Beautiful, Private Berkshires Retreat w Magic View! 5min to Lake Garfield Beach

Photo gallery for Beautiful, Private Berkshires Retreat w Magic View! 5min to Lake Garfield Beach

A wooden-paneled bedroom with a bed, two bedside lamps, a mirror, and a window with blinds.
A wooden cabin with a balcony, a red door, and a staircase leading to the entrance.
A cozy cabin interior with a kitchen, dining area, and seating space.
A wooden interior with a dining table, chairs, a shelf with dishes, and a view through large windows.
A modern living room with a sectional sofa, a coffee table with remotes, a bookshelf, a painting, and a staircase.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Family fun awaits
    Top-rated for families.
  • Games at the ready
    One of the few properties with video games available for guests.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
Sleeps 83 bedrooms4 beds

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue
  • Balcony or patio

Explore the area

View map
Monterey, MA
  • Place, Lake Garfield
    ‪9 min walk‬
  • Place, Lee Premium Outlets
    ‪29 min drive‬
  • Place, Tanglewood Music Center
    ‪44 min drive‬
  • Airport, Pittsfield, MA (PSF-Pittsfield Municipal)
    ‪52 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

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.

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House Rules

Check in after 4:00 PM
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

Property Registration Number C0129641930
Property # 7407484
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

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 Lenox Arts Center. Berkshire Scenic Railway Museum and Berkshire Botanical Garden are also worth visiting.
Map
Monterey, MA

What's nearby

  • Lake Garfield - 9 min walk - 0.8 km
  • Lee Premium Outlets - 29 min drive - 34.2 km
  • National Shrine of the Divine Mercy - 36 min drive - 33.7 km
  • Tanglewood Music Center - 44 min drive - 46.9 km
  • Eastern States Exposition - 53 min drive - 67.1 km

Getting around

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

Restaurants

  • ‪Paige's Place - ‬12 min drive
  • ‪The Old Inn On The Green - ‬18 min drive
  • ‪Gedney Farm - ‬18 min drive
  • ‪Roadhouse - ‬8 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 22 Aug 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 1 Nov 2026 start from AU$1,086, 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 0.5 mi (0.9 km) from Lake Garfield and 2.6 mi (4.1 km) from Bidwell House Museum. McLennan Reservation and Ashintully Gardens are also within 6 miles (10 km).

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

Premier Host

They consistently provide great experiences for their guests
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