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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Beautiful Berkshire Home W Tennis Court; Close to Skiing!

Bedrooms 4
Space 3,800 sq ft
Property type house
Minimum Stay 3 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:
April 20, 2018

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
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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 -
(64 traveler reviews)

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Beautiful Berkshire Home W Tennis Court; Close to Skiing!
average rating of 4.984375 based on 76 reviews

Magical Country Home in the Berkshires

  • 5 of 5

Our family of 7 adults and a dog just returned from a 4 night stay at August Moon over the Thanksgiving holiday. We had the most amazing time. The house is beautifully setup to just spread out, relax and enjoy yourself. Every amenity you would possibly need was provided--games, books, tv, kitchen tools, and enough children's toys to keep tots busy for a long time. My only disappointment was to not be able to see all the gardens in full bloom, which I'm sure is going to require a return trip for us. The property is expansive and we hiked through the forest trails every day, even to a local waterfall trail that was stunning. We had camp fires at night and played bocce ball every day. The solar accent lights around the property really gave it a magical feel. It truly was just spectacular all the way around.

The hosts, Jill and Trey, were fabulous with their communications and were always quick to respond with any questions we had. The expansive information packet/book they provide is very complete, and I had the sense that they just wanted you to relax and enjoy yourself and surroundings.

We didn't go out to eat much because we just wanted to stay at the house. Brought pizza home one night, but then just used the grill or ate leftover turkey. We enjoyed a day of exploration in Great Barrington and a couple of us went to the Norman Rockwell museum in Stockbridge which I would highly recommend.

The beds were all comfortable and the linens high quality. The master bedroom was expansive, and the bathroom spa like. Great selection of soaps, lotions, etc.

All of us would highly recommend August Moon for an unforgettable vacation getaway. We would all go back!

  • Submitted: Nov 28, 2017
  • Stayed: November 2017
  • Source: VRBO, from HomeAway
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Beautiful wedding venue and peaceful escape!

  • 5 of 5

I cannot say enough great things about this property! My husband and I hosted our intimate wedding here this Columbus Day weekend. We stayed for 4 nights with some friends and had the wedding in the yard with invited guests on Saturday. The house is surrounded by many acres of quiet, relaxing scenery so this is the perfect location for a quiet, romantic getaway as well as a setting for a wedding. The house is absolutely GORGEOUS. It is well maintained, very open with a ton of natural light. The house was stocked with everything we could need. It is also impeccably decorated. The grounds are also absolutely perfect! The gardens are filled with flowers and as we were near peak foliage, the colorful trees and mountain view served as the perfect backdrop for the wedding. The fire pit was a huge hit for smores, after the formal reception ended. The nighttime sky was also amazing, especially for us coming in from the city. Luckily, the last day my husband and I were able to have a few minutes to explore the property more after everyone left. We chose to walk some of the trails on the backside of the property and were lucky enough to find some salamanders and frogs!

In addition to the property, Jill and Trey were also wonderful. They responded to all emails in a timely manner and were available to answer any questions that we had. They were very knowledgeable about all of the technical aspects of hosting a wedding that were needed to be taken care of prior to the party.

Overall, this has been the most perfect wedding weekend I could have imagined and a large portion of that was due to the property. All of our guests commented on how wonderful a venue it was and how they wish that they had chosen something similar instead of their more traditional venues. We will definitely be coming back to enjoy a more quiet vacation. It was so hard to leave to get back to the hustle and bustle of the city after being in this peaceful oasis all weekend. We cannot wait to go back!

  • Submitted: Oct 10, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
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Best wedding venue ever!

  • 5 of 5

We just spent 4 nights at August Moon and hosted our wedding on the breathtaking grounds and 1 week later we can't stop reliving our incredible weekend. We were not able to see the house in person before we booked it as our venue, but the pictures online were so beautiful we took the chance. When we arrived we quickly realized that even though the pictures we saw were incredible, there is no way to capture all of this home's beauty in a photo. The house is so cozy it truly felt like ours during our visit and the grounds are perfectly maintained and made for a wedding. All of our guests were blown away and many of them asked for information on how they can rent out the house. Everything about the house is perfect!

There is honestly not a negative thing we can say about August Moon, it is the perfect place to stay and just relax, host a small family gathering, or a wedding. It was so hard to leave, everyone who stayed at the house was very emotional when it was time to go. This home has given my family the most wonderful memories and we plan to go back!

  • Submitted: Oct 1, 2017
  • Stayed: September 2017
  • Source: VRBO, from HomeAway
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Cambridge, MA

Berkshire experience like no other!

  • 5 of 5

It is hard to find words to express all that this exceptional property and most importantly the two owners, Jill and Trey, encompass. From the expansive property to the stunning and whimsical gardens (those dahlias!) to the curated interior, it was nothing but top-notch. My (now) husband and I decided to hold our August wedding there, and it couldn't have been a more perfect site. After searching over 100 venues (!), we were ecstatic to have learned about this space. Once meeting Jill and Trey, there was no question that this would be the place for us to hold our special day. One distinguishing aspect that August Moon offers is the opportunity to have a memorable experience vs. strictly an event--something quite rare amongst wedding venues and sites! The house offers both an aesthetic (that all were envious of!) and an inviting warmth that brought our friends together from around the world. The property offered multiple vignettes to create a magical weekend--from the tennis court to the hiking trails to the outdoor patio amongst the butterflies to the garden to the fire pit--and importantly each of which were in nothing but in the best condition. As you can imagine, our wedding guests were in awe as well. Many raved at its beauty and many of our younger friends wondered how they could get this site for their own memorable day!

While the location, setting, and site hold a unique and stunning presence, more importantly the owners, Jill and Trey, were those that you want to call dear friends. From their generosity to their warmth to their support and ease in scheduling and planning, it was nothing but a pleasure and privilege to work with them on all fronts. They shared their generous and fun spirit as we were gearing up for our big day, which made it all the more special and helped allow for the pre-wedding anxiety to slip away. This spirit could also be felt within the property--as you could imagine their desire to bring people from near and far together to step away from the hustle and bustle and truly enjoy one another's presence. Again, nothing but magical.

To say that I would recommend this setting for a getaway or one of your most memorable moments would be an understatement. There is no question that you will find the magic and the beauty within all things August Moon. We can't wait to come back!

  • Submitted: Sep 30, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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The Perfect Getaway and Wedding Venue

  • 5 of 5

August Moon is so incredible, I don't know where to start! We were introduced to the property by our wedding planner, 42 North, for our September nuptials and took the trip from Boston to check it out in the dead of winter. While there, we met a couple staying at the house who had been married there in the past and could not stop gushing about how beautiful the property, and the Berkshires, is in the Summer and Fall (Always a good sign to see repeat renters!). Even that didn't prepare me for how wonderful this place is. The landscaping is this perfect mix of wild and organized, with the most incredible dahlias! The grass is green and soft and the garden is flourishing with veggies and flowers. The grounds are straight out of a dream with a big lilac hedge and a huge, well-manicured field in the back perfect for a tent of any size with extra space for an al fresco cocktail hour. There is a stunning natural ceremony site with a grass aisle that runs from the house to the site and the cutest tennis house, perfect for cocktails and lounging. If you get the chance, take a walk on the paths behind the field and you'll become enamored with the old forest, high-strung vines and vibrant moss. We even saw a huge brown owl!

Now for the house - I actually pretended I lived a life as rustic-chic as this house during my stay. Jill and Trey's eye for design is unreal. Everyone who entered the house was blown away with how gorgeous it is. I was actually taking design notes in my phone. And the beds? I am so picky about this and I slept better than I've slept in a long time here. Everything you need for a perfect getaway is here and it's not old, mismatched stuff that you sometimes find in rental properties. Everything is high-end, clean and obviously cared-for. August Moon is amazing and Jill couldn't have been more accommodating and responsive. You will not regret booking a weekend, a wedding or a week here! We will definitely be back.

  • Submitted: Sep 26, 2017
  • Stayed: September 2017
  • Source: VRBO, from HomeAway
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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: August 2017
  • Source: VRBO, from 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

Refundable damage deposit $500
Housecleaning $150

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.