Entire chalet

Newly discounted for SPRING! Private Berkshires Hilltop Getaway w/ Magic View!

Newly discounted for SPRING! Private Berkshires Hilltop Getaway w/ Magic View!

Photo gallery for Newly discounted for SPRING! Private Berkshires Hilltop Getaway w/ Magic View!

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

Overview of Newly discounted for SPRING! Private Berkshires Hilltop Getaway w/ Magic View!

Reviews
9.8 out of 10 Exceptional
3 bedrooms1 bathroomSleeps 8167 sq m

Popular amenities

  • KitchenKitchenKitchen
  • Barbecue grillBarbecue grillBarbecue grill
  • Free WiFiFree WiFiFree WiFi
  • WasherWasherWasher
  • DryerDryerDryer
  • Air conditioningAir conditioningAir conditioning

Check out the area

Map
Monterey, MA
  • Popular LocationSki Butternut16 min drive
  • Popular LocationJacob's Pillow22 min drive
  • Popular LocationNational Shrine of the Divine Mercy27 min drive
  • AirportAlbany, NY (ALB-Albany Intl.)77 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

Newly discounted for SPRING! Private Berkshires Hilltop Getaway w/ Magic View!

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
Premier Host
Premier Host

Languages

English, Spanish

Amenities

Kitchen
Washer
Dryer
Free WiFi
Air conditioning
Outdoor space

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

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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

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
  • Jacob's Pillow - 22 min drive
  • Lee Prime Outlets - 22 min drive
  • National Shrine of the Divine Mercy - 27 min drive
  • Tanglewood Music Center - 32 min drive

Getting around

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

Restaurants

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

Frequently asked questions

Is Newly discounted for SPRING! Private Berkshires Hilltop Getaway w/ Magic View! pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Newly discounted for SPRING! Private Berkshires Hilltop Getaway w/ Magic View!?

Check-in begins at 4:00 PM.

What time is check-out at Newly discounted for SPRING! Private Berkshires Hilltop Getaway w/ Magic View!?

Checkout is at 11:00 AM.

Where is Newly discounted for SPRING! Private Berkshires Hilltop Getaway w/ Magic View! located?

Situated on a lake, this chalet is 2.3 mi (3.7 km) from Beartown State Forest and 2.6 mi (4.1 km) from Bidwell House Museum. McLennan Reservation and Ashintully Gardens are also within 6 miles (10 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. 17 out of 20 reviews" "
Rating 8 - Good. 3 out of 20 reviews" "
Rating 6 - Okay. 0 out of 20 reviews" "
Rating 4 - Poor. 0 out of 20 reviews" "
Rating 2 - Terrible. 0 out of 20 reviews" "

9.2/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

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

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

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

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

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

Premier Host
They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback

People also search for

More Holiday Rentals ideas