Cliffwood Cottage by Evergreen Home
Guest house near Tanglewood Music Center in Lenox
Choose dates to view prices
Photo gallery for Cliffwood Cottage by Evergreen Home





Popular amenities
- Free WiFi
- Air conditioning
- Laundry
- Kitchen
Explore the area

Lenox, MA
- The BookstorePlace, The Bookstore5 min walk
- Lenox LibraryPlace, Lenox Library6 min walk
- Ventfort Hall Mansion and Gilded Age MuseumPlace, Ventfort Hall Mansion and Gilded Age Museum13 min walk
- Pittsfield, MA (PSF-Pittsfield Municipal)Airport, Pittsfield, MA (PSF-Pittsfield Municipal)13 min drive
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About the area
Lenox
Heart of Lenox.Within a 10-minute walk of the guesthouse, you'll find The Bookstore and Lenox Library. Ventfort Hall Mansion and Gilded Age Museum and Shakespeare and Company are also within 2 miles (3 km).
What's nearby
- The Bookstore - 5 min walk - 0.4 km
- Lenox Library - 6 min walk - 0.6 km
- Ventfort Hall Mansion and Gilded Age Museum - 13 min walk - 1.1 km
- Shakespeare and Company - 2 min drive - 1.8 km
- Wyndhurst Golf & Club - 3 min drive - 2.9 km
Getting around
- Pittsfield Intermodal Transportation Center - 13 min drive
- Pittsfield, MA (PSF-Pittsfield Municipal) - 11 min drive
Restaurants
- Antimony Brewing - Craft Brewery & Kitchen - 3 min drive
- Haven Cafe & Bakery - 3 min walk
- Bernstein Shack - Tanglewood - 6 min drive
- Olde Heritage Tavern - 5 min walk
- Ombra - 6 min walk
About this property
Cliffwood Cottage by Evergreen Home
9 MINUTES FROM BOUSQUET
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.
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.
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Property amenities
Internet
- Available in all rooms: Free WiFi
- In-room WiFi speed: 250+ Mbps (good for 3–5 people or up to 10 devices)
- Available in some public areas: Internet access
Room amenities
Entertainment
- Smart TV
Bedroom
- Bedsheets provided
Bathroom
- Hair dryer
- Towels provided
Food and drink
- Coffee/tea maker
- Cookware, dishware, and utensils
- Dining table
- Dishwasher
- Kitchen
- Kitchen island
- Oven
- Refrigerator
- Stovetop
- Toaster
More
- Air conditioning
- Desk
- Desk chair
- Dryer
- Heating
- Office
Policies
Check-in
Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 23
Check-out
Check-out before 11:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
-No Smoking or vaping -No parties or events on the property -No commercial photography or filming allowed without prior authorization
Pets
- No pets allowed
Children and extra beds
- Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
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
Onsite parties or group events are strictly prohibited
Safety features at this property include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
- This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.
Property Registration Number C0522371520
Property is also known as
28ff9585-7ed5-4859-847e-c1c655376c49