Cliffwood Cottage by Evergreen Home

Just a 5-minute stroll from downtown Lenox and set on one of its most coveted streets, this charming guest house offers private off street parking, two beautifully appointed bedrooms, a chef’s kitchen, central A/C, and washer/dryer. A private courtyard patio provides the perfect spot to relax or entertain. Blending comfort with character, it’s an ideal Berkshire retreat close to hiking, dining, museums, theater, and Tanglewood. Long-term availability, please inquire.

If you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.

Lenox is central to The Berkshires; anywhere you want to explore in the greater area, like museums, hikes, skiing, and theater is just a short drive away.

Guests will have access to the entire carriage house and patio outside, except for the artist studio located at the back of the home. The artist studio will remain vacant, and is not rented or setup as a rentable space.

This thoughtfully designed two-bedroom, one-bath home offers both comfort and convenience for your stay in the Berkshires.

On the main level, an open-concept kitchen and dining area invite you to gather and entertain. The chef’s kitchen is fully stocked for meals at home, while nearby restaurants offer endless options for dining out. French doors bathe the space in natural light and open to a charming patio, perfect for al fresco meals.

Upstairs, the landing transforms into a cozy living area with plush seating and a flat-screen TV, ideal for movie nights or relaxed afternoons. A dedicated workspace with desk and supplies ensures seamless remote work. The serene primary bedroom features a queen bed, a seating nook, and an additional desk for private productivity. The second bedroom includes two twin beds, while the adjacent full bath offers a walk-in shower.

Perfectly situated, this home places you moments from the very best of the Berkshires—boutiques, farm-to-table dining, world-class theater, museums, hiking, skiing, and more. Everything you need for an inspired stay is just minutes away.

Minutes from downtown Lenox
5 minutes from Tanglewood
10 minutes from Bousquet Mountain Ski Area
20 minutes from Jacob's Pillow



The Village of Lenox is walkable, but you will want a vehicle if you plan to explore all the Berkshires has offer.

LOCATION: The property is approximately a 3 minute walk into downtown Lenox from its location on Cliffwood Street.
Lenox is central to The Berkshires; anywhere you want to explore in the greater area, like museums, hikes, skiing, and theater is just a short drive away.
PETS: No pets.
PARKING: Guests can use the shared driveway, which includes a designated bump-out for convenient guest parking.
CLEANING: Depending on length of stay, management may require a mid-stay clean, to be discussed.

**Your reservation includes a $20 insurance fee to cover any accidental damage during your stay, allowing you to relax and enjoy your vacation with peace of mind. If any damage does occur, please let us know so we can arrange timely replacements for the next guest.

This guesthouse offers its guests laundry facilities. The front desk is open around the clock.

This Lenox guesthouse is smoke free.