Apartment

Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

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

A modern house with a dark gray exterior, a black front door, and a small porch with steps leading to the entrance.
A modern two-story house with large windows and a well-maintained lawn.
A bedroom with a sloped ceiling, a bed with a patterned bedspread, a bedside table with a lamp, and a chair.
large bath
A spacious living area with a wooden floor, a kitchen in the background, a blue leather sofa, a patterned rug, and a wooden staircase.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Discover nearby landmarks
    Walk to Housatonic River

Popular amenities

  • Air conditioning
  • Internet
  • Refrigerator
  • Onsite parking available
  • Dryer
  • Firepit

Explore the area

View in a map
Sheffield, MA
  • Place, Lime Kiln Farm Wildlife Sanctuary
    ‪3 min walk‬
  • Place, Housatonic River
    ‪17 min walk‬
  • Place, Ski Butternut
    ‪23 min drive‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪49 min drive‬

Rooms & beds

1 bedroom (sleeps 2)

Bedroom 1

1 Queen Bed

1 bathroom

Bathroom 1

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Spaces

Kitchen

Add dates for prices

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About the neighborhood

Sheffield

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.
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Map
Sheffield, MA

What's nearby

  • Lime Kiln Farm Wildlife Sanctuary - 3 min walk - 0.3 km
  • Housatonic River - 17 min walk - 1.5 km
  • Ski Butternut - 23 min drive - 22.2 km
  • National Shrine of the Divine Mercy - 34 min drive - 31.0 km
  • Tanglewood Music Center - 45 min drive - 43.0 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 does it cost to stay at Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts ?

As of Oct 26, 2026, prices found for a 1-night stay for 2 adults at Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts on Sep 1, 2027 start from $233, 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?

Onsite 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 ?

Check-out 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 mi (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
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

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

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
Response from VrboOwner on Oct 13, 2025
Thank you for being such a wonderful guess we should look forward to hosting you again in the future!
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
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