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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

Reviews

10 out of 10
Exceptional
4 bedrooms3 bathroomsSleeps 9353.0 sq m

Popular amenities

  • Ski-in/ski-out access
  • Garage parking available
  • Dogs and cats allowed
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View map
Sheffield, MA
  • Place, Mount Everett State Reservation
    ‪8 min drive‬
  • Place, National Shrine of the Divine Mercy
    ‪37 min drive‬
  • Place, Tanglewood Music Center
    ‪48 min drive‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪46 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.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
An Event Fee will apply for any parties or events
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Pets

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

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

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.
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Map
Sheffield, MA

What's nearby

  • Mount Everett State Reservation - 8 min drive - 7.1 km
  • Lime Rock Park - 25 min drive - 25.0 km
  • Norman Rockwell Museum - 36 min drive - 36.4 km
  • National Shrine of the Divine Mercy - 37 min drive - 35.0 km
  • Tanglewood Music Center - 48 min drive - 47.3 km

Getting around

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

Restaurants

  • ‪Dunkin' - ‬18 min drive
  • ‪McDonald's - ‬18 min drive
  • ‪Roma Pizzeria - ‬17 min drive
  • ‪Industry Kitchen & Bar - ‬17 min drive
  • ‪Homegrown Café - ‬17 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 3 May 2026, prices found for a 1-night stay for 2 adults at Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly on 27 July 2026 start from AU$1,215, 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 116 out of 120 reviews
Rating 8 - Good. 4 out of 120 reviews
Rating 6 - Okay. 0 out of 120 reviews
Rating 4 - Poor. 0 out of 120 reviews
Rating 2 - Terrible. 0 out of 120 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Alexandra P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Such a beautiful property in a gorgeous setting.
Stayed 3 nights in Nov 2025
Verified

10/10 Excellent

Cynthia P.

This is a lovely home- a beautiful mix of rich historical
Stayed 4 nights in Nov 2025
Verified

10/10 Excellent

Marian O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful family getaway

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 .
Stayed 4 nights in Nov 2024
Archival

10/10 Excellent

Bria A.

Such a lovely vacation at August moon

The house was perfect for a family trip! Stocked with everything you could need. The only drawback were the mosquitos!
Stayed 7 nights in Jun 2017
Verified

8/10 Good

Ruth C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family wedding weekend

Lovely location. Very responsive host.
Stayed 2 nights in Sep 2023
Verified

10/10 Excellent

Cindy L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

August Moon is a gem!

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!
Stayed 3 nights in May 2024
Verified

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
Verified

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
Verified

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
Verified

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
Verified

10/10 Excellent

Carl W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A cozy, well-appointed, spacious delight

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.
Stayed 4 nights in Nov 2022
Verified

10/10 Excellent

Laura H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Berkshires in the Fall

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!
Stayed 4 nights in Oct 2022
Verified

10/10 Excellent

Lauren S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Our Magical Dream Wedding

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!
Stayed 5 nights in Sep 2022
Verified

10/10 Excellent

Meg S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Delightful

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.
Stayed 10 nights in Aug 2022
Verified

10/10 Excellent

David S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful and relaxing

Lovely
Stayed 7 nights in Aug 2022
Verified

10/10 Excellent

Bill C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Could not have been better

thoroughly enjoyable stay
Stayed 3 nights in Jun 2022
Verified

10/10 Excellent

joy

Liked: Cleanliness, check-in, communication, location, listing accuracy

LOVED it!!!

August Moon is awesome!! We loved every bit of it, and the property is spectacular. Wish we owned it
Stayed 3 nights in May 2022
Verified

10/10 Excellent

Jennifer O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Property and Home

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!
Stayed 3 nights in Apr 2022
Verified

10/10 Excellent

Mia S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic for families, relaxing for adults

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?!
Stayed 3 nights in Apr 2022
Verified

10/10 Excellent

NICOLE M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Magical place

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.
Stayed 4 nights in Dec 2021
Verified

10/10 Excellent

Umrao S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Stunning Getaway!

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!
Stayed 3 nights in Dec 2021
Verified

10/10 Excellent

Jackson C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Fall Stay

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.
Stayed 3 nights in Oct 2021
Verified

10/10 Excellent

Alana B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Such a special place!!

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!!
Stayed 3 nights in Oct 2021
Verified

10/10 Excellent

John E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Sheffield, MA

Terrific place, wonderful host, lovely few days with friends.
Stayed 4 nights in Sep 2021
Verified

10/10 Excellent

Tynan L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Warm, vibrant and chic!

We held our wedding at August Moon and it was amazing! The property is absolutely stunning. The gardens and grounds are perfectly manicured and the house is top notch. Every room exudes style. Jill and Trey have fabulous and eclectic taste. Most notably, their record collection, which we enjoyed listening to out on the patio. They were also super accommodating and easy to get in touch with. They provided us with robes, towels, bubble bath, shampoos, conditioners, face wash and lotions - all of which I will be purchasing to keep my house stocked with from now on! Whether you’re looking to host a snazzy event on the lawn (that your guests will rave on and on about), or you’re looking for a quiet place to relax/reset, this is the place to go. Would highly recommend! ***10/10***
Stayed 3 nights in Sep 2021

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.
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