Entire home
Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly
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Reviews
10 out of 10
Exceptional
4 bedrooms 3 bathrooms Sleeps 9 353.0 sq m
Popular amenities
Explore the area

Sheffield, MA
- Taconic State Park
- Catamount Ski Area16 min drive
- Bash Bish Falls State Park28 min drive
- Pittsfield, MA (PSF-Pittsfield Municipal)58 min drive
Rooms & beds
4 bedrooms (sleeps 9)
3 bathrooms
Bathroom 1
Bathroom 2
Bathroom 3
Spaces
Deck or patio
Porch or lanai
Kitchen
Kitchenette
Balcony
Separate dining area
Outdoor play area
Garden
Dining area
About this property
Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly
Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hours north of New York City, this circa-1770s center chimney colonial will charm and delight your family and guests.
The rarest of New England homes, with historic bones and bright contemporary additions, August Moon sits on 88 acres of private and peaceful land in the heart of the Berkshires with mountain views from various parts of the property. Just steps away from beautiful hiking trails, it features a perfect blend of new and old, urbane and rustic, and with an eternal quality that is felt throughout the home and the vast property. Enjoy western views of Mount Race and Mount Everett from the grounds, or explore the walking trail through the woods. The trailhead to Racebrook Falls can be accessed by walking down the dirt road where the house is located.
With 3100 sq. ft of wood floors and cozy decor, this spacious house was renovated with two additions: sunroom with master bedroom above, and a gourmet kitchen. The original portion of the house includes a den with fireplace and 42" plasma tv with satellite surround sound home theater system. Built-in bookshelves have loads of great reading and an eclectic DVD library that should have something for everyone. The Parlor is a wood-paneled room with a wood-burning stove, opening up to a small deck with Adirondack chairs for lounging. This is a great room for entertaining with a stereo, turntable, and vinyl record collection. Connecting to the parlor is the traditional dining room which has a table that can seat 10 and a candle fireplace.
A bright sunroom opens up to a back patio with teak outdoor furniture, an umbrella, and vast flower gardens that bloom in every season.
In the Master Suite, wake up to beautiful mountain views particularly spectacular during fall foliage season, and go to bed relaxed after taking a soak in the private master bath jacuzzi. Bath and shower products and candles along with luxurious bath robes complete the experience. Vaulted ceilings, cherry hardwood floors, and walk-around deck make this room a relaxing retreat. All bedrooms feature down comforters, high thread count sheets and fans. All bathrooms feature hair dryers, robes, plush towels, Shampoo, Conditioner and Shower Gel.
Bedrooms: In addition to the spacious master, there are three guestrooms with great architectural details like original wood beams and hardwood floors. The upstairs landing with skylights and gas stove features a day bed perfect for reading in the afternoon.
Kitchen: The gourmet kitchen features top-notch equipment like a WOLF eight-burner stove and is fully stocked with cookware, utensils, barware, dishware and other essential cooking tools. A secondary kitchen with another refrigerator makes entertaining for larger groups easy.
Flower gardens are in abundance and you will be enticed to the hammock to unwind and soak in the incredible mountain views. After playing a round of tennis on the clay court, enjoy a glass of iced-tea on the outdoor porch furniture at the tennis house bar. Or retreat to the shaded seated area behind the cutting garden or shady hideaway under the canopy of the weeping Katsura tree.
Other amenities include: walking trails, tennis court, two fireplaces, wood-burning stove, gas stove, air conditioning in the tv room, master suite, sunroom, and kitchen. WI-FI, cable HDTV, DVD, VCR, stereo, CDs, Jacuzzi tub, microwave, dishwasher, linens, washer/dryer. The three-story garage features a ping-pong and pool table game room on the 2nd story. In the garage, find bikes and helmets for kids and adults, and loads of outdoor games like bocce, croquet, corn hole, badminton, and more. A kids' outdoor playhouse and secret playroom in the twin bedroom are great places for the little ones to play.
Smoking is **strictly not permitted.** Large Parties are prohibited.
*** No Longer accepting Wedding Inquiries.
Keywords: skiing, snow, fall foliage, tanglewood, berkshires, mountains, hiking, tennis, peace, privacy, country roads, escape, country living.
The rarest of New England homes, with historic bones and bright contemporary additions, August Moon sits on 88 acres of private and peaceful land in the heart of the Berkshires with mountain views from various parts of the property. Just steps away from beautiful hiking trails, it features a perfect blend of new and old, urbane and rustic, and with an eternal quality that is felt throughout the home and the vast property. Enjoy western views of Mount Race and Mount Everett from the grounds, or explore the walking trail through the woods. The trailhead to Racebrook Falls can be accessed by walking down the dirt road where the house is located.
With 3100 sq. ft of wood floors and cozy decor, this spacious house was renovated with two additions: sunroom with master bedroom above, and a gourmet kitchen. The original portion of the house includes a den with fireplace and 42" plasma tv with satellite surround sound home theater system. Built-in bookshelves have loads of great reading and an eclectic DVD library that should have something for everyone. The Parlor is a wood-paneled room with a wood-burning stove, opening up to a small deck with Adirondack chairs for lounging. This is a great room for entertaining with a stereo, turntable, and vinyl record collection. Connecting to the parlor is the traditional dining room which has a table that can seat 10 and a candle fireplace.
A bright sunroom opens up to a back patio with teak outdoor furniture, an umbrella, and vast flower gardens that bloom in every season.
In the Master Suite, wake up to beautiful mountain views particularly spectacular during fall foliage season, and go to bed relaxed after taking a soak in the private master bath jacuzzi. Bath and shower products and candles along with luxurious bath robes complete the experience. Vaulted ceilings, cherry hardwood floors, and walk-around deck make this room a relaxing retreat. All bedrooms feature down comforters, high thread count sheets and fans. All bathrooms feature hair dryers, robes, plush towels, Shampoo, Conditioner and Shower Gel.
Bedrooms: In addition to the spacious master, there are three guestrooms with great architectural details like original wood beams and hardwood floors. The upstairs landing with skylights and gas stove features a day bed perfect for reading in the afternoon.
Kitchen: The gourmet kitchen features top-notch equipment like a WOLF eight-burner stove and is fully stocked with cookware, utensils, barware, dishware and other essential cooking tools. A secondary kitchen with another refrigerator makes entertaining for larger groups easy.
Flower gardens are in abundance and you will be enticed to the hammock to unwind and soak in the incredible mountain views. After playing a round of tennis on the clay court, enjoy a glass of iced-tea on the outdoor porch furniture at the tennis house bar. Or retreat to the shaded seated area behind the cutting garden or shady hideaway under the canopy of the weeping Katsura tree.
Other amenities include: walking trails, tennis court, two fireplaces, wood-burning stove, gas stove, air conditioning in the tv room, master suite, sunroom, and kitchen. WI-FI, cable HDTV, DVD, VCR, stereo, CDs, Jacuzzi tub, microwave, dishwasher, linens, washer/dryer. The three-story garage features a ping-pong and pool table game room on the 2nd story. In the garage, find bikes and helmets for kids and adults, and loads of outdoor games like bocce, croquet, corn hole, badminton, and more. A kids' outdoor playhouse and secret playroom in the twin bedroom are great places for the little ones to play.
Smoking is **strictly not permitted.** Large Parties are prohibited.
*** No Longer accepting Wedding Inquiries.
Keywords: skiing, snow, fall foliage, tanglewood, berkshires, mountains, hiking, tennis, peace, privacy, country roads, escape, country living.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
An Event Fee will apply for any parties or events
Pets
Pets allowed: dogs and cats less than 23 kg per pet (limit one pet total)
A pet fee will apply
Smoking
Smoking is not permitted
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
Note from host: An Event Fee will apply for any parties or events
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Property Registration Number C0119902670
We should mention
A car is required for transport to and from this property
About the area
Sheffield
Located in Sheffield, this holiday home is in the mountains and on a river. Ashley House and Great Barrington Historical Society & Museum are cultural highlights, and some of the area's landmarks include W.E.B. Du Bois Boyhood Homesite and Scoville Memorial Library. Travelling with kids? Consider Harney and Sons Tea Tasting Room, or check out an event or a game at Lime Rock Park. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Sheffield, MA
What's nearby
- Magnolia Bluffs Casino - 15 min drive - 12.7 km
- Catamount Ski Area - 16 min drive - 15.9 km
- Ski Butternut - 26 min drive - 24.0 km
- Lime Rock Park - 27 min drive - 23.9 km
- Bash Bish Falls State Park - 28 min drive - 21.9 km
Getting around
Restaurants
- McDonald's - 18 min drive
- Dunkin' - 18 min drive
- Caddie Shack - 15 min drive
- Industry Kitchen & Bar - 17 min drive
- Roma Pizzeria - 17 min drive
Frequently asked questions
About the host
Hosted by Jill Gregory

We are a family of four based in NYC with a passion for travel and hospitality. We have lovingly shared this family home with guests for 15 years. Nothing brings us more joy than hearing our guests discover a bit of its magic during their stay.
Why they chose this property
Discover a haven, a bit of an enchanted world, where families and friends slow down, hold and treasure each other for a brief moment in time. There have been many joys baked into the walls of this home and you, your family and friends will likely feel closer because of it.
We welcome you to enrich its foundation with your own love, joy, and laughter.
SETTLE IN to a home with all the comforts of your own. August Moon is replete with all the necessities you require and the niceties you desire- enjoy two kitchens stocked to host family and friends, living quarters with hidden nooks for quiet conversations and secret joys. Loving care has been taken to outfit this home for a truly relaxing respite.
Explore the trails protected by the Nature Conservancy that lead to to the edges of the property while listening to the sounds of unique fauna and observing many varieties of flora.
We welcome you to enrich its foundation with your own love, joy, and laughter.
SETTLE IN to a home with all the comforts of your own. August Moon is replete with all the necessities you require and the niceties you desire- enjoy two kitchens stocked to host family and friends, living quarters with hidden nooks for quiet conversations and secret joys. Loving care has been taken to outfit this home for a truly relaxing respite.
Explore the trails protected by the Nature Conservancy that lead to to the edges of the property while listening to the sounds of unique fauna and observing many varieties of flora.
What makes this property unique
August Moon is on a quiet dirt road and sits on 88 acres so you'll enjoy the peace and privacy. August Moon is also furnished with a host of kid-friendly essentials and more than a few surprises the children will love. Explore our family-friendly side.
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