Berkshire County Vacations & Trips from ￥395,412

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The Latest Berkshire County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

2.5 out of 5
Downtown Albany
per person
Aug 6 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Albany (ALB)
8.6/10 Excellent! (1,001 reviews)
Clean room and good breakfast

Reviewed on Jun 17, 2025

Hampton Inn Schenectady Downtown

Hampton Inn Schenectady Downtown

2.5 out of 5
Seward Place
per person
Aug 6 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Albany (ALB)
9/10 Wonderful! (915 reviews)
Clean room. Friendly staff.

Reviewed on Jun 24, 2025

DoubleTree by Hilton Schenectady Downtown

DoubleTree by Hilton Schenectady Downtown

4 out of 5
Seward Place
per person
Aug 6 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Albany (ALB)
8.4/10 Very Good! (662 reviews)
Overall nice clean hotel . Need to update tvs so you can use streaming services. Need to update website about complimentary breakfast and late check out .

Reviewed on Jun 1, 2025

Homewood Suites by Hilton Albany Crossgates Mall, NY

Homewood Suites by Hilton Albany Crossgates Mall, NY

3 out of 5
per person
Aug 6 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Albany (ALB)
8.8/10 Excellent! (411 reviews)
We enjoyed our staff from our spacious & clean room to the excellent amenities and walk ability to restaurants and shopping!

Reviewed on Jun 21, 2025

Tru By Hilton Albany Crossgates Mall

Tru By Hilton Albany Crossgates Mall

2.5 out of 5
per person
Aug 6 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Albany (ALB)
8.6/10 Excellent! (1,000 reviews)
Nice and clean hotel. Lots of variety for breakfast

Reviewed on Jun 21, 2025

Berkshire County Hotel Deals

Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
8.6/10 Excellent! (1,836 reviews)
"The property was perfect for a getaway. 1 bedroom suite or more with balconies. Non heating Fireplace for aesthetics. The suite was a jack and Jill! Shower, but also a jet tub separate from shower. All dishes and cooking utensils that you needed. You can grill onsite or cook in your suite as take ..."

Reviewed on Jun 24, 2025

Get rates
Vacation Village in the Berkshires
Quality Inn
Quality Inn
2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is ￥17,082 per night from Jul 27 to Jul 28
￥17,082
￥19,080 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"The gentleman working at the front desk was extremely helpful when were in a pinch and needed assistance late at night! The second-level room was comfortable, clean, and quiet, and the location is amazing, just a short walk to all the restaurants, cafes and shops that downtown Great Barrington has ..."

Reviewed on Jun 26, 2025

Quality Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3 out of 5
One West Street, Pittsfield, MA
Fully refundable
The price is ￥15,767 per night from Jun 30 to Jul 1
￥15,767
￥17,612 total
Jun 30 - Jul 1
includes taxes & fees
7.8/10 Good! (797 reviews)
"All was great, except parking was quiet of walk"

Reviewed on Jun 13, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 1,100 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.

Frequently asked questions

How much does a Berkshire County vacation package cost?
Less than you might think --- from as low as ￥395,412, 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.