Entire home

Walk to Dining: Downtown Lenox Guest House!

Photo gallery for Walk to Dining: Downtown Lenox Guest House!

A two-story house with a front porch, a brick pathway leading to the door, and a well-maintained lawn.
A living room with a sofa, armchairs, a coffee table, a TV, and a lamp.
A kitchen with white cabinets, a stainless steel sink, a stove, and a trash can.
A kitchen with white cabinets, a stainless steel refrigerator, and a coffee maker on the counter.
A dining area with a table, chairs, and a chandelier.

Reviews

9.6 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Shakespeare and Company

Popular amenities

  • Yard
  • Barbecue grill
  • Internet access
  • Air-conditioning
  • Refrigerator
  • Onsite parking available

Explore the area

View in a map
Lenox, MA
  • Place, Lenox Library
    ‪5 min walk‬
  • Place, Ventfort Hall Mansion and Gilded Age Museum
    ‪6 min walk‬
  • Place, Shakespeare and Company
    ‪14 min walk‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪52 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Double Bed

2 bathrooms, 1 half bathroom

Full Bathroom

Full Bathroom

Half Bathroom

Spaces

Kitchen

Add dates for prices

Similar properties

Breakfast Nook - wake up to the best sunshine ever!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Stockbridge
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
10.0 out of 10, Exceptional, (152 reviews)
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

About the area

Lenox

Lenox is home to this holiday home. Wyndhurst Golf & Club and Kennedy Park are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Berkshire Performing Arts Center and Berkshire Scenic Railway Museum. Lenox Arts Center and Ebenezer II Gifts and Antiques are also worth visiting. Take the opportunity to explore the area for outdoor excitement like hiking/biking trails.
View more Holiday homes in LenoxOpens in a new window
Map
Lenox, MA

What's nearby

  • Lenox Library - 5 min walk - 0.5 km
  • Berkshire Performing Arts Center - 6 min walk - 0.6 km
  • Ventfort Hall Mansion and Gilded Age Museum - 6 min walk - 0.6 km
  • Shakespeare and Company - 14 min walk - 1.2 km
  • Wyndhurst Golf & Club - 3 min drive - 2.5 km

Getting around

  • Pittsfield Intermodal Transportation Center - 13 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 12 min drive

Restaurants

  • ‪Antimony Brewing - Craft Brewery & Kitchen - ‬4 min drive
  • ‪Tanglewood Cafe - ‬4 min drive
  • ‪Bistro Zinc - ‬4 min walk
  • ‪Haven Cafe & Bakery - ‬7 min walk
  • ‪Chocolate Springs Cafe - ‬4 min drive

Frequently asked questions

Is Walk to Dining: Downtown Lenox Guest House! pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Walk to Dining: Downtown Lenox Guest House!?

As of 3 Nov, 2026, prices found for a 1-night stay for 2 adults at Walk to Dining: Downtown Lenox Guest House! on 4 Apr, 2027 start from S$1,883, 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 Walk to Dining: Downtown Lenox Guest House!?

On-site parking is available at the property.

What time is check-in at Walk to Dining: Downtown Lenox Guest House!?

Check-in begins at 4:00 PM.

What time is check-out at Walk to Dining: Downtown Lenox Guest House!?

Checkout is at 11:00 AM.

Where is Walk to Dining: Downtown Lenox Guest House! located?

Situated in Lenox, this holiday home is within a 5-minute walk of Lenox Library and Berkshire Performing Arts Center. Ventfort Hall Mansion and Gilded Age Museum and Shakespeare and Company are also within 15 minutes.

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 28 out of 37 reviews
Rating 8 - Good. 7 out of 37 reviews
Rating 6 - Okay. 2 out of 37 reviews
Rating 4 - Poor. 0 out of 37 reviews
Rating 2 - Terrible. 0 out of 37 reviews

9.6/10

Cleanliness

8.0/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

9.8/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful weekend away in Lenox Ma the fall colors were beautiful and the hiking in the area even better. the house was clean and had everything we needed. Location was perfect for easy walk to a number of fantastic restaurants each night
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Welcoming layout with plenty of room. Walkable to town and shops.
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was fantastic- great location- clean- comfy beds- fully stocked kitchen. All great!
Stayed 5 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location. Walking to restaurants and short drive to Tanglewood
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful place and great location
Stayed 3 nights in Jul 2025
Verified review

8/10 Good

Liked: Cleanliness, amenities, property conditions & facilities, communication
Great location and convenient walking distance to downtown Lenox.
Stayed 3 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location. Everything was as advertised
Stayed 5 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
So adorable! Quiet, beautiful, close to everything! The beds were the best part. They were so comfortable!!
Stayed 5 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Another great stay!

We were happy to return with our 3 generations of family. Love the blackout curtains and great AC!
Stayed 3 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location!

My friends and I had a great time in Lenox. The location can’t be beat. We walked to all the shops and restaurants in under 5 min.
Stayed 3 nights in Mar 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

Large downstairs rooms
Stayed 6 nights in Aug 2023
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Thanksgiving stay

Some cosmetic repair needed to the front steps, but overall a nice property. A three minute walk from the center of town, shops and restaurants.
Stayed 3 nights in Nov 2023
From a partner site

10/10 Excellent

fall getaway

The house was very comfortable and very clean. It is set back from the street. The Gps said we had arrived, but we couldn't see a house, parked the car and walked around, and found it behind an inn.
From a partner site

10/10 Excellent

excellent as always~

This is our 3rd year staying here. We LOVE it!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location! We had a wonderful time

Steps away from Main strip in Lenox. House is literally in the back parking lot of the Gateway Inn but the parking is fine. The Gateway Inn is there for drinks. The house was clean. The air conditioners were loud, but besides that the place suited us very well.
Stayed 3 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house / location

Prime location in Lenox right behind the Gateway Inn. We had five adults in our group but easily could have fit more as the house was larger than expected and had a pull out couch downstairs and a cot in the closet upstairs. Check in was a breeze and there was plenty of parking. The kitchen was well stocked with pans, plates, utensils, etc. The bathrooms had plenty of towels and great water pressure. We highly recommend this property.
Stayed 3 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lenox getaway

We were five women who were supposed to be in Iceland this week. We canceled that trip due to the state of emergency Iceland had. We decided to meet in Lenox (one of us lives there) and had a wonderful time!
Stayed 3 nights in Nov 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent

We enjoyed our stay here in Lenox. This house was incredibly clean and great location to downtown and the shops and sights. Plenty of towels and well stocked kitchen. The beds were all very comfortable. We had small children and they enjoyed the yard and all the space the house had. Michelle the caretaker was very responsive and available. We will be back!!
Stayed 4 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Holiday Week Downtime

Loved this house tucked away in downtown Lenox. Everything was better and bigger than expected. Lots of fresh towels available and very comfy beds/bedding. Decor was a contemporary minimalist vibe that was conducive to relaxation. We lingered over a jigsaw puzzle, built a gingerbread house, and gathered for holiday movies. (I even brought a few Christmas decorations to make it feel like the holidays!) Walks through town and runs on nearby sidewalks kept us moving. Highly recommend this spot for de-stressing and reconnecting with a small group of people you love!
Stayed 5 nights in Dec 2022
Verified review

6/10 Okay

Liked: Cleanliness, check-in, communication, location, listing accuracy

The location was great

We were close to everything. The Mr. Coffee coffee maker was enough for only 1 person, but there were 4 adults. Fortunately, we found a Chemex in one of the cabinets. The kettle's lid was wobbly and after 2 or 3 days it broke off. They replaced it with a very nice kettle. We didn't have bath towels at first. When we requested them, they appeared.
Stayed 7 nights in Aug 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice, central location

Location is nice both for town activities and getting around the berkshires. Walk to town is easy and 5-10 min walk to coffee, restaurants, and shops, and walking to Tanglewood is doable, though the hill back would be tough. Plenty of clean towels and sheets, kids liked the chairs in the living room and going to the playground next door. Plenty of room for 6 person multigenerational family. About 5-10 min by car to supermarkets in Pittsfield, slow charging available at the police station and fast chargers 10 min away at Lee outlets. 30 min to Williamstown, 45 to North Adams and Mass Moca.Owners were responsive and helpful-we accidentally left something there and they mailed it back quickly! stairs are a little steep for both my 4 year old and my 80 parents. The views aren’t great from the house (mostly parking lots) but there is a yard kids can play in and the community center next door has a playground and pickleball courts
Stayed 4 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We were in Lenox, MA for a wedding. Many of the guests were staying at The Whitlock, so the location of this house was perfect. Parking was convenient and check in was easy. The house was very clean, with plenty of room on the first floor. The master bedroom was adorable, and the beds were very comfortable. It was a great stay!
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Enjoyable and convenient

The house was quiet and convenient and comfortable for six people. Some of the check-in directions for Wi-Fi seemed to be out of date or for a different house, but we were able to figure everything out and the weekend/vacation property manager on duty was responsive and helpful.
Stayed 3 nights in Nov 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fall Trip

The property overall was great. Good location, plenty of space, was even upgraded vs the photos on VRBO. Our only problem was we we did not have WiFi for 90% of the trip and did not get great cell service.
Stayed 3 nights in Nov 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent location!

Wonderful place to stay! Love the yard and grill. Will be back for sure!
Stayed 3 nights in Jul 2022
Tell us how we can improve our siteShare feedback