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Book Online or call HomeAway Booking Assistance 888-640-7927
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Beautiful Berkshire Home W Tennis Court; Close to Skiing!

Bedrooms 4
Space 3,800 sq. ft.
Property type house
Minimum Stay 3 - 7 nights


About the property

House, 4 Bedrooms + Other (See Description), 3 Baths, (Sleeps 8-9)

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. 88 acres of land with views of Mt. Washington and Mount Everett promises privacy, peace and quiet. Search 'Berkshire Winter Rental' on Vimeo to see a winter video of the house.

With 3100 sq. ft of wood floors and elegant decor, this spacious house was renovated with two additions: sunroom with master bedroom above, and the 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 wood-burning stove and door opening up to a small deck with adirondack chairs for lounging. This is a great room for entertaining. Connecting to the parlor is the traditional dining room which has a table that can seat 10 and a fireplace.

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. Ethics Supply Co. bath 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, body soaps, R&Co Shampoo and Conditioner and Kiehl's 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 Subzero refrigerator and is fully-stocked with cookware, utensils, barware, dishware and other essential cooking tools. Hook up your IPod to the kitchen stereo system and whistle while you cook! 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 plan your summer bbq with friends and family gathered around the teak patio furniture with umbrella.

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, and three-story, two-car garage and ping-pong game room on the 2nd story. In the garage, find three bikes, and loads of outdoor games like bocce, croquet, corn hole, badminton, and more. A kids' out door playhouse and secret playroom in the twin bedroom are great places for the little ones to play.

Smoking is **strictly not permitted.**

Keywords: skiing, snow, fall foliage, tanglewood, berkshires, mountains, hiking

More Details

Member since: 2006
Speaks: english
Response time:
Within a few days
Response rate:
Calendar last updated:
September 19, 2017

Guestbook comments from the owner

Jill's place was amazing! Jill was super helpful since we first contacted her and made everything go smoothly. The kids loved all the toys both inside and out and my husband and I loved all the luxurious touches throughout the house. Would definitely return!
Jul 2017
  • 1 of 12


Sheffield House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 3800 sq. ft.
House Rules:
  • Max. occupancy: 9
  • Minimum Age Limit for Renters ...
  • pets considered ...
  • Events Allowed
  • children welcome
  • non smoking only
Location Type:
  • Mountain
  • Mountain View ...
  • River
  • Ski-In ...
  • Away From It All
  • Family
  • Activities Guide
  • Air Conditioning ...
  • Alarm Clock
  • Basic Soaps
  • Broadband Access ...
  • Ceiling Fans
  • Clothes Dryer
  • Fireplace
  • Firewood
  • Free Long Distance
  • Garage ...
  • Gas Fireplace ...
  • Hair Dryer
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided ...
  • Living Room
  • Local Restaurant Guide
  • Paper Towels
  • Parking
  • Parking Off Street
  • Shampoo
  • Sunbed
  • Telephone
  • Thermos Bottle
  • Toilet Paper
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Wood Fireplace ...
  • Wood Stove ...
  • Blender
  • Catering Available ...
  • Coffee Grinder
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishwasher ...
  • Freezer
  • Grill
  • Ice Maker
  • Kitchen ...
  • Lobster Pot
  • Microwave
  • Oven
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Stove
  • Toaster
  • Child's Highchair
  • Dining Room
  • seating for 12 people
  • 3 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 3 -
  • 4 Bedrooms, Sleeps 9
  • Queen size Beds (3), Twin or Single Beds (2), Baby Cribs (1) Pack n play , Sleep Sofa or Futons (1) In addition to the bedrooms, there is a twin-size day bed in the upstairs landing,
  • Books
  • CD Player
  • DVD Player
  • Music Library ...
  • Ping Pong Table
  • Radio
  • Satellite / Cable ...
  • Stereo
  • Television
  • Toys ...
  • VCR
  • Video Library ...
  • Balcony ...
  • Barbecue
  • Beach Towels
  • Bicycles
  • Deck / Patio ...
  • Large Cooler
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • Patio
  • Raft
  • Small Cooler
  • Tennis ...
  • Tennis Court
  • Unscreened Porch / Veranda
  • Wood Deck
  • 3 bicycles
Pool / Spa:
  • Indoor Hot Tub
  • Jacuzzi
  • jetted tub ...
  • autumn foliage
  • cinemas
  • forests
  • live theater
  • museums
  • pond
  • restaurants
  • waterfalls
Leisure Activities:
  • antiquing
  • bird watching
  • horseback riding
  • scenic drives
  • shopping
  • sight seeing
  • sledding
  • walking
  • wildlife viewing
Local Services & Businesses:
  • fitness center
Sports & Adventure Activities:
  • cross country skiing
  • cycling
  • fishing
  • golf
  • hiking
  • kayaking
  • mountain biking
  • mountain climbing
  • rafting
  • rock climbing
  • skiing
  • snowboarding
  • swimming
  • tennis
On-site activities: Tennis (picturesque HAR-TRU shared-use court), nature walks through forest protected by a conservation easement. **Opening of the court in the spring is dependent upon winter and spring weather (usually mid-May to October). Please inquire when booking. SKI RESORTS: For the winter ski season, the house has close proximity to two local family-friendly mountains. Catamount Ski Resort is just 6 miles away and Butternut is 12 miles away in Great Barrington. Jiminy Peak Ski Resort is a larger mountain with more advanced terrain and is 1 hour away. After your day on the hill, stop for dinner at the cozy Stagecoach Tavern, less than a mile from the house and serving wonderful farm-to-table cuisine. HIKING: Race Brook Falls trailhead is a short walk down the dirt road where you'll discover a beautiful 3-tier waterfall It's not a stretch to say thatto say that "Hawaiian waterfall" comes to mind when you visit Race Brook during the summer months.


Exceptional! 5/5 -
(59 traveler reviews)

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Beautiful Berkshire Home W Tennis Court; Close to Skiing!
average rating of 4.983051 based on 71 reviews

A Perfect Wedding and Relaxing Stay

  • 5 of 5

Both home and grounds of August Moon are exceptional. The house is incredibly comfortable (and is equipped with everything you need) and has so many beautiful decorative touches. A tasteful mix of old farmhouse and contemporary brightness. The rugs are wonderful! And then there are the gardens, the meadow, the woods, views, the fire pit – all magnificent.

We had a wedding at August Moon and it was a perfect choice. The property is laid out ideally for weddings (and other events). All our guests were blown away by the setting, from the wedding arbor in the meadow to the views of Mount Everett to the gardens and beautiful trees scattered throughout to the hidden seating areas and to the tennis house which doubles as a bar. Being able to stay at August Moon a few days before and after the wedding made the venue so much more meaningful as we felt as if we were entertaining in our own home rather than a commercial event space.

Jill and Trey are exceptional hosts. From our first contact they demonstrated a warmth, openness and flexibility that made us feel very comfortable. All the vendors they recommended were top notch. Jill and Trey cared that the wedding would go off without a hitch…and it did.

We were sad to be leaving August Moon but we truly loved our time there. We will definitely be back.

  • Submitted: Sep 1, 2017
  • Stayed: Aug 2017
  • Source: VRBO, from HomeAway
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Beyond magical

  • 5 of 5

My husband and I got married here in August and stayed on the property for a week. There are no sufficient words for how beautiful and magical this place is. Every single guest commented on how breathtaking it was ("How did you find this place?!" "This place is unbelievable!" "Is it okay if I copy off of you and have my wedding here too?!")—the pictures do not do it justice (and the pictures are pretty damn good). The house itself is decorated top-to-bottom like it should be in Domino or Kinfolk Magazine....we were there for a whole week and I kept finding new remarkable details every single day. The grounds are immaculate with multiple little sitting areas under trees, in gardens, around fire pits, etc.—and that's to say nothing of the phenomenal views of the mountains.

To say that Jill and Trey were generous, thoughtful hosts is an understatement. Jill responded quickly to every single one of my questions and even helped me suss out a lot of wedding details (which she did NOT have to do). Plus, she was extremely responsive while we were staying on the property. They provided everything we could have ever needed and much, much more—sorry, am I gushing? I can't help it—August Moon is one of the most remarkable properties on planet Earth. On one hand, I want to keep it as a secret for ourselves, and on the other hand, I want everyone to experience it.

Despite the fact that we just got married there, we're already hoping we'll be able to return for our one year anniversary. How far out can we book this place?! <3

  • Submitted: Aug 18, 2017
  • Stayed: Aug 2017
  • Source: VRBO, from HomeAway
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Fabulous Berkshire Home

  • 5 of 5

My family and I loved our week in Sheffield. It was not long enough! I am the mom of four adult children (with significant others) and two young grandchildren. The house fit us perfectly for our mini family reunion. August Moon is the perfect spot to unwind, enjoy your family, and soak in the beauty of the Berkshires. Rainbows provided!!

  • Submitted: Jul 14, 2017
  • Stayed: Jul 2017
  • Source: VRBO, from HomeAway
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Such a lovely vacation at August moon

  • 5 of 5

The house was perfect for a family trip! Stocked with everything you could need.

The only drawback were the mosquitos!

  • Submitted: Jul 6, 2017
  • Stayed: Jun 2017
  • Source: HomeAway
Owner's Response: Bria, we are so sorry about the mosquitos and the lack of effect of the spraying. We've contacted the company and the owner is looking into this. This is the first time in all our years of spraying that the mosquitos were not controlled. We will refund the additional cost of the spraying along with your full security deposit. Happy you enjoyed yourselves despite the nuisance!
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We loved August Moon

  • 5 of 5

We had a beautiful time here with our adult kids and relatives. The house is clean quaint and comfortable, the kitchen is fully stocked, there is a great record collection, as well as a nice sunny family room and a TV room for relaxing indoors. We enjoyed the patio, gardens and tennis courts daily, and one night had a fire and roasted marshmallows in the fire pit -- haven't done that since our kids were little! Our dogs loved the big open yard and did not want to leave. So all in all, it was the perfect spot for our family and we definitely hope to rent August Moon again in the future.

  • Submitted: Jun 19, 2017
  • Stayed: Jun 2017
  • Source: HomeAway
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Our 2nd visit to August Moon!

  • 5 of 5

Just fabulous the second time! All three generations love this beautiful country house because it's the perfect blend of old (1770'S) and new (2017 technology), fabulous kitchen, proximity to good restaurants, beautiful gardens and acres to explore, bicycles, children's playhouse, tree swings, tennis court, great books on the shelves, music collection for everyone, nearby movie theatre, Tanglewood, Jacobs Pillow and on and on. We're looking forward to our 3rd visit!

  • Submitted: Apr 17, 2017
  • Stayed: Apr 2017
  • Source: HomeAway
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Car: necessary

Our Welcome Book features a list of local information related to: antiques shopping, dining, Berkshire Theatre Festival, Tanglewood, and art exhibits in the area.

SWIMMING: In the summer months, a refreshing dip is a must for cooling off. Here are some ideas:

Green River Water Hole: amazing spot! (2.5 miles north from S. Egremont on Route 23)

Lake Mansfield: a 40 acre body of water less than a mile from downtown Great Barrington. The lake has historically been a site for recreation, social gatherings, and solitude. Generations of swimmers have enjoyed its cool waters. A small beach with lifeguard and roped off swimming area is great for families with children.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $150
Damage Deposit $500

Higher rates will apply for holiday weekends. Site fee applies for weddings and group events.

Owner's Cancellation Policy

100% refund if canceled at least 90 days before arrival date.

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