Bathtub or shower · Bathtub · Toilet · Shower only
Spaces
Deck or patio
Porch or lanai
Kitchen
Garden
Dining area
About this property
Beautiful, Private Berkshires Retreat w Magic View! 5min to Lake Garfield Beach
Please enjoy our little slice of paradise! Perched just up the hill from Lake Garfield, The Hupi House offers a truly magical view of the lake and mountains for miles beyond. Let breathtaking sunsets be your evening entertainment! Inside you will find a stocked kitchen, high-quality appliances and bedding, fast wifi, and wooded seclusion. Outside you will find swimming, kayaking, hiking, leaf-peeping, star-gazing, skiing...Minutes to Ski Butternut, Great Barrington, Jacob s Pillow, Tanglewood.
The Space
Our place is a beautiful rustic house in the woods with quiet privacy, the modern amenities you need to feel at home, and a view you will talk about after your visit ends. Easy access to Lake Garfield (lake access included), 10 Minutes from Ski Butternut, 15 minutes from Great Barrington.
The main first floor living area is a lovely open space with galley kitchen, woodstove, ample seating for dining and relaxing. Sliding doors lead to the deck with lounge chairs and grill. Two bedrooms and a bathroom with tub round out the main level.
Upstairs you have a master suite: a lovely tucked away loft with proper closing door, king bed, tv, and en suite bath with shower.
Downstairs is a finished lower level with two twin beds, a queen sleeper sofa, den area w tv/video games, piano, laundry area, and doors that open to the outside under the deck. This is a flexible area, perfect for kids, well-appointed for adults.
Guest Access
Our house is a conveniently situated location from which to visit countless Berkshires attractions, including Tanglewood, Jacob s Pillow, Norman Rockwell Museum, W.E.B. Dubois National Historic Site, The Bidwell House Museum, Animagic Museum of Animation, Bard College at Simon s Rock, Berkshire Theater Festival, Berkshire Int l Film Festival, hiking at Umpachene Falls and Beartown State Forest, and a bit over an hour drive from MassMOCA. The charming towns of Great Barrington, Lenox and Stockbridge are all 15-20 minutes away. Lake Garfield Beach is a 20-minute walk or 4-minute drive down the hill. Ski Butternut, a hub for Northeast skiers, is a 10-minute drive, and a major attraction for winter travelers.
Interaction with Guests
The house is yours and you will not be disturbed by us. Should you need anything we are always available over phone/text/email, and we have reliable local help, should problems arise.
Other things to note:
--The kitchen/main living space is only accessed by stairs, so keep that in mind for those with additional accessibility needs.
--The driveway is quite twisty! We recommend, minimally, a front wheel drive vehicle for winter stays.
--Parents with small children should be advised that any playing on the deck or at the foot of the deck/front side of the house must be monitored for safety, as there are spaces for a wee one to sneak thru the deck railing, and as there is a steep drop off into woods in front of the house.
—We aim to allow people to feel as comfortable here as possible, always are trying to improve guests’ experiences, and are almost always reachable and quickly responsive to any issues that arise. While we are here to help, guests should know it is not a hotel, but a lovely, rustic house in the woods. There are quirks; our patio door leaves a small crack which does not create any noticeable draft but does not seal tight. Some light switches were installed in strange places. We are as diligent as possible in the battle vs critters, as the woods is their home too, but there will occasionally be signs of a country mouse. It is on the side of a small mountain and there are storms that take the power out a few times a year. Workers can be hard to get here quickly. This is just life up here in the Berkshires, and we want guests to come with appropriate expectations so everyone is happy.
Our prices include all fees. No hidden fees.
Add dates for prices
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Similar properties
Fabulous Renovated Log Cabin: the perfect getaway with new pickleball court!
Monterey
Fabulous Renovated Log Cabin: the perfect getaway with new pickleball court!
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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, a first aid kit and a deadlock
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
Property Registration Number C0129641930
About the area
Monterey
Located in Monterey, this chalet is in a rural area and on a lake. National Shrine of the Divine Mercy and Bidwell House Museum are local landmarks, and some of the area's attractions include Ashintully Gardens and Mahaiwe Performing Arts Center. Lenox Arts Center and Berkshire Scenic Railway Museum are also worth visiting.
Pittsfield, MA (PSF-Pittsfield Municipal) - 39 min drive
Restaurants
Paige's Place - 12 min drive
Grouse House - 10 min drive
The Old Inn On The Green - 18 min drive
Gedney Farm - 18 min drive
Red Truck Bbq - 17 min drive
Frequently asked questions
Is Beautiful, Private Berkshires Retreat w Magic View! 5min to Lake Garfield Beach pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Beautiful, Private Berkshires Retreat w Magic View! 5min to Lake Garfield Beach?
As of 2 Apr 2026, prices found for a 1-night stay for 2 adults at Beautiful, Private Berkshires Retreat w Magic View! 5min to Lake Garfield Beach on 6 May 2026 start from £189, 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 Beautiful, Private Berkshires Retreat w Magic View! 5min to Lake Garfield Beach?
On-site parking is available at the property.
What time is check-in at Beautiful, Private Berkshires Retreat w Magic View! 5min to Lake Garfield Beach?
Check-in begins at 4:00 PM.
What time is check-out at Beautiful, Private Berkshires Retreat w Magic View! 5min to Lake Garfield Beach?
Checkout is at 11:00 AM.
Where is Beautiful, Private Berkshires Retreat w Magic View! 5min to Lake Garfield Beach located?
Situated on a lake, this chalet is 2.6 mi (4.1 km) from Bidwell House Museum and within 6 miles (10 km) of McLennan Reservation and Ashintully Gardens. Otis Ridge and Tyringham Cobble are also within 9 miles (15 km).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Idyllic, beautiful vistas, full relaxation and fun a reality for all ages, with a wonderful lake, forest, ponds, trails, and towns nearby, but not too close :-)
Greg and Meg were super responsive and on it. We loved the wood stove and the view and spent a lot of time looking through their gorgeous art and object books. We stayed at their cozy, comfortable home on one of the coldest days of the year (-5 degrees F, felt like -20). The basement got cold but not unmanageable and there were lots of warm blankets and a space heater. Greg was super accessible to coordinate with us and the plow guy (we got 2-3 inches of snow! it was gorgeous). I am very grateful for this home!
Greg and Meg’s cabin is a perfect place for a getaway. Location is great and tucked away in the middle of the Berkshires with lots of things to see and do. The wood stove and old school record player made for an amazing ambience.
Tastefully decorated, great view, and lots of peace and quiet. All the amenities worked, and the house was equipped with everything you need. A great place for families or a larger group of close friends. Would definitely recommend
Geert e.
Stayed 2 nights in May 2025
Response from VrboOwner on 28 May 2025
Thank you, Geert! You were great guests, and so happy you loved the situation as much as we do. Best wishes to you and yours, Meg and Greg
Short couples getaway to recharge. The house was perfect and the wood stove kept the house toasty through the cold windy stay. HINT: coming from NY/NJ, buy your groceries as you pass through Great Barrington and save that extra trip.
We had a wonderful time at this house (our second time visiting) and really appreciate how responsive the hosts are to any small issues that arise! It is a great space for families with a cozy living room and an excellent basement for kids to relax in, and it's proximity to Butternut makes it a great choice for skiers.
What a wonderful place to call “home” for a long ski weekend with friends, 4 adults and 4 kids. The finished basement was perfect for the kids to sleep and play while the adults enjoyed the main floor and upstairs bedroom. The view of the mountains, lake and sunset was icing on the cake. The location of the house to Butternut Ski and Great Barrington made it a great place to get away but have access to fun activities, shopping, and restaurants.
I stayed three nights at Greg & Meg’s Monterey cabin with best friends of 30+ years and we had a wonderful time. The home is well-appointed and comfortable, with beautiful lake and mountain views. Our hosts were communicative but gave us space. It rained the entire four days, but we were cozy with the wood stove and enjoyed a movie night in the downstairs space the last night. Not a ton to do in the area but that’s what we wanted — a wine tasting and a brewery, a restaurant meal here and there, and the Norman Rockwell museum was more interesting than I’d expected. It was just enough, really - totally relaxed weekend. We even had a movie star sighting while eating brunch at the Southfield Store (delicious French toast btw!). Already looking forward to our next visit. Thank you!
Tori B.
Stayed 3 nights in Apr 2023
Response from VrboOwner on 5 May 2023
We are so happy you enjoyed your time at our place, and had a wonderful reunion with old friends. Next time hopefully the weather will cooperate! Thanks for sharing your experience, best wishes, Meg and Greg
We stayed here with our daughter and son-in-law and their two boys, 6 and 3. The house was spotlessly clean and very well supplied, and we loved the pictures and books. The view really is extraordinary, and sitting on the deck looking out at the lake and listening to the wind in the trees was totally restorative. We went to the town beach daily, which was a great pleasure. The only cultural thing we did was to visit the beautiful garden at the Bidwell House Museum, highly recommended!
We enjoyed our week here, a very comfortable house that is well equpped for both good weather and the occasional rainy day. Great view of the mountains and lake, nearby farm stands and all the cultural attractions of Western Mass in the summer. We hope to visit again.
Highly recommend! Cabin/house is very nice, clean and specious. Having no pats allowed was the major reason I picked this place it was a great decision. Ski areas are near by, beautiful view and house has everything you need (dishes, spices, paper towels, towels, blankets, coffee maker, Wi-Fi, board games for kids, books, wood for wood stove, soap/shampoo..) it’s awesome. Owner was very responsive and helpful every time I had a question.
Great house for a New Years gathering with friends. Although fogged in the entire weekend, the spacious welcoming basement provided all the room we needed to welcome in the new year. Greg is a very understanding and welcoming host, promptly responding to and if possible accommodating requests. Just a pleasure to communicate with. The lot of land itself does not provide much outside area for games etc. but given the weather and the opportunities in the Berkshires, it was not an issue. The house is well stocked with supplies and cooking needs and was very clean. We had a great stay.
Jane C.
Stayed 3 nights in Dec 2021
Response from VrboOwner on 4 Jan 2022
So glad you enjoyed your stay, Jane. Thanks for the review and for leaving the house so tidy, we really appreciate it. Happy new new year!
Really wonderful home with a great view. Check in was very easy and Greg and Meg were available and quick to respond to any questions. Would absolutely stay here again. Thank you for a fantastic week relaxing with family.
JOSEPH G.
Stayed 5 nights in Nov 2021
Response from VrboOwner on 10 Nov 2021
Thank you so much, so happy you enjoyed yourselves, would welcome you back anytime! Best wishes, Meg and Greg
Wonderful place to relax and check out The Berkshires
I rented this absolutely beautiful home with 4 other friends to celebrate my 60th birthday. It had amazing views of the morning moonrise and the sunset looking out over Lake Garfield and the mountain ridges. So spectacular. The house is so cozy especially with the wood burning stove. Beds are super comfortable and the house is very clean. It also has a great location! I'd love to return in a different season and explore the lake too.
Nancy W.
Stayed 2 nights in Jan 2021
Response from VrboOwner on 3 Feb 2021
Thanks so much, Nancy! So glad you had a nice time. Come back anytime!
This was an awesome house to get away for a weekend. It has enough space for several people to stay comfortably, and was clean and as advertised. It's secluded but you can take a quick drive to get groceries, go hiking, or check out one of the cool towns nearby. The view is incredible too, as is the woodstove! Communication with the owners was also great, and they were quick to respond to the few questions we had. I would definitely stay here again and recommend anyone who is looking for a quiet weekend with friends or a basecamp for exploring the Berkshires to do the same.
Sam M.
Stayed 3 nights in Oct 2020
Response from VrboOwner on 18 Nov 2020
Thanks for your thoughtful review, and being such great guests!
Nice country cabin. Plenty of room for the four of us. Great internet connection for our two adults who were on "working vacations."
James M.
Stayed 4 nights in Oct 2020
About the host
Hosted by Greg Glassman
Both of us grew up in homes that were the center of social life, and we love sharing our modest dreamhouse with others. Our goal is for you to be able to relax, gather, decompress, and feel at home.
Greg is a professional performer and teacher of music who loves cooking, games, and has been lucky to see much of the world. Greg's parents ran a longtime (pre-Air) B'n'B in the Hudson Valley, so hosting is in his blood. His favorite place in the house is: Pantry!
Meg, a public servant, is everyone's good friend, an avid film and theater goer, knitter, and master organizer of people and things. Her favorite place in the house is: Deck with a book!
We have a small child, Soji, who enjoys carrying kindling and collecting rocks.
Why they chose this property
We fell in love with Monterey when we stumbled upon the beach at Lake Garfield during a summer trip to the area.
What makes this property unique
In the summer, enjoy grilling outside, lounging on the deck and swimming in Lake Garfield. In the winter, cozy inside with the wood stove burning after a day of skiing. In the Fall, apple-picking and harvest festivals. Breathtaking views year-round!
Languages:
English, Spanish
Premier Host
They consistently provide great experiences for their guests