Cliffwood Cottage by Evergreen Home
Photo gallery for Cliffwood Cottage by Evergreen Home





Popular amenities
- Free Wi-Fi
- Air-conditioning
- Laundry room
- 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
Room options
Similar properties

Heart of Lenox!! - renovated downtown apartment
Heart of Lenox!! - renovated downtown apartment
Lenox
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
4.9 out of 5, Exceptional, 73 reviews
4.9
Exceptional
73 reviews

Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
Hancock
- Pool
- Spa pool
- Parking included
- Free Wi-Fi
4.1 out of 5, Very good, 987 reviews
4.1
Very good
987 reviews
The price is AU$364
AU$364
includes taxes & fees
4 Jan - 5 Jan 2026

The Ponds at Foxhollow
The Ponds at Foxhollow
Lenox
- Pool
- Spa pool
- Kitchen
- Parking included
4.3 out of 5, Excellent, 137 reviews
4.3
Excellent
137 reviews

The Constance by the Lenox Collection
The Constance by the Lenox Collection
Lenox
- Pet-friendly
- Parking included
- Free Wi-Fi
- Air-conditioning
4.2 out of 5, Very good, 564 reviews
4.2
Very good
564 reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
- Breakfast included
- Pet-friendly
- Parking included
- Free Wi-Fi
4.5 out of 5, Wonderful, 1,001 reviews
4.5
Wonderful
1,001 reviews
The price is AU$173
AU$173
includes taxes & fees
7 Jan - 8 Jan 2026

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
South Lee
- Pool
- Spa pool
- Air-conditioning
- Tennis court
4.5 out of 5, Wonderful, 812 reviews
4.5
Wonderful
812 reviews
The price is AU$242
AU$242
includes taxes & fees
4 Jan - 5 Jan 2026

The Red Lion Inn
The Red Lion Inn
Stockbridge
- Pool
- Spa
- Pet-friendly
- Free Wi-Fi
4.4 out of 5, Excellent, 1,002 reviews
4.4
Excellent
1,002 reviews
The price is AU$314
AU$314
includes taxes & fees
26 Jan - 27 Jan 2026

The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
Lenox
- Pool
- Spa pool
- Breakfast included
- Parking included
4.6 out of 5, Wonderful, 1,002 reviews
4.6
Wonderful
1,002 reviews
The price is AU$168
AU$168
includes taxes & fees
6 Jan - 7 Jan 2026

Berkshires Untold
Berkshires Untold
Lenox
- Pet-friendly
- Parking included
- Free Wi-Fi
- Restaurant
4.5 out of 5, Wonderful, 821 reviews
4.5
Wonderful
821 reviews
The price is AU$211
AU$211
includes taxes & fees
4 Jan - 5 Jan 2026

Vacation Village in the Berkshires
Vacation Village in the Berkshires
Williamstown
- Pool
- Parking included
- Free Wi-Fi
- Air-conditioning
4.4 out of 5, Excellent, 2,190 reviews
4.4
Excellent
2,190 reviews
The price is AU$189
AU$189
includes taxes & fees
4 Jan - 5 Jan 2026
About the area
Lenox
With a stay at this guesthouse, you'll be centrally located in Lenox, within a 5-minute drive of Tanglewood Music Center and The Bookstore. .This guesthouse is 0.3 mi (0.4 km) from Lenox Library and 0.6 mi (1 km) from Ventfort Hall Mansion and Gilded Age Museum.
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.
A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless internet access keeps you connected, and a Smart television is provided for your entertainment. Conveniences include a desk and a coffee/tea maker.
Guests will find features like internet access.
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
Conveniences
- Laundry facilities
More
- Smoke-free property
Room amenities
Bedroom
- Bedsheets provided
Bathroom
- Hair dryer
- Towels provided
Entertainment
- Smart TV
Food and drink
- Coffee/tea maker
- Cookware, dishware, and utensils
- Dining table
- Dishwasher
- Hob
- Kitchen
- Kitchen island
- Oven
- Refrigerator
- 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
Pets
Pets not allowed
Children and extra beds
Children are welcome
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
Property Registration Number C0522371520
Property is also known as
28ff9585-7ed5-4859-847e-c1c655376c49