Set along the riverbank, this vacation home features 4 bedrooms and 3 bathrooms, accommodating 9 guests. It includes 3 bicycles for outdoor exploration and offers ski-in/ski-out access. Enjoy mountain views from the patio while engaging in activities like rafting and fishing near Mount Everett State Reservation and Mount Riga State Park. This property is pet-friendly.
Highlights
Family fun awaits
Top-rated for families.
Ski access
A rare find - hit the slopes directly from your doorstep!
4 bedrooms3 bathroomsSleeps 9
Popular amenities
Ski-in/ski-out access
Arcade/game room
Balcony
Barbecue
Garage parking available
Internet
Explore the area
Sheffield, MA
Mount Riga State Park
Place, Mount Riga State Park
6 min drive
Mount Everett State Reservation
Place, Mount Everett State Reservation
9 min drive
Housatonic River
Place, Housatonic River
13 min drive
Pittsfield, MA (PSF-Pittsfield Municipal)
Airport, Pittsfield, MA (PSF-Pittsfield Municipal)
55 min drive
Where you'll sleep
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.
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Pets allowed: dogs and cats less than 23 kg per pet (limit one pet total)
A pet fee will apply
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Smoking
Smoking is not permitted
Important information
You need to know
Property Registration Number C0119902670
Property # 95599vb
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
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. Take in the nearby slopes with cross-country skiing and snowboarding, or try out other outdoor activities such as snowmobiling and sledging.
Mount Everett State Reservation - 9 min drive - 7.1 km
Washinee Lake - 11 min drive - 10.6 km
Housatonic River - 13 min drive - 7.1 km
Catamount Ski Area - 15 min drive - 16.6 km
Getting around
Hudson, NY (HCC-Columbia County) - 42 min drive
Restaurants
McDonald's - 18 min drive
Dunkin' - 18 min drive
ILSE Coffee - 17 min drive
Mom's Country Cafe - 9 min drive
Bistro Box - 16 min drive
Frequently asked questions
Is Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly pet-friendly?
Yes, this property allows cats and dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.
How much does it cost to stay at Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly ?
As of 18 Sept 2026, prices found for a 1-night stay for 2 adults at Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly on 26 Jan 2027 start from AU$4,759, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly ?
On-site parking is available at the property.
What time is check-in at Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly ?
Check-in begins at 4:00 PM.
What time is check-out at Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly ?
Checkout is at 11:00 AM.
Where is Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly located?
Located in the mountains, this Sheffield holiday home offers ski-in/ski-out access within 3 miles (5 km) of Mount Everett State Reservation, Lime Kiln Farm Wildlife Sanctuary and Mount Riga State Park. Housatonic River is 3.1 mi (5 km) away.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
August Moon is a beautiful place that combines historical context, state-of-the-art updates, warm personal touches and spectacular gardens and grounds. The host was wonderful to work with. We would highly recommend this lovely home and hope to return in the future.
Jill was a wonderful host. She answered all of our questions and concerns immediately. The property and the gardens are gorgeous. We really enjoyed the use of the tennis court. It was fun to stay in an historic home with lots of the original architectural details. With the exception of the master bedroom, the upstairs bedrooms are very small and ceilings are treacherously low. There are 2 staircases leading to the second floor. One has very steep, short steps and high risers, so navigating them for older guests and small children could be problematic. The second staircase does not have any handrails, so that was difficult as well. It is difficult to see that on the website photos. Because it is an older home, the air conditioning (or lack there of) in the smaller rooms can be tricky. Because the nights are cool, it was ok. There is only 1 small bathroom upstairs for the 3 bedrooms so that was a bit inconvenient for the 4 adults and one child. I feel badly calling these things out on my review but feel that future guests should know about these issues so they can plan accordingly. The house is probably perfect for a family with 2 adults and children older than 5 or 6 because it is really lovely.
Stayed 6 nights in Aug 2026
Response from VrboOwner on 1 Sept 2026
Thank you so much for staying with us and for your lovely comments about the house, gardens, tennis court, and your experience with us as hosts. We’re so glad you enjoyed your stay!
As you noted, ours is a true 18th-century home, and many of the original architectural details have been preserved, including the staircases, lower ceiling heights in some rooms, and the wonderfully quirky proportions that come with a house of this age. It also means it lives quite differently from a modern house. We do our best to represent these historic characteristics in our listing and photos, and appreciate you sharing your perspective for future guests.
Just to clarify a couple of details for those considering a stay: the primary bedroom has its own Fujitsu air-conditioning unit, and there is a second Fujitsu unit on the upstairs landing that cools the three guest bedrooms with the help of the provided fans to circulate the air. Fortunately, Berkshire evenings tend to cool down considerably, so this system has worked very well for us and our guests. The upstairs bathroom serving the three guest rooms is a standard-size full bathroom with a tub and shower. The primary bedroom also has a full bathroom. And there is an additional bathroom with a shower downstairs.
We’re so happy you were able to enjoy the property and experience the character of this very special old house. It was a pleasure hosting you and your family!
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 .
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!
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.
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.
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.
The home and property is everything advertised and so much more. From the minute we entered the driveway and saw the home surrounded by the stunning gardens we knew we were in for a treat. We loved sitting in the Adirondack chairs in the side yard and walking and exploring the large acreage surrounding the home. But then as you set foot inside the house, you discover the treasures in every room of the house. Designed to be comfortable to friend groups, families, couples, this house will please everyone. The kitchen is fully equipped and we enjoyed making breakfast on the griddle of the Wolf Stove, then looking out the gorgeous windows into the garden and yard surrounding us. We loved candlelight dinners in the dining room, all the warmth of this home in the fireplace room. There's a sun room to enjoy in the day and a living room with television for others. The bedrooms are all upstairs and each bed is very comfortable and carefully furnished with quality bedding. This home is so unique; farmhouse but modernized and it has everything. We loved it so much and highly recommend August Moon!
My (now) husband and I attempted to rent August Moon to share with a bunch of friends in spring 2020, which we obviously had to cancel. Fast forward 1.5 years after eloping in California and having our twins, we decided to have a real wedding celebration with family and friends, and knew August Moon was the perfect spot. The house itself is charming and elegant without feeling too precious to drag in some dirt and grass from the yard. As many wedding guests commented, the grounds are ideal for entertaining with multiple distinct areas to sit or play lawn games. We were able to host a morning brunch, wedding ceremony, cocktails, and reception all in distinct areas, and with plenty of lawn games to spare. The weekend itself felt magical and almost unreal. Many thanks to Jill for accommodating us and for being so responsive whenever questions came up. We can’t make it back soon enough!
Our extended family of 6 adults and 2 children (1 toddler, 1 infant) spent 10 days at August Moon in late August. The property is lovely, with several seating areas, including an outdoor dining area and a fire pit. There are walking trails through the woods. The kitchen is well-equipped and amply stocked. The beds were very comfortable. There is no air conditioning in 3 of the 4 bedrooms, but as it cooled off in the evening, the fans were enough to keep the rooms comfortable. Jill, our host, answered our questions promptly and was a pleasure to work with.
We stayed here for the weekend and did not want to leave. The house is a beautiful historic home with all the charm of early American architecture preserved and yet the convenience of a well equipped modern kitchen and a comfy entertainment room have not been overlooked. The style is true to the heritage with modern touches and beautiful art. The property is stunning and private, dozens of acres of fields, garden, flora and fauna to explore on foot and also to be enjoyed from every window. The stars at night are visible as you fall asleep from the master bed. Note, there are no window coverings in most bedrooms which I was worried about initially but it is so dark at night you really don't need them and it was lovely to have the sun wake us gently. Many activities and games for all ages including tennis, a see-saw, tether ball, horseshoes, board games. The stairs are typical of the period and might be more difficult to navigate for someone with decreased mobility. We look forward to a return visit!
We had a fantastic time staying at August Moon. My kids literally didn’t stop running around and playing in the multitude of different activities and toys - they were in heaven! The house has kept the old charm while being equipped with literally anything you could want! Beds were super comfortable and all of the rooms were so well set out - each with a different vibe and purpose. Jill was no more than a text away and the advance information for the house was probably the best I have ever received! My husband referred to the house as ‘life goals’ - so I suspect he’ll be asking when we are next going back?!
We had an amazing family vacation in this beautiful place. The kids loved to hide away and play for hours in the secret play room or wonder around the property to discover the enchanted tree house. The kitchen was so well equipped and it was great fun to cook family recipes for a larger group. We would love to come back in the summer when everything is in full bloom. Thank you so much for having us.
The house was so beautiful! Every room has so much character, the kitchen is wonderfully stocked and has bowls and pots and pans of every possible size. The master bedroom is truly stunning and waking up to the sunrise over the mountains was perfect. We would certainly go back!
We had a great weekend with a group of 8 adults, two infants and a dog. The property is in a great location with a ton of space and privacy while being close to things to do.
We got married at august moon and it was the perfect setting for our celebration. The gardens are absolutely gorgeous and the home is cozy, stylish, and very comfortable. Thank you!!
Terrific place, wonderful host, lovely few days with friends.
Stayed 4 nights in Sep 2021
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.
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.