Deals on vacations and trips to The Berkshires

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Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
Price was $750, price is now $646 per person
$646
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Albany (ALB)
This hotel features a gym and an outdoor tennis court. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $858, price is now $663 per person
$663
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Albany (ALB)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A garden, a lobby fireplace, and a communal living room are also on offer.
Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center

3 out of 5
Price was $1,515, price is now $1,292 per person
$1,292
per person
Oct 2 - Oct 6
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
This smoke-free resort features 2 restaurants, a bar/lounge, and an indoor pool. Traveling on business? Take advantage of the 24-hour business center, laundry service, and airport shuttle. There's a seasonal outdoor pool on site, and a 24-hour front desk and a terrace are also provided.
27 Lincoln

27 Lincoln

2 out of 5
Price was $989, price is now $845 per person
$845
per person
Oct 2 - Oct 6
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
Free WiFi in public areas is available at this motel. Take advantage of the free self parking.
Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was $1,336, price is now $1,161 per person
$1,161
per person
Oct 2 - Oct 6
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
A restaurant and a 24-hour gym are featured at this lodge. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A business center, a terrace, and a picnic area are also on offer.

Top The Berkshires hotels deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$134 nightly
The price is $150 total per night
$150 total
Aug 19 - Aug 20
Total with taxes and fees
This aparthotel features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
Pool
Parking included
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Free Cancellation
$161 nightly
The price is $179 total per night
$179 total
Aug 16 - Aug 17
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express check-out. Enjoy the hot tub and free perks like continental breakfast and free self parking.
Pool
Hot Tub
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$142 nightly
The price is $158 total per night
$158 total
Aug 23 - Aug 24
Total with taxes and fees
This aparthotel features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Free Cancellation
$118 nightly
The price is $132 total per night
$132 total
Aug 16 - Aug 17
Total with taxes and fees
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A picnic area and barbecue grills are also provided.
Breakfast included
Parking included
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$145 nightly
The price is $162 total per night
$162 total
Aug 5 - Aug 6
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$152 nightly
The price is $170 total per night
$170 total
Aug 23 - Aug 24
Total with taxes and fees
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. A terrace, a lobby fireplace, and express check-in are also on offer.
Pet friendly
Parking included
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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.

Stay near popular The Berkshires attractions

A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.

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.
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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, as well as flights and hotels, starting from an impressive $646. With all that extra cash, you could purchase some cool tours or possibly add a couple of extra days to your exciting getaway.
Where can I get the best vacation package deals for The Berkshires?
Travelocity has endless ways to score an incredible The Berkshires package deal. Choose from 400 partner airlines and 1,000,000 properties around the globe and craft a vacation package that's right for you. With so much choice, you have inspiration galore for your next big getaway.
Why should I purchase my The Berkshires vacation package via Travelocity?
Fantastic savings, an abundance of breathtaking destinations and a team of customer service experts available 24/7 — that's why. And with our Price Match Guarantee, you can rest assured knowing that you'll always get the best possible deal with Travelocity.
Will I save money on my The Berkshires car rental if I combine it with a hotel or flight?
Combining your bookings into a The Berkshires vacation package will save you some serious money. Book a flight and car; a flight, car and hotel; or a car and hotel. You won't find a better way to discover the greater The Berkshires region than with your own set of wheels. You can also add experiences and activities to your Travelocity package.
Which airport is best for The Berkshires?
Bradley Intl. Airport (BDL) is a popular choice for many travelers to the region. But depending on your itinerary, Albany Intl. Airport (ALB) or Hartford, CT (HFD-Hartford - Brainard) could work better for you.
What is there to do in The Berkshires?
The Berkshires boasts hidden gems at every turn, but be sure you plan a visit to both Williams College and National Shrine of the Divine Mercy while you're here. These landmarks are a must-see for visitors to the region.

Photos of local treasures

Browse The Berkshires vacation photos for more inspiration

A person snowboarding down a snowy slope.
A large white building with multiple chimneys, surrounded by lush gardens with various flowers.
A golf course with a man and a woman preparing to putt, surrounded by autumn-colored trees and historic buildings.
A wooden dining table with breakfast items, a vase with flowers, and a fireplace in the background.
A street lamp with a sign reading "VENTFORT HALL" and "LENOX 1767" against a backdrop of autumn-colored trees.

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