Berkshire County Holidays

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Your Berkshire County Holiday

Book a holiday package to Berkshire County and make planning your getaway quick and easy. With all the details organised before you leave, you can focus on enjoying every moment in this amazing destination. Trying to put together a travel schedule for your trip to Berkshire County? Start with top cities like Lenox, Hancock and Williamstown. From the instant you book your Berkshire County holiday to the second you come back home, Expedia has you covered each step of the way.

Top destinations in Berkshire County

Lenox featuring an administrative building
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Lenox

Lenox
Great Barrington
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Great Barrington

Great Barrington

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

Our pick of the best Berkshire County Hotel Deals

Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking and breakfast. Our guests praise the helpful staff and the clean rooms in their reviews. ...
9/10 Wonderful! (221 reviews)
"Really nice place. Very nicely renovated, and a real bargain in the off season. My only issue was no shops/restaurants near to walk to and the highway it’s on is fast and busy making left turns out of the place a real challenge."

Reviewed on 15 Apr 2024

Life House Berkshires
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Stay at this 3.5-star spa hotel in Stockbridge. Enjoy free WiFi, 3 restaurants and a full-service spa. Our guests praise the pool and the restaurant in their ...
8.8/10 Excellent! (865 reviews)
"What a pleasure to have the opportunity to stay in an historic inn such as the Red Lion."

Reviewed on 13 Apr 2024

The Red Lion Inn
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
9/10 Wonderful! (1,001 reviews)
"I would highly recommend the Yankee. The front desk person was kind and welcoming. As soon as I opened the door to my room, I was pleased to see how clean and cozy it was. The breakfast room was well stocked, and the pool was being enjoyed by families with children. I would definitely stay again. ..."

Reviewed on 16 Apr 2024

The Yankee, Trademark Collection by Wyndham
See all 1,017 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.