Chalet

Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.

Photo gallery for Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.

Main level open space (old setup)
Sunsets can be your evening entertainment!
Main level open space
Kitchen/dining area, table extends to seat 8 or 10
View from inside

Reviews

9.8 out of 10
Exceptional
3 bedrooms1 bathroomSleeps 8167.2 sq m

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Barbecue grill
  • Kitchen
  • Outdoor space

Explore the area

Map
Monterey, MA
  • Ski Butternut
    ‪16 min drive‬
  • Jacob's Pillow
    ‪22 min drive‬
  • National Shrine of the Divine Mercy
    ‪27 min drive‬
  • Great Barrington, MA (GBR-Walter J. Koladza)
    ‪24 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Queen Beds

1 bathroom

Loft

Shower only

Main floor

Bathtub or shower · Bathtub · Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden
Dining area

About this property

Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.

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.

Property manager

Greg Glassman

Languages

English, Spanish

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Free WiFi
Air conditioning
Outdoor space

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
Should mind young children on deck/loft/outside
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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

Important information

You need to know

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
Property Registration Number C0129641930

About the area

Monterey

Located in Monterey, this chalet is in a rural area and on a lake. Bidwell House Museum and Mahaiwe Performing Arts Center are local landmarks, and some of the area's attractions include Ashintully Gardens and Berkshire Scenic Railway Museum.
Map
Monterey, MA

What's nearby

  • Ski Butternut - 16 min drive - 13.3 km
  • Jacob's Pillow - 22 min drive - 17.9 km
  • Lee Premium Outlets - 22 min drive - 16.2 km
  • National Shrine of the Divine Mercy - 27 min drive - 21.6 km
  • Tanglewood Music Center - 32 min drive - 26.1 km

Getting around

  • Pittsfield, MA (PSF-Pittsfield Municipal) - 39 min drive

Restaurants

  • ‪Grouse House - ‬10 min drive
  • ‪The Old Inn On The Green - ‬18 min drive
  • ‪Gedney Farm - ‬18 min drive
  • ‪Farmington River Country Store - ‬12 min drive
  • ‪Fratelli's Restaurant & Pizza - ‬11 min drive

Frequently asked questions

Is Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut. pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.?

Check-in begins at 4:00 PM.

What time is check-out at Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.?

Checkout is at 11:00 AM.

Where is Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut. 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.
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Rating 10 - Excellent. 20 out of 23 reviews
Rating 8 - Good. 3 out of 23 reviews
Rating 6 - Okay. 0 out of 23 reviews
Rating 4 - Poor. 0 out of 23 reviews
Rating 2 - Terrible. 0 out of 23 reviews

9.4/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Joe B.

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

Peace and quiet with a fantastic view

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.
Stayed 3 nights in Jan 2025

10/10 Excellent

Elspeth C.

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

Beautiful view

Exactly as it seems in the photos. I spent most of my time on the couch, soaking in the view.
Stayed 3 nights in Jan 2025

10/10 Excellent

Daniel C.

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

Beautiful home in Monterey, MA

Beautiful well kept house in the Berkshires, great view and layout. Close to amazing nature and Great Barrington if you need anything. Wonderful trip!
Stayed 3 nights in May 2024

10/10 Excellent

Andrew R., Pelham, US

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

Peaceful Getaway

The space was great for our family and gave us a nice relaxing trip away from the city.
Stayed 3 nights in May 2023

10/10 Excellent

Hugh M.

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

Great Berkshires Getaway

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.
Stayed 2 nights in Dec 2023

10/10 Excellent

sheila g.

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

Great R&R

Fantastic home to unwind and enjoy the beauty of true peace and quiet.
Stayed 6 nights in Jun 2023

10/10 Excellent

Jamie Z.

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

A great ski house!

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.
Stayed 8 nights in Feb 2023

8/10 Good

Nicole T.

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

Ski weekend

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.
Stayed 3 nights in Dec 2022

10/10 Excellent

Tori B.

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

Perfect quiet getaway

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!
Stayed 3 nights in Apr 2023

10/10 Excellent

Elizabeth P.

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

Family refresher

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!
Stayed 4 nights in Aug 2022

10/10 Excellent

Frank G.

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

Beautiful view, peaceful lake

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.
Stayed 7 nights in Jul 2022

10/10 Excellent

Justin E.

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

Great property

Great property & house. Very clean, good amenities & sleeps a group of people easily.
Stayed 2 nights in May 2022

10/10 Excellent

Envera E.

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

Super cozy

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.
Stayed 3 nights in Feb 2022

10/10 Excellent

Jane C.

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

New Years Eve Fun

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.
Stayed 3 nights in Dec 2021

10/10 Excellent

JOSEPH G.

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

Ideal Berkshire Home

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.
Stayed 5 nights in Nov 2021

8/10 Good

Alice P.

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

Beautiful views! Responsive host!

Thank you for a lovely stay. Beautiful views and Greg was available whenever we had questions. Thanks!
Stayed 4 nights in May 2021

10/10 Excellent

Marc U.

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

Ideal 4 Day Get Away

This property was perfect for our first venture out in over a year. The views were wonderful, the neighborhood quiet and the hosts were fantastic.
Stayed 4 nights in May 2021

10/10 Excellent

Nancy W.

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

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.
Stayed 2 nights in Jan 2021

10/10 Excellent

Sam M.

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

Great spot for a getaway

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.
Stayed 3 nights in Oct 2020

8/10 Good

James M.

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

Great View Off the Deck

Nice country cabin. Plenty of room for the four of us. Great internet connection for our two adults who were on "working vacations."
Stayed 4 nights in Oct 2020

10/10 Excellent

Verified traveller

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

Amazing weekend!

We had such an amazing stay at the Hupi Views house :) Myself and my friends escaped the city for a weekend to enjoy some foliage and fall fun at the Hupi Road house in the Berkshires and we were not disappointed. The view from the deck alone made the whole weekend worth it! There was plenty of space for my group and the house had everything we needed. Greg was very responsive and helpful the whole weekend. The house is super cozy and we couldn't of had a better time. Will definitely be staying again in the future! :)
Stayed 3 nights in Oct 2020

10/10 Excellent

Karen S., Georgia

Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness

Outstanding View of Garfield Lake and Rolling Mountains

Everything was so homey. Waking up to That View was Exhilarating! Glass from floor to ceiling. Beds were comfy and plenty of warm blankets. Didn't get to use the woodstove because the house was toasty even though it was 47 degrees at night. It is fully stocked with most any dishes and cookware that you may need for cooking. We cooked in every meal. It was one of the best vacations I have ever had.

10/10 Excellent

JT B., Boston

Great Cabin!

Our group had an amazing holiday weekend! The view of the lake and the wood stove made for a cozy, relaxing and fun stay!
Stayed 3 nights in Dec 2018

About the host

Hosted by Greg Glassman

Host profile image
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