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.

The Berkshires Holidays 2026 from £776

Top The Berkshires Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.

Vacation Village in the Berkshires

£776

per person

22 Aug - 28 Aug

found 10 hours ago

Return flight included

London (LON) to Albany (ALB)

8.8/10 Excellent! (2,411 reviews)

We spend 5 days and we had a good time . + : the location is beautiful with nice views of the mountains . It’s quiet and peaceful . Good amenities for the kids and the 2 pools are clean and nice . Spacious room ! - : I had ongoing problems with my key door . Almost every day I would get stuck because the key door was not working anymore . Really annoying when you traveled alone pregnant with 2 kids . The room was outdated , I think it’s time for an update . No laundry machine A market inside the resort is missing . There is no food at all except a vending machine and if you want to grab decent food for take out you need to drive at least 20 mn . A marketplace inside the resort with coffee shop would make a big difference

Reviewed on 3 Jul 2026

Berkshire Mountain Lodge

£786

per person

22 Aug - 28 Aug

found 10 hours ago

Return flight included

London (LON) to Albany (ALB)

9/10 Wonderful! (1,009 reviews)

One night stay was enjoyable! Close enough to Tanglewood to Uber.

Reviewed on 3 Jul 2026

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

£880

per person

22 Aug - 28 Aug

found 10 hours ago

Return flight included

London (LON) to Albany (ALB)

9.2/10 Wonderful! (915 reviews)

We had a lovely, one night stay here. I went with my adult son and his girlfriend to see Paul Simon at Tanglewood (which turned out to be an amazing show!) The front desk staff at the resort were friendly and accommodating; they let us use the amenities early before we could check in, which was GREAT! We hung around the outdoor pool, met a lot of nice people, and had a blast. Our suite was great. Parking was easy and plentiful and we had 2 bedrooms and each had it's own bathroom for full privacy. Full kitchen with fridge and freezer, a little living room and a nice outdoor deck overlooking the woods and a brook. It was clean, comfortable, and we had a wonderful stay. There is a grocery store just a few miles down the street for everything you need and Lenox is about 10-15 minutes away. We even saw a bear in the parking lot and he went out back in the woods where our porch was. I've never had a bear sighting. It was awesome! The only thing I can comment is the windows in the front bedroom were pretty dirty. It would have been nice it they were cleaned up. Honestly it didn't make or break our trip, just a business owner myself, I always like the feedback. But all in all, I would definitely recommend and definitely stay there again.

Reviewed on 3 Jul 2026

The Yankee Inn

£921

per person

22 Aug - 28 Aug

found 10 hours ago

Return flight included

London (LON) to Albany (ALB)

9.2/10 Wonderful! (1,011 reviews)

The Yankee Inn was a convenient and affordable option for our visit to Tanglewood. The check-in staff was friendly and advised us of breakfast and checkout hours. The room was clean and thankfully well air conditioned during our stay there in 90 degree weather! The included breakfast was typical fare: eggs, cereal, yogurt, fresh fruit, bread/pastries, etc. As we were there for only one night, we did not take advantage of the outdoor pool or fire pit, but both appeared to be clean and well maintained.

Reviewed on 2 Jul 2026

Quality Inn Lee - Lenox South

£805

per person

22 Aug - 28 Aug

found 10 hours ago

Return flight included

London (LON) to Albany (ALB)

8.4/10 Very good! (1,003 reviews)

A great budget stay in Berkshires.

Reviewed on 2 Jul 2026

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	22.8°F (-5.1000000000000005°C)	Light Rain	Mostly Cloudy	Slightly Low	Average
February	24.6°F (-4.1000000000000005°C)	Light Rain	Mostly Cloudy	Average	Average
March	32.5°F (0.3°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	44.2°F (6.800000000000001°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
May	56.3°F (13.5°C)	Light Rain	Mostly Sunny	Average	Average
June	64.0°F (17.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	70.3°F (21.3°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	68.4°F (20.200000000000003°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
September	61.3°F (16.3°C)	Light Rain	Mostly Sunny	Average	Average
October	50.0°F (10.0°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	37.8°F (3.2°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
December	29.5°F (-1.4°C)	Light Rain	Mostly Cloudy	Slightly Low	Average

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.

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

Language

English

Currency

U.S dollars

Closest Airport

Bradley Intl. Airport (BDL)

Top hotels in The Berkshires

The Yankee Inn

461 Pittsfield Rd Lenox MA

Fully refundableReserve now, pay when you stay

£106

6 Jul - 7 Jul

includes taxes & fees

9.2/10 Wonderful! (1,000 reviews)

"The Yankee Inn was a convenient and affordable option for our visit to Tanglewood. The check-in staff was friendly and advised us of breakfast and checkout hours. The room was clean and thankfully well air conditioned during our stay there in 90 degree weather! The included breakfast was typical ..."

Reviewed on 2 Jul 2026

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Fully refundableReserve now, pay when you stay

£112

21 Jul - 22 Jul

includes taxes & fees

8.8/10 Excellent! (2,415 reviews)

"We spend 5 days and we had a good time . + : the location is beautiful with nice views of the mountains . It’s quiet and peaceful . Good amenities for the kids and the 2 pools are clean and nice . Spacious room ! - : I had ongoing problems with my key door . Almost every day I would get stuck because ..."

Reviewed on 3 Jul 2026

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Fully refundableReserve now, pay when you stay

£129

2 Aug - 3 Aug

includes taxes & fees

9/10 Wonderful! (1,012 reviews)

"One night stay was enjoyable! Close enough to Tanglewood to Uber."

Reviewed on 3 Jul 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.

Stay near popular The Berkshires attractions