Dilly Dally Chalet

Welcome home to Dilly Dally Chalet, a spacious 5-bedroom, 3.5-bathroom home in Winter Park’s Roam neighborhood. With room for up to 17 guests, this three-level home offers plenty of space for families and larger groups, with multiple living areas, a private hot tub, chef’s kitchen, dedicated workspace and easy access to downtown Winter Park, the Fraser River Trail and Winter Park Resort.

Head inside to the main living level, where the open-concept great room gives everyone a comfortable place to gather. The living room is centered around a fireplace with plenty of seating, while large windows bring in mountain views and plenty of natural light. The dining area sits just off the kitchen, making it easy to gather for meals after a day out exploring. The kitchen is well equipped for larger groups, with a large island for prep and seating, high-end appliances and plenty of space to spread out while cooking. Whether you’re making a quick breakfast before heading out or sitting down for a long dinner together, this main level keeps everyone connected. Upstairs, you’ll find a second living area that gives the home even more room to spread out. It’s a great spot for movie nights, games or letting the kids have their own space while everyone else enjoys the main living area. Downstairs, a secondary kitchenette and lounge provide another convenient gathering space, making the home especially comfortable for families traveling together or multi-generational groups.

After a day of skiing, hiking or biking, head outside to the private hot tub and relax under the Colorado sky. There’s also a BBQ grill and outdoor space for enjoying a quiet morning coffee or an evening together. Need to get a little work done while you’re away? A dedicated workspace with a custom desk provides a quiet place for remote work, taking a meeting or catching up on emails without having to take over the dining table.

When you're ready to rest easy, the primary King Suite is located on the third floor and includes a futon, ensuite bathroom and peaceful mountain views. Also upstairs is a second King bedroom and a Queen bedroom, both with a shared bathroom. The upstairs living area includes two Twin-over-Twin bunk beds, giving you four additional Twin beds. On the ground floor, another guest room features a custom Twin-over-Queen bunk, and a ADA bedroom includes a Twin bed and a full-size pullout sofa.

And when you’re ready to get outside, you won’t have to go far. Downtown Winter Park’s shops and restaurants are about a 5-minute walk away, as is Hideaway Park. The free town shuttle stop is also approximately a 5-minute walk from the home, while Winter Park Resort is about a 5-minute drive. The Fraser River Trail is nearby for walking and biking, and the Grand Park Community Recreation Center is just a short drive away.

The home also includes a 2-car garage, additional parking in front and dedicated ski and snowboard storage with wall-mounted racks in the garage.

Sleeping Arrangements: King Primary Suite with futon on the third level, King Guest Room on the third level, Queen Guest Room on the third level, two Twin-over-Twin bunk beds in the upstairs living area, Twin-over-Queen bunk on the ground level, and Twin bed with full-size pullout sofa in the ground-floor ADA bedroom. Sleeps up to 17 guests.

Luxury Linen Package Included: Premium linens and towels are provided for your stay.

RENTAL LICENSE NO: XX

There is construction going on near this property. Ask our vacation planners for details.