio with outdoor sofa, open floor plan with a modern themed interior design, gourmet kitchen, washer and dryer and will sleep 8 guests comfo

Timber Fox Building C Unit 3308

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This affordable condominium located in Winter Park, Colorado, features two bedrooms and encompasses 899 square feet of living area. Additionally, it offers the attractive benefit of a private balcony that overlooks the river. Constructed in 1976, the property retains several original characteristics in its furnishings but with updated bathrooms.

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Hi Country Haus Unit 1908

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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

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Beaver Village Unit #1734

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