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.
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.
Highlights:
- 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
14 Master King Bed Rm Suite
14A Master King Bed Rm Suite 2
15 Master Bath 2
15A Master Bath 1
16 Queen Bedroom1
Downstairs Twin 3
9A Kitchen2
18A Downstairs Movie Rm-Game rm 2
12 B Outdoor-Great -Yoga deck 1
9B Kitchen 1
18 Movie Room 1
20 Downstairs Bathroom Main 1
Hot Tub 4 with Bear tree
4 Great Rm -Fire place 1
19B Downstairs Game-Movie Rm 3
Downstairs New Bathroom 2
21 D DownStairs Queen 2
21 A Downstairs Queen 3
Downstairs Twin 1
20A Downstairs Bathroom Main 2
Downstairs Bunk (4) Room 1
Downstairs New Bath Rm 1
21 B Downstairs Queen 1
Downstairs Newbath room 4
DownStairs Bunk 2
DownStairs Bunk 1
Downstairs Twin 2
3 Great Rm Living Rm3
9 Great Rm Dining Rm2
7 Great Room Living Rm 1
6 Great Rm Living Rm 2
12 Back Open Yoga Rm 4
9C Kitchen 3
8 Great Rm Dining Rm1
13 Back Open Yoga Rm 3
Firepit 1
10 Back Open Room-Yoga Deck 1
17 Great Room Bear on wall
Great Rm with view of Round Table
6 Great Rm Living Rm 2
Hot Tub 1
Hot Tub 3
12 A Outdoor Great Yoga Deck 2
Hot Tub 2
11 Back Open Yoga Rm 2
King BedRm at 23 MRR with AirP1
Queen BedRm with AirP at 23MRR
Austin Air P at 23 MRR Kit photo 2
Yoga Deck over looking Green Mountain 3
Yoga Deck over looking Green Mountain 4
Sauna 1
Movie -Game Rm 2
Austin Air P at 23 MRR Kit photo 2
13 Back Open Yoga Rm 3
1 Front View 4 w Lightpost Chalet O'Bear
2 Front of Chalet O'Bear 2
Due to COVID-19, access to the fitness facilities is currently restricted.
Sports Center Outdoor Tennis
Sports Center Indoor Pool
Sports Center Cardio
Shuffleboard Courts at Rising Bear
Basketball Court at RB
Outdoor Heated Pool for RB
Front View Rising Bear Lodge
Golf Fairway
Golf Course at Stratton Mountain
Mountain Biking Trails
Mountain Biking Trails
Stratton Mountain Village
Grout Pond in Fall
Grout Pond in Fall
Stratton Lake
Sports Center Shop
Amenities & Info
Our response to COVID-19
Enhanced Safety Procedures
With the evolving coronavirus, we are taking extra efforts to keep our spaces safe and clean for you. Our cleaning staff have put CDC recommend practices in place. This includes cleaning with EPA registered disinfectants and in addition to typical sheet and towel washing and full wipe downs, now includes removal and washing of bedding covers, shower curtains and other fabrics and particular attention to high touch surfaces for deep cleaning.
We also have acquired UV sanitizing wands to further cleanse counter tops, switches, handles and other high contact areas. Lastly each of our properties have been equipped with medical grade EPA approved air purifiers; one in each bedroom and one in the common area.
Why Book with Blue Sky?
What makes us the top choice for luxury vacation rentals?
01. Luxury Accommodations
Relax after a day at the slopes with your favorite show in front of a 4K HD Smart TV, or enjoy the mountain views with a cup of coffee on your private covered patio.
02. Less Walking, More Skiing
Go from your chalet to a private shuttle that will take you to and from the slopes. Spend more time having fun instead of traveling!
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.
04. Incredible Journey
The amazing atmosphere of the Stratton Mountain Resort will be an unforgettable experience. Book today to make memories that will last a lifetime!
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
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!
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!
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.