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

Sheffield, Massachusetts
$1180 avg/night
Minimum Stay 3 Nights
Bed 4

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 9

Max Sleeps

Night 3 nights

Min Stay

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.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • SKI

    Cross-country Skiing And Snowboarding Nearby Ski-in/ski-out Access
  • PETS

    1 Total (up To 50 Lbs Per Pet) Pet Friendly Service Animals Exempt From Fees Welcoming Cats And Dogs Only
  • BEACH

    Beach Towels
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 3800 Sq Ft (353 Sq M)
  • KITCHEN

    Coffee Grinder Coffee/tea Maker Dishwasher Lobster/crab Pot Microwave Oven Refrigerator Spices Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Required Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Firepit Garden Outdoor Furniture
  • BATHROOMS

    3 Bathrooms Hair Dryer Shampoo Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • THINGS TO DO

    Bicycle On Site Birdwatching Nearby Cycling Nearby Fitness Facilities Nearby Golf Nearby Hiking Nearby Hiking/biking Trails Nearby Kayaking Nearby Rock Climbing Nearby Snow Sports Gear Snowmobiling Nearby Swimming Nearby Tennis On Site
  • ENTERTAINMENT

    Arcade/game Room Books DVD Player Foosball Table Music Library Pool Or Billiards Table Stereo Table Tennis Video Library Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Fireplace Wood Stove
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Books Children's Dinnerware Children's Games Children's Toys Highchair Playground Travel Crib
  • LOCATION HIGHLIGHTS

    In A Village In The Mountains Near A Hospital On The River
  • SERVICES AND CONVENIENCES

    Housekeeping (on Request) Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 9

Map Map

School District Availability

Review Review

  • Cynthia P.

    Submitted Dec 26, 2025

    Stayed Nov 26, 2025

    This is a lovely home- a beautiful mix of rich historical

  • Alexandra P.

    Submitted Nov 10, 2025

    Stayed Nov 6, 2025

    Such a beautiful property in a gorgeous setting.

  • Marian O.

    Submitted Dec 2, 2024

    Stayed Nov 27, 2024

    The house is old but well -maintained and very clean. There are many different areas inside and outside for family members to hang out together and relax and tons of toys and games for the children .

  • Cindy L.

    Submitted May 26, 2024

    Stayed May 22, 2024

    I feel so fortunate that I found this gem for Berkshire graduation weekend! Word to the wise, book in advance as it’s a popular spot!

  • Betsy F.

    Submitted Jan 4, 2024

    Stayed Dec 28, 2023

    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.

  • David S.

    Submitted Nov 16, 2023

    Stayed Nov 9, 2023

    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.

  • Jamie H.

    Submitted Oct 23, 2023

    Stayed Oct 12, 2023

    It is a serene and lovely getaway. The home is warm and welcoming. It was perfect!

  • Donna D.

    Submitted Sep 25, 2023

    Stayed Sep 22, 2023

    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!

  • Ruth C.

    Submitted Sep 10, 2023

    Stayed Sep 8, 2023

    Lovely location. Very responsive host.

  • Carl W.

    Submitted Nov 30, 2022

    Stayed Nov 23, 2022

    August Moon was the perfect spot to host our Thanksgiving weekend. The kitchen had all the tools we needed, and we loved going on long hikes on the property and nearby. The house is so warm and comfortable and there are endless things to do, from building fires, to listening to records, or playing in games with kids of all ages. Jill was very communicative, and check-in was seamless. I would stay again, perhaps in summer, so that we could enjoy more of the outdoor activities.

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Total

Includes taxes and fees
$1,180+
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