Save up to ₹100,000 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
Plan, book, and manage your trip all in one place
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/...
"As of late we have been traveling with our small dog. Most hotels that accept pets you end up in the most dinghy room and not kept well. Not here the room was clean well kept and no odor. "
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.
How to find a pet-friendly holiday in The Berkshires
How can I book the best pet-friendly holidays in The Berkshires?
As a pet parent, you want your best bud along for your The Berkshires holiday, right? So use our pet-friendly filter to find all the places that are purr-fect for cats, dogs or even well-trained rabbits. Think stacks of outside space, welcome treats and maybe something lovely that keeps the travel time to a minimum.
Can I book a cheap The Berkshires pet-friendly holiday?
The Berkshires pet-friendly package holidays start at , but prices and availability are subject to change, and additional terms may apply. To narrow down the best deals, sort by price and use the filters to find cheap places with tail-wag-worthy amenities.
How can I book holiday lets in The Berkshires that are pet friendly?
The space and seclusion of a holiday let is great for holidaying as a family or bigger group, and if your furry friends are with you, even better. Use both the private holiday home and pet-friendly filters to find all the options that tick both boxes.
How can I find pet-friendly holidays in The Berkshires with hot tubs?
Pet-friendly holidays aren’t just about the animals – you deserve to indulge yourself, too! Filter our The Berkshires properties using the hot-tub and pet-friendly holiday options and find somewhere you can relax while the pooches snooze.
Can I book a pet-friendly holiday in The Berkshires with a car?
For hassle-free pet-friendly travel, a car is a no-brainer. Book both your car hire and accommodation with Expedia and you’ll sniff out some great savings.
How can I book last-minute pet-friendly holidays in The Berkshires?
A spontaneous last-minute getaway to The Berkshires with your pet is what holiday dreams are made of. You might even dig up discounted rates on some hotels by booking close to the date.
Can I book a pet-friendly holiday in The Berkshires with free cancellation and/or flexible dates?
We offer several places to stay with free cancellation in The Berkshires, just use the fully refundable filter to find the ones available on your dates. Make sure you read the terms and conditions, too.
Why should I book The Berkshires pet-friendly travel with Expedia?
Thanks to our dedicated pet-friendly filter, it’s incredibly easy to find accommodation in The Berkshires that welcomes fur babies. Search, choose and book in just a few clicks. Purr-fect!