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Happy Trails: A Four Seasons Woodland Lodge

Entire house hosted by Amber
8 guests5 bedrooms5 beds3 bathrooms
Entire home
You’ll have the house to yourself.
Enhanced Clean
This host committed to Airbnb's 5-step enhanced cleaning process.
Self check-in
Check yourself in with the keypad.
Ryan is a Superhost
Superhosts are experienced, highly rated hosts who are committed to providing great stays for guests.
Happy Trails, located in Great Barrington, MA is a humble, yet country-contemporary, renovated home well-suited for all travelers during any time of year for any purpose.

Whether its vacationing in the winter to ski or snowboard at Butternut, or to catch a concert at Tanglewood and the Mass Moca Museum in the spring, you can enjoy the fall foliage while visiting a local farm or orchard in Autumn, Happy Trails offers all of the right amenities to enjoy everything The Berkshires has to offer.

The space
Situated on 5.3 acres of land, with hiking trails, babbling brooks, & ponds, this private country-contemporary home has 5 bedrooms, 3 bathrooms, a screened in porch as well as an indoor Hot Tub & Sauna that have recently been updated. As of October 2020, we have a brand new BBQ and outdoor firepit for you to enjoy during your stay.

The kitchen is newly renovated and equipped with anything you need to cook meals while enjoying the property. Each bedroom has it's own bed and fresh linens and each room is deep-cleaned and sanitized between guests for your comfort and safety. All bathrooms are also newly renovated.

The living room is fully equipped with a LED Smart TV, equipped with Netflix, Disney+ and cable TV service. We have the highest-speed spectrum internet, making our home ideal for remote-working/learning.

*To be more flexible to your needs, we have recently opened our property to be pet-friendly, on a case-by-case basis.*

Sleeping arrangements

Bedroom 1
1 double bed
Bedroom 2
1 queen bed
Bedroom 3
1 queen bed


Free parking on premises
Hot tub
Pets allowed
TV with standard cable/satellite
Washing machine
Patio or balcony

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5.0 out of 5 stars from 37 reviews



Great Barrington, Massachusetts, United States

The Berkshire House is only 2 miles from growing, popular Main Street of Great Barrington, where you can find great shopping, coffee spots, and great new restaurants opening all the time.

We are located at the foot of Butternut Mountain, 30 minutes from Catamount and 60 minutes from Jiminy Peak. Enjoy the greenery, and view-able wildlife on a day-time hike through one of the local lakes or public walking trails.

Hosted by Amber

Joined in September 2014
  • Identity verified
Music industry professional. Brooklyn, NY transplant living in Nashville, TN.
  • Richard
  • Ryan
During your stay
The hosts will not be available on-site, but do have a local caretaker that will be available for any emergencies or anything urgent that needs to be taken care of during your visit.
  • Response rate: 100%
  • Response time: within an hour
To protect your payment, never transfer money or communicate outside of the Airbnb website or app.

Things to know

House rules
Check-in: After 3:00 PM
Check out: 11:00 AM
Self check-in with keypad
No smoking
No parties or events
Pets are allowed
Health & safety
Committed to Airbnb's enhanced cleaning process. Show more
Airbnb's social distancing and other COVID-19-related guidelines apply
May encounter potentially dangerous animals
Carbon monoxide alarm
Smoke alarm
Cancellation policy