Chalet
Beautiful, Private Berkshires Retreat w Magic View! 5min to Lake Garfield Beach
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Reviews
9.8 out of 10
Exceptional
3 bedrooms1 bathroomSleeps 8167.2 sq m
Popular amenities
Explore the area
Monterey, MA
- Place, Bidwell House Museum10 min drive
- Place, Otis Ridge11 min drive
- Place, Ski Butternut18 min drive
- Airport, Westfield, MA (BAF-Barnes Municipal)42 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.
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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10.0 out of 10, Exceptional, (76 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Should mind young children on deck/loft/outside
Events
No events allowed
Pets
No pets allowed
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
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. 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.
Monterey, MA
What's nearby
- Bidwell House Museum - 10 min drive - 4.6 km
- Otis Ridge - 11 min drive - 10.4 km
- Lake Buel - 16 min drive - 13.2 km
- County Beach - 16 min drive - 17.2 km
- Ski Butternut - 18 min drive - 15.7 km
Getting around
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
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 window9.6/10
Cleanliness
10/10
Check-in
10/10
Communication
9.8/10
Location
9.8/10
Listing accuracy
Reviews
11 January 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in Jan 2026
10/10 Excellent
JoAnn M.
25 August 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
JoAnn M.
Stayed 7 nights in Aug 2025
10/10 Excellent
Andrew R.
30 May 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Peaceful Getaway
Andrew R.
Stayed 3 nights in May 2023
10/10 Excellent
Geert e.
26 May 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Large and cozy cabin in an enchanted landscape
Geert e.
Stayed 2 nights in May 2025
10/10 Excellent
Daniel C.
6 May 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home in Monterey, MA
Daniel C.
Stayed 3 nights in May 2024
10/10 Excellent
sheila g.
18 June 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great R&R
sheila g.
Stayed 6 nights in Jun 2023
10/10 Excellent
Hugh M.
4 January 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Berkshires Getaway
Hugh M.
Stayed 2 nights in Dec 2023
10/10 Excellent
Joe B.
12 January 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Peace and quiet with a fantastic view
Joe B.
Stayed 3 nights in Jan 2025
10/10 Excellent
Elspeth C.
4 January 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful view
Elspeth C.
Stayed 3 nights in Jan 2025
10/10 Excellent
Jamie Z.
1 March 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
A great ski house!
Jamie Z.
Stayed 8 nights in Feb 2023
8/10 Good
Nicole T.
5 January 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Ski weekend
Nicole T.
Stayed 3 nights in Dec 2022
10/10 Excellent
Tori B.
5 May 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect quiet getaway
Tori B.
Stayed 3 nights in Apr 2023
10/10 Excellent
Monica S.
23 February 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Monica S.
Stayed 4 nights in Feb 2026
10/10 Excellent
Emma S.
12 February 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Emma S.
Stayed 3 nights in Feb 2026
10/10 Excellent
Elizabeth P.
16 August 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family refresher
Elizabeth P.
Stayed 4 nights in Aug 2022
10/10 Excellent
Frank G.
6 August 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful view, peaceful lake
Frank G.
Stayed 7 nights in Jul 2022
10/10 Excellent
Justin E.
7 May 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property
Justin E.
Stayed 2 nights in May 2022
10/10 Excellent
Envera E.
20 February 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Super cozy
Envera E.
Stayed 3 nights in Feb 2022
10/10 Excellent
Jane C.
3 January 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
New Years Eve Fun
Jane C.
Stayed 3 nights in Dec 2021
10/10 Excellent
JOSEPH G.
9 November 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Ideal Berkshire Home
JOSEPH G.
Stayed 5 nights in Nov 2021
8/10 Good
Alice P.
31 May 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful views! Responsive host!
Alice P.
Stayed 4 nights in May 2021
10/10 Excellent
Marc U.
16 May 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Ideal 4 Day Get Away
Marc U.
Stayed 4 nights in May 2021
10/10 Excellent
Nancy W.
3 February 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful place to relax and check out The Berkshires
Nancy W.
Stayed 2 nights in Jan 2021
10/10 Excellent
Sam M.
16 November 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great spot for a getaway
Sam M.
Stayed 3 nights in Oct 2020
8/10 Good
James M.
26 October 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great View Off the Deck
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.
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!
Breathtaking views year-round!
Languages:
English, Spanish
Premier Host
They consistently provide great experiences for their guests
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