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12 guests
7 beds
3 bathrooms
12 guests
6 bedrooms
7 beds
3 bathrooms
Wander Berkshires Highlands is a peaceful mountain retreat set on four acres of rolling countryside, just minutes from skiing at Catamount and the vibrant dining scene of Great Barrington.

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Check-in after 4:00pm • Check-out before 10:00am • Dogs allowed
Cancel within 24 hours for a full refund.
Arrive to five star cleaning • No chores at checkout • Just lock up and go
Wander is the best of both worlds. The quality of a luxury hotel with the comfort of a private vacation home just for you and your guests.
Hot tub
Forest view
Game Room
Patio
Free parking
Long term stays allowed
BBQ Area
Ping pong table
Fire place
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 queen bed
Bedroom 5
1 queen bed
Bedroom 6
2 full beds
Surrounded by the natural beauty of the Berkshires, this home offers easy access to the best of Western Massachusetts. Spend your days skiing or hiking at nearby Catamount Mountain, exploring the charming shops and art galleries of Great Barrington, or discovering local treasures like Bash Bish Falls and the Mahaiwe Performing Arts Center.
Hy's Fried
The Well Restaurant + Bar
Little Cat Lodge
French Park
River Walk
Catamount Aerial Adventure Park
Choose your check-in & check-out dates

based on 4 reviews
Guests love the home for its relaxing hot tub, sauna and lively game room with ping pong. They praise the peaceful woodland location yet easy access to downtown and outdoor activities. Visitors also note sparkling cleanliness, thoughtful host communication and roomy, comfortable layout.
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Here are some things which you should know before booking Wander Berkshires Highlands
Check-in: after 4:00 pm
Check-out: before 10:00 am
12 guests maximum
Dogs allowed
No smoking - fees will apply
Events require approval
Cancel within 24 hours for a full refund.
Check-in: after 4:00 pm
Check-out: before 10:00 am
12 guests maximum
Dogs allowed
No smoking - fees will apply
Events require approval
Cell service is generally available, but the home is in a remote area, and connectivity issues or service interruptions may occur. Weather-related power outages are also possible. These interruptions are outside our control, and we’re unable to offer refunds for disruptions caused by external providers or weather conditions.
The mountains is home to a variety of amazing creatures, including deer, coyotes, foxes, bears, and other wildlife. It is incredible for those who love to nature-watch from afar, but may not be for everyone. Use caution and do not touch wildlife. Avoid leaving food outside (including residue in grills or fires), secure all garbage, and keep doors and windows closed.
Quiet hours are from 10 PM to 10 AM. We kindly ask that you refrain from hosting parties or creating excessive noise during your stay, as we strive to maintain a peaceful environment for both our guests and neighbors. Amplified outdoor sounds are strictly prohibited.
Weather Accessibility
If you are planning a stay with us from December to March, we strongly recommend arriving in an all-wheel-drive or four-wheel-drive vehicle, as roads leading to the property may be icy or snow-covered during this time. Ensuring your vehicle is equipped to handle winter conditions and driving carefully will help make your arrival as smooth and safe as possible.
PWD Accesibility
This home contains features that may be difficult for elderly and guests with mobility challenges - including climbing a set of stairs to access additional levels.
This home follows a strict maximum occupancy rule of 12 guests. Please make sure that the total number of guests accompanying you (including both children and adults) doesn’t exceed the indicated maximum occupancy above to avoid cancellation of your stay and additional fees.