The Berkshires Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Photo courtesy of Berkshire Visitors Bureau

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Your The Berkshires Holiday

Embark on your next adventure with a The Berkshires holiday package, and leave knowing the finer details are organised. And with the ability to tailor your getaway, it'll be one to remember! Your trip to The Berkshires wouldn't be complete without getting to some of its leading cities, starting with Lenox. Some of the most popular attractions here include National Shrine of the Divine Mercy and Norman Rockwell Museum. Williamstown is another favourite with The Berkshires travellers. Visitors to this destination love Massachusetts Museum of Contemporary Art and Mount Greylock. Quit dreaming and get packing, because your The Berkshires holiday is only a few clicks away with Expedia.

Things to do near The Berkshires

The Berkshires offers a delightful blend of outdoor adventures and scenic beauty, ideal for a memorable vacation. Visitors can enjoy skiing at local resorts, explore picturesque hiking trails, and embark on enjoyable vineyard trips. Additionally, leisurely strolls through charming towns and engaging day trips enhance the experience, making it a perfect destination for those seeking both relaxation and adventure.

Shopping

Visit Hoffman's Pottery, located 25.7km from The Berkshires, for unique handcrafted items. Lee Premium Outlets, 16.1km away, offers a variety of brand-name shops in a vibrant environment. Don't miss the Berkshire Mountain Country Store, 17.7km from The Berkshires, for charming gifts and local goods.

Recreation

Explore Lake Mansfield Park, a serene recreational area perfect for relaxation and rejuvenation amidst nature. Experience the enchanting performances at Jacob's Pillow, a cultural hub for dance, or enjoy a captivating show at the Mahaiwe Performing Arts Center, where family-friendly entertainment meets romance and culture.

Adventure

Experience the scenic Housatonic River Walk, an invigorating hiking trail located 17.7km from The Berkshires, perfect for outdoor enthusiasts. Enjoy thrilling skiing at Blandford Ski Area, 19.3km away, or at Ski Butternut, 14.5km from The Berkshires, where the sports vibes are electric.

Nightlife

The Berkshires offers a charming nightlife with venues like the vibrant Barrington Stage Company for live theatre and the intimate Club Helsinki for music. Enjoy a relaxed evening at the Tavern at the Aloha or sip cocktails at the picturesque Red Lion Inn, perfect for unwinding after a day of exploration.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near The Berkshires

The Berkshires is a fantastic destination for outdoor and adventure enthusiasts, offering stunning scenery and a rich cultural experience. Explore historic houses, serene lakes, and the local library, while also visiting the picturesque Berkshire Hills and the intriguing Berkshire Museum. These attractions provide a perfect blend of nature and culture, making your visit to The Berkshires truly memorable.

  • Norman Rockwell Museum: Nestled 20.9km from The Berkshires, this museum showcases the charming and nostalgic works of Norman Rockwell, capturing the spirit of American culture and everyday life. Visitors will enjoy a variety of exhibitions and a serene outdoor sculpture garden.
  • Ventfort Hall Mansion and Gilded Age Museum: Located 24.1km away, this historic mansion offers a glimpse into the opulent lifestyle of the Gilded Age. With its stunning architecture and richly decorated interiors, it's a perfect place for history enthusiasts.
  • National Shrine of the Divine Mercy: Situated 19.3km from The Berkshires, this serene shrine provides a tranquil space for reflection and prayer, featuring beautiful gardens and inspiring religious art.

Best time to go to The Berkshires

The best time to visit The Berkshires is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.8°F (-5.1000000000000005°C)Light RainMostly CloudySlightly LowAverage
February24.6°F (-4.1000000000000005°C)Light RainMostly CloudyAverageAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.800000000000001°C)Light RainMostly CloudyAverageSlightly Low
May56.3°F (13.5°C)Light RainMostly SunnyAverageAverage
June64.0°F (17.8°C)Light RainMostly SunnySlightly HighAverage
July70.3°F (21.3°C)Light RainMostly SunnySlightly HighSlightly High
August68.4°F (20.200000000000003°C)Light RainMostly SunnySlightly HighSlightly High
September61.3°F (16.3°C)Light RainMostly SunnyAverageAverage
October50.0°F (10.0°C)Light RainMostly SunnyAverageSlightly High
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowSlightly Low
December29.5°F (-1.4°C)Light RainMostly CloudySlightly LowAverage

Tips to save on your trip to The Berkshires

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to The Berkshires.
  • Consider traveling to The Berkshires during the low season (March to April and November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

The Berkshires Essential Information

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

Top hotels in The Berkshires

Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA
£80
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (2,545 reviews)
"The location was great and the pools and hot tub were nice. Besides for linens, our room looked like it hadn't been cleaned in a couple months. Spider webs and dead spiders in bath tub, cobwebs in multiple parts of suite, and dust/debris all over entry and kitchen counters (I think from replacement ..."

Reviewed on 17 Aug 2026

Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
£130
14 Sept - 15 Sept
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
"The stay was very good however the rooms are dated though well maintained. I felt the price was very high for the accommodations. I had expected more for the price ($350) but it was their peak season and they need to price accordingly. Certainly this Inn did not offer the feel or quality level of ..."

Reviewed on 17 Aug 2026

The Yankee Inn
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA
£95
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (1,077 reviews)
"The rooms were spotless and a good size. And is not far from Lenox which was our focus. I’d suggest that guests bring some food with them and there is a supermarket nearby. There is not a morsel of food in the ‘resort’. The tv is complicated and I’m not sure why it is set up the way it is. Check ..."

Reviewed on 17 Aug 2026

Berkshire Mountain Lodge
See all 1,086 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
Golf Holidays
Golf Holidays
Luxury Holidays
Luxury Holidays
gay friendly holidays
LGBTQ+ Holidays
LGBTQ+ Holidays
Romantic Holidays
Romantic Holidays
Ski Holidays
Ski Holidays
Pet Friendly Holidays
Pet Friendly Holidays
Holiday in Month
Where to go when
Where to go when

Stay near popular The Berkshires attractions

A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.

Tanglewood Music Center

9.6/10 (457 reviews)
Tanglewood enchants as the summer home of the Boston Symphony Orchestra, set in the picturesque Berkshire Hills. Enjoy world-class performances while picnicking on the expansive lawns as the sun sets over the mountains.
See properties
A hillside with autumn-colored trees and five wind turbines against a blue sky with clouds.

Jiminy Peak Mountain Resort

8.8/10 (311 reviews)
Southern New England's largest ski resort transforms into a summer playground with thrilling attractions. Glide down 45 winter trails or ride the Mountain Coaster through Berkshire Mountain scenery.
See properties
A building with 'MASS MoCA' written on it, surrounded by greenery and hills.
Photo by Caminante

Massachusetts Museum of Contemporary Art

9.4/10 (246 reviews)
This converted factory houses one of America's largest contemporary art museums. Wander through MASS MoCA's vast industrial galleries to experience thought-provoking works that transcend artistic boundaries.
See properties
A historic building with ivy-covered brick walls, a large lawn, and a clear blue sky.

Williams College

9.4/10 (534 reviews)
Williams College offers a prestigious liberal arts education amid the scenic Berkshire Mountains. Visitors can explore the renowned Williams College Museum of Art and attend public lectures in this intellectual haven.
See properties
A calm river surrounded by autumn foliage.
Photo by Adnan Kakazai

Norman Rockwell Museum

9.4/10 (347 reviews)
This gallery houses the world's largest collection of Norman Rockwell's iconic American illustrations. Explore his relocated studio on the scenic Berkshire estate for insight into his creative process.
See properties
A tall, conical tower with a spherical top, surrounded by a grassy field and a stone staircase leading up to it.
Photo by Caitlin Reese

Mount Greylock

9.4/10 (180 reviews)
Massachusetts' highest peak rewards hikers with panoramic views stretching 90 miles on clear days. Explore the Appalachian Trail segment or stay overnight at the historic Bascom Lodge for a summit sunrise experience.
See properties

National Shrine of the Divine Mercy

9.0/10 (83 reviews)
This serene sanctuary in the Berkshire Mountains is a centre for Divine Mercy devotion inspired by Saint Faustina. Visitors can join the daily 3:00 PM Chaplet or walk contemplative trails.
See properties

Lee Premium Outlets

8.2/10 (265 reviews)
You can do some window-shopping at Lee Premium Outlets during your visit to Lee. Amble around the area's gardens or attend a sporting event.
See properties

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.

Explore a world of travel with Expedia

* 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.