Elena Mallia 
The Berkshires are three mountain ranges located in western Massachusetts, New England. Loved for their breathtaking views and outdoor activities, from hiking in the summer to skiing in the winter, if you’re looking for weekend getaways nestled in the tranquility of nature, this is the place to be!
But where to stay in the Berkshires to have easy access to all the great activities it has to offer? There are many towns and villages just nearby, offering different vibes and accommodation options, for any budget and taste!
Lenox is the best place to stay in the Berkshires, New England for the first time, but there are many other options too like the affordable Pittsfield, the family-friendly North Adams, the quiet Stockbridge, and the nature paradise Great Barrington. I am sure you’ll find the best place for a great holiday.
But you don’t have to do any effort, I’ve already done the job for you and spilled this guide with the best areas and hotels in the Berkshires, researching through all the best booking websites.
The only thing you have to remember is to book them far in advance if you don’t want to lose the spot.
So let’s jump right in!
Contents
- Quick Picks for Your Stay
- 1. Lenox – where to stay in the Berkshires for the first time
- 2. Pittsfield – where to stay in The Berkshires on a budget
- 3. Adams – where to stay in the Berkshires with the family
- 4. Stockbridge – the most laid-back area in the Berkshires
- 5. Great Barrington – best area in the Berkshires for nature
- Frequently asked questions about hotels in the Berkshires
- Conclusion
Quick Picks for Your Stay
If you need to take a quick decision and book immediately, I got your back, check this list with the best hotels located in Lenox:
Here’s a map to help you have a mental image of all the areas that I will be talking about in this post:
- Lenox: for first-timers
- Pittsfield : on a budget
- Adams : for families
- Stockbridge : for quietness
- Great Barrington : for nature
1. Lenox – where to stay in the Berkshires for the first time
The historic village Lenox is the heart of culture in the Berkshires, located south of the mountain ranges. If you’re interested in cultural activities, rich history and you want to be well connected to the whole area at the same time, this is the place to be, featuring many tours providers.
In fact, here you will find countless art galleries and interesting attractions like the ancient Lenox Library, the Ventfort Hall Mansion & Gilded Age Museum, and the Boston Symphony Orchestra, a hub for theater and visual arts.
But if you just want to spend a lazy afternoon, the town offers many creative boutiques to do some shopping and amazing restaurants where you can enjoy a delicious meal. And while you’re wandering around Lenox streets, you won’t be able to stop gazing at the amazing architecture of the buildings!
And if all this wasn’t enough, from Lenox you can access soo many outdoor experiences, from challenging hiking in Monument Mountain, to the 15 miles of tree-lined trails in Kennedy Park and the breathtaking views of Mahanna Cobble Summit.
With such a wide offer, Lenox, New England, is definitely the best place where to stay in the Berkshires for first-time visitors!
This adults-only hotel is the perfect place if you want to enjoy all the comforts of a luxurious stay! Here you’ll start your morning with a delicious complimentary breakfast and finish it with free cocktails and cheese for the happy hour! The hotel also has a great position close to the Tanglewood Musical Center and Kripalu Center for Yoga and Health!
Other accommodation options in Lenox
Lovely hotel with a good location close to Cranwell Spa & Golf Resort, perfect to explore the hiking trails nearby!
Enjoy the swimming pool, spa, and hot tub of this great hotel, also offering an on-site restaurant
Feel like at home in this cozy house with a hot tub, just a few minutes away from town but very quiet and private.
Things to do in Lenox
- Take a hike, a walk, a swim or have a picnic at Laurel Lake
- Check out the special collections of the historic Lenox Library!
- Relieve some life stress at Kripalu Center for Yoga and Health
- Have the best views at the Mahanna Cobble Summit
- Go for a picturesque hike in Kennedy Park!
- Have the dinner at Blantyre, offering an award-winning menu
- Visit Edith Wharton’s estate (known as The Mount) historic museum
2. Pittsfield – where to stay in The Berkshires on a budget
Pittsfield is the largest town in The Berkshires, located about 30 minutes driving north of the mountain ranges.
Here there’s truly something for any kind of traveler and taste, from world-class theaters to live music, art shows, museums, unique shopping, and top dining options, all super close to the scenic beauty.
If you’re here and you love art, go see some cool performances at the Colonial Theater or at Barrington Stage Company!
And what is better than having access to all of this at very affordable prices? In fact, often overlooked by tourists, Pittsfield offers hotels and restaurants at way cheaper fares compared to the rest of the area, perfect if you want to stay on a budget!
So what are you waiting for? Check them out and don’t forget to book them as soon as you can… you could even find some good offers!
Berkshire’s Sweet Spot- New year-round spa, enjoy
You will absolutely love this house, with the perfect location to visit the Mass MoCa or explore the natural beauty in the Berkshires, including beautiful public lakes and hiking trails. Here you can relax in the outdoor pool or in the hot tub, and choose from many dining options nearby were to have a delicious dinner!
Other accommodation options in Pittsfield
Pet-friendly hotel featuring spacious suites, a tennis court, and a fitness center to stay in shape!
Offering suites with a private patio, this hotel is within walking distance of the best shopping and dining options!
Enjoy this family and pet-friendly apartment, perfect for skiing weekend getaways, close to Bousquet Mountain!
Things to do in Pittsfield
- Check out the amazing shows of the Colonial Theater
- See the best performances at the Barrington Stage Company
- Hit the ski slopes of Bousquet Mountain
- Have a delicious meal with live entertainment at Underground
- Hike The Boulders for dramatic views!
- Attend the Jacob’s Pillow Festival, with cool dance and music!
Subscribe here to get up to 35% off your accommodation for your next trip!
3. Adams – where to stay in the Berkshires with the family
Adams is a picturesque town in Berkshire County, nestled between Mount Greylock on the west and by the Hoosac Range on the east.
Here you’ll be overwhelmed by natural splendor and tranquility, but at the same time, you’ll have access to the most various outdoor activities, from sightseeing to hiking in the Appalachian Trail during summer and skiing at Mount Greylock in the winter months!
To not talk about all the touristic attractions the city has to offer: great restaurants, theaters, and touristic landmarks such as the Susan B. Anthony Museum and the Massachusetts Museum of Contemporary Art (Mass MoCA) … Adams is a worthy destination all year round!
With its leafy streets, laid-back vibe, and countless activities for any age and taste, Adams is the perfect destination for a family vacation in New England!
This luxurious hotel has everything you need and more: a restaurant where to enjoy a delicious dinner, a seasonal outdoor pool for some deserved relaxation, and spacious suites for the best sleep. This is also a great starting point to explore the great hiking and dining options in and around North Adams!
Other accommodation options in Adams
The porches inn offers a swimming pool to relax, a fitness center to stay active, and the best breakfast ever!
Enjoy the best location close to great dining options and the Massachusetts Museum of Contemporary Art
Enjoy the amazing suites of this house located on the top of a forested hill, overlooking the Mass MoCA
Things to do in North Adams
- Check out the Clark Art Institute, Williams College Museum of Art!
- Visit the Massachusetts Museum of Contemporary Art (Mass MoCA)
- Learn new things at the Susan B. Anthony Birthplace Museum!
- Go hiking in the Appalachian Trail in summer
- Have fun with the snow at Mount Greylock, the highest point in Massachusetts!
4. Stockbridge – the most laid-back area in the Berkshires
The charming village of Stockbridge, located in western Massachusetts, is known as the quintessential small-town of America. This is the perfect place if you want to enjoy some peace and slow-paced life!
The town is famous for being home to the artist Norman Rockwell, who painted Stockbridge Main Street: a MUST to take a stroll… you’ll be immediately brought back in time!
Here you can spend your days exploring the boutiques, art galleries, and specialty food shops of the center or venture into the stunning nature preserves and hiking trails just nearby.
But if you’re looking for cultural attractions, the options here are endless: from Norman Rockwell Museum to The Lenox Station Museum or The Historic Naumkeag Mansion And Gardens… you’ll just be spoiled for choice!
This 4-star bed and breakfast will strike you with its tastefully decorated rooms and delicious, varied breakfast… the best way to start your day full of energy and happiness! Here you’ll have access to on-site massage services as well as a swimming pool, a fitness center, and a games room… What more do you need?
Other accommodation options in Stockbridge
Find the best value in this great hotel offering spacious suites and great dining!
Historic hotel with antique furnishings and gourmet on-site dining options.
Cozy, intimate, and magical apartment equipped with all the comforts of home!
Things to do in Stockbridge
- Check out Gilded Age architecture in The Berkshire Botanical Garden
- Hike at the Goodrich Memorial Park
- Learn at the Norman Rockwell Museum
- See the historic trains of The Lenox Station Museum
- Marvel at The Historic Naumkeag House
5. Great Barrington – best area in the Berkshires for nature
If you drive South of the Berkshires and east of the Hudson River, you will find the charming town of Great Barrington, blessed with breathtaking nature, mountain views, and outdoor activities in the close surroundings!
One of the most popular destinations for tourists in Great Barrington is the magnificent Monument Mountain, whose beauty inspired many poets like Herman Melville: he got the idea to write “Moby-Dick” right in this place… maybe it deserves a hike, right?
Here you can stay in contact with nature literally all year round, having access to ski slopes like the Ski Butternut during winter and many trails such as the Housatonic River Walk or the walking path within the forest in Lake Mansfield!
If nature and peace are what you’re looking for, Great Barrington is where you’ll find it!
Choose from the many beautiful suites of the Barrington, all offering free WiFi and free private parking. Here you will enjoy a delicious morning breakfast served in the elegant dining room and impeccable service… This luxurious hotel has one of the best value for price in the whole Berkshires area!
Other accommodation options in Great Barrington
Enjoy the large indoor heated pool, hot tub, and fitness center of this great hotel!
Travel on a budget staying at this hotel featuring suites with a sofa bed or a spa bath.
Beautiful, studio apartment within walking distance of the center, perfect for families!
Things to do in Great Barrington
- Hit the ski slopes of the Ski Jiminy Peak!
- Do a challenging hike in Monument Mountain
- Go trekking in the panoramic trail Housatonic River Walk
- Follow the charming walking path within the forest in Lake Mansfield
- Check out the Ski Butternut resort for some of the best ski in the area
| 👑 Luxury price: | $250 |
| 💵 Mid Range: | $200 |
| 🛏️ Budget: | $150 |
| 🏠 Airbnb: | $200 |
| 💰 Accommodation prices: | High |
| 📍 Best area: | Lenox |
| 👪 Best area for families: | North Adams |
| 🛎️ Best luxury hotel: | 33 Main |
| 🧳 Best mid-range hotel: | Birchwood Inn |
| 👛 Best budget hotel: | Courtyard by Marriott Lenox |
Frequently asked questions about hotels in the Berkshires
📍 Which is the best place to stay in the Berkshires?
The best place where to stay in the Berkshires is Lenox, the heart of culture in the Berkshires, offering access to many outdoor activities and interesting attractions. Stay at the luxurious 33 Main or the Gateways Inn!
🐕 What are the best dog-friendly hotels in Berkshires?
The best dog-friendly hotels in Berkshires are the midrange option Hotel on North or the more affordable Berkshire Yankee Suites, both located in Pittsfield, the largest town in The Berkshires.
🧳 Are the Berkshires worth visiting?
Yes, the mountain ranges of Berkshires are definitely worth a visit, offering you everything you need for weekend getaways in nature: from hiking trails to ski slopes, breathtaking panoramic views, and lots of culture in the towns of the areas!
💆 What are the best spa hotels in Berkshires?
There are no proper spa hotels in The Berkshires but a great option with spa-like facilities is the Courtyard by Marriott, in Lenox.
☀️ Where to stay in The Berkshires in summer?
The best places to stay in The Berkshires in summer are the Birchwood Inn, in Lenox, or Berkshire’s Sweet Spot in Pittsfield, both offering you access to outdoor hiking trails: the best way to enjoy the warmer months!
Conclusion
Here we are at the end of this extensive guide on where to stay in the Berkshires, including the best towns in the area and accommodation options for any budget and taste!
Whether you want to have access to cultural and artistic attractions, outdoor activities, and adventures in the snow, or simply enjoying some quietness nestled in nature, there is for sure the right place for you!
If you are still undecided about which hotel suits more your interests, check out my 2 absolute favorites, located in Lenox, the heart of culture in the Berkshires:
- 33 Main – the best place in the Berkshires if you want to enjoy all the comforts of a luxurious stay!
- Birchwood Inn – Lovely hotel with a good location, perfect to explore the hiking trails nearby!
Just remember to book them as soon as possible or you could lose the spot: places here sell out super fast!
Now you have everything you need to plan your amazing holiday in the Berkshires, but if you have any doubts or questions for me, please leave them in the comments below: I am looking forward to answering you!
Have a great holiday!
Elena
