Berkshire County Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Your Berkshire County Holiday
With a Berkshire County holiday package, you can forget about the stress of planning and simply focus on experiencing what this exciting destination has on offer. Kick off your trip to Berkshire County with a few nights in Lenox visiting popular attractions like National Shrine of the Divine Mercy and Norman Rockwell Museum. Williamstown is another city that draws crowds from far and wide. Massachusetts Museum of Contemporary Art and Mount Greylock are two of the leading places to see in this destination. If you're ready to stop daydreaming and start doing, Expedia will help turn your Berkshire County holiday into reality.
Top destinations in Berkshire County
Berkshire County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Bradley Intl. Airport (BDL) |
Top Sights | Bash Bish Falls State Park, Pittsfield State Forest and Tolland State Forest |
Top hotels in Berkshire County
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
£81
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (2,691 reviews)
"Great place great price!"
Reviewed on 1 Oct 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
£91
18 Oct - 19 Oct
includes taxes & fees
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
£64
1 Nov - 2 Nov
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"I typically do not reserve in motel with parking in front of each space due to security, I was mistaken at this facility. Pleasant neighborhood and the building was situated well off the main street."
Reviewed on 28 Sept 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
How much does a Berkshire County travel package cost?
From just . Yes, you read that correctly. Our Berkshire County packages are an easy way to make your budget stretch further. Combine your preferred hotels, flights and rental car and get to know this popular destination.
If I'm not able to travel, can I cancel my Berkshire County travel package?
Whether it's your hotel or flight, yes, you can cancel or amend it. Locked in your Berkshire County travel package in the last 24 hours? You may be able to make changes at no cost. For older bookings, you may be charged a fee by your hotel, airline or car rental company. For more information, visit our Customer Service Portal. We'll help you every step of the way.
How do I get a cheap travel package to Berkshire County?
Book everything all in one place with our Berkshire County travel packages. You'll find deals on hotels, flights and more that'll keep your pocketbook happy and your spirit of adventure alive. And, with more than 550 air carriers and 1,000,000 properties globally to choose from, you'll have the flexibility to mix and match all you want.
Does Expedia offer Book Now, Pay Later Berkshire County holidays?
We certainly do. Expedia has partnered with online lender Klarna to help you easily pay for your trip in instalments. Simply choose the payment plan that suits best during checkout and take away the stress of budgeting for your trip. Make sure you bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your holiday buck. Take a look at our flexible payment options below:
- Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's convenient monthly instalment plans. If making small repayments each month sounds right for you, choose this option during the checkout process.
- Pay in instalments holidays: If you'd like to pay for your getaway in multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: Pressing the "book now" button is easier with this plan. Put down a small deposit on your holiday and then start packing your bags.
What are the top hotels in Berkshire County?
When it comes to hotels in Pittsfield, Holiday Village In The Berkshires and The Black Swan Lee - Lenox, Ascend Hotel Collection are two fantastic options. If you're also staying in New Marlborough, Holiday Village In The Berkshires and The Black Swan Lee - Lenox, Ascend Hotel Collection will make you feel right at home.
How far in advance should I book my Berkshire County holiday?
While not all air carriers advertise tickets early, you can normally start comparing international flights on Expedia up to 12 months in advance. This is the time you can score some incredible bargains. If you're booking at the last minute, there's a chance you could get lucky. Sometimes the cheapest prices become available only weeks before departure.
What does an Expedia Berkshire County travel package include?
Car rentals, hotels and flights — we connect you to the best deals. All you have to do is figure out your favourite combination. Once you've made your booking, you can add on the fun stuff like tours and experiences. Our travel packages make it simple to craft an awesome Berkshire County trip.
What should I know before booking a Berkshire County travel package?
Whether it's relaxation or adventure you're chasing, a Berkshire County travel package lets you organise your escape your way. Plus, you'll score great discounts just for combining your accommodation with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Berkshire County Expedia travel package?
With a travel package, the choice is in your hands. Whether you're hoping to fly to Berkshire County in economy or business class, simply select from the available airline options. Expedia has access to over 550 airline partners worldwide.
Stay near popular Berkshire County attractions
Jiminy Peak Mountain Resort
8.8/10 (311 reviews)
Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this family-friendly area.
Tanglewood Music Center
9.6/10 (457 reviews)
You can make plans for a show at Tanglewood Music Center during your stay in Lenox. While you're in the area, stroll along the lakeside.
Williams College
9.4/10 (534 reviews)
Explore the campus of Williams College during your trip to Williamstown. In the area, take in the fascinating museums and mountain views.
Photo by Caminante
Massachusetts Museum of Contemporary Art
9.4/10 (246 reviews)
You can spend time studying the exhibits at Massachusetts Museum of Contemporary Art in North Adams. Take in the fascinating museums while you're in the area.
Photo by Adnan Kakazai
Norman Rockwell Museum
9.4/10 (347 reviews)
You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to Stockbridge. Wander the lakeside in this quaint area.
Photo by Caitlin Reese
Mount Greylock
9.4/10 (180 reviews)
Explore the great outdoors at Mount Greylock and enjoy the mountain views during your trip to Adams. You can seek out the ski slopes while in the area.
Ski Butternut
9.0/10 (134 reviews)
Hit the slopes in Great Barrington with a visit to Ski Butternut. While you're in the area, stroll along the lakeside.
National Shrine of the Divine Mercy
9.0/10 (83 reviews)
Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
