Entire home

Berkshires Retreat in Lenox - Main House

Photo gallery for Berkshires Retreat in Lenox - Main House

A house with a sloped roof, large windows, and a porch with potted plants.
A covered picnic table with benches, large windows, and hanging light fixtures.
A cabin surrounded by tall trees and a well-maintained lawn.
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.

Reviews

9.8 out of 10
Exceptional
On the lake, this vacation home features 6 bedrooms and 3 bathrooms, accommodating 13 guests. Enjoy activities like birdwatching, snowboarding, and hiking nearby. The property includes a balcony, porch, and patio, with mountain views throughout. It also offers games and is located near Pleasant Valley Wilderness Sanctuary and Tanglewood Music Center.

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.
6 bedrooms3+ bathroomsSleeps 13

Popular amenities

  • Balcony
  • Toys
  • Barbecue
  • Air-conditioning
  • Internet
  • Onsite parking available

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, Pittsfield, MA (PSF-Pittsfield Municipal)
    ‪20 min drive‬

Where you'll sleep

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

About this property

Berkshires Retreat in Lenox - Main House

A private retreat in Berkshires set on 5 acres in prime location in Lenox - our all-season property offers secluded luxury whilst offering close proximity to Tanglewood, ski slopes, hiking trails, lakes, the historic town of Lenox and other Berkshire towns. Please note, the expansive grounds are set in a nature setting and occasional sighting of bears, wild turkey, deer's etc. is normal in the Berkshires.

This listing is for the Main House that accommodates a maximum of 13 (you can also rent this property in a larger format - Main House + the Studio - which accommodates 15. VRBO ID. 1266558).

Main House [4400sqft]: This charming 1920s log cabin has an expansive layout with a breezeway connecting a newer section. Inside you will find 6 well-appointed bedrooms, three full bathrooms and a powder room. The heart and soul of the house is an expansive living room with a brick fireplace, big comfortable sofas, a TV area, and a grand piano. Right behind the living room there are two king bedrooms sharing a full bath. The second floor has two spacious bedrooms (one king and three twins respectively) which share a full bath with a claw foot tub and a separate shower. At the other end of the house, you will find an inviting country kitchen that opens up to a large dining area. The farm table seats 10 comfortably, and there is an adjoining dining area for children. Above the kitchen are two queen bedrooms, a hall bathroom with shower, and a TV den.

Gazebo: We have built a screened-in living space by the woods' edge, with a 16 seat dining table and seating for lounging. In this substantial new space you will be able to enjoy long, leisurely meals al fresco, and then curl up for a nap while listening to birds and crickets sing. During the cold season, you can enjoy a fire in the large in-ground fire pit right outside the Gazebo.

Not just a conventional vacation rental, we’ve set up this property as our own retreat with a lot of thought and care. Choosing to rent a home instead of booking a hotel room allows you the space to get together with friends and family in comfort and privacy. But you shouldn't have to sacrifice the luxury you may enjoy during a hotel stay. At the end of your stay, all you need to do is pack your bags and walk out the door. We don't expect you to strip the beds, empty the fridge, or take out the garbage. We offer a worry-free experience right up to the last moment!

** BEFORE YOU INQUIRE**
Thank you for understanding that we have no flexibility on these points:
- We require a 3 night minimum during July and August and long weekends.
- This house is pet free, there are absolutely NO exceptions to the pet policy.

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House Rules

Check in after 4:00 PM

Minimum age to rent: 26

Check out before 11:00 AM

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Children

Children allowed: ages 0–17

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Events

No events allowed

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Pets

No pets allowed

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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:

Load and start the dishwasher

Remove personal items, remove leftover food and drinks and take out the rubbish

Lock the doors and return the keys

The trash is in the far garage - you can access the garage through the side door. Please keep the garage door closed to avoid bears.

Failure to complete these may result in a negative review from the host.

Unfortunately, due to repeat issues in the past with larger gatherings, we strictly do not allow functions like weddings etc. on the property.

Important information

You need to know

Property Registration Number C0214901520
Property # 660967vb
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 has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

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 snowmobiling and sledging.
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
  • The Mount - 11 min drive - 7.1 km
  • National Shrine of the Divine Mercy - 18 min drive - 14.2 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
  • ‪Amazing Pho - ‬10 min drive
  • ‪Tanglewood Cafe - ‬7 min drive
  • ‪Lenox Coffee - ‬5 min drive

Frequently asked questions

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

No, pets are not allowed at this property.

How much does it cost to stay at Berkshires Retreat in Lenox - Main House?

As of 19 September 2026, prices found for a 1-night stay for 2 adults at Berkshires Retreat in Lenox - Main House on 16 March 2027 start from NZ$4,940, 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 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.
Learn moreOpens in a new window
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

About the host

Hosted by Caitlin Yadav

Host profile image

We live a few hours away, in Westchester, NY. We've been coming to the Berkshires ever since we first started dating, 18 years ago. And now we are thrilled to have our own place to bring our three children.

Why they chose this property

We couldn't resist this place! The house itself has tons of character. The surrounding woods are great for admiring or exploring. And the proximity to both Tanglewood and town could not be beat. As the previous owner explained to us, this is a very special place in the universe. So we feel lucky to have discovered it, and look forward to sharing it with you!

What makes this property unique

We bought this house as it feels like a true escape from the daily routine and gives you a vacation feel. The large living room is a great place for everyone to come together and hangout and at the same time there are so many spaces that everyone can spread out. The surrounding nature setting is ideal for quiet relaxation. And the location is so convenient for all the attractions that the Berkshires and Lenox have to offer. For more firsthand guest experiences, you can read the reviews this property has drawn over more than a decade.

Languages:

English

Premier Host

They consistently provide great experiences for their guests

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