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
Top Berkshire County Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Weathervane Motel
£1,224
per person
16 Oct - 25 Oct
found 24 hours ago
Return flight included
London (LGW) to Albany (ALB)
6.8/10 (790 reviews)
Nice clean place to stay a few days. Hard to find staff to check in and out as the reception isn’t manned full time. However they are friendly and helpful when you find them. Large comfortable rooms and nice sitting area behind the room. If there was a breakfast available it would be an excellent and reasonable choice
Reviewed on 14 Aug 2026
Toll Road Inn
£1,553
per person
16 Oct - 25 Oct
found 24 hours ago
Return flight included
London (LGW) to Albany (ALB)
9.2/10 Wonderful! (531 reviews)
We loved it! This is a small, 16 room hotel which maintains all of its 70’s vibe. Everything was vintage and immaculate. The room was spacious and well-lit, the bathroom was tiled (!) and gorgeous. We especially loved the coffee bar area, the cozy den space with fireplace and vintage board games, and the pristine swimming pool. We will definitely come back!
Reviewed on 14 Aug 2026
Hotel Vervana, Trademark Collection by Wyndham
£1,396
per person
16 Oct - 25 Oct
found 24 hours ago
Return flight included
London (LGW) to Albany (ALB)
8.2/10 Very good! (1,004 reviews)
The staff was great and welcoming. The room was comfortable and clean. The shower was strong and wonderful. The hotel was walking distance to pubs and restaurants. Overall a great night.
Reviewed on 14 Aug 2026
The Palmer House Resort, an Ascend Collection Hotel
£1,602
per person
16 Oct - 25 Oct
found 24 hours ago
Return flight included
London (LGW) to Albany (ALB)
8.2/10 Very good! (983 reviews)
Property is very run down. Our room was filthy. Bedding stained, toilet seat stained and floor was extremely dirty. My kids were very much looking forward to the fishing pond advertised as an amenity. Unfortunately the dock was sinking, a rowboat was full of water and beer cans, and the pond was covered entirely in weeds. We didn’t even stay the night.
Reviewed on 9 Aug 2026
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
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
£80
31 Aug - 1 Sept
includes taxes & fees
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! (1,003 reviews)
"It was very convenient for an overnight with pool and close to downtown. Affordable. I stayed in the annex so no noise from other guests!"
Reviewed on 14 Aug 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
£95
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (1,074 reviews)
"A real gem. Wonderfully situated. Spacious rooms. Friendly service. I forgot a camera battery charger in the room and the hotel staff kept it for my son to pick up. So very efficient and honest staff. We will definitely consider staying here again."
Reviewed on 15 Aug 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.
Frequently asked questions
How much does a Berkshire County travel package cost?
From just £1,224. 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.
Stay near popular Berkshire County attractions
Tanglewood Music Center
9.6/10 (457 reviews)
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.
Jiminy Peak Mountain Resort
8.8/10 (311 reviews)
Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this quaint area.
Photo by Caminante
Massachusetts Museum of Contemporary Art
9.4/10 (246 reviews)
You can spend time studying the exhibits at Massachusetts Museum of Contemporary Art in North Adams. Take in the fascinating museums while you're in the area.
Williams College
9.4/10 (534 reviews)
Explore the campus of Williams College during your trip to Williamstown. In the area, take in the fascinating museums and mountain views.
Photo by Adnan Kakazai
Norman Rockwell Museum
9.4/10 (347 reviews)
You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to Stockbridge. Wander the lakeside in this quaint area.
Photo by Caitlin Reese
Mount Greylock
9.4/10 (180 reviews)
Explore the great outdoors at Mount Greylock and enjoy the mountain views during your trip to Adams. You can seek out the ski slopes while in the area.
National Shrine of the Divine Mercy
9.0/10 (83 reviews)
Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.
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.
* 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.
