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Discover the most popular places to visit in The Berkshires
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.
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.
Photo by Caminante
Open 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.
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.
Photo by Adnan Kakazai
Open 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.
Photo by Caitlin Reese
Open 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.
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.
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.
Top Pet-friendly The Berkshires Hotels
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
"Its an interesting experience in that we thought we were staying at a hotel/ inn. The pictures and the website lead one to believe that but when we got there, we saw a motel. Nothing wrong with that but we felt we had been misinformed. They push the pcitures of the Club room which looks like an inn/ restaurant but that is the front of the building but attached to it is the motel where you stay. Again, once we knew that, we were fine but honestly, we were looking for more of an Inn or a hotel/...
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.
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.
Can you take a dog on holiday with you in The Berkshires?
Yes, you can take your dogs on holiday with you. Many accommodations and holiday packages now cater to pet owners by offering pet-friendly services. Just use the filter on the left to find The Berkshires pet-friendly holiday accommodation on Expedia.
How can I find pet-friendly holiday packages in The Berkshires on Expedia?
The easiest way to find pet-friendly holidays in The Berkshires is to use Expedia’s filter options. Just click on “Pet-friendly”, under “Amenities” in the filters on the left to narrow down your search. For more information, read the details of the accommodation’s pet-friendly policy and for the real down-low, look at the guest reviews from travellers with pets.
How to book a pet-friendly holiday in The Berkshires?
Once you’ve found your ideal The Berkshires pet-friendly holiday accommodation, check for any extra charges and restrictions when you place your booking, and state that you are bringing a pet, with any necessary details.
Are there many pet-friendly holiday options in The Berkshires?
Holidaying with dogs has become a popular choice, and you can find various kinds of accommodation options, including pet-friendly holiday rentals in The Berkshires.
What are some tips for selecting the ideal pet-friendly package in The Berkshires?
If you want to make pupper really happy on holiday, look for The Berkshires pet-friendly holiday accommodation with amenities like welcome treats, dog parks, or walking services. See if there are nearby pet-friendly activities or parks. Read reviews from other pet owners. Check the pet policy for size or breed restrictions and additional fees.
How can I find excellent deals on The Berkshires pet-friendly holidays in The Berkshires?
One way to find great deals for 2026 is to book in off-peak seasons, when the rates are lower. If you’re an Expedia member, you can also access package holiday deals, which may include pet-friendly holiday rentals in The Berkshires.
How can I discover last-minute pet-friendly holiday deals in The Berkshires?
You can find last-minute deals on The Berkshires pet-friendly holiday accommodation by entering your dates and other relevant information into the search function and seeing what options come up.
How can I find pet-friendly spa holiday packages in The Berkshires?
If you want to spend some quality time in the spa while your doggo relaxes in your room, search for spa resorts in The Berkshires and filter for pet-friendly ones.
How to locate pet-friendly family holiday packages.
If you’re looking for a package holiday that includes your four-legged family member, use the filter options to look for resorts or holiday packages that offer both family-friendly and pet-friendly amenities.
How can I find great weekend The Berkshires pet-friendly holiday packages in The Berkshires?
Your dog may be your best friend, but Expedia’s filters are your second-best friend because you can use them to filter for pet-friendly holiday rentals in The Berkshires that offer short stays. Just enter your dates and use the filters on the left to find The Berkshires pet-friendly holiday accommodation for those dates.
Why book pet-friendly holiday packages in The Berkshires with Expedia?
Expedia offers a wide range of options and the ability to filter for pet-friendly accommodations. They provide customer reviews, which can offer insights into how pet-friendly the package truly is. By booking your The Berkshires pet-friendly holiday accommodation through Expedia, you can also get exclusive deals or points for future travel.