The Berkshires, nestled within the idyllic heartland of western Massachusetts, have long been recognized as an enchanting year-round playground for nature enthusiasts, culture vultures, and families. It’s also one of the best New England vacation destinations.
Our five favorite Berkshire Vacation Rentals
Bordered by Vermont to the North, New York to the West, and Connecticut to the South, this easily accessible New England destination is popular year-round, and for a good reason! There’s always something to see and do here, no matter the season.
Western Massachusetts is home to many beautiful accommodations, but in today’s article, we will focus on the wild, the wacky, and the downright fun Berkshire vacation rentals your family will surely enjoy on your next trip.
Ready? Buckle in; #5 is bananas!
Berkshire Vacation Rentals: Goose Pond Off-Grid Cottage – Lee, MA
This “cottage” is located on the shores of Goose Pond in Lee. It has two bedrooms and 1.5 baths and can sleep up to six guests. The aesthetic interior of the house is a traditional New England Camp vibe that meets Coastal Chic exterior, so there are lots of pine inside and clapboard multi-story vibes outside.
While the kitchen is small, it’s fully equipped, and your family will enjoy seeing the sunset over the lake at dinner time from the dining room table. Open the deck’s sliding windows on the warmer nights to enjoy the fresh air, or keep toasty with a wood-burning fireplace on those cooler fall evenings.
Amenities include air conditioning, limited wifi, a hammock, and kyacks to glide across the river. This two-bedroom features two queen bedrooms and a two-person pull-out couch in the living room, so everyone in the family will get a good night’s sleep here.
Things to do in Lee, MA – Lee is a waypoint of the Berkshires and a place for kicking back. There are plenty of hiking and outdoor activities to enjoy here, including mountain biking, hiking, and fishing, but it’s less of a focus here.
Lee, in my mind, is the destination you want to visit if you want to combine fine dining, art, and music. Lee’s premium outlets are an excellent shopping destination for those that like great deals. While not as extensive as Maine’s Kittery outlet stores and not as upscale as Wrenthem’s outlet stores, Lee’s outlet offers known brands great values.
The big draw for me is in the Summer when the Boston Symphony Orchestra and many other globally known entertainers flock to Tanglewood.
Berkshire Vacation Rentals: The Babbling Brook House – Monterey, MA
If venturing even further off the beaten path and into the wilderness is your family’s vibe, the Babbling Brook might be the spot for you. This remote home is a traditional farmhouse with a natural stone fireplace, wide plank floorboards, and a bridge over the moat (aka brook) to enter.
The galley-sized kitchen is well equipped to meet your family’s mealtime needs, and the decor mixes luxurious furniture fabrics and minimal/rustic furniture. This house offers one king bedroom and two queen bedrooms, so there’s plenty of space here for larger families or families with older children to spread out and get comfy.
One thing to consider, the vehicle parking is a bit of a hike to the house. You will need to pack your things in and out for this one, but if you’re the type that prefers to be truly isolated from the world on your vacations, this one’s it.
Things to do in Monterey, MA – Take a trip back to 1760 and visit the Bidwell House Museum, where you can stroll or hike 192 acres of land and learn about the life, death, and beliefs of Adonijah Bidwell.
Berkshire Vacation Rentals: Woodland Haven – Becket, MA
If off-grid isn’t your family’s vibe and you’d rather spend your Berkshire vacation with a few more creature comforts, Woodland Haven could be the right spot for you.
Combining rustic wood interior with high-end appliances, this two to three-bedroom stunner has high-end appliances, a well-manicured lawn, a gorgeous stone fireplace, and a heated inground swimming pool.
Though private, this retreat is located on a larger estate, giving your family the utmost privacy in their stay; it’s just a quick 5-10 minute walk to a shared beach area, tennis court, hiking trails, playground, and basketball court for your enjoyment.
Things to do in Becket, MA – Dancers take note; this one’s for you. Becket is home to the iconic Jacob’s Pillow dance festival, where performers worldwide come together each summer to learn, teach, and showcase creative dance performances. This is the epicenter of dance’s free expression, from classical ballet to modern hip-hop.
Berkshire Vacation Rentals: The Tree House – New Marlborough, MA
I will admit it, after spending 18 years of my youth outdoors in the northern woods of Maine, I don’t like “roughing it,” and this one isn’t for me. However, this three-bedroom treehouse literally brings the outdoors in, with a ginormous tree growing through the middle of the house.
This is the camp house of my youth, and it personifies rustic, unlike any other thing I’ve seen in my travels, with plenty of little nooks and crannies for the kids to get lost in.
There’s one bedroom with a queen bed, one with a double and a single bed, and a third with one single bed. In addition, there’s a fully equipped kitchen, outdoor hammock, grill, and patio set, as well as private parking.
The beautiful glass window panes allow the house to receive plenty of light, perfect for the artist in your family to draw, paint, or explore light textures, and the loft-style upper is sure to be a hit with your little ones as well.
Things to do in New Marlborough, MA –
New Marlborough is your destination if you like rocks, hikes, and waterfalls! Unlike most Massachusetts “waterfalls,” New Marlborough has a collection of waterfalls reaching up to 50 feet high on a backdrop of evergreen forest.
Spend a day hiking to and having lunch by Campell Falls, a zig-zagging river with multiple drops set on a pine needle forest background – better bring the bug spray. Or, take a dip with your family in the Umpachene Falls, with its gentle tide pools and crips, cool water, and enjoy one of the only falls in Massachusetts with swimming is *encouraged*.
Berkshire Vacation Rentals: Mid-Century Glass Octagon – Otis, MA
Ok, now we’re speaking my love language 😉 This mid-century octagonal Otis house is my family’s ultimate Berkshire vacation rental. It’s cool. It’s unique. It’s modern, and it’s cozy.
While this rental is smaller than the others on our list, this “tiny” house comes packed with amenities, including:
- Fast Wi-Fi
- A Modern Kitchen
- Stream enabled television
- Washer/Dryer
- Huge private deck with seating and BBQ Grill
- Bluetooth surround sound
- An EV Charger
Here you can enjoy everything the Berkshires offer without sacrificing a single creature’s comfort. While you will be limited on the number of guests this place can accommodate (2 adults, one pack-and-play, one double pullout bed), you will not find a better location for balancing your desire to unplug and your need for modern amenities.
Things to do in Otis, MA –
Otis is located in a somewhat awkward location. If you’re visiting in the summertime, you can easily take advantage of and visit all of the other recommendations I’ve listed above.
If you’re visiting in Winter, Otis offers a rather special gift, Otis Ridge, one of the last family-friendly small and locally operated ski mountains in Massachusetts. The Berkshires used to be an incredible family destination for skiers of all ages and abilities; sadly, the pattern of weather changes and lack of interest have all but killed this traditional locally.
The Berkshires’ enduring appeal lies in its unique fusion of natural beauty, cultural richness, culinary delights, and a vibrant local community. Whether you’re a history buff, a foodie, an art enthusiast, or a nature lover, the Berkshires offer an unforgettable experience that will make you fall in love with this New England gem. So, pack your bags, set your GPS, and prepare for the quintessential Berkshires adventure.