The Berkshires are three different mountain ranges along the western border of Massachusetts. This peaceful region has long been a favourite for staycationers from New York and Boston thanks to the gorgeous views, epic adventure activities, and snowy ski slopes in the winter. With everyone opting to have a vacation at home this year, the Berkshires should definitely be on your list.

Despite its popularity locally, the relative obscurity internationally means there isn’t a lot of information out there about the different destinations within the Berkshires. There are loads of towns and villages in the area, with each offering something a little different. For this reason, it’s important to do a little research in advance.

Which is where we come in! We’ve combined our personal experience with information from locals and tourism experts to bring you the lowdown on the three best places to stay in The Berkshires. Whether you’re on a budget, want to stay close to the action, or are trying to plan a family-friendly vacay, we’ve got you covered.

So let’s jump right in!

Where to Stay in The Berkshires

Calm Cabin in The Berkshires – Stockbridge Home

Stockbridge Home

This gorgeous cabin in the heart of The Berkshires is one of the best-rated accommodation picks in the region. Visiting in the winter? The rustic fireplace and cosy furnishings will keep you nice and snug in the evenings. If you prefer a summer escape, the outdoor area comes with gorgeous views and a barbecue deck. It really does offer the best of both worlds.

Cosy Home in The Berkshires – Mt. Greylock

Mt Greylock

If you’re visiting for the ski resorts in the winter, this is our top pick! Guests will have quick access to the Mt Greylock pistes, with regular skiing and snowshoeing available. It’s also close to some major hiking trails, so you will have plenty to do all year-round. Inside, you’ll find a peaceful and inviting space.

Affordable Hotel in The Berkshires – Hotel on North

Hotel on North

The Berkshires can get a little pricey, but thanks to this cute hotel in Pittsfield you’ll get to enjoy comfort without breaking the bank. They offer spacious rooms and luxury extras that will make you feel like you’re staying in a lavish resort. It’s also in a super central location, so you’ll have no problem getting to all the best attractions.

The Berkshires Neighborhood Guide

FIRST TIME IN THE BERKSHIRES
Lenox
FIRST TIME IN THE BERKSHIRES

Lenox

In the south of the Berkshires, Lenox is a popular gateway to the region for visitors from New York City. This creative hub is a must-visit for anyone interested in discovering cultural highlights. Home to the Boston Symphony Orchestra, it’s also a hub for theatre and visual arts.

ON A BUDGET
Pittsfield
ON A BUDGET

Pittsfield

Pittsfield is the largest town in The Berkshires, so it might seem surprising that it’s our top budget pick. The thing is, The Berkshires are known for their quaint villages and stunning scenery, so most people tend to give Pittsfield a miss and travel elsewhere.

FOR FAMILIES
Adams
FOR FAMILIES

Adams

With wide leafy streets, a peaceful town centre, and spacious accommodation, Adams is the perfect destination for a family staycation! North of Pittsfield, it’s well connected to the rest of the region, but limited tourist numbers mean it maintains a calm and easy-going vibe.

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Top 3 Places to Stay in The Berkshires

The Berkshires provide a laid-back kind of natural beauty perfect for a staycation in the United States. The towns are pretty easy to get to, and public transport connections are actually pretty good. This means you don’t need a car, but having one would certainly make things a little easier for you.

Pittsfield is the largest town in The Berkshires, and a major gateway into the region. Despite this, it’s also one of the most affordable destinations. Many visitors opt to stay in the quaint little towns and villages dotted around the mountains, so accommodation is surprisingly modest in Pittsfield. This is a fantastic choice for those visiting on a budget.

Just south of Pittsfield, Lenox is a great option for your first-time in The Berkshires. It’s still well connected, but maintains a small-town charm that will help you settle into the region. Home of the Tanglewood Music Centre, it’s also an artistic hub in the region, making it a firm favourite with creatives.

Last, but certainly not least, is Adams! This is a little more peaceful than the other destinations in this guide, making it a great option for families heading to the Berkshires. Visiting in the winter? Adams is also home to Mt Greylock, a popular ski resort in the area. During the warmer weather, it’s also a gateway to the Appalachian Trail. For this reason, we reckon it’s an excellent choice for adventure addicts.

Still not quite decided? It’s important to get it right before you spend money on booking everything, so we totally understand you might need a little bit more information. Keep reading for some more advice for each destination – including our top accommodation and activity picks in each.

#1 Lenox – Best Place to Stay in The Berkshires for Your First Time

Lenox
source: James Kirkikis (Shutterstock)

In the south of The Berkshires, Lenox is a popular gateway to the region for visitors from New York City. This creative hub is a must-visit for anyone interested in discovering cultural highlights. Home to the Boston Symphony Orchestra, it’s also a hub for theatre and visual arts. Simply walking around the town will get your creative juices oozing thanks to its historic architecture.

So, why do we recommend it for first-time visitors? Lenox is well connected to the whole region, and there are plenty of tour providers in the area. It has managed to weather the tide of increasing tourism numbers and maintain its charming small-town vibe.

Gorgeous Cabin near Lenox: Stockbridge Home

Stockbridge Home

Nestled among the trees of The Berkshires, this cabin is a short drive outside of Lenox on the route towards Stockbridge. This makes it a fantastic choice for people that desperately need some secluded calm, though you will need a car. The cosy interiors create a homely space perfect for unwinding and letting your troubles melt away.

Stylish Home in Lenox: Quintessential Cape

Quintessential Cape

This gorgeous holiday home has recently been renovated and comes with peaceful interiors and wide-open spaces. It’s located right in the heart of Lenox, but on a calm side street that means you get to enjoy some peace and quiet in the evenings. The beautifully restored fireplace is perfect for cosying up around the fire on a cold winter night.

Luxurious Hotel in Lenox: Seven Hills Inn

Seven Hills Inn

Let yourself be whisked away into the fairytale realm with this charming hotel on the outskirts of Lenox. With plenty of quaint little walks nearby, you’re also only a couple of minutes away from Edith Wharton’s Home. An à la carte breakfast is available every morning, and the on-site sun terrace gives you unbeatable views across the Berkshires.

Things to See and Do in Lenox:

Things to See and Do in Lenox
Lenox is the perfect destination for art-lovers!
source: T photography (Shutterstock)
  • Rucking – another name for walking with a weighted backpack – is a great way to get your exercise in, and this experience will let you enjoy some stunning scenery, too.
  • Tanglewood is home of the Boston Symphony Orchestra, as well as smaller music and theatre performances throughout the year.
  • Lenox Athenaeum and Shakespeare & Company are also two fantastic theatres – the latter of which is a particularly excellent choice if you have kids.
  • There are a few organisations offering horseback riding in the area, with Undermountain Farm Riding Stable offering both horses and ponies to suit all levels and ages.
  • You’ll have to splurge, but with five stars and an award-winning wine menu, you’ll have the meal of your life at Blantyre.

#2 Pittsfield – Where to Stay in the Berkshires on a Budget

Pittsfield
source: James Kirkikis (Shutterstock)

Pittsfield is the largest town in The Berkshires, so it might seem surprising that it’s our top budget pick. The Berkshires are known for their quaint villages and stunning scenery, so most people tend to give Pittsfield a miss and travel elsewhere. This means that many of the accommodation and restaurant options are cheaper than the rest of the area.

That’s not to say affordability is the only reason you should visit! Pittsfield is home to some interesting cultural attractions, including a few museums. There are also more shopping destinations here – ranging from national chains to local boutiques.

Central Apartment in Pittsfield: Berkshires Charm

Berkshires Charm

This modern apartment might seem a little basic, but it maintains an air of style and is in an excellent location. The affordable rates make this a great choice for couples and small families heading to the region on a budget. There are several delightful restaurants nearby including Mission Restaurant – a vibrant tapas bar. The luxury bathroom also adds a nice touch.

Spacious Conversion in Pittsfield: Historic Schoolhouse

Historic Schoolhouse

Looking for something a bit more unique? Look no further than this charming converted schoolhouse deep in the forests surrounding Pittsfield. If you’re visiting during the theatre festival, Tanglewood is within quick driving distance of this property. It’s animal friendly – a great pick for small families and couples struggling to find a pet-sitter. We particularly love the idyllic outdoor space – your own calm oasis away from the tourist crowds.

Cute Hotel in Pittsfield: Hotel on North

Hotel on North

Right in the heart of Pittsfield, you’ll only be a short walk from the most popular attractions in town. The facilities are a little basic, but the spacious rooms have luxurious furnishings that add a sense of class. Hotel on North comes with outstanding guest reviews thanks to their above-and-beyond service and unmatchable comfort. They also have a small business centre, making it a great choice for corporate guests.

Things to See and Do in Pittsfield:

Things to See and Do in Pittsfield
Nope – no boat here.
  • Berkshire Museum features exhibits from art, science and history – the only museum of its kind in the entire region.
  • For something a bit more specific, Arrowhead – the Home of Herman Melville, hosts a fascinating exhibit dedicated to his work, including the world-famous Moby Dick.
  • Head down to Onota Lake where you can hire boats, fishing poles and kayaks for a fun day out among the stunning scenery.
  • There are plenty of delicious (and affordable!) restaurants in the town centre – we love the Underground in particular, who also provide live entertainment.
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#3 Adams – Best Area in The Berkshires for Families

Adams, The Berkshires
Relax among the gorgeous scenery

With wide leafy streets, a peaceful town centre and spacious accommodation, Adams is the perfect destination for a family staycation! It’s well connected to the rest of the region, but limited tourist numbers mean it maintains a calm and easy-going vibe. With activities to suit all ages, this is the perfect spot for a much-needed break.

Beyond family-friendly attractions, Adams is also the best area in the Berkshires for adventurous travellers. Mt Greylock is home to a huge ski resort in the winter, and is also a gateway into the Appalachian Trail for epic hikes during the warmer months. History buffs will also rejoice at the unique attractions on offer.

Historic Hideaway in Adams: 1890 House

1890 House

Step back in time with this traditional hideaway in the heart of Adams. With stunning views of Mt Greylock, the house is super close to the main hiking and adventure activities in the town. Inside, you’ll find quirky furnishings and classic design. The rooms are comfortable and spacious, with enough room to fit up to five guests. The master bedroom comes with an en-suite.

Cosy Family Home in Adams: Mt. Greylock

Mt Greylock

Of course, when it comes to skiing, you can’t go wrong with this peaceful home within walking distance of Mt Greylock! Sleeping up to six people, this one is popular with groups heading to the slopes – but it’s also a great pick for families. The modern kitchen is equipped with basics prior to arrival, making it super convenient for those arriving late.

Charming B&B in Adams: Harbour House Inn

Harbour House Inn

Kick back and relax in this rustic bed and breakfast just outside the town. The traditional décor gives this accommodation a historic charm, while the surrounding scenery is nothing short of breathtaking. There are major hiking trails within walking distance, and ski resorts can be reached in less than five minutes by car. The complimentary hot breakfast is highly rated and comes with vegetarian and vegan options.

Things to See and Do in Adams:

Things to See and Do in Adams
  • Feminist icon Susan B. Anthony was born in Adams, and you can visit her birthplace to learn more about her life and fight for women’s suffrage.
  • Mount Greylock is the start of the Appalachian Trail – but even those looking for a short hike will be stunned by the gorgeous scenery from the summit.
  • If you’re visiting in the winter, once you get to the top of Mount Greylock, the only way back down is via the epic ski trail running down the centre of the hill.
  • Simply walking down the town centre, you will discover quirky boutiques, gorgeous Victorian architecture, and the inviting smells of locally sourced cuisine.

Final Thoughts on Where To Stay in The Berkshires

The Berkshires are home to some cute destinations perfect for a laid-back USA travel experience. Nestled between three mountain ranges, you’ll discover scenic panoramas everywhere you look. The towns and villages provide a fascinating insight into local life in Massachusetts, and you’re sure to experience a warm welcome from the second you arrive.

If we had to pick one destination that really stands out to us, it would be Adams! With awe-inspiring hiking trails and adrenaline-pumping ski slopes, it offers a little something for everyone throughout the year. The town itself is quite peaceful, while still having great connections to other parts of the region. The Berkshires is a safe travel destination, but keep an eye on the weather, especially if you’re traveling during winter.

That being said, Lenox is a good alternative if you want to get creative, and Pittsfield is a great way to experience the Berkshires without breaking the bank. The best place for you really depends on what you want to get out of your trip, but we hope this guide has managed to help you narrow down your options.

Did we miss anything? Let us know in the comments.

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