Enjoy Your Vacation in the Lap of Luxury


Leave the car keys on the dresser. Everything you need is right here or just outside the doorstep. This newly renovated, spacious 5 bedroom chalet is perfectly located, only a 6 minute walk across the road from Stratton Village and the base lodge and lifts. Close enough to everything for top convenience and far enough for privacy and relaxation. If walking isn’t your thing, no problem - the house is serviced by the Black Bear shuttle which runs every 15 minutes.

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Ready for the experience of a lifetime?

Stay Minutes Away from Skiing, Snowboarding, and More

This special house offers amenities at every level. Guests are greeted on the first floor by a light filled, open air living room with a stonework wood fireplace and comfortable seating. The space flows to an adjacent open kitchen and dining area with seating for 12. The layout suits socialization in whatever form – après ski with tales of the day’s adventures, group cooking or family style dining. Continue through to the back door and enjoy a brand new covered deck providing space for morning meditation, yoga or just grab your coffee and ease into the day your own way with beautiful views of the Green Mountains. This level also contains two bedrooms. A King bedroom suite and a Queen bedroom, and a full bath, all of which sit behind French doors for extra quiet and privacy. There’s an additional half bathroom off the hallway.

Luxury Ski Rental Chalet O'Bear

Everything You Need in One Place

Head downstairs to find the den with Movie projector entertainment and abundance of seating. Or try your hand at the table games. To truly wind down after a full day on the slopes, you'll no doubt find the invitation of the newly built sauna or the outdoor hot tub, or maybe both to be irresistible. And for the outdoor enthusiasts who didn’t get enough fresh air on the mountain, the backyard fire-pit beckons. This level contains three more bedrooms, one with 4 bunks, the other with twin beds and the third with a Queen bedroom and two full bathrooms.


  • Five bedroom, three and a half bath, high-end upgraded unit
  • Walk to Village for Skiing, Shopping, - Restaurants, Spa and Activities
  • Walk to Athletic Center and Tennis
  • Close to Golf, Nordic Skiing, Snowmobiling, Hiking, Canoeing, and more
  • Shared outdoor heated pool + outdoor sitting area and 2 hot tubs available to use with 3 night stays at Chalet O' Bear

See our virtual tour of Chalet O'Bear

Amenities & Info

5 Bedrooms

3.5 Bathrooms

3,940 Sq. Ft. Chalet

No Pets

2 Night Minimum Stay

Children Welcome

Sleeps 12

Mountain Views

Walk to Ski Lifts

Backyard Firepit

Covered Deck

Beautiful Balcony

Granite Countertops

4K HD Smart TVs

High Speed Internet

On-Site Gym

Private Hot Tub

Private Sauna

Ice Skating Rink

Heated Swimming Pool

Board Games




Washer & Dryer in Unit

Why Book with Blue Sky?

What makes us the top choice for luxury vacation rentals?

01. Luxury Accommodations

Our properties are outfitted with top of the line appliances, luxurious linens, beautiful outdoor spaces, and everything you need for your entertainment and relaxation.

02. Exclusive Locations

We feature homes and condos in the most exclusive and sought after communities in each of our resort areas with beautiful views and access to every convenience offered.

03. No Hidden Fees

With our upfront and transparent pricing, you don't have to worry about being hit with any unexpected fees or charges. Booking directly through us can save you money.

04. Reliable Responsiveness

We value our guest and our owners and work hard to answer any questions in a timely, welcoming, and effective manner.

See What Our Previous Guests Think

Karen S.

"The condo is perfect! Great location, well supplied, love the parking and the locker. I felt like I was in my own home!"

Josh W.

"Nice property. Spacious, well-maintained and good location. Perfect for a family ski weekend."

Ethan L.

"This was a perfect location and great spot for our group of 6 for a ski vacation. We definitely would like to come back!"

Book Now!

100% refund if canceled at least 60 days before arrival date.

50% refund if canceled at least 30 days before arrival date.

Cleaning Fee $ 175

Property Damage Insurance $ 59

Where is Chalet O'Bear?

Leave a Review

Rated 5 out of 5
October 29, 2021

This house is everything you could wish for in a vacation home. Beautiful setting with amazing views – especially from the hot tub. We loved the back covered deck – large and so peaceful. The two levels offered privacy and separation, when we needed it. TV room on the bottom floor was great for the kids! Decor is so warm and cozy. Location, couldn’t have be better! We were a large group but didn’t feel crowded. Great open kitchen/dining/family room floor plan. We’ll be back!!

Helene M
Rated 5 out of 5
March 19, 2020

We had a great stay here and could not have asked for a better location! I so appreciated that the pictures were very accurate and the house was very well maintained. This was the perfect spot for our family vacation. We would stay at this property again for sure!

Megan S.
Rated 5 out of 5
March 1, 2020

The property is just as nice as it looks. The owners did a really great job renovating it, and it has every comfort and convenience you could want. We enjoyed the sauna in particular, and the well-equipped kitchen (particularly the fact that there are THREE coffee makers!). The walk to the slopes was slightly more taxing than I thought it would, as a bit of the walk is uphill, but nonetheless perfectly easy to walk to and from skiing. The owner was extremely responsive when I had a hard time getting into the property upon arrival (totally my own fault, not his), but we solved the issue within minutes. I’d definitely stay there again!

Gwyn W.
Rated 5 out of 5
January 15, 2019

We really enjoyed our stay in this home. The house was beautiful, the distance from the mountain perfect, and the overall experience delightful. The manager, Reggie, checked on us and made the stay very pleasant. We will certainly stay here again when we return! We had a group of 8 consisting of family ages 11-57 and everyone had a memorable stay.

Nelda Y.