The Berkshires Vacation Packages

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Top The Berkshires Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
per person
Aug. 1 - Aug. 4
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.4/10 Good! (350 reviews)
Check-in experience was pretty awful. I waited in a line for more than an hour in order to check-in. Two staff members at reception were working together to check folks in; one person making keys for the rooms, the other for everything else. Also very easy to hear people in the hallways and through the room walls.

Reviewed on Apr. 9, 2024

Equinox Resort Residences

Equinox Resort Residences

4.5 out of 5
Save 100% on your flight
per person
Aug. 1 - Aug. 4
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
No reviews
Valley Craft Ales

Valley Craft Ales

2 out of 5
per person
Jun. 14 - Jun. 16
Roundtrip non-stop flight included
Ottawa (YOW) to Albany (ALB)
9/10 Wonderful! (36 reviews)
Pros: Good location near to Mt Snow, responsive host when issues come up, clean, bar downstairs with a fire is nice, pretty views over the river and v close to a few nice restaurants in the town. Not so good: Uncomfortable - quite rough sheets and hard bed, v thin walls and could be quite loud from bar downstairs and people and cars on the road outside (check if there's an event on!), no reserved guest parking so could be hard to find a nearby space early-evening (but fine all other times), Fine for a few nights stay but overall just a bit expensive for what it was.

Reviewed on Feb. 21, 2024

Kimpton Taconic Hotel, an IHG Hotel

Kimpton Taconic Hotel, an IHG Hotel

4 out of 5
per person
Jun. 14 - Jun. 16
Roundtrip non-stop flight included
Ottawa (YOW) to Albany (ALB)
9.4/10 Exceptional! (677 reviews)
Always love it here!

Reviewed on May 10, 2024

The Berkshires Hotel Deals

Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from May 20 to May 21
CA $135
CA $151 total
includes taxes & fees
May 20 - May 21
9/10 Wonderful! (233 reviews)
"It’s the perfect place to go for a weekend or weeklong stay and be as isolated as social as you want. The towns nearby are fantastic. Will definitely be back a lot"

Reviewed on May 1, 2024

Life House Berkshires
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from May 21 to May 22
CA $190
CA $243 total
includes taxes & fees
May 21 - May 22
8.8/10 Excellent! (880 reviews)
"Great service from the staff and a beautiful place to relax and unwind"

Reviewed on May 10, 2024

The Red Lion Inn
Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from May 13 to May 14
CA $204
CA $228 total
includes taxes & fees
May 13 - May 14
8.4/10 Very Good! (915 reviews)
"Near Mass MoCA, friendly staff, great view from my room"

Reviewed on May 6, 2024

Hotel Downstreet
See all 1,024 properties in The Berkshires
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.

Explore other types of vacation packages

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Frequently asked questions

How much does a The Berkshires vacation package cost?
We make it simple to travel somewhere new, with The Berkshires packages starting from as little as CA $953. You’ll have the flexibility to bundle your favorite airlines, hotels and car rental. For the ultimate getaway, why not add a few tours and experiences to your itinerary?
How do I get a cheap travel package to The Berkshires?
Just imagine all the thrilling things you could do in The Berkshires with extra cash in your wallet. Watch your savings stack up when you combine your flights, hotels and extras into a The Berkshires vacation package. You have plenty of choice when you book with Expedia too. In fact, you can pick from more than 550 airlines and 1,000,000 properties around the world. Whether you’re vacationing with the family or embarking on a solo adventure, exploring The Berkshires is better with a package.
What are the top hotels in The Berkshires?
Hampton Inn Boston - Logan Airport and Boston Park Plaza know how to make their guests feel welcome in Great Barrington. If you also plan to explore Hancock, have a look at Hilton Boston Logan Airport and Sheraton Boston, a Marriott Hotel. Both are top picks with travelers.
How far in advance should I book my The Berkshires vacation?
Travelers are normally able to browse international flights on Expedia up to a year in advance of departure. Booking last minute? With a stroke of luck, it’s still possible to purchase a cheaper ticket only weeks before your flight.
What does an Expedia The Berkshires travel package include?
Flights, hotels and a cool car for all your road trip adventures. Simply select your preferred bundle and get access to great discounts. Once you’ve made your booking, add on a couple of tours and experiences and watch your savings stack up. When it comes to organizing your The Berkshires trip, you’re in charge!
What should I know before booking a The Berkshires travel package?
Booking all the parts of your trip together is a simple way to save. Combine car rentals, airfares and hotels into a tidy little package. But hotels aren’t your only option. Expedia has all kinds of properties, including vacation rentals such as beachside villas and serviced residences. You’ve got loads of choices!
Can I choose my airline with a The Berkshires Expedia vacation package?
Yes — that’s one of the best things about an Expedia package. You’re the boss! We have access to more than 550 airline partners across the globe, so you have options galore when putting together your The Berkshires escape.
If I'm not able to travel, can I cancel my The Berkshires vacation package?
Don’t stress if you’re rethinking your The Berkshires vacation package — it’s possible to cancel or amend your booking. And if you’ve booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We totally understand life can sometimes throw a spanner in the works, so make your way to our Customer Service Portal if that happens. When you’re ready to make changes, we’re ready to help.

Discover the most popular places to visit in The Berkshires

Image for Tanglewood Music Center

Tanglewood Music Center

5/5(6 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.

Tanglewood Music Center
Image for Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this quaint area.

Jiminy Peak Mountain Resort
Image for Norman Rockwell Museum

Norman Rockwell Museum

4.5/5(6 reviews)

You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.

Norman Rockwell Museum

What to do in The Berkshires

Image for Stockbridge Showdown MA Scavenger Hunt

Stockbridge Showdown MA Scavenger Hunt

CA $37
Per adult
Stockbridge Showdown MA Scavenger Hunt
See all activities in The Berkshires

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.