Entire home

Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly

Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly

Photo gallery for Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly

View of Mount Everett from tennis court
Evening with outdoor lights
Front entrance to the house
Summer Evenings on the patio
Entrance to the house with fall gardens

Overview of Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly

Reviews
10 out of 10 Exceptional
4 bedrooms3 bathroomsSleeps 9353 sq m

Popular amenities

  • Pet-friendlyPet-friendlyPet-friendly
  • FireplaceFireplaceFireplace
  • Free WiFiFree WiFiFree WiFi
  • WasherWasherWasher
  • DryerDryerDryer
  • KitchenKitchenKitchen

Check out the area

Map
Sheffield, MA
  • Popular LocationMagnolia Bluffs Casino13 min drive
  • Popular LocationCatamount Ski Area15 min drive
  • Popular LocationBash Bish Falls State Park25 min drive
  • AirportAlbany, NY (ALB-Albany Intl.)77 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.

Property manager

Jill Gregory

Amenities

Kitchen
Washer
Dryer
Pet-friendly
Free WiFi
Air conditioning

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 50 lbs per pet (limit one pet total)
A pet fee will apply

Smoking

Smoking is not permitted

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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
Onsite parties or group events are strictly prohibited
Note from host: An Event Fee will apply for any parties or events
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
Property Registration Number C0119902670

We should mention

A car is required for transportation to and from this property

About the area

Sheffield

Located in Sheffield, this vacation home is in the mountains and on a river. Ashley House and Mahaiwe Performing Arts Center are cultural highlights, and some of the area's landmarks include W.E.B. Du Bois Boyhood Homesite and Scoville Memorial Library. Traveling with kids? Consider Harney and Sons Tea Tasting Room, or check out an event or a game at Lime Rock Park. Be sure to check out the area's animals with activities such as game walks and birdwatching.
Map
Sheffield, MA

What's nearby

  • Magnolia Bluffs Casino - 13 min drive
  • Catamount Ski Area - 15 min drive
  • Ski Butternut - 22 min drive
  • Bash Bish Falls State Park - 25 min drive
  • Taconic State Park - 37 min drive

Getting around

  • Hudson, NY (HCC-Columbia County) - 42 min drive

Restaurants

  • McDonald's - 18 min drive
  • Dunkin' - 18 min drive
  • Industry Kitchen - 17 min drive
  • Picante S - 15 min drive
  • Great Falls Brewing Company - 17 min drive

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 111 out of 115 reviews" "
Rating 8 - Good. 4 out of 115 reviews" "
Rating 6 - Okay. 0 out of 115 reviews" "
Rating 4 - Poor. 0 out of 115 reviews" "
Rating 2 - Terrible. 0 out of 115 reviews" "

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Betsy F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Family Gatherin
A perfect place for our family get together! Almost equidistant from Boston and New York City (and just a bit farther from Philadelphia), August Moon was a wonderful setting to spend time together. We especially loved the size and workability of the kitchen as we cooked together. Having both a "formal" dining room and an eat-in kitchen gave us lots of options to hang out. The living/family rooms, too, were very comfortable and made for a great few days. Being in the Berkshires provides so many fun activities. We were 9 people and had plenty of space in this lovely farmhouse.
Stayed 3 nights in Dec 2023

10/10 Excellent

David S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
beautiful weekend in the Berkshires
This is the second time we have stayed at this beautiful rural property about 15 minuts from Great Barrington. The host has always been extremely attentive and drove up from NYC to attend to a heater problem when we had trouble. The house is large and fully stocked with every amenity, particularly the kitchen. There are lots of rooms downstairs to be together or separate. The outdoor space is large and well maintained with hiking trials and lots of space for lawn games, including a tennis court. Close to lots of antique shops and good groceries. Extremely relaxing. My family is already asking when we will go back.
Stayed 4 nights in Nov 2023

10/10 Excellent

Jamie H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect!
It is a serene and lovely getaway. The home is warm and welcoming. It was perfect!
Stayed 5 nights in Oct 2023

10/10 Excellent

Donna D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Breathtaking home and property
This home is beautiful and sparkling clean! Perfect location from our daughter’s wedding venue! The property is gorgeous with a fabulous view! Wish we had more time to spend at the house, it had 2 outdoor sitting areas, tennis court, huge barn with a pool table. The beds were super comfortable, kitchen was state of the art, and numerous rooms for sitting areas. Definitely would return in the future!
Stayed 2 nights in Sep 2023

8/10 Good

Ruth C., Lexington

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family wedding weekend
Lovely location. Very responsive host.
Stayed 2 nights in Sep 2023

About the host

Hosted by Jill Gregory

Host profile image
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.

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.
Tell us how we can improve our siteShare feedback