Entire home

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

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

A modern kitchen with white cabinetry, a marble island, and pendant lighting. - 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)
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 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 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)
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

Entire home

6 bedrooms4 bathrooms

Popular amenities

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

Add dates for prices

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

Property amenities

Internet

  • Available in the house: WiFi

Parking and transport

  • Parking on site

Kitchen

  • Dishwasher
  • Hob
  • Microwave
  • Oven

Bedrooms

  • 6 bedrooms
  • Bedsheets provided

Bathroom

  • 3.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • TV

Outdoor areas

  • Barbecue grill

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • Up to 23 kg per pet

Suitability/Accessibility

  • Smoke-free property

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)

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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you to complete the following before checking out:
Load and start the dishwasher
Strip any used beds and gather used towels
Remove leftover food and drinks and take out the rubbish
Turn off the lights, lock the doors and return the keys
1. Clean BBQ thoroughly. Scrape off food. Dump grease trap in woods 2. Close BBQ & protect with cover 3. Close umbrella Failure to clean the BBQ results in immediate $100 additional cleaning fee.
Failure to complete these may result in a negative review from the host.

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total (up to 23 kg per pet)

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Property Registration Number C0581482670
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

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 wooden bridge over a river, surrounded by lush greenery and large rocks.
    Housatonic River
    3 min drive - 1.8 miles
  • A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.
    Tanglewood Music Center
    51 min drive - 30.7 miles
  • Ashley Falls Woods
    18 min walk - 1.0 mile
  • Ski Butternut
    29 min drive - 17.8 miles
  • National Shrine of the Divine Mercy
    40 min drive - 23.0 miles

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

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
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

10

Cleanliness

8.0

Location

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