Berkshire County Vacation Packages

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Your Berkshire County Vacation

With a Berkshire County vacation package, you can forget about the stress of planning and simply focus on experiencing what this exciting destination has on offer. Kick off your trip to Berkshire County with a few nights in Lenox visiting popular attractions like National Shrine of the Divine Mercy and Norman Rockwell Museum. Williamstown is another city that draws crowds from far and wide. Massachusetts Museum of Contemporary Art and Mount Greylock are two of the leading places to see in this destination. If you're ready to stop daydreaming and start doing, Expedia will help turn your Berkshire County vacation into reality.

Top vacation destinations in Berkshire County

FlightsFlightsHotelsHotels

Great Barrington

Great Barrington

Top Berkshire County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

2 out of 5
Price was CA $899, price is now CA $776 per person
CA $776
per person
Jun 15 - Jun 19
found 19 hours ago
Roundtrip flight included
Buffalo (BUF) to Hudson (HCC)
9.2/10 Wonderful! (349 reviews)
Ski, spa and staff made my trip enjoyable thank you.

Reviewed on Mar 10, 2026

Mins to Hunter Mountain Sleeps 36 Pool, Spa, Games & Bar Cozy Peaks Lodge by Avantstay

Mins to Hunter Mountain Sleeps 36 Pool, Spa, Games & Bar Cozy Peaks Lodge by Avantstay

3 out of 5
Price was CA $12,071, price is now CA $9,136 per person
CA $9,136
per person
Jun 15 - Jun 19
found 19 hours ago
Roundtrip flight included
Buffalo (BUF) to Hudson (HCC)
No reviews
Game Farm Villa by Avantstay 10bdr, Private Pond, Spa, Pool Family-friendly

Game Farm Villa by Avantstay 10bdr, Private Pond, Spa, Pool Family-friendly

3 out of 5
Price was CA $5,932, price is now CA $4,771 per person
CA $4,771
per person
Jun 15 - Jun 19
found 19 hours ago
Roundtrip flight included
Buffalo (BUF) to Hudson (HCC)
No reviews
The Old Catskill Game Farm Inn

The Old Catskill Game Farm Inn

3.5 out of 5
Price was CA $1,140, price is now CA $960 per person
CA $960
per person
Jun 15 - Jun 19
found 19 hours ago
Roundtrip flight included
Buffalo (BUF) to Albany (ALB)
9.8/10 Exceptional! (31 reviews)
The uniqueness and beauty of the transformation

Reviewed on Mar 2, 2026

The Haüs Windham

The Haüs Windham

2 out of 5
Price was CA $1,044, price is now CA $887 per person
CA $887
per person
Jun 15 - Jun 19
found 19 hours ago
Roundtrip flight included
Buffalo (BUF) to Hudson (HCC)
7.6/10 Good! (25 reviews)
Mainly the location and the solitude.

Reviewed on Feb 7, 2026

Berkshire County Hotel Deals

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
The price is CA $194 per night from Mar 30 to Mar 31
CA $194
CA $217 total
Mar 30 - Mar 31
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Great location. Within walking distance to MOCA, and a few restaurants that were open during our stay. The town is post industrial and post manufacturing. Walking around MOCA is a wonderful experience in itself as much of the history of the building and surrounding area comes alive and is fascinating.The ...

Reviewed on Mar 22, 2026

Hotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Apr 26 to Apr 27
CA $120
CA $165 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (888 reviews)
very clean and friendly staff

Reviewed on Mar 24, 2026

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is CA $96 per night from Mar 31 to Apr 1
CA $96
CA $108 total
Mar 31 - Apr 1
includes taxes & fees
9/10 Wonderful! (881 reviews)
Berkshires Untold is an old roadside motel that has been very spiffed up. The rooms are small but clean, comfortable, and nicely decorated and updated. Our bed was comfy with high end linens and a nice updated bathroom. The major drawback to the room is the very noisy HVAC unit. There's a super cozy, ...

Reviewed on Mar 26, 2026

Berkshires Untold
See all 1,119 properties in Berkshire County
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.
All Inclusive Vacations
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Frequently asked questions

How much does a Berkshire County vacation package cost?
Less than you might think — from as low as CA $776, actually! By bundling hotels, flights and car rentals into a custom-made package, your Berkshire County escape is only clicks away.
How do I get a cheap travel package to Berkshire County?
Booking a Berkshire County vacation package with Expedia is a smart way to save. We have over 550 air carriers and 1,000,000 hotel options globally. With such a fabulous range to choose from, you'll have no trouble creating your dream adventure.
What are the top hotels in Berkshire County?
For properties in Great Barrington with cozy beds and friendly service, look up Hampton Inn Boston - Logan Airport and Boston Park Plaza. If you're visiting Hancock as well, you can look forward to a good night's sleep at Hilton Boston Logan Airport or Sheraton Boston, a Marriott Hotel.
How far in advance should I book my Berkshire County vacation?
While not all air carriers release ticket prices early, it's usually possible to compare international airfares on Expedia up to a year in advance. This is the time when you can score some fantastic deals. If you've left everything to the last minute, you might still be in luck. Low prices occasionally emerge a few weeks before departure.
What does an Expedia Berkshire County travel package include?
Choose from a combination of hotels, flights and rental cars. Once you've made your booking, you can add some activities and experiences. Want to pick your fare class? That's easily done too. The choice is yours when it comes to arranging your perfect Berkshire County getaway.
What should I know before booking a Berkshire County travel package?
Our prices are already low. However, you'll score even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Berkshire County Expedia vacation package?
Most definitely. Expedia has over 550 airline partners to choose from around the world. With so many choices, finding the ideal carrier to get you to Berkshire County will be easy.
If I'm not able to travel, can I cancel my Berkshire County vacation package?
It's difficult to predict what tomorrow might bring, so it's comforting to know that you can change or cancel your Berkshire County vacation package. If you made your booking in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for further details.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.