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Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $836, price is now $702 per person
$702
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
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.
South Shire

South Shire

4 out of 5
Price was $1,227, price is now $972 per person
$972
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
A restaurant and a bar/lounge are featured at this bed & breakfast. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, express check-in, and express check-out are also on offer.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,198, price is now $997 per person
$997
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $849, price is now $726 per person
$726
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Albany (ALB)
This smoke-free hotel features a casino, a nightclub, and a restaurant. Enjoy the indoor pool and perks like free self parking and a free area shuttle. You'll appreciate the 24-hour gym, bar/lounge, and snack bar/deli.
The White House Inn

The White House Inn

3.5 out of 5
Price was $1,318, price is now $1,129 per person
$1,129
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace and a garden are also provided.

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
$128 nightly
The price is $143 total per night
$143 total
Aug 31 - Sep 1
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
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$159 nightly
The price is $178 total per night
$178 total
Aug 9 - Aug 10
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
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$138 nightly
The price is $155 total per night
$155 total
Aug 30 - Aug 31
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
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
$61 nightly
The price is $68 total per night
$68 total
Aug 10 - Aug 11
Total with taxes and fees
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.
Parking included
Free WiFi
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $161 total per night
$161 total
Sep 7 - Sep 8
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
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Free Cancellation
$131 nightly
The price is $146 total per night
$146 total
Sep 7 - Sep 8
Total with taxes and fees
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 hot tub and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
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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.
See properties

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 $702. 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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