Deals on vacations and trips to The Berkshires

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Top The Berkshires hotel deals

Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
The price is $110 per night
$110
per night
May 5 - May 6
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. Express check-in is provided and the front desk is staffed around-the-clock.
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Free Cancellation
Reserve now, pay when you stay
The price is $108 per night
$108
per night
May 6 - May 7
A full-service spa, 3 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the gym, bar/lounge, and concierge services.
Pet friendly
Breakfast available
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
The price is $118 per night
$118
per night
May 8 - May 9
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Hot Tub
Breakfast included
The Lenox Collection

The Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
The price is $78 per night
$78
per night
May 27 - May 28
This hotel features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A library, express check-out, and wedding services are also on offer.
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

3.5 out of 5
190 Meadow Street, South Lee, MA
Free Cancellation
The price is $139 per night
$139
per night
May 2 - May 3
This smoke-free hotel features 2 restaurants, 2 outdoor pools, and 2 indoor pools. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and visit the 2 bars/lounges and poolside bar for drinks.
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3 out of 5
One West Street, Pittsfield, MA
Free Cancellation
The price is $104 per night
$104
per night
May 5 - May 6
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
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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.

Popular places to visit

Image for Tanglewood Music Center

Tanglewood Music Center

5/5(150 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.

Tanglewood Music Center
Image for Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

4.5/5(98 reviews)

Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this quaint area.

Jiminy Peak Mountain Resort
Image for Norman Rockwell Museum

Norman Rockwell Museum

4.5/5(193 reviews)

You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.

Norman Rockwell Museum

The Berkshires Vacations

The highlands known as The Berkshires are situated in Western Massachusetts and Connecticut and are some of the best-known tourist attractions in the region. With impressive mountains, scenic hills, and beautiful autumn foliage, experiencing a vacation in The Berkshires is one of the best ways to get to know one of the Northeast's most beautiful regions.

Major Attractions

After you've checked into your hotel in the Berkshires, dive right into your vacation with a visit to the Massachusetts Museum of Contemporary Art. Located in a converted factory in nearby North Adams, this unique space is one of the largest and most notable spaces for contemporary visual and performing arts in the country. This museum's 100,000 square feet of space hosts a rotation of exhibitions from artists from around the world. When you're done exploring the Berkshires' ample art scene, get intimate with nature in the area's extensive wild spaces. One of the standouts is the Mt. Everett State Reservation, a 1,356-acre natural space in the southwest corner of the state. In addition to climbing to this mountain's summit, Mt. Everett offers its visitors picnicking and the chance to explore the 90-mile Appalachian Trail that wanders through the site.

Recurring Festivals and Events

Tourists planning their Berkshires vacations should prepare for the annual festivals in the region. For instance, the nearby Bay State Winter Games showcases some of winter's best sports, including ice skating, skiing, and more. Summer's annual Berkshire Arts Festival in July displays some of the works of some of the region's most innovative visual artists and allows visitors the chance to purchase many works.

It's easy to get Berkshires vacation packages and even rental cars in the Berkshires through Travelocity. When you book through us, you can take advantage of our Travelocity Price Guarantee: If you find a better deal through a competitor, we'll match their price and refund you the difference.

Frequently asked questions

How much are vacation packages to The Berkshires?
Prepare to be surprised — you can unwind in The Berkshires for as low as . At Travelocity, we save you money and time with our awesome vacation package deals. With flights, hotels and experiences all ready to go, what’s holding you back?
Where can I get the best vacation package deals for The Berkshires?
Travelocity can help you get an unbeatable The Berkshires package deal. With 400 airlines and 1,000,000 properties across the globe, we’re sure you’ll find one that works for you.
Why should I book my The Berkshires vacation bundle via Travelocity?
From our 24/7 support to our range of terrific destinations, we are dedicated to fulfilling your travel dreams. All you need to do is click and book — our Price Match Guarantee will make sure you lock in the cheapest price.
Can I save money on my The Berkshires car rental if I combine it with my hotel or flight?
Combining your bookings into a The Berkshires vacation package will leave you with a nice chunk of spare change. Bundle a flight and car; a flight, hotel and car; or a car and hotel. There’s no better way to discover the greater The Berkshires region than from the driver’s seat of your own rental car. You can also add tours and experiences to your Travelocity package.
What is the best time of year to go to The Berkshires?
That comes down to whether you’d like to save cash or visit The Berkshires at its most exciting. The quietest time to explore this part of the world is October, November and December. But if you want to experience this destination in peak season, consider February, March and May. More interested in saving your hard-earned cash? The most affordable month is . usually has the highest prices.
Which airport is best for The Berkshires?
That largely depends on where you depart and where you’re going — Bradley Intl. Airport (BDL), Albany Intl. Airport (ALB) or Hartford, CT (HFD-Hartford - Brainard) are where you’re most likely to land.