The Black Bear Den at Okemo

04/24/2024

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10/24/2023

https://seekadventure.beehiiv.com/p/autumn

When fall and autumn come and go and we find our own light in the muted mornings.

08/17/2023

Hey all!

While things are booking up, just wanted to throw a reminder out there to all the Facebook friends, if you need a fall or winter escape, we have you covered.

With

- a single bedroom king bed apartment
- 4 bedroom with hot tub sleeps up to 8
- 7 bedroom with hot tub and fire pit sleeps up to 15
- 2 bedroom sleeps up to 4
- And 4 bedroom log home sleeps up to 8

Options. If anyone is in need of Vermont this weekend. I will work special discounts for Facebook friends.

All locations within 5-15 minutes of ludlow.

06/08/2023

This is, by far, a favorite place to have the morning coffee. The sun rises and slowly fills the porch with morning glow. And it’s in that moment, the coffee tastes even better. So when you stay at the black bear den, and when you have your coffee in this spot, know that it’s magic.

05/11/2023

Can you spot the corgi?
Good spring morning from and !
Doing some spring work while cleaning from last weeks guests and getting ready for a big Jeep event happening right here with us! So excited!!! And then the rest of May is booked up so maybe you want to come stay in June?

04/20/2023

The stories that this truck keeps as secrets. From the conversations within its cab to the shoe still resting on the passenger side seat… the stories. The forgotten.
Things you find around Vermont

04/18/2023

We are interrupting Vermont posts for a baby sloth. Because. I mean. Baby sloth.
Disclaimer. You will not find baby sloth when staying at 😂

04/16/2023

Blue making his springtime appearance over here. Enjoying a beautiful weekend getting some things done and so excited for all the spring and summer guests coming! Heck, fall guests have already booked some stays. 2023 will be a year with so many stories and memories made at - - - huge thank you to everyone choosing our homes for your stays!
****le

04/12/2023

A few more runs happening on the slopes but let’s be honest, spring is here and life is about to pop and animals about to be twitterpated all over the green mountains. Oh, and of course we will literally be chasing waterfalls again!

04/03/2023

WHAT WILL YOU DO!??!
No snow, not ski season? What are you going to do???
We love this time of year too too because we have all the things. From the private yard with custom crafted corn hole, grill, hot tub and more! To the large fire pit area surrounded by garden life. has you covered for fun and relaxing all year!
Unfortunately dates are filling quick but if you need a Vermont retreat, reach out for special options. From our 2 guest king bed apartment - 4 bedroom 8 guest log home to the main 6500sf inn. We have you covered.
Keep shining! Tim and Caitlin

04/03/2023

Entering day 1! 4 more to go and then it’s some pond skimming at Okemo! You got this!

03/24/2023

pushing every day to boil down 2000 gallons of sap into the sweetest of sweet.
Did you know that this weekend and next are open sugar house weekends? Where you can enjoy the process and learn all the steps?
“Exploring” link in bio - read all about it and find the direct map to all the open sugar houses in Vermont this weekend.

03/24/2023

We can not wait to get to doing all the exterior work this spring and continuing to elevate the interior with a couple new bathrooms and more. All that being said, we will also miss the beauty of winter and the property being snowed in.

03/23/2023

One of the best parts about all the spring snow??? The gazebo over the hot tub keeps everything ready for those sore bodies after a day on the slopes. And yea, that’s the firepit in the background, unfortunately can’t put a gazebo over that so it’s currently snowed in.

03/14/2023

Some live music and a pond skim coming to a mountain near you!!! Or at least near us because it’s time to shine for
Do we skim the pond? I think yes.

03/13/2023

We won’t lie. It would be a fun game if guests all got competitive over who could leave the best note on departure. 😂 This crew leveled it up! Haha

03/08/2023

💜💜💜 our fuel to this passion💜💜💜

03/07/2023

What’s that!?!? A Jeep weekend? That’s right, we had our Jeep weekend in the fall and now it’s time for our spring dust off. Rooms at our main property are already booked but we do have a few rooms at open. Sleep there but join us for dinner and breakfast at the inn.
Or just come for breakfast and the drive.
Or if that doesn’t suit your needs, just come for the drive and adventure!!!
DM for details.

03/02/2023

Winter has arrived and we have one thing to remind you of. You can’t buy happiness but you can buy a lift ticket and we all know what a lift ticket brings.

03/02/2023

‘Merica….
Those winter storm moments when you will stop for any photo op and that’s why camera is always on hand for us.
🇺🇸

03/02/2023

Our first open weekend since before Xmas is coming up in a couple weeks and we won’t lie. We are looking forward to getting in and doing some work and enjoying the home and the mountain! Till then, we are gonna keep loving every new memory that our guests get to create!

02/27/2023

And this sums it up. The ability to give families a home that is large enough with space for everyone. Not having to jam 6 people into one room on three beds etc. The ability to create a home for families to create memories in. This is why we do what we do.

02/06/2023

When you get to unwind from a day on the slopes in our second dining room. The more intimate option for dining with a pop of color and mountainside art which we hand painted. Just wait till you see how the spring and summer unfold here at and

02/03/2023

Ahhhh! It’s gonna be frigid!!! Good morning all you winter people!!! Layers upon layers with a few more layers will be the key this weekend. Think of yourself as lasagna…..

01/30/2023

We are both in love and insanely envious of our guests who checked out this morning. They sent us a pic of their 14.5’ long table nacho set up! And one, now we want nachos. Two, next year we need them to invite us up for nacho night. 😂 🌮

01/24/2023

Okay. Listen. About a mile down the road is the company. They’re tucked back off the streets. You’ll go in, meet the nicest of folks, and you’ll buy a pie. You sorta need to buy a pie. And some donuts while you’re at it. The pie is going to be not the cheapest pie at all. Here’s the thing though, just do it. Don’t question it. Because the VT Apple pie Co. makes the best dang apple pie we have ever tasted in this country. No, in the world! NO! In the universe!!! Like, your grandmother may actually be mad that her apple pie is no longer your favorite. Don’t blame us.

01/23/2023

And that’s a wrap on another great Vermont weekend. Big week ahead with booked solid with a couple different groups of guests coming and then a weekend with and also with guests.
Going to be lots of laughs, memories, and trails had this week!

01/22/2023

One of our favorite things to do when we get back to our home is to read the stories or thoughts left in one of our guest books. Brings joy to the soul knowing that other souls are making memories and loving their stays.

12/28/2022

Did you know that we offer 3 different property options???

We have our main house which is the 6500 sf 7 bedroom sleeps 14 located 5-10 minutes from Okemo.

We have a 1 bedroom apartment located in the carriage house (aka above garage) at the same location.

And then we have The Ascutney Retreat which is a 4 bedroom log home nestled into 6 acres and located about 15 minutes from Okemo.

You can learn more at

5 minutes from okemo, 20-30 minutes from Killington. Both ski mountains are near by for your enjoyment. vt ski vaction properties

12/20/2022

What did today look like at Okemo, just 5 or so
Minutes away? Well, this! Great conditions and all the goodness!