Deals on vacations and trips to The Berkshires

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The Berkshires flight + hotel vacation packages

Surfside On The Lake

Surfside On The Lake

2.5 out of 5
Price was $879, price is now $782 per person
per person
Jul 27 - Jul 30
Roundtrip non-stop flight included
Indianapolis (IND) to Albany (ALB)
This hotel features a private beach and 2 restaurants. Dine at the beachfront restaurant and relax with sun loungers. Enjoy the a rooftop terrace and perks like free self parking.
The Springs Motel

The Springs Motel

2 out of 5
Price was $840, price is now $748 per person
per person
Jul 27 - Jul 30
Roundtrip non-stop flight included
Indianapolis (IND) to Albany (ALB)
Free WiFi in public areas is available at this motel. Take advantage of the free self parking.
Amsterdam Castle

Amsterdam Castle

3.5 out of 5
Price was $740, price is now $663 per person
per person
Jul 27 - Jul 30
Roundtrip non-stop flight included
Indianapolis (IND) to Albany (ALB)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace and express check-out are also provided.
Nordick's Inn

Nordick's Inn

2.5 out of 5
Price was $792, price is now $710 per person
per person
Jul 27 - Jul 30
Roundtrip non-stop flight included
Indianapolis (IND) to Albany (ALB)
This motel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a picnic area, and luggage storage are also on offer.
Park Manor Hotel

Park Manor Hotel

4 out of 5
Price was $681, price is now $618 per person
per person
Jul 27 - Jul 30
Roundtrip non-stop flight included
Indianapolis (IND) to Albany (ALB)
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A 24-hour business center, a coffee shop, and a lobby fireplace are also on offer.

Top The Berkshires hotels deals

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 $115 per night
$115
per night
Jun 15 - Jun 16
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.
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 $190 per night
$190
per night
Jun 12 - Jun 13
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Berkshire Inn

Berkshire Inn

2 out of 5
150 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
The price is $79 per night
$79
per night
Jun 19 - Jun 20
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A picnic area is provided and the front desk is staffed around-the-clock.
Hotel Downstreet

Hotel Downstreet

3 out of 5
40 Main St, North Adams, MA
Free Cancellation
Reserve now, pay when you stay
The price is $120 per night
$120
per night
Jul 9 - Jul 10
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 2 conference rooms, as well as the 24-hour business center and free WiFi in public areas. Enjoy the spa tub and perks like free self parking.
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

3 out of 5
435 Laurel St, Lee, MA
Free Cancellation
Reserve now, pay when you stay
The price is $118 per night
$118
per night
Jun 15 - Jun 16
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A 24-hour business center, a picnic area, and laundry facilities are also on offer.
Econo Lodge

Econo Lodge

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Get rates
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. The front desk is staffed around-the-clock and laundry facilities are on offer.
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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?
Travelocity has great package deals to The Berkshires, including hotels and flights, starting from as low as $618. With the cash you save, you could book some popular tours or maybe even tack on a few extra nights to your vacation.
Where can I get the best vacation package deals for The Berkshires?
No matter your travel style, Travelocity can help you get an unbeatable The Berkshires package deal. All you need to do is mix and match from our 400 air carriers and 1,000,000 worldwide properties.
Why should I book my The Berkshires vacation package via Travelocity?
Whether you’re planning a month-long vacation or a last-minute escape, we have many tempting destinations to choose from at an affordable price. And on top of that, we provide round-the-clock support, quality service and a Price Match Guarantee. Save yourself the effort and time and lock in your dream vacation now.
Can I save money on my The Berkshires car rental if I combine it with hotels and flights?
You sure can with our The Berkshires vacation packages. With one of these, there are loads of ways to stretch your vacation budget further. Combine any two or more car, hotel, flight and tour bookings and watch the savings start to pile up. With a rental car, all the key sights in and around The Berkshires are within your reach.
What is the best time of year to go to The Berkshires?
If you really want to wander wisely, is the perfect time to do it. That’s when hotel rates are at their cheapest. By way of comparison, prices are at their highest around . are the most popular months to vacation in The Berkshires, so expect big lines at top attractions. Want to avoid high season? You’ll find fewer crowds in .
Which airport is best for The Berkshires?
There are three main hubs for anyone heading to and from The Berkshires — Bradley Intl. Airport (BDL), Albany Intl. Airport (ALB) and Hartford, CT (HFD-Hartford - Brainard).
Can I go on vacation to The Berkshires at this time?
Our team has the local know-how to ensure your travel dreams come true, so before booking a ticket to The Berkshires, look over our Covid-19 Travel Advisor. Here you’ll find all the current info about quarantine policies, travel restrictions and other useful advice.