The Berkshires Vacation Packages
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Your The Berkshires Vacation
Leave the travel planning to us with a The Berkshires vacation package. With everything organized before you head off, the only thing left for you to do is relax and enjoy this destination's countless delights. A trip to The Berkshires wouldn't be complete without exploring some of its most renowned cities, starting with Lenox. A couple of the top attractions here include National Shrine of the Divine Mercy and Norman Rockwell Museum. Williamstown should also be on the itineraries of all The Berkshires travellers. Visitors to this city enjoy Massachusetts Museum of Contemporary Art and Mount Greylock. Expedia has flights, hotels, car rentals and more to help you organize your own customized The Berkshires vacation today.
Top The Berkshires Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Toll Road Inn
CA $2,021
per person
Oct 1 - Oct 8
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (541 reviews)
We absolutely loved the toll road hotel! Mike was amazing behind the desk, extremely friendly and welcoming! Enjoyed all the amenities and would highly recommend it as a place to stay
Reviewed on Aug 28, 2026
Ready to book your vacation to The Berkshires?
The Berkshires Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
CA $120
CA $150 total
Aug 31 - Sep 1
includes taxes & fees
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
CA $177
CA $198 total
Sep 16 - Sep 17
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"One of the quietest rooms we have ever stayed in. The location was very convenient to sites in both Lenox and Stockbridge."
Reviewed on Aug 27, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
CA $131
CA $177 total
Aug 31 - Sep 1
includes taxes & fees
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
Tanglewood Music Center
9.6/10 (457 reviews)
You can get tickets for a performance at Tanglewood Music Center during your trip to 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 browsing 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)
Take a campus tour or just explore the area of Williams College, during your travels in 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 studying the exhibits at Norman Rockwell Museum during your travels in 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 find the perfect gifts to bring home at Lee Premium Outlets during your trip to Lee. Amble around the area's gardens or attend a sporting event.
Frequently asked questions
How much does a The Berkshires vacation package cost?
We make it simple to travel somewhere new, with The Berkshires packages starting from as little as CA $1,414. You'll have the flexibility to bundle your favorite airlines, hotels and car rental. For the ultimate getaway, why not add a few tours and experiences to your itinerary?
How do I get a cheap travel package to The Berkshires?
Just imagine all the thrilling things you could do in The Berkshires with extra cash in your wallet. Watch your savings stack up when you combine your flights, hotels and extras into a The Berkshires vacation package. You have plenty of choice when you book with Expedia too. In fact, you can pick from more than 550 airlines and 1,000,000 properties around the world. Whether you're vacationing with the family or embarking on a solo adventure, exploring The Berkshires is better with a package.
What are the top hotels in The Berkshires?
Hampton Inn Boston - Logan Airport and Boston Park Plaza know how to make their guests feel welcome in Great Barrington. If you also plan to explore Hancock, have a look at Hilton Boston Logan Airport and Sheraton Boston, a Marriott Hotel. Both are top picks with travelers.
How far in advance should I book my The Berkshires vacation?
Travelers are normally able to browse international flights on Expedia up to a year in advance of departure. Booking last minute? With a stroke of luck, it's still possible to purchase a cheaper ticket only weeks before your flight.
What does an Expedia The Berkshires travel package include?
Flights, hotels and a cool car for all your road trip adventures. Simply select your preferred bundle and get access to great discounts. Once you've made your booking, add on a couple of tours and experiences and watch your savings stack up. When it comes to organizing your The Berkshires trip, you're in charge!
What should I know before booking a The Berkshires travel package?
Booking all the parts of your trip together is a simple way to save. Combine car rentals, airfares and hotels into a tidy little package. But hotels aren't your only option. Expedia has all kinds of properties, including vacation rentals such as beachside villas and serviced residences. You've got loads of choices!
Can I choose my airline with a The Berkshires Expedia vacation package?
Yes — that's one of the best things about an Expedia package. You're the boss! We have access to more than 550 airline partners across the globe, so you have options galore when putting together your The Berkshires escape.
If I'm not able to travel, can I cancel my The Berkshires vacation package?
Don't stress if you're rethinking your The Berkshires vacation package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We totally understand life can sometimes throw a spanner in the works, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we're ready to help.
Explore a world of travel with Expedia
- Sheffield Hotels
- West Stockbridge Hotels
- Motels in Granville
- Great Barrington Hotels
- Hotels near National Shrine of the Divine Mercy
- Quality Inn Great Barrington
- B&B in Russell
- Cheap Hotels in Lee
- Becket Hotels
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- Southwick Hotels
- Condo Rentals in Otis
- Pet-Friendly Hotels in The Berkshires
- Westfield Hotels
- Holiday Inn Express & Suites Pittsfield
- Resorts in Mount Washington
- Pet-Friendly Hotels in Stockbridge
- Hotels near Frelinghuysen Morris House and Studio
- B&B in Lee
- Pet-Friendly Hotels in Pittsfield
- Chalets in Becket
- The Whitlock
- 3 Star Hotels in Pittsfield
- Hupi House
- Family Hotels in The Berkshires
- Lenox Hotels
- Cottages in Mill River
- Lee Hotels
- Historic Rectory Retreat in Stockbridge – Getaway for 8
- Motels in Egremont
- Resorts in Lenox
- Cheap Hotels in Sandisfield
- Private Island
- Villas in Beartown State Forest
- Historic 1804 house in N Becket Village in the Berkshires
- Cabin Rentals in Westfield
- Apartments in Huntington
- Chalets in Mount Washington
- One Bedroom Luxury Cottage at Blantyre
- Pittsfield Hotels
- Stockbridge Hotels
- Luxury Hotels in Berkshire County
- Chestnut Lodge
- Cheap Hotels in Lenox
- Hotels near Tanglewood Music Center
- Country Houses in Alford
- Relais & Chateaux Hotels in The Berkshires
- Washington Hotels
- Cheap Hotels in The Berkshires
- The Egremont Village Inn
- Springfield Hotels
- Pet-Friendly Hotels in Sheffield
- Luxury Hotels in The Berkshires
- Hotels near Lee Premium Outlets
- Cottages in The Berkshires
- Hotels near Maple Corner Farm Cross Country Ski Area
- Quality Inn Westfield
- Resorts in The Berkshires
- The Red Door B&B
- Flights from Ithaca (ITH) to Pittsfield (PSF)
- Flights from Lenox
- Flights to Westfield
- Flights to Lenox
- Flights to Springfield
- Flights from Phoenix (PHX) to Pittsfield (PSF)
- Flights to Stockbridge
- Flights to Pittsfield
- Flights to West Stockbridge
- Flights to Great Barrington
- Flights from Becket
- Flights from Toronto (YYZ) to Pittsfield (PSF)
- Flights from Plattsburgh (PBG) to Pittsfield (PSF)
- Flights from Boston (BOS) to Pittsfield (PSF)
- Flights to Sheffield
- Flights to The Berkshires
- Flights from Seattle (SEA) to Pittsfield (PSF)
- Flights from Dalton
- Visit South Lee
- Visit South Egremont
- Visit October Mountain State Forest
- Great Barrington Vacations
- Springfield Vacations
- Visit Great Barrington
- National Shrine of the Divine Mercy
- Adams Vacations
- Florida Vacations
- Visit Stockbridge
- Naismith Memorial Basketball Hall of Fame
- Norman Rockwell Museum
- Ventfort Hall Mansion and Gilded Age Museum
- Lenox Library
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
