Dilly Dally Chalet

Modern Alpine Home

  • Winter Park
  • 17 Guests
  • 5 Bdrms
  • 3.5 Baths
  • 5 (2)

About Dilly Dally Chalet

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.
The space

Welcome to Dilly Dally Chalet: A Refined Mountain Home

Welcome to Dilly Dally Chalet, an Elysian 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 Elysian 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.

Check in and out

Check in: 4:00 pm

Check out: 10:00 am

Sleeping Situation

  • KING_BEDSINGLE_BED
    Primary Suite

    1 King bed
    1 Single bed

  • KING_BED
    King Guest Room

    1 King bed

  • QUEEN_BED
    Queen Guestroom

    1 Queen bed

  • SINGLE_BED
    3F Bunk Room

    4 Single beds

  • QUEEN_BEDSINGLE_BED
    GF Guest Room

    1 Queen bed
    1 Single bed

  • SINGLE_BEDSOFA_BED
    Ground Floor ADA

    1 Single bed
    1 Sofa bed

  • Big Views
  • Coffee maker
  • Dining table
  • Dishwasher
  • High chair
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Carbon Monoxide Detector
  • Fishing
  • Mountain climbing
  • Rock climbing
  • Fire Extinguisher
  • First Aid Kit
  • Horseback riding
  • Shopping
  • Mountain view
  • Private Entrance
  • Smoke Detector

Availability

  • Today
  • Unavailable
  • Available

Location

Reviews (2)

Natalie Dybzinski
Jul 08 2026
We had a beautiful stay ! Every detail was well thought out, the property was beautiful and perfectly located. I believe it may be a new property, so it had some kinks to work out. The property said it had a highchair and pack and play and there was not-it took them awhile to respond to bring one, but they did bring one. Also the downstairs shower flooded while we were there, but they were quick to respond. For the size of the house, they could use a few more towels and wash cloths for guests, but otherwise, really no complaints. It is a beautiful property with tons of amentiies and we would absolutely stay there again!
Olena Chokan
Jun 23 2026
Amazing peaceful retreat. Location is walkable to a little river, Fraser trail and also nice playground with clean water and bathrooms. We walked 5 min to rent ebikes, it was so fun to go on a trail. Nice vibe small towm with good coffee and food options. Kids have enjoyed having 2 living rooms, lots of room to sit together. Adults enjoyed the deck and jacuzzi. Luxury kitchen island and pots. Kitchen was a dream come true. Colorado light roast cofee is my all time favorite so I was so happy to find it locally too. Made the trip memorable with food quality. Bathrooms are very spacious, all was very clean. We also had a vaccum and napkins for in between selfcleaning. Provided laundry pads, dishwasher pads too. I mean it was fully stocked!! Home has lots of windows - just breathtaking views from every one of them! They had no screens and with no AC it was the only challenge we had in the middle of the summer. Still best home we ever stayed and team was above and beyond. 10 out 10!

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