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Walk to Dining: Downtown Lenox Guest House!

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

A spacious living room with a wooden staircase, a chandelier, a white armchair, and a floor lamp. - Walk to Dining: Downtown Lenox Guest House! (Lenox)
A bedroom with a bed, a dresser, a mirror, and a bedside table. - Walk to Dining: Downtown Lenox Guest House! (Lenox)
A two-story white house with a front porch and a brick pathway leading to the entrance. - Walk to Dining: Downtown Lenox Guest House! (Lenox)
TV, books - Walk to Dining: Downtown Lenox Guest House! (Lenox)
A living room with a sofa, two armchairs, a coffee table, and a patterned rug. A staircase is visible in the background leading to another room. - Walk to Dining: Downtown Lenox Guest House! (Lenox)
Immerse yourself in the charm of Lenox at this private 3-bedroom, 2.5-bath house with a yard and grill. This warm vacation rental is perfect for family trips to Massachusetts country, offering easy access to Appalachian Trail and ski mountains.

Reviews

9.4 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 61900 sq ft

Popular amenities

  • Kitchen
  • Dryer
  • Air-conditioning
  • Outdoor space
  • Parking available
  • Barbecue grill

Add dates for prices

About this property

Walk to Dining: Downtown Lenox Guest House!

  • Steps to Main Street | 2 Mi to Tanglewood | Private Yard w/ Grill

    This Lenox vacation rental places you in the heart of the Berkshires! Steps from shops and restaurants and minutes from Tanglewood, you’ll enjoy easy access to world-class arts, culture, and outdoor adventure. The 3-bedroom, 2.5-bath home is also conveniently located within a short drive of the Appalachian Trail and ski resorts. After exploring, relax with a backyard barbecue or unwind inside with all the comforts of home.

    -- THE PROPERTY --

    C0514291520

    SLEEPING ARRANGEMENTS
    - Bedroom 1: 1 king bed
    - Bedroom 2: 1 queen bed
    - Bedroom 3: 1 full bed

    STEP OUTSIDE
    - Private yard w/ gas grill
    - Front yard w/ garden

    INDOOR LIVING
    - Hardwood flooring
    - Smart TVs
    - Natural sunlight

    KITCHEN
    - Refrigerator, stove/oven, dishwasher, microwave
    - Drip coffee maker, toaster oven
    - Cooking basics

    GENERAL
    - Free WiFi
    - Central heating & A/C
    - Linens & towels, complimentary toiletries

    FAQ
    - Quiet hours (10:00 PM-8:00 AM)

    ACCESSIBILITY
    - 2-story home, 3 steps to enter

    PARKING
    - Designated parking spaces (2 vehicles)
    - Additional vehicles must be parked in public parking (not at the nearby inn)

    -- THE LOCATION --

    - Close to hiking trails, skiing resorts & golf courses
    - 2 miles to The Mount, Edith Wharton's Home
    - 5 miles to Bousquet Ski Area
    - 10 miles to Fountain Pond State Park
    - 13 miles to Appalachian Trail
    - 51 miles to Albany International Airport

    -- REST EASY WITH US --

    Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

    -- POLICIES --

    - No smoking
    - No pets allowed
    - No events, parties, or large gatherings
    - Additional fees and taxes may apply
    - Photo ID may be required upon check-in
    - Please observe quiet hours from 10:00 PM and 8:00 AM

    ADDITIONAL INFORMATION
    - This 2-story home requires 3 steps to enter

Property amenities

Internet

  • Available in the house: Internet access

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Refrigerator
  • Toaster oven

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • Books
  • TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Yard

Laundry

  • Dryer
  • Laundry facilities

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Things to do

  • Hiking/biking trails nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Unit size: 1,900 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 18

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

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher 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 C0264961520
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

About the area

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 The Bookstore. Berkshire Scenic Railway Museum and Lenox Arts Center are also worth visiting. Take the opportunity to explore the area for outdoor excitement like hiking. Visit our Lenox travel guide
View more Holiday homes in Lenox
Map
Lenox, MA

What's nearby

  • A grassy field with a prominent tree and a small house in the distance.
    Wyndhurst Golf & Club
    3 min drive - 1.6 miles
  • The Bookstore
    5 min walk - 0.3 miles
  • Lenox Library
    5 min walk - 0.3 miles
  • Ventfort Hall Mansion and Gilded Age Museum
    6 min walk - 0.4 miles
  • Shakespeare and Company
    14 min walk - 0.8 miles

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
  • Lenox Coffee
    7 min walk
  • Harvest Moon
    4 min drive
  • Firefly
    6 min walk
  • Olde Heritage Tavern
    5 min walk

Frequently asked questions

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

No, pets are not allowed at this property.

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 steps from The Bookstore and 1.4 mi (2.3 km) from Tanglewood Music Center. Lenox Library and Berkshire Performing Arts Center are also within 5 minutes.

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Walk to Dining: Downtown Lenox Guest House! Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 25 out of 34 reviews
Rating 8 - Good. 7 out of 34 reviews
Rating 6 - Okay. 2 out of 34 reviews
Rating 4 - Poor. 0 out of 34 reviews
Rating 2 - Terrible. 0 out of 34 reviews

9.6

Cleanliness

9.8

Location

10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

jen o.

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

8/10 Good

marian g.

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
Verified

10/10 Excellent

Megan L.

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

10/10 Excellent

Karen B.

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

8/10 Good

Ryan B.

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

10/10 Excellent

Irene N.

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

10/10 Excellent

Mary Beth R.

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

8/10 Good

Thomas

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

10/10 Excellent

Vetta M.

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
From a partner site

10/10 Excellent

SUZANNE

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.
Verified

10/10 Excellent

Gabrielle F.

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

8/10 Good

Michael L.

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

Great location

Large downstairs rooms
Stayed 6 nights in Aug 2023
From a partner site

10/10 Excellent

Gabrielle

excellent as always~

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

10/10 Excellent

David S.

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

10/10 Excellent

Kathleen C.

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

10/10 Excellent

Judith D.

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

6/10 Okay

Dalia G.

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

10/10 Excellent

Naomi L.

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

10/10 Excellent

Brittany B.

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

10/10 Excellent

Gabrielle F.

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
Verified

8/10 Good

Jill F.

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

Clean and comfortable. Great location!

A clean and comfortable property. Should have toilet paper supply in each bathroom. Also, window shades should have some sort of lining especially in bedrooms. Lights from the inn shone through bedroom windows all night!
Stayed 3 nights in Dec 2021
Verified

10/10 Excellent

HELENA B.

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

Anniversary Leafing Adventure

The small towns with friendly shop owners, restaurant and other tourist was a very pleasant vacation
Stayed 3 nights in Oct 2021
Verified

10/10 Excellent

Christie P.

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

Ideal location

Our family loved staying in the heart of Lenox. We could stroll to great restaurants, shopping, and bakeries. It’s hard even to imagine a better location. We found the home to be clean and spacious with comfortable beds. It’s not a “homey” or cozy atmosphere, like some rentals, but that didn’t bother us. Even the occasional noise from a nearby community center and the inn and restaurant was no problem. We hope to return.
Stayed 3 nights in Oct 2021
Verified

10/10 Excellent

Amy A.

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

great

very nice!
Stayed 3 nights in Sep 2021
Verified

10/10 Excellent

joseph m.

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

The house is nicer than the listing portrayed it. Very comfortable in all aspects.

Great location. Very comfortable, simple and clean. Great for our family of 4. We will be back for any of our Berkshire adventures.
Stayed 4 nights in Feb 2021