A private retreat in Berkshires set on 5 acres in prime location in Lenox - our all-season property offers secluded luxury whilst offering close proximity to Tanglewood, ski slopes, hiking trails, lakes, the historic town of Lenox and other Berkshire towns. Please note, the expansive grounds are set in a nature setting and occasional sighting of bears, wild turkey, deer's etc. is normal in the Berkshires.
This listing is for the Main House that accommodates a maximum of 13 (you can also rent this property in a larger format - Main House + the Studio - which accommodates 15. VRBO ID. 1266558).
Main House [4400sqft]: This charming 1920s log cabin has an expansive layout with a breezeway connecting a newer section. Inside you will find 6 well-appointed bedrooms, three full bathrooms and a powder room. The heart and soul of the house is an expansive living room with a brick fireplace, big comfortable sofas, a TV area, and a grand piano. Right behind the living room there are two king bedrooms sharing a full bath. The second floor has two spacious bedrooms (one king and three twins respectively) which share a full bath with a claw foot tub and a separate shower. At the other end of the house, you will find an inviting country kitchen that opens up to a large dining area. The farm table seats 10 comfortably, and there is an adjoining dining area for children. Above the kitchen are two queen bedrooms, a hall bathroom with shower, and a TV den.
Gazebo: We have built a screened-in living space by the woods' edge, with a 16 seat dining table and seating for lounging. In this substantial new space you will be able to enjoy long, leisurely meals al fresco, and then curl up for a nap while listening to birds and crickets sing. During the cold season, you can enjoy a fire in the large in-ground fire pit right outside the Gazebo.
Not just a conventional vacation rental, we’ve set up this property as our own retreat with a lot of thought and care. Choosing to rent a home instead of booking a hotel room allows you the space to get together with friends and family in comfort and privacy. But you shouldn't have to sacrifice the luxury you may enjoy during a hotel stay. At the end of your stay, all you need to do is pack your bags and walk out the door. We don't expect you to strip the beds, empty the fridge, or take out the garbage. We offer a worry-free experience right up to the last moment!
** BEFORE YOU INQUIRE** Thank you for understanding that we have no flexibility on these points: - We require a 3 night minimum during July and August and long weekends. - This house is pet free, there are absolutely NO exceptions to the pet policy.
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The host requires you to complete the following before checking out:
Load and start the dishwasher
Remove personal items, remove leftover food and drinks and take out the rubbish
Lock the doors and return the keys
The trash is in the far garage - you can access the garage through the side door. Please keep the garage door closed to avoid bears.
Failure to complete these may result in a negative review from the host.
Unfortunately, due to repeat issues in the past with larger gatherings, we strictly do not allow functions like weddings etc. on the property.
Important information
You need to know
Property Registration Number C0214901520
Property # 660967vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Lenox
Located in Lenox, this holiday home is near a water park and on a lake. Tanglewood Music Center and Ventfort Hall Mansion and Gilded Age Museum are cultural highlights, and some of the area's landmarks include Lenox Library and The Mount. Travelling with kids? Consider The Bookstore and Berkshire Performing Arts Center. Take in the nearby slopes with cross-country skiing and snowboarding, or try out other outdoor activities such as sledging and snowmobiling.
Pleasant Valley Wilderness Sanctuary - 14 min walk - 1.3 km
Tanglewood Music Center - 6 min drive - 3.2 km
Lenox Library - 7 min drive - 3.9 km
The Mount - 11 min drive - 7.1 km
Jiminy Peak Mountain Resort - 43 min drive - 46.9 km
Getting around
Pittsfield Station - 18 min drive
Pittsfield, MA (PSF-Pittsfield Municipal) - 15 min drive
Restaurants
McDonald's - 17 min drive
Market 32 by Price Chopper - 10 min drive
Guido's Fresh Marketplace - 10 min drive
Parkside - 16 min drive
Flo's Diner - 18 min drive
Frequently asked questions
Is Berkshires Retreat in Lenox - Main House pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Berkshires Retreat in Lenox - Main House?
As of 20 Aug, 2026, prices found for a 1-night stay for 2 adults at Berkshires Retreat in Lenox - Main House on 6 Jan, 2027 start from S$3,690, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Berkshires Retreat in Lenox - Main House?
On-site parking is available at the property.
What time is check-in at Berkshires Retreat in Lenox - Main House?
Check-in begins at 4:00 PM.
What time is check-out at Berkshires Retreat in Lenox - Main House?
Checkout is at 11:00 AM.
Where is Berkshires Retreat in Lenox - Main House located?
This family-friendly Lenox holiday home is located on a lake, within 2 mi (3 km) of Pleasant Valley Wilderness Sanctuary, The Bookstore and Tanglewood Music Center. Berkshire Performing Arts Center and Lenox Library are also within 3 miles (5 km).
About the host
Hosted by Caitlin Yadav
We live a few hours away, in Westchester, NY. We've been coming to the Berkshires ever since we first started dating, 18 years ago. And now we are thrilled to have our own place to bring our three children.
Why they chose this property
We couldn't resist this place! The house itself has tons of character. The surrounding woods are great for admiring or exploring. And the proximity to both Tanglewood and town could not be beat. As the previous owner explained to us, this is a very special place in the universe. So we feel lucky to have discovered it, and look forward to sharing it with you!
What makes this property unique
We bought this house as it feels like a true escape from the daily routine and gives you a vacation feel. The large living room is a great place for everyone to come together and hangout and at the same time there are so many spaces that everyone can spread out. The surrounding nature setting is ideal for quiet relaxation. And the location is so convenient for all the attractions that the Berkshires and Lenox have to offer. For more firsthand guest experiences, you can read the reviews this property has drawn over more than a decade.
Languages:
English
Premier Host
They consistently provide great experiences for their guests