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

143 properties available

Perfect for families looking for a homey feel in their vacation rental in this two bedroom two bathroom condo with a mountain theme with a personal touch.The solid hardwood flooring in dining room which will seat 4 to 6 people comfortably, for additional seating try using the kitchen counter that doubles as an extra eating place. The kitchen offer

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Beaver Village Unit #0521

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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

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Beaver Village Unit #0721

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This Bear Crossing three-bedroom townhome features a remarkably spacious interior, high-quality finishes throughout, and a multi-level layout. Spanning 2,000 square feet, it provides ample room for a group of eight to spread out, enjoy the nearby outdoor activities, and admire the stunning mountain views from the large windows in the main living ro

HOT 12

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A remarkably spacious 4 bedroom townhome in downtown Winter Park, located at the Arrow development, offers stunning views from the private rooftop hot tub of the Continental Divide. Its prime location on Main Street ensures convenient access to summer festivals at the Rendezvous Event Center as well as a short stroll to various restaurants, nightl

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Arrow At Winter Park Unit 280

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Welcome to your cozy mountain retreat at Timber Fox Building C Unit 3404, nestled in the heart of Winter Park. This luxurious 2-bedroom, 2-bathroom condo offers a perfect blend of comfort and elegance, ideal for families or groups of friends seeking a memorable getaway.Step inside to discover a thoughtfully designed living space, complete with a mo

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Timber Fox Building C Unit 3404

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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

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Beaver Village Unit #0623

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The living area features exotic jewel tones on the walls, complemented by furnishings and accessories in similarly warm and rich hues. This ground floor unit offers the enjoyment of a gas fireplace, a flat screen TV and a private patio. This vacation rental boasts modern enhancements in the kitchen, including new cabinetry and fixtures, as well a

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Beaver Village Unit #1113R

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The living room features a fireplace that is ideal for chilly evenings in both summer and winter. Take a look at the collection of books in the owner’s library, neatly arranged along the wall, perfect for days when you feel like staying indoors and reading a book or watching a movie on the flat screen TV. Guests also have access to the private pat

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Beaver Village Unit #0711R

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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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Hi Country Haus Unit 0701

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Situated on the third floor of the structure, the arched ceilings in the primary living area create a sense of openness and grandeur. Adorned in a serene and relaxing neutral color palette, this one bedroom one bathroom condominium showcases contemporary western aesthetics and furniture, perfect for a mountain retreat in Colorado.The living room sp

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Beaver Village Unit #0232R

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This Winter Park condo is ideal for guests looking to experience the beauty of the Rockies! Completely renovated, a ground floor corner unit offers a forest view from the private patio and dining table, plenty of bedding that is ideal for families wanting to experience the mountains and wonderful outdoor activities.There is hardwood flooring in the

Beaver Village Unit #0611

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Beaver Village Condominiums represent the ideal blend of comfort and convenience, situated a mere 1.5 miles from the Ski Area, and only a five minute walk from the vibrant downtown shopping and dining district of Cooper Creek Square. In the summer, a bike path provides direct access from the property to the extensive mountain biking trail system i

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Beaver Village Unit #1821

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