High Field Farm


Entire home hosted by Jennifer

  1. 8 guests
  2. 4 bedrooms
  3. 5 beds
  4. 2 baths
Self check-in
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Come to High Field Farm to getaway and unwind in a beautiful, classic New England farmhouse. Set on over 500 acres of land, enjoy a spacious, tasteful and pristine country vacation home, lovingly cared for by the same family for over 50 years.

The house offers four bedrooms and two full bathrooms, and endless outdoor opportunities like hiking or fly-fishing. You'll enjoy spectacular mountain views in an idyllic and private country setting that will enchant and nourish your heart and soul.

The space
The farmhouse and barns of High Field Farm were built in the late 1700’s by the Buck’s, one of the very first settler families of the Hilltowns, and as one of the oldest houses in town, it is quaint, full of charm and steeped in history. Art and antiques, lovingly selected over the decades to tastefully decorate this family vacation home, can be found throughout High Field Farm, which is large enough to gather easily with friends or extended family for a long and enjoyable getaway. There are a total of four (4) big bedrooms that can sleep up to eight (8) people quite comfortably, and two full baths, along with a full laundry, too.

The first floor has one bedroom with a lovely antique Queen bed for two people, adjacent to a full bathroom with laundry facilities. There are three upstairs bedrooms, plus another full bath, as well as a small sitting room that can easily fit a Pack n’ Play for a baby or toddler. The upstairs bedrooms are large and airy, and include one bedroom with a large Shaker style Queen bed for two; a second bedroom with a spindle Double bed for two; and a third bedroom with two maple Twin/single beds. Although all the beds are antiques, the mattresses are newer and very comfortable, and they boast new pillows, fresh new bed linens, and you’ll also enjoy plush new bath towels during your stay, too.

High Field Farm has a simple eat-in country kitchen with all the knives, utensils, dishes, flatware, pots and pans you’ll need to cook a big meal for yourselves (we also provide guests with kitchen basics: salt, pepper, oil, vinegar, sugar, tea bags and ground coffee.) There’s a big farm table where up to eight people can enjoy long, leisurely dinners—or epic card or board games. Outside, we provide a gas grill for all your BBQ needs, too.

A large first floor living room and adjacent comfy den provide big couches for lounging or napping, plus books and board games for evening fun. The house has Broadband WiFi, and there is a TV and a DVD player in the den. You can connect to your favorite streaming service, or watch one of the DVDs we provide - which include a small selection of classic movies. There is a Bose Radio with an AUX cable and a bluetooth Ultimate Ears speaker on the bookcase in the living room. You can connect your phone and stream music, or listen to one of the CDs provided.

The extensive grounds of High Field Farm include two large barns, and a fenced-in, full size in-ground swimming pool. The pool has dreamy views of the blue sky and the surrounding countryside, and is large enough to do laps—or if you want to relax, simply grab a float and soak in the sun! There’s also a fire pit up near the pool, surrounded by several Adirondack chairs, where you can sit and enjoy the fire or roast marshmallows to make S’Mores, as the cool summer and fall evenings bring your day to a close.

Right outside the kitchen door is the large breezeway, which has long been a favorite spot for family and friends to gather and visit, to play a game of Scrabble, or to simply sit quietly and read a book. It offers magnificent field, hilltop, and forested views for miles and miles to the North and West. And, uphill past the small barn, pool, and the blueberry patch (where guests can pick blueberries when they’re in season) guests can gaze towards the very top of the Farm, to the highest hilltop on the property.

It’s the land that makes High Field Farm truly special, it offers miles of private trails and lanes for hiking and meandering, through fields and forests that are criss crossed by old stone walls which harken back to the region’s earliest settlement. A naturalist’s paradise, High Field Farm is home to a variety of flora and fauna: besides majestic white pines, old maple trees, and beautiful birches, the rolling fields are covered in masses of green grass, clover, rye and wildflowers in season. As for critters, you might get lucky and see deer, fox, porcupines, beavers, hawks, barn swallows, owls and more—perhaps even a moose or a bear!

One of the best “walks" is just above and beyond the pool yard: it’s a steep trail to the top of the open mountain, where you can get a bird’s eye, 280-degree view of the surrounding hills. If you happen to come around a full moon, climb up to the top, where you will be amazed at how close and magical the moon looks as it rises over the hills from the East. Stargazers will be dazzled by the number of stars you can see on a clear night.

The Road up to High Field Farm is steep enough for a rigorous cardio workout! It continues for another, somewhat easier ½ mile or so into the woods for a beautiful and enjoyable hike or run to the old beaver pond, where you can explore the old beaver dam and lodge. While a few family members have homes on the Road, and nearby, every home is far enough away that you will have plenty of privacy during your stay.

Where you'll sleep

1 of 3 pages

What this place offers

Mountain view
Valley view
Free parking on premises
Private pool
Free washer
Free dryer

7 nights in Chesterfield

Nov 24, 2022 - Dec 1, 2022

4.94 out of 5 stars from 18 reviews


Where you’ll be

Chesterfield, Massachusetts, United States

Nearby natural amenities include the gorgeous Westfield River and the nine+ mile long East Branch Trail, which includes the spectacular and popular Chesterfield Gorge; it’s a fantastic location for fly-fishing, hiking, biking and swimming. For the adventurous, we can even recommend a few local swimming holes to take a dip on the hottest days if you feel like experiencing the cold waters of this region! Worthington Golf Course is a few miles away, and provides a relaxing 9-hole course that’s open to the public from May to late October. There are public tennis courts and a playground in the center of Chesterfield about 5 minutes away by car. The Cummington Fairgrounds, which provide a variety of nostalgic events throughout the summer, like sheep trials and an old fashioned country fair at the end of August, is only a few minutes down the road, too.

There are also several charming local restaurants and stores within a 10 minute drive, including The Rabbit Hole in Worthington, the Chesterfield General Store & Cafe (which boasts excellent baked goods and wood fired pizza) and the Cummington Creamery, which offers fantastic prepared foods, home made ice cream, baked goods and more. Both stores have a selection of beer & wine, and most provisions you will need. For larger grocery stores and more extensive food shopping, we suggest you head to Northampton (try River Valley Market) or Pittsfield (try Market 32).

At Highfields, you are close enough to the Berkshires (including Lenox, Pittsfield and North Adams and Williamstown) to take an easy day trip and access any of the institutions that make up the famous Berkshire arts and cultural scene, including Tanglewood, Jacob’s Pillow, Kripalu, The Mount, MassMoCA, Barrington Stage and Williamstown Theater Festival, as well as the Norman Rockwell Museum and Hancock Shaker Village.

The wonderful small city of Northampton is approximately 30 minutes away, and has excellent galleries, a vibrant music scene, and lots of shops (check out Thorne’s Market, a great one-stop location with a variety of fun stores and eateries) plus dozens of great restaurants and pubs, including East Side Grill, Haymarket Cafe, Spoleto, Nourish, the Northampton Brewery, Paul & Elizabeths, Amanouz and Woodstar Cafe, as well as a variety of excellent Asian, Indian and Thai restaurants, too. In Florence, try the croissants at Bread Euphoria, or the bagels and smoothies at Tandem Bagel. Look Park is great fun for families with kids - it offers a spray park, paddle boats, tennis and playground.

Hosted by Jennifer

  1. Joined in October 2012
  • 18 Reviews
  • Identity verified
  • Superhost
Member of Airbnb since 2012, I’ve enjoyed staying at people’s homes. It’s a richer experience to be in a home or a neighborhood, where you can get a better sense of a place. Plus, it's fun to be able to buy groceries, cook meals and have added space to gather with friends or family. The place I’m sharing, has been in my family for over 50 years, and is a magical place that we cherish.

Many of us have always thought it would be a great house for guests to rent because it’s such a unique place. There are endless rooms in the house, and being out in the country on vacation - makes you want to exercise, craft, read, play games, swim, fish, hike or simply have an outdoor fire!

High Fields is a place to slow down for a few days, and let the outside world slip away. The vantage point of the house, set up over the hills of West Chesterfield, will instantly mesmerize you. Please contact me to schedule your visit!
Member of Airbnb since 2012, I’ve enjoyed staying at people’s homes. It’s a richer experience to be in a home or a neighborhood, where you can get a better sense of a place. Plus…

Jennifer is a Superhost

Superhosts are experienced, highly rated hosts who are committed to providing great stays for guests.
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Things to know

House rules

Check-in: After 4:00 PM
Checkout: 11:00 AM
Self check-in with lockbox
No smoking
No pets
No parties or events

Health & safety

Airbnb's COVID-19 safety practices apply
Carbon monoxide alarm
Smoke alarm

Cancellation policy