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Berkshires Retreat with Private Pickleball Court – Perfect for Large Groups!

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A modern kitchen with white cabinetry, a marble island, and pendant lighting. - Berkshires Retreat with Private Pickleball Court – Perfect for Large Groups! (Sheffield)
A modern living room with a flat-screen TV, a sectional sofa, a round coffee table, and a wooden ceiling. - Berkshires Retreat with Private Pickleball Court – Perfect for Large Groups! (Sheffield)
A modern kitchen with a long wooden table, black chairs, white cabinets, and a hanging light fixture. - Berkshires Retreat with Private Pickleball Court – Perfect for Large Groups! (Sheffield)
A bedroom with a bed, bedside lamps, a framed picture, and a window with blinds. - Berkshires Retreat with Private Pickleball Court – Perfect for Large Groups! (Sheffield)
A tennis court with a net, ceiling lights, and a table with chairs. - Berkshires Retreat with Private Pickleball Court – Perfect for Large Groups! (Sheffield)
Berkshires Retreat with Private Pickleball Court – Perfect for Large Groups! provides laundry facilities and more. Stay connected with in-room WiFi.

Reviews

10 out of 10
Exceptional

Popular amenities

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

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About this property

Berkshires Retreat with Private Pickleball Court – Perfect for Large Groups!

  • Welcome to Greenwood Gables, a one-of-a-kind Berkshires retreat for large groups & family getaways

    Originally built in the 1960s as a community church, our beautifully reimagined home offers 6 bedrooms and a sleepable office, 2 more offices, 2 kitchens, 2 living spaces, and an indoor Pickleball court for year-round fun!

    Host the holidays with our 10ft dining table, cozy up in our sprawling TV room, or prove your Pickleball dominance on the court!

    15min to Great Barrington
    20min to Hotchkiss

    Primary Bedroom: King with Private Bathroom
    2nd Bedroom: Queen, upstairs
    3rd Bedroom: Queen & Twin Trundle, upstairs
    4th Bedroom: Full, upstairs
    5th Bedroom: Queen, downstairs
    6th Bedroom: Full, downstairs
    7th Bedroom: sleepable office with couch turned single or double bed. Access via Primary Bedroom

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About the area

Ashley Falls is home to this holiday home. Land of Nod Vineyard and Winery and Umpachene Falls Park are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Harney and Sons Tea Tasting Room and Mahaiwe Performing Arts Center. Visit our Ashley Falls travel guide
View more Holiday homes in Ashley Falls
Map
Sheffield, MA

What's nearby

  • A red covered bridge spanning a river with autumn foliage in the background.
    Housatonic River
    3 min drive - 2.9 km
  • A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.
    Tanglewood Music Center
    51 min drive - 49.4 km
  • Ashley Falls Woods
    18 min walk - 1.5 km
  • Ski Butternut
    29 min drive - 28.6 km
  • National Shrine of the Divine Mercy
    40 min drive - 37.0 km

Getting around

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

Restaurants

  • McDonald's
    6 min drive
  • Dunkin'
    6 min drive
  • ILSE Coffee
    5 min drive
  • The Southfield Store
    20 min drive
  • State Line Pizza
    4 min drive

Frequently asked questions

Is Berkshires Retreat with Private Pickleball Court – Perfect for Large Groups! pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 23 kg per pet.

How much is parking at Berkshires Retreat with Private Pickleball Court – Perfect for Large Groups!?

On-site parking is available at the property.

What time is check-in at Berkshires Retreat with Private Pickleball Court – Perfect for Large Groups!?

Check-in begins at 4:00 PM.

What time is check-out at Berkshires Retreat with Private Pickleball Court – Perfect for Large Groups!?

Checkout is at 10:00 AM.

Where is Berkshires Retreat with Private Pickleball Court – Perfect for Large Groups! located?

Situated in Ashley Falls, this holiday home is 0.9 mi (1.5 km) from Ashley Falls Woods and within 3 miles (5 km) of Housatonic River and Ashley House. Eddy Field and Connecticut Railroad Historical Museum are also within 3 miles (5 km).

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Reviews

Berkshires Retreat with Private Pickleball Court – Perfect for Large Groups! Reviews

10

Exceptional

10

Cleanliness

8.0

Location
Rating 10 - Excellent. 1 out of 1 reviews
Rating 8 - Good. 0 out of 1 reviews
Rating 6 - Okay. 0 out of 1 reviews
Rating 4 - Poor. 0 out of 1 reviews
Rating 2 - Terrible. 0 out of 1 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful time staying here. The property was spacious, comfortable, and clean. If you have a large group it’s perfect.
Stayed 3 nights in Sep 2026