Entire apartment·Private host

Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

Photo gallery for Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

A modern two-story house with large windows and a well-maintained lawn. - Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts  (Sheffield)
A kitchen with wooden beams, white cabinets, a central island with a sink, and a stainless steel refrigerator. - Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts  (Sheffield)
A modern house with a dark gray exterior, a black front door, and a small porch with steps leading to the entrance. - Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts  (Sheffield)
A staircase with wooden beams and a television on a cabinet. - Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts  (Sheffield)
A spacious living area with a wooden floor, a kitchen in the background, a blue leather sofa, a patterned rug, and a wooden staircase. - Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts  (Sheffield)
Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts provides amenities, such as a firepit and laundry facilities. Guests can connect to in-room WiFi.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Parking available

Add dates for prices

About this property

Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

  • This private Luxurious Guest house will Amaze you, with full kitchen, living area and large bedroom with Luxurious Queen bed and plenty of storage only 10 miles to Ski Resorts.
    Sheffield, Mass. is only 5 miles to Great Barrington with wonderful shops, restaurants and grocery stores. You will have a FULL SIZE kitchen in this wonderful guest house.
    The first level has a kitchen, living area with recliners and TV, large bath and laundry.
    Upstairs is a large bedroom with queen bed. The kitchen is fully stocked with anything and everything you could possibly need. We have a Keurig and K-cups but you might want to bring your favorite flavors. We also provide ALL kinds of spices, pam, tin foil and zip locks. If you stay awhile and run out of these items, please replace.
    The firepit out back is great for spring or fall nights.
    You have a private entrance away from the main home. The space is very large and comfortable and very private.
    Way better than any hotel, with all the special comforts of home. Also, includes a brand new Black Samsung washer and dryer for your convenience.

    This is a 2 person guest home.

    House rules:
    1. no smoking pot or cigarettes inside the home
    2. NO PETS
    3. no parties or events
    4. Trash goes in a black garbage bag in front of the washer and dryer on check out.

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About the area

Sheffield is home to this apartment. Ashley House and Great Barrington Historical Society & Museum are cultural highlights, and some of the area's activities can be experienced at Umpachene Falls Park and Land of Nod Vineyard and Winery. Mahaiwe Performing Arts Center and Harney and Sons Tea Tasting Room are also worth visiting. Visit our Sheffield travel guide
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Map
Sheffield, MA

What's nearby

  • A red covered bridge spanning a river with autumn foliage in the background.
    Housatonic River
    17 min walk - 1.5 km
  • A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.
    Tanglewood Music Center
    45 min drive - 43.0 km
  • Lime Kiln Farm Wildlife Sanctuary
    3 min walk - 0.3 km
  • Ski Butternut
    23 min drive - 22.2 km
  • National Shrine of the Divine Mercy
    34 min drive - 31.0 km

Getting around

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

Restaurants

  • Guido’s Kitchen
    10 min drive
  • McDonald's
    9 min drive
  • Dunkin'
    8 min drive
  • Mom's Country Cafe
    10 min drive
  • ILSE Coffee
    7 min drive

Frequently asked questions

Is Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts pet-friendly?

No, pets are not allowed at this property.

How much is parking at Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts ?

On-site parking is available at the property.

What time is check-in at Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts ?

Check-in begins at 4:00 PM.

What time is check-out at Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts ?

Checkout is at 11:00 AM.

Where is Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts located?

Situated in Sheffield, this apartment building is within a 15-minute walk of Housatonic River and Lime Kiln Farm Wildlife Sanctuary. Drury Preserve and Thom Reed UFO Monument Park are also within 3 miles (5 km).

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Reviews

Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts Reviews

10

Exceptional

10

Cleanliness

10

Location
Rating 10 - Excellent. 9 out of 9 reviews
Rating 8 - Good. 0 out of 9 reviews
Rating 6 - Okay. 0 out of 9 reviews
Rating 4 - Poor. 0 out of 9 reviews
Rating 2 - Terrible. 0 out of 9 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This bungalow was perfect for us! Very clean and setup with everything needed. The host was kind and helpful, too.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

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

Well maintained, quiet spot

Lovely quiet spot with plenty of eating options around the area. Well maintained.
Stayed 3 nights in Jan 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had an excellent stay at Black Bear Bungalow! The home is just as lovely as advertised and had every thing we needed for our time there. The space was clean and cozy, the skylights were an extra treat, and Karen was a great, communicative host.
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

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

Lovely

Very well- appointed. Comfortable and clean with warm and inviting decor on a lovely property.Thoughtful touches for comfort and convenience. Great location with lots to do and see. Highly recommend Bear Bungalow!
Stayed 2 nights in Jul 2025
Verified review

10/10 Excellent

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

Karen is a great host

We had a great time in the unit. It was just as nice in person as it is in the pictures. Karen was great with communication and provided local information, which was helpful.
Stayed 2 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
My stay was wonderful. The place was immaculate beautifully appointed with everything that we could possibly need including spices coffee. Everything was perfect. Communication was great. I was able to get in with the keypad no problem very nice and I plan to stay there again and it’s really pretty.
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was the absolute best equipped kitchen I have ever been in, including my own! The description is accurate, exactly as pictured. Karen was very attentive; and gave excellent dining options. The bed was comfy, the shower had great water pressure, the Patriots won. It was a great 5 day stay.
Stayed 5 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location. Clean and cozy. Washer dryer and full kitchen. There was an issue when we arrived with the AC and Karen took care of it ASAP. Very easy and relaxing. Highly recommend it
Stayed 11 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our stay in the Black Bear Bungalow could not have been nicer! It’s a great location with so many cultural and outdoor possibilities. The host was gracious and communication was prompt and helpful. The bungalow was clean, charming with a beautifully appointed kitchen. Everything exceeded our expectations!
Stayed 3 nights in Jun 2026