Deals on vacations and trips to Berkshire County

Save when you book Berkshire County, MA package deals

Choose two or more items and save on your trip:

Search vacation packages deals in Berkshire County's top destinations

Lenox showing fall colors

Lenox

Vacations
Lenox

Berkshire County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $655, price is now $515 per person
$515
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Free WiFi in public areas is available at this guesthouse. Take advantage of the free self parking.
Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $1,018, price is now $735 per person
$735
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Albany (ALB)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a picnic area are also on offer.
The Old Catskill Game Farm Inn

The Old Catskill Game Farm Inn

3.5 out of 5
Price was $875, price is now $645 per person
$645
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
A sauna, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. A communal living room, a picnic area, and free newspapers are also on offer.
Gedney Farm

Gedney Farm

3.5 out of 5
Price was $812, price is now $624 per person
$624
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) 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, a garden, and a communal living room are also on offer.
The Dewey

The Dewey

3.5 out of 5
Price was $851, price is now $667 per person
$667
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Albany (ALB)
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

Top Berkshire County 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
$126 nightly
The price is $141 total per night
$141 total
Jan 28 - Jan 29
Total with taxes and fees
This condo 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
$126 nightly
The price is $140 total per night
$140 total
Feb 10 - Feb 11
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 perks like 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
$121 nightly
The price is $136 total per night
$136 total
Feb 25 - Feb 26
Total with taxes and fees
This lodge 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
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$195 nightly
The price is $217 total per night
$217 total
Feb 8 - Feb 9
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking, a coffee shop, and a terrace are also offered.
Pet friendly
Parking included
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free Cancellation
$98 nightly
The price is $109 total per night
$109 total
Jan 30 - Jan 31
Total with taxes and fees
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.
Pool
Pet friendly
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$90 nightly
The price is $101 total per night
$101 total
Jan 29 - Jan 30
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
Don't see what you're looking for?
See all available properties in Berkshire County
View all properties
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.

Photos of local treasures

Browse Berkshire County vacation photos for more inspiration

Under a mile walk up the creek to this nice waterfall! Small parking area at the end of Marion St. Walk on the creek side of the fence past the driveway of the private residence.
Under a mile walk up the creek to this nice waterfall! Small parking area at the end of Marion St. Walk on the creek side of the fence past the driveway of the private residence.
Hidden away in the city is a beautiful piece of 19th century architecture. Not far up the rails is the infamous five mile long Hoosac Tunnel.
Hancock Shaker Village, Hancock Massachusetts beautiful place; description Shakers, all supported themselves by the proceeds of their farmland. The Hancock Shakers were primarily dairy farmers. The raising and sale of garden seeds was perhaps the most lucrative of their early businesses.Land acquisition and conversion continued for decades, with the area peaking at 3,000 acres (12 km2) and the population rising to over 300.After reaching peak membership in the 1840s, the Shaker movement gradually dwindled, partially due to the urban migration that accompanied the Industrial Revolution, and by the westward migration of New England's youth. By the early twentieth century, the population of the village had fallen to around 50, most of whom were children. The remaining Shakers sold off their excess land, and many buildings were destroyed.The decision was eventually made in 1960 to close the village and sell the property and buildings. Non-Shakers were impressed by the Hancock Shaker property—scrupulously clean, neat, and well-tended—and their innovations in farming, such as the round barn that attracted much attention Visitors also praised Hancock Shakers' products, including boxes "of beautiful workmanship" and garden seeds. Before 1820, the village was prosperous and the Shakers were respected as good neighbors.
Two beautiful cascades that combine and form several crystal clear pools along the stream.

Frequently asked questions

How much are vacation packages to Berkshire County?
With vacation packages being sold from just $515, you won't need to wipe out your bank balance for your getaway to Berkshire County. Travelocity is here to help. Bundle your flights, hotels and tours into a convenient package and walk away with fantastic discounts. The more you book, the more you save.
Where can I get the best vacation package deals for Berkshire County?
Travelocity has endless ways to score an awesome Berkshire County package deal. Choose from 400 air carriers and 1,000,000 hotels worldwide and create a vacation package that's right for you. With this amount of choice at your fingertips, you'll have plenty of inspiration for your next big adventure.
Why should I book my Berkshire County vacation package via Travelocity?
Incredible savings, countless enticing destinations and 24/7 customer service — that's why. And with our Price Match Guarantee, you can rest easy knowing that you'll always score the best possible deal with Travelocity.
Can I save money on my Berkshire County car rental if I bundle it with hotels and flights?
You can with our Berkshire County vacation packages. With one of these, there are lots of ways to make your hard-earned cash go further. Combine any two or more car, flight, hotel and tour bookings and watch your savings add up. With a rental car, all the popular attractions around Berkshire County are a fun road trip away.
Which airport is best for Berkshire County?
Bradley Intl. Airport (BDL), Albany Intl. Airport (ALB) and Hartford, CT (HFD-Hartford - Brainard) are the most frequented airports for those traveling in and out of Berkshire County.
What is there to do in Berkshire County?
Berkshire County has hidden gems around every turn, however ensure you visit Williams College and National Shrine of the Divine Mercy while you're here. These landmarks are very popular with visitors to the region.

Where to stay in Berkshire County: Best areas for travelers

Explore More Ways to Travel with Travelocity