Peaceful Views | Hot Tub | Board Games

Welcome to Dilly Dally Chalet, a refined mountain home in Winter Park’s Roam neighborhood, thoughtfully designed for elevated summer living and effortless connection. This five-bedroom retreat offers open gathering spaces, private sleeping areas, multiple living zones, and a dedicated workspace, all finished with modern alpine style. Spend your days exploring nearby hiking and biking trails, enjoying downtown restaurants and summer events, then return to unwind in the private hot tub, host with ease in the chef’s kitchen, and soak in the fresh alpine air with seamless access to town, trails, and the resort. Welcome to Dilly Dally Chalet: A Refined Mountain Home Welcome to Dilly Dally Chalet, an Property Manager Destination Properties home thoughtfully designed for elevated summer mountain living and effortless connection. Located in Winter Park’s Roam neighborhood, this 5-bedroom home blends modern alpine design with relaxed comfort, offering generous gathering spaces, private retreats, and curated details that elevate every moment of your stay. Spend your days exploring nearby hiking and biking trails, downtown dining, and seasonal events, then return to unwind in the private hot tub, enjoy multiple living areas, and take in the fresh mountain air through seamless indoor-outdoor flow. Dilly Dally Chalet is designed for connection, relaxation, and unforgettable summer memories. From the moment you step inside, the home opens into a light-filled gathering space where clean lines, rich textures, and intentional design set the tone for a memorable stay. A Space Made for Gathering The main living level sets the tone with an expansive open-concept layout anchored by a striking fireplace and comfortable seating designed for conversation and unwinding after a day of summer adventure. Large windows bring the surrounding mountain landscape inside, while the dining area invites long meals and shared stories after days spent hiking, biking, and exploring Winter Park. The chef’s kitchen is beautifully finished and fully equipped, featuring an oversized island with seating, high-end appliances, and everything needed to host with ease. Upstairs, an additional living space offers flexibility for families and groups, creating a dedicated area for movie nights, games, or quiet downtime after sunny days outdoors. Downstairs, a secondary kitchenette and lounge provide another layer of privacy and convenience, making this home exceptionally well suited for multi-generational stays or groups traveling together. After a day exploring alpine trails, festivals, and mountain air, retreat outdoors to the private hot tub, perfectly positioned for relaxation under the Colorado stars. Work from the Mountains A dedicated workspace with a custom desk and comfortable seating offers a quiet place to focus, take meetings, or ease into the morning with natural light and mountain views. Thoughtfully positioned away from the main living areas, it provides a peaceful setting for remote work while still keeping you connected to the energy of your summer mountain getaway. Bedroom Layout Every sleeping space is thoughtfully appointed to support rest, privacy, and flexibility: 󠁯•󠁏󠁏 Primary Suite (3rd Floor): King bed with an additional futon, ensuite bathroom, and peaceful views 󠁯•󠁏󠁏 King Guest Room (3rd Floor) : King Bed 󠁯•󠁏󠁏 Queen Guest Room (3rd Floor): Queen Bed 󠁯•󠁏󠁏 Bunk Area (3rd Floor): Two twin over twin bunks located in the upstairs living area 󠁯•󠁏󠁏 Ground Floor Guest Room: Custom Built Twin over Queen bunk 󠁯•󠁏󠁏 Ground Floor ADA : Twin bed & Full Pullout This layout comfortably accommodates multi generational groups, families traveling together, or friends seeking both shared moments and personal space. Location and Access Located in the Roam neighborhood, Dilly Dally Chalet places you close to everything while maintaining a sense of calm and privacy. 󠁯•󠁏󠁏 Winter Park Resort: 5-min drive 󠁯•󠁏󠁏 Downtown Winter Park dining and shops: 0.3 mi/ 5 min walk 󠁯•󠁏󠁏 Hideaway Park: 0.3 mi/ 5 min walk 󠁯•󠁏󠁏 Fraser River Trail access: nearby 󠁯•󠁏󠁏 Free town shuttle stop: 0.3 mi/ 5-min walk 󠁯•󠁏󠁏 Grand Park Community Rec Center: 5-min drive Parking Information 󠁯•󠁏󠁏 2-car garage 󠁯•󠁏󠁏 The garage is accessed through the home and opened from inside. 󠁯•󠁏󠁏 Additional parking in front. Ideal For • Families and multi-generational summer stays and reunions • Groups seeking space, comfort, and elevated mountain design • Remote workers blending productivity with a refreshing mountain escape • Summer adventures, hiking, biking, festivals, and extended Colorado stays The Property Manager Difference As a guest of Dilly Dally Chalet, you’ll receive: 󠁯•󠁏󠁏 Premium Ritz Carlton linens and elevated bath amenities 󠁯•󠁏󠁏 A dedicated local concierge team 󠁯•󠁏󠁏 Curated welcome touches to begin your stay 󠁯•󠁏󠁏 Access to exclusive partnerships and personalized recommendations Dilly Dally Chalet is prepared to a high standard so guests can arrive, exhale, and simply enjoy. Reserve your stay at Dilly Dally Chalet and experience a summer in Winter Park with space to gather, room to breathe, and comfort that feels quietly exceptional, whether you’re hiking alpine trails, biking through mountain paths, or enjoying long, sun-filled days in the Rockies. License number: 029992