Berkshire County Holidays

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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

FlightsFlightsHotelsHotels

Lenox

Lenox

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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is £90 per night from 24 May to 25 May
£90
24 May - 25 May
includes taxes & fees
9/10 Wonderful! (934 reviews)
Clean and great job staffing

Reviewed on 15 May 2026

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is £105 per night from 20 May to 21 May
£105
20 May - 21 May
includes taxes & fees
9/10 Wonderful! (948 reviews)
All was good

Reviewed on 16 May 2026

Berkshires Untold
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is £81 per night from 20 May to 21 May
£81
20 May - 21 May
includes taxes & fees
8.8/10 Excellent! (2,358 reviews)
Hank, quickly responded and corrected a chirping CO monitor. He was friendly, efficient and prompt with fix. Thank you, Hank.

Reviewed on 16 May 2026

Vacation Village in the Berkshires
See all 1,122 properties in Berkshire County
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

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.

* 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.