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Cypress Sky

5-bedroom chalet with panoramic mountain views

Position Cypress Place
Outdoor Covered Patio
Slope Access shuttle-access

— Located in Cypress Place, Whistler, Cypress Sky Retreat is just a 5-minute drive from Whistler Village and the renowned Whistler Blackcomb ski domain. The chalet's elevated position grants panoramic views of the surrounding mountains.

Amenities & Features

What the chalet includes

Premium amenities are highlighted; everything else supports a self-contained, well-staffed stay.

Outdoor & Terraces
  • Covered Patio
  • Firepit
Services & Staff
  • Parking
Indoor Living
  • Games Room
  • Media Room
  • Ping Pong
Wellness & Leisure
  • Close To Village
  • Hot Tub
  • Infrared Sauna

Direct Booking Benefits

What's included & available on request

Included With Direct Booking

With your booking

  • Direct coordination with the owner or local manager
  • Dedicated chalet specialist
  • Arrival and check-in coordination
  • Daily housekeeping where listed
  • Catering options confirmed at booking
  • Concierge coordination from inquiry to check-out
Available on Request

Tailored to your stay

  • Private ski instructor
  • Ski & boot rental delivery
  • Helicopter transfers
  • In-chalet massage therapist
  • Private ski guide
  • Michelin-starred dining reservations

Location & Access

Cypress Place, Whistler

Cypress Sky is located in Cypress Place, Whistler.

We manage curated Cypress Place chalets sleeping 6 to 12 guests in forested lots with private hot tubs and access to both mountain bases. Our concierge team arranges Vancouver airport transfers, lift passes for both peaks, equipment delivery, and private chef services.

Part of the Canada ski area.
Explore Whistler

Frequently Asked

Questions Before Booking

What dates are you planning? How many guests are in your group? Preferred area or setting priorities?
How many guests does Cypress Sky sleep?

Cypress Sky sleeps up to 14 guests across 5 bedrooms, with 6 bathrooms. What a group can comfortably use depends on the room-by-room configuration rather than the bedroom count alone, so we confirm the layout against your party before you book.

Where is Cypress Sky located?

Cypress Sky is in Cypress Place, Whistler. We can confirm drive times from the airport and what is within reach on foot before you commit to the location.

Can we have a private chef at Cypress Sky?

Yes, a private chef can be arranged at Cypress Sky. Chef service is booked on request and quoted separately from the chalet rate, so it is never assumed to be included.

Who is Cypress Sky best suited to?

Cypress Sky works particularly well for families with children and large groups travelling together. Tell us how your group is made up and we will say plainly whether this chalet fits, or point you to one that does.

How much does Cypress Sky cost, and how do we book?

Rates are quoted per stay rather than published as a single number, because they move with the season, the length of stay and the size of the group, and taxes and fees vary by destination. Send your dates and we confirm availability and the rate with the owner before anything is charged.

Concierge Inquiry

Plan your stay at Cypress Sky

Send your details and our concierge will confirm availability, share options, and tailor the stay around your group and dates.

Owner-direct coordination
Direct contact with a property specialist
Concierge planning from first inquiry
Discreet handling of every request

Your inquiry goes directly to our concierge team. We match you with the right chalets for your stay goals, not just what is available.

Minimum stay requirements vary by property and season — we’ll confirm what’s possible for your dates.

We respect your privacy. Your details are handled discreetly and never shared.

Owner-direct coordination · Concierge-led planning · Discreet, personal service

Every stay is concierge-handled. Chef, transfers, wellness, excursions, provisioning — all coordinated through a single specialist.
See all services
Direct Booking · Concierge Planning

Every chalet. Every stay. Handled personally.

Owner-direct coordination · Concierge from inquiry to check-out · Discreet, personal service