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Berkshires Retreat in Lenox - Main House

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A house with a sloped roof, large windows, and a porch with potted plants.
A spacious living room with a fireplace, bookshelves, a piano, and a dining table.
A spacious outdoor area with wooden flooring, a long table, two chairs, and a bench.
A covered picnic table with benches, large windows, and hanging light fixtures.
A cabin surrounded by tall trees and a well-maintained lawn.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Firepit available
    One of the few properties with a dedicated outdoor firepit.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Balcony
  • Toys
  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Internet

Explore the area

View map
Lenox, MA
  • Place, Pleasant Valley Wilderness Sanctuary
    ‪14 min walk‬
  • Place, Tanglewood Music Center
    ‪6 min drive‬
  • Place, The Mount
    ‪11 min drive‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪53 min drive‬

Rooms & beds

6 bedrooms (sleeps 13)

#1 Ground Floor Bedroom

1 King Bed

#2 Ground Floor Bedroom

1 King Bed

#3 Master Bedroom

1 King Bed

#4 Kids Upstairs Bedroom

3 Single Beds

#5 Bedroom Above Kitchen

1 Queen Bed

#6 Bedroom Above Kitchen

1 Queen Bed

3 bathrooms, 1 half bathroom

#1 Clawfoot Jack & Jill

Soap · Towels provided · Bathtub · Toilet · Shower only · Shampoo · Hair dryer

#2 Hall bath above Kitchen

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

#3 First Floor Bathroom

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

#4 Powder Room

Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Garden
Dining area

Add dates for prices

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Living room
Spacious Central Berkshires Home for Groups
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  • Kitchen
  • Washing machine
  • Dryer
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9.6 out of 10, Exceptional, (4 reviews)
Spacious Central Berkshires Home for Groups

About the area

Lenox

Located in Lenox, this holiday home is near a water park and on a lake. Tanglewood Music Center and Ventfort Hall Mansion and Gilded Age Museum are cultural highlights, and some of the area's landmarks include Lenox Library and The Mount. Travelling with kids? Consider Berkshire Performing Arts Center and Berkshire Scenic Railway Museum. Take in the nearby slopes with cross-country skiing and snowboarding, or try out other outdoor activities such as sledging and snowmobiling.
View more Holiday homes in LenoxOpens in a new window
Map
Lenox, MA

What's nearby

  • Pleasant Valley Wilderness Sanctuary - 14 min walk - 1.3 km
  • Tanglewood Music Center - 6 min drive - 3.2 km
  • Shakespeare and Company - 8 min drive - 5.0 km
  • The Mount - 11 min drive - 7.1 km
  • Jiminy Peak Mountain Resort - 43 min drive - 46.9 km

Getting around

  • Pittsfield Station - 18 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 15 min drive

Restaurants

  • ‪Burger King - ‬10 min drive
  • ‪Antimony Brewing - Craft Brewery & Kitchen - ‬7 min drive
  • ‪Tanglewood Cafe - ‬7 min drive
  • ‪Amazing Pho - ‬10 min drive
  • ‪Bistro Zinc - ‬6 min drive

Frequently asked questions

Is Berkshires Retreat in Lenox - Main House pet-friendly?

No, pets are not allowed at this property.

How much is parking at Berkshires Retreat in Lenox - Main House?

On-site parking is available at the property.

What time is check-in at Berkshires Retreat in Lenox - Main House?

Check-in begins at 4:00 PM.

What time is check-out at Berkshires Retreat in Lenox - Main House?

Checkout is at 11:00 AM.

Where is Berkshires Retreat in Lenox - Main House located?

This family-friendly Lenox holiday home is located on a lake, within 2 mi (3 km) of Pleasant Valley Wilderness Sanctuary, Tanglewood Music Center and Lenox Library. Berkshire Performing Arts Center and Ventfort Hall Mansion and Gilded Age Museum are also within 3 miles (5 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 61 out of 65 reviews
Rating 8 - Good. 3 out of 65 reviews
Rating 6 - Okay. 0 out of 65 reviews
Rating 4 - Poor. 0 out of 65 reviews
Rating 2 - Terrible. 1 out of 65 reviews

9.8/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was a bit unusual but nice kitchen and lots of space. Location excellent. Host was very responsive.
Stayed 4 nights in Jul 2026
Response from VrboOwner on 24 July 2026
Hi Roger - we would love to hear what was unusual about it. For us, it’s an amazing tranquil retreat for our family that we love sharing with other guests. You had an issue with the gas is bbq grill, we did supply a full replacement cylinder. In addition we will be replacing it with a new grill for next season. Thanks, Caitlin & Vik.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property is outstanding. Beautiful house. Spacious kitchen and other common areas. Clean and well equipped kitchen and bathrooms. The property is quiet and a five minute drive to Lenox with Lee and Pittsfield also close by. Highly recommended. Hosts were phenomenal and responsive. Would absolutely stay here again.
Stayed 6 nights in May 2026
Verified review

10/10 Excellent

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

Wonderful prperty

Very lovely and spacious, well appointed home in a fabulous location. We had a wonderful stay and hope to return.
Stayed 3 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family friendly home in great location to downtown Lenox. Close to Stockbridge and Lee. House is perfectly equipped for children with plenty of books and toys. Our kids loved getting to see tons of wildlife right outside the house.
Stayed 5 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We were a group of 11 senior women, in the Berkshires for biking. The location was great for our needs. The house was clean and spacious, with a large kitchen, dining area and living room. We were very comfortable there, and communication with the hosts was excellent. The grounds are beautiful, and there are decks one can go out on to take in the views. It is well stocked with kitchen equipment, which was great because we prepared most of our meals there. We never used the outdoor gazebo, but I could imagine it would be fun to spend time there with a large group of people. The only thing to point out is that one of the upstairs queen rooms has a ceiling the slants down low over the bottom of the bed, so the person on the far side must bend down low when getting out. We only had one person sleeping in that room, so it was not a problem at all, but if 2 adult people were sleeping in the room it may have been a bit difficult to get in and out. In our 17 years of annual bike trips, this was the nicest house we have stayed in. Also, the most expensive - but well worth it.
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

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

Always Happy to Return

A group of 9 friends just ended our 7th return weekend to this property. We look forward to it every year and it never disappoints. The beautiful house provides plenty of space for each of us, the location is perfect, and the hosts are very responsive and always helpful ! We are already planning our long weekend again next year for year number 8! Can’t wait!
Stayed 3 nights in Jan 2023
Verified review

10/10 Excellent

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

ladies weekend

If you are looking for a private retreat with a fabulous large screen house that will accommodate your group of people, this is the place. The pictures of the screen house do not do it justice. The home is very large and kept very nicely. Kitchen is well appointed with everything you need.
Stayed 3 nights in Jun 2023
Verified review

10/10 Excellent

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

Wonderful winter break

We just returned from our amazing stay in this heavenly retreat. The house was just perfect in every way, the setting, the furnishings, and every accessory you could ever need. So close to town with the amazing restaurants of Haven, Brava. Boeme, and Zinc, yet remote enough to really feel relaxed. We cross country skied at Canterbury Farms, skied at Butternut and Catamount and just loved every second of it. Caitlin and Vik are such attentive hosts. Would love to return
Stayed 5 nights in Feb 2021
Verified review

10/10 Excellent

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

Fabulous and Spacious Farm House Property

What a delightful property on the most beautiful street and within a stoll to town or a five minute drive, your choice. Surrounded by other spacious properties, farms, and beautiful views, this was the ideal spot for five of us college friends celebrating our 60th birthday together. The hosts were gracious and extremely easy to communicate with. Everything was exactly as portrayed, but even better. An amazing year-round, kitchen, outside space both screened inside and outdoor fire pit that was ideal, and each bedroom had incredibly comfy beds and sheets. Plenty of bathrooms, a great office to hook up and work and peaceful, restful, and incredibly well appointed. I highly recommend and thank you for our beautiful day.
Stayed 2 nights in Apr 2025
Verified review

10/10 Excellent

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

Awesome Christmas!

We thoroughly enjoyed our week-long stay! It is a very charming place with comfortable beds for all 10 of us and we stayed warm without touching the thermostats. One huge attraction was the table for 10 on the “kitchen/dining” side which we used for eating, crafting and game playing. The pantry had a nice variety of cooking essentials. The other side had a functional wood-burning fireplace, gathering areas and a main floor bedroom suite for the grandparents. The owners were ideal—responsive and accommodating. We arrived just after a moderate snowfall and it snowed during our stay; snow tires or four wheel drive came in handy around the area. This place was ideal for all three generations ranging in age from 10 to 78. Snow sports, great restaurants, museums and shopping within 20 minutes, a lot within 10. We highly recommend this cabin to anyone visiting the Berkshires, especially first-timers like us.
Stayed 7 nights in Dec 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a great house for any sort of gathering of friends/family - spacious and comfortable with everything you need. Fabulous location.
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

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

Girls Weekend

We are a group of 10+ women who travel from NY, NH, ME and MA to get together for a girls weekend every year. This property is fantastic! Great location, plenty of room inside and out. The hosts are very accomodating. We hope to return next year!
Stayed 3 nights in Jun 2022
Verified review

10/10 Excellent

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

Terrific stay at great house in Lenox

We were three generations (grandparents, adult kids, and toddler grandchildren) on vacation for a long weekend. The house is very spacious so that we were not cramped and on top of one another. There were plenty of bedrooms and bathrooms for all of us. The kitchen was large and well stocked with cookware, dishes, utensils, and anything you would possibly need. The kids play/dining area was a big attraction and the toddlers loved all the toys. The kitchen had non glass dishes for the kids and little kids’ utensils - greatly appreciated. One night we sat around the fire pit after the kids went to bed. The house is in a great location - closed to the town of Lenox and also great for running/walking. One day we went to MASS MOCA. Another day we found a toddler playground and spent a few hours at Balderdash Cellars, which is nearby. Other times we just sat outside at the house while the kids rode their scooters or played ball. We’d love to rent this place again. Thank you, Caitlin.
Stayed 3 nights in May 2022
Verified review

10/10 Excellent

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

Perfect family getaway

We had an amazing time with our friends and children. The house was perfect for our group and had every thing you need for kids games, Cooking dinners, and a big open space to hang out. Even got enough snow to go sledding
Stayed 3 nights in Jan 2022
Verified review

10/10 Excellent

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

The best 50th birthday celebration!

We were 10 women celebrating a birthday. The house was perfect, large enough that no one felt like they didn’t have privacy. Kitchen was well equipped and bathrooms were all clean. Would highly recommend. Proximity to Lenox was amazing while still feeling like you were in the country.
Stayed 3 nights in Oct 2021
Verified review

10/10 Excellent

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

A retreat into beauty and peace

This Berkshire retreat becomes your home away from home the moment you cross the threshold. The home is artfully decorated and clean and welcoming. There are features that easily accommodate adults and children. We were traveling as a three generation family with two boys, ages two and six. There are exceptional play spaces for children and many different rooms and outdoor spaces for family to come together and find time for themselves. Everything you can need is fresh and within easy reach. Each of the rooms are beautifully functional.The kitchen is well appointed and an easy space in which to prepare all meals. The bedrooms are large, the beds are supremely comfortable and the newly renovated bathrooms are a dream! The outside space is large and private. From the expanse of well maintained lawns and gardens along with a rippling brook, it works just as well for quiet meditation as active lawn games. The fire pit is fun and the screened in additional building is a superb bonus spot. We all felt very happy to have this exceptional home and setting for our long awaited family get together.
Stayed 7 nights in Jul 2021
Verified review

10/10 Excellent

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

Great for family reunion

This property was perfect for our family reunion. We had grandparents and two families (total of 10) under the one roof. We all had our own private space and bathrooms. The house was well furnished and clean. The screened in eating area was perfect for our large family meals. We look forward to staying there again some day!
Stayed 5 nights in Jul 2021
Verified review

10/10 Excellent

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

Wonderful property

We had a fantastic long weekend at this beautiful house. From the moment of booking, the owners, Caitlin and Vik, were extremely helpful and informative. The house itself is wonderful - spacious and really well appointed. Lots of room to cook, eat, spread out, play board games and relax. The beds were extremely comfortable and the kitchen is really well stocked. The property around the house is great, lots of room to explore. We took a very pretty walk into Lenox and also visited nearby Pleasant Valley Wildlife sanctuary which is an easy walk from the house. Also convenient to Jay Peak ski resort. Overall we had a wonderful break and would highly recommend this vacation rental.
Stayed 3 nights in Jan 2021
Verified review

10/10 Excellent

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

Clean and comfortable

We had a great stay in Lenox. The house was very clean, the beds were comfortable, and there was lots of space to spread out. The kids enjoyed the rope swing and the firepit. It was a short ride to the Mount and other local attractions. The owners were very responsive.
Stayed 6 nights in Aug 2020
Verified review

10/10 Excellent

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

Beautiful!

We loved renting Caitlin’s house in Lenox. We stayed with our three young girls and their grandpa. The girls loved the rope swing and play room(s)! We all enjoyed the screen porch and beautiful, unique house, and well appointed kitchen. We found plenty to do in the area and appreciated the short drive to restaurants and Guidos. The owners were very responsive. Check out was super easy - we didn’t even have to empty the fridge. Would def rent again!
Stayed 5 nights in Aug 2020
Verified review

10/10 Excellent

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

Our favorite getaway

We are a group of 10 professionals who love to get away for the long weekend in January every year. We have tried different properties in the Berkshires but this is by far our favorite, which explains why we have now stayed here 4 times. We look forward to it every year. Caitlin, the owner, is wonderful, and extremely responsive to any requests or concerns we may have. The house itself is immaculate and comfortable, with plenty of room for 10 people to coexist without getting in each other ‘s way. We are always sad to leave.
Stayed 3 nights in Jan 2020
Verified review

10/10 Excellent

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

Perfect place for a peaceful family getaway

We loved that this home was luxurious and kid friendly; it had classic country house charm and came equipped with toys, children’s books and a crib. The fire place room was our favorite place to congregate - plenty of couch space and things to do for people of all ages. We ate very well in Lenox - It’s roughly a 5-10 minute drive to reach a number of outstanding restaurants and the kitchen is fully equipped for cooking at home too. A wonderful time was had by all!
Stayed 3 nights in Nov 2019
Verified review

10/10 Excellent

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

Wonderful

This was our second vacation in this wonderful home. We love the layout for our multi generational extended family. Everything that we could want is in the house. We cook most meals in and the kitchen is very much a cooks kitchen! Exploring the area is very convenient given the home's location. We would love to return in the future!
Stayed 7 nights in Aug 2019
Verified review

2/10 Terrible

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

Beautiful place!

We love Lenox and found this home to be extremely well-equipped for our group of 5 adults, 4 children (ages 5-11) and a 6-mos old. The house had wonderful toys, dress-up clothes, pack-and-play, great beds, privacy for all, very well-equipped kitchen, fabulous rope swing, lovely hammock, grill, and any thing we could have wished for! Some hiked thru the woods up to Pleasant Valley! Up the road from Tanglewood. With bird sanctuary, Tanglewood, Shakespeare, and Lenox center so close, what more could one want! It was perfect! Thank you!
Verified review

10/10 Excellent

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

Perfection

The perfect place to stay in every way especially if you love concerts , dance, Shakespeare etc. house was perfect as well
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