Where to Stay in the Berkshires, Western Massachusetts

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Seven Hills Inn

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The sprawling mountain vistas of the Berkshires in Western Massachusetts have been attracting creative types (and outdoorsy types) for centuries.

No matter what season you visit, there’s lots to do. In the summer months, city folks flee nearby Boston and even New York City to head to the low-lying hills of the Berkshires to soak up big nature while hiking or festival hopping. The famous Jacob’s Pillow Dance Festival is here. In the winter season, these peaks give way to ski resorts and other outdoor fun.

So where should you stay in the Berkshires? Let’s dive in.

Where to Stay in Berkshires

The Berkshires encompasses a significant area, so this guide is broken out into towns or regions. Travel times between destinations can vary, so make sure you plan your travels in advance.

None of these places will leave you disappointed. For this guide, I partnered with Hotels.com to share where to stay in the Berkshires. Here you’ll find a breakdown of each area of the Berkshires, along with some of the best accommodations for your budget in the region.

Stockbridge

Stockbridge is quintessential small-town New England, and for many people it’s a familiar sight: Norman Rockwell’s famous painting Stockbridge Main Street at Christmas captures that classic American scene of snow-dusted beautiful homes. At The Norman Rockwell Museum, you’ll learn all about his creative process, from start to finish.

Stockbridge is easily one of the most idyllic towns the Berkshires. Peruse the manicured gardens, admire the Gilded Age architecture, and explore the many art galleries, restaurants, and boutiques around town.

Once you leave Downtown Stockbridge, you’ll find lots of nature reserves and hiking trails to explore. This is one of my favorite areas in the Berkshires simply because it has a little bit of everything to offer.

Red Lion Inn

The Red Inn Stockbridge

The Red Lion Inn is a mainstay in the Berkshires, and is easily one of the best Berkshires hotels in town. Each room and suite here has a completely unique style; no two are alike! Antiques and charming decor give the feel of having stepped back in time, but modern amenities like fluffy bathrobes and luxurious linens will keep you nice and comfy throughout your Berkshires stay.

The Red Lion Inn is truly a testament to the Gilded Age of luxury. Plus, when you stay here you’re just a few minutes walk to Housatonic River and the iconic Mission House, which you should definitely work into your travel plans. Don’t forget to see what’s on the menu at the Lion’s Den Pub.

The Inn at Stockbridge

The Inn at Stockbridge

The Inn at Stockbridge is another charming area to stay in Stockbridge, full of antique furniture and period details. There are 15 smoke-free guest rooms here, as well as a giant outdoor pool and a fitness room. If you want an upgraded experience, book one of the Barn Suites: you’ll get extra amenities like a working fireplace and a lounge sofa.

Another thing to love about the Inn at Stockbridge—all guests are invited to a wine and cheese reception daily. Oh, there’s also a library and an extensive record collection belonging to the owner. You’ll feel right at home here.

North Adams

North Adams is a little quieter than the other towns in the Berkshires, but it does stand out for one good reason: it’s home to Mass MoCA, a contemporary art museum that draws visitors from across the country. People come all the way to the Berkshires just for this museum. If your artistic spirit still isn’t filled, the Clark Art Institute is also nearby.

This New England town also has tons of shopping and dining options, as well as art galleries and studios. Even old factory buildings and mills have been converted to artist studios around here—Berkshires folks really know how to beautify an area.

If art isn’t your thing, hit the Ashuwillticook Rail Trail. This converted rail bed now stretches over 12 miles and you’ll travel through several towns in the Berkshires when you walk or bike it.

The Porches Inn

The Porches Inn

The Porches Inn is a must-see when you stay in the Berkshires, even if you don’t end up booking a room. It’s a Berkshire institution, making up a row of 19th-century Victorian houses ringed with (you guessed it) porches. And it’s located right across from Mass MoCA.

The Porches Inn in the Berkshires has just seven rooms, but each with a distinct design and style. Some come with spiral staircases or even fireplaces. There’s also a year-round heated pool, hot tub, sauna, and fire pit to complete your Berkshire getaway.

Holiday Inn Berkshires

If you’re looking for hotels in the Berkshires that are more budget-friendly, you can’t go wrong with the Holiday Inn Berkshires. This is one of the most family-friendly places to stay in the Berkshires (kids stay and eat for free), with 90 rooms, a dining room and restaurant, and even free parking.

You’re also close to the town center area when you stay here. The Holiday Inn Berkshires might not be a fancy cottage house, but you’re guaranteed a great travel experience with everything right at your fingertips.

Mount Greylock

Mount Greylock is home to the highest point in Massachusetts at 3,491 feet. On a clear day at the summit, you’ll get perfect views stretching across the Berkshire hills all the way to New York.

If you’ve come to the Berkshires to tick some physical activity off your list, Mount Greylock is the place to be. If you feel like hiking or camping, the State Reservation is a popular area to hit the trails—but it’s also a great spot for skiing or snowmobiling in the winter months.

While here, visit the stunning War Memorial Tower. The spiral staircase takes you up to a viewing platform with a 360-degree view around Massachusetts and the region. Pack a picnic, and enjoy your day exploring the area.

Harbour House Inn Bed and Breakfast

Harbour House Inn Bed and Breakfast

Who doesn’t love a good bed and breakfast? The Harbour House Inn Bed and Breakfast is technically on the outskirts of the park reserve, but it’s one of the nicest inns in the Berkshires area and will complete your Berkshire getaway.

This Georgian Colonial inn welcomes guests with comfortable rooms, dreamy beds, and antique furnishings. Soak up the lush garden with its mountain views and enjoy a homemade breakfast before heading out to travel around the area. You’ll get freshly baked muffins, brewed coffee, and other dishes made from local ingredients to get your day started off right.

Renovated Barn in the Berkshires

Renovated Barn

Also located in the park reserve area, the owners of this Berkshire property spared no expenses in turning a rustic barn into a comfortable, open-concept vacation home. If you’re not interested in staying in hotels, definitely check out this place.

Wifi, a barbecue grill, a full kitchen and seating area and more are all included here. And yes, this is still a working farm area—you’ll be treated to fresh eggs for breakfast on your visit!

Lenox

Located in the southern part of the Berkshires, Lenox is best known for being home to former literary figure Edith Wharton. In fact, you can visit her home known as The Mount.

It’s no wonder Wharton found the Berkshires inspiring—beauty is all around. Nature lovers, this Massachusetts getaway is right up your alley. Don’t forget to visit Lake Mahkeenac (the Stockbridge Bowl) or hit a hiking trail around town.

Lenox is an ideal area to stay in the Berkshires, and it’s a personal favorite of mine thanks to its convenience. You’ll never be too far from a restaurant or a gallery, and the town is chock full of historical landmarks. Be sure to check out the Berkshire Cottages, the Church on the Hill, and more. The Tanglewood in Lenox is also the summer residence of the Boston Symphony Orchestra, so don’t forget to visit and see what’s on.

Seven Hills Inn

Seven Hills Inn

The Seven Hills Inn is one of the best Berkshires hotels in the region. This year-round boutique is set on 27 acres of gardens, making it the ideal Berkshire getaway for anyone (while still being in the heart of Lenox). All the rooms are modern and recently upgraded with plush new bedding, flat-screen TVs, and plenty more.

This Inn is basically a retreat, and an impressive retreat at that. You can stroll the tree-lined lanes, sunbathe, hang out at the pool, see what’s on the breakfast menu, or hang out at the wine bar. The Plunkett Lounge dining room in the main house is the perfect spot to grab a cheese tray (or something else on the menu) while enjoying the Berkshire surroundings.

Birchwood Inn

Birchwood Inn

Complete your stay in the Berkshires with a bit of luxury at the Birchwood Inn—one of the nicest inns in the Berkshires. Believe it or not, it started out as a tavern in the 1700s and now has turned into this Berkshires getaway. Each room is named for a previous owner and is adorned with its own style. And the bed? You’ll find it hard to leave behind.

If your travel plans include the Berkshires, you might as well pamper yourself at a place like this in Lenox. No matter the season, hang out by the fire, order some room service, and enjoy the gardens.

Pittsfield & Great Barrington

This area of the Berkshires is near Lenox but has a much busier, upbeat vibe than the slower pace of the other Berkshire travel destinations. Here, you’re at the center of the Berkshires with tons of restaurants, shopping options, and entertainment venues right at your fingertips. Some of the finest Berkshires hotels are also here.

See what’s on at the Barrington Stage Company, travel back in time at the Berkshire Museum, or simply treat yourself to a fine dining experience at a local restaurant. There are plenty to choose from.

Pittsfield makes a great hopping off spot for exploring the rest of the Berkshires.

Hotel on North

Hotel on North

Let’s take a break from all the inns! The Hotel on North is one of the best Berkshires hotels around. It’s smack dab in the middle of all the action, and each room has its own unique style. It’s got a lot of quirky edginess: you can admire all the exposed brick while sipping cocktails in a birdcage elevator, for example. And the restaurant is fantastic.

This hotel has stayed true to its Berkshires heritage while also adding touches of modernity. You’ll get lightning fast wifi, gas fireplaces, wet bars, and more. There’s even a library suite with literally a full library of books.

The Berkshire Inn

The Berkshire Inn

Last on our list of Berkshires hotels is this fairly affordable inn with basic but comfortable amenities. All rooms here come with plush beds, air conditioning units, wifi, and more. There are a handful of rooms that are also accessible for people with disabilities.

If you want an affordable hotel to stay as you travel around the Berkshires, this is it. There’s lots to see and do right outside the front door, and believe me, the Berkshires do not disappoint. The friendly staff are always on hand to offer additional information before you head out to explore.

***

There you have it, these are some of the best towns and accommodations in the Berkshires. If you’re itching to travel to a quintessentially American destination, this is it. You’ll get all the small-town feels combined with the epic landscape of the Berkshires mountains, and you won’t return home disappointed.

It’s worth nothing that Berkshires is a pretty popular destination, especially in the summer months. So make sure you secure your travel dates early, and book your accommodations!

As travel today remains uncertain, please keep your safety and the safety of others in mind. If you are comfortable with traveling, please travel responsibly and within regulation as any travel is at your own risk. Travel restrictions may apply.

If you do decide to travel at this time, here are our recommendations:

  • Wear a face mask. 
  • Bring hand sanitizer and wash your hands on a regular basis.
  • Check official websites before your trip for the latest information on policies, closures and status of local businesses. There may be travel restrictions.
  • Book a hotel with free cancellation in case you need to change your plans at the last minute.

Jeremy Scott Foster
Jeremy Scott Foster
Jeremy Scott Foster is an adventure-junkie, gear expert and travel photographer based in Southern California. Previously nomadic, he’s been to ~50 countries and loves spending time outdoors. You can usually find him on the trail, on the road, jumping from bridges or hustling on his laptop working to produce the best travel and outdoors content today. You can read more about Jeremy at his bio.

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