The Berkshires Holidays

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to £195 when you book a flight and hotel together*
  • lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your The Berkshires Holiday

Check one more big thing off your travel bucket list with a holiday package to The Berkshires. Visited by many for its cultural experiences, laid-back lifestyle and spectacular views, this mountainous destination is where your next awesome adventure begins. Why not organise your trip to The Berkshires around one or two of its most well-known cities? Lenox, Hancock and Williamstown are excellent places to begin. Stop dreaming and start packing, because your The Berkshires holiday is only a few clicks away with Expedia.

The Berkshires Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)

Our pick of the best The Berkshires 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! (204 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 1,011 properties in The Berkshires
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

Why should I book my The Berkshires holiday with Expedia?
Choose Expedia to arrange your next escape easily and all in one convenient place. Our top tip for scoring an unbeatable deal on a The Berkshires getaway? Bundle your hotel, flights and/or hire car into a package holiday. Then throw in a couple of awesome tours and activities. Many bookings also include flexible cancellation policies, so there’s no need to panic if you have to switch up your travel itinerary. Round-the-clock help with making changes to your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in The Berkshires?
If you like the buzz of peak season, visit The Berkshires in February, March and May. Travelling during the quieter months of October, November and December will help you skip the crowds. To get an idea of the type of weather you can experience, the average temperature during the day in January, the coolest month in The Berkshires, is -5ºC. The warmest time here is July, when temperatures average 21ºC.
What are the top hotels for my holiday in The Berkshires?
When it comes to properties in Great Barrington, Boston Park Plaza and Hilton Boston Logan Airport are two fantastic options. If you’re spending time in Hancock, Harborside Inn Of Boston and Club Quarters Hotel Faneuil Hall, Boston look forward to welcoming you.
How do I get a cheap holiday to The Berkshires?
Booking a The Berkshires holiday with Expedia is a great way to save. We have more than 400 airlines and 321,000 properties around the globe. With such a huge range to pick from, you’ll have no difficulty creating your next dream adventure. Learn more about how you can save money on your holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my The Berkshires holiday?
Organise your holiday in The Berkshires around leading attractions like Jiminy Peak Mountain Resort and Tanglewood Music Centre. Many travellers also highly recommend Williams College and National Shrine of the Divine Mercy.
Do I need a visa for my The Berkshires holiday?
Official government websites are the best source of information on visa requirements, application procedures and any necessary documentation. Your nationality and the purpose of your visit, whether it be for work or pleasure, will determine if you’ll need a visa for The Berkshires. Also double-check that your passport is up to date and has at least six months validity remaining after your date of return. Do all your travel planning well ahead of time to avoid any nasty last-minute surprises.
What should I wear on my The Berkshires holiday?
Though everyone’s personal style differs, it can help to have some guidelines for what to bring on your holiday in The Berkshires. Consider looking up style blogs before you go for inspiration on fashion trends or dress codes. It’s also a good idea to take a look at the forecast so you can pack the right clothes. July is the warmest month in The Berkshires, with average temperatures of 21ºC. January is when much of this destination is at its coolest, so get packing for daytime temperatures of around -5ºC.
What does an Expedia The Berkshires holiday include?
Flights, hotels and car hires, or any combination of the three — it’s your pick! Whether you’re exploring The Berkshires with the kids or travelling with your friends, there’s a package to match every budget and style. Once you’ve made your booking, why not add on some activities? Explore a variety of styles on Expedia and discover the perfect fit for you and your travel companions. From the most sought-after property types, like private holiday homes and condos, to everything in between, you’ll find loads of holiday retreats in The Berkshires to choose from so you can customise your stay to suit your taste.
Does Expedia offer Book Now, Pay Later The Berkshires holidays?
We sure do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in instalments. Simply select the payment plan best suited to your needs during checkout and take the stress out of budgeting for your trip. Remember to bundle your flights, hotel and car hire with Expedia to get the biggest bang for your holiday buck. Consider these flexible payment options below:

  • Pay monthly holidays: If paying across multiple transactions sounds right for you, Klarna offers just that! Paying in easy monthly instalments will make your holiday dreams come true.
  • No-deposit holidays: When you spot an awesome deal but your budget doesn’t quite cover it yet, Klarna’s no-deposit holiday plan will allow you to Book Now, Pay Later to lock it in.

Can I choose my airline with a The Berkshires Expedia holiday?
Yes — and it’s simple too. Expedia has access to more than 400 partner airlines all over the world. Our holiday packages give you the freedom to take your pick of available flights, hotels and activities that suit you.

Discover the most popular places to visit in The Berkshires

Image for Tanglewood Music Center

Tanglewood Music Center

4/5(1 review)

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.

Tanglewood Music Center
Image for Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

4/5(1 review)

Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this quaint area.

Jiminy Peak Mountain Resort
Image for Norman Rockwell Museum

Norman Rockwell Museum

5/5(1 review)

You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to Stockbridge. Wander the lakeside in this quaint area.

Norman Rockwell Museum

Unmissable things to do in The Berkshires

Image for Stockbridge Showdown MA Scavenger Hunt

Stockbridge Showdown MA Scavenger Hunt

£21
Per adult
Stockbridge Showdown MA Scavenger Hunt
See all activities in The Berkshires

* 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.