Book Exclusive The Berkshires Vacation Packages

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The Berkshires flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
per person
Jul. 12 - Jul. 14
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
Book a stay at this business-friendly hotel in Latham. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
per person
Jul. 12 - Jul. 14
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Courtyard by Marriott Albany Troy/Waterfront

Courtyard by Marriott Albany Troy/Waterfront

3 out of 5
per person
Jul. 12 - Jul. 14
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Troy. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Troy Waterfront Farmers' Market and Arts Center of the Capital Region are located nearby.

Top The Berkshires hotels deals

Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $162 per night
CA $162
per night
Jun. 3 - Jun. 4
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.
Pet-friendly
Breakfast available
Hotel Downstreet

Hotel Downstreet

3 out of 5
40 Main St, North Adams, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $195 per night
CA $195
per night
Jun. 24 - Jun. 25
Stay at this hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Massachusetts Museum of Contemporary Art and Studio 21 South are located nearby.
Hot tub
Pet-friendly
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $254 per night
CA $254
per night
Jun. 5 - Jun. 6
Stay at this 3.5-star spa hotel in Stockbridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the pool and the restaurant in our reviews. Popular attractions Tanglewood Music Center and Schantz Galleries are located nearby.
Pet-friendly
Spa
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $165 per night
CA $165
per night
Jun. 16 - Jun. 17
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Hot tub
Breakfast included
The Lenox Collection

The Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
The price is CA $134 per night
CA $134
per night
Jun. 12 - Jun. 13
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Lenox Library are located nearby.
Breakfast included
Parking included
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $141 per night
CA $141
per night
Jun. 9 - Jun. 10
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Mahaiwe Performing Arts Center and Housatonic River Walk are located nearby.
Breakfast included
Parking included
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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.

Popular places to visit

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

Frequently asked questions

How much are vacation packages to The Berkshires?
CA $1,029 is all you’ll need for a memorable vacation in The Berkshires. Bundle your hotel and flights into a vacation package with Travelocity and see your savings add up. With prices this good, there’s never been a better time to travel.
Where can I get the best vacation package deals for The Berkshires?
For a fun and affordable package deal to The Berkshires, head straight to Travelocity. Take your pick from as many as 400 partner airlines and 665,000 worldwide properties to create the ultimate trip — it’s as easy as that.
Why should I book my The Berkshires vacation bundle with Travelocity?
Whether you’re on the hunt for the ultimate unplugged getaway or you crave the fun and excitement of the big smoke, booking everything with Travelocity saves you time, money and hassle. No need to search through hundreds of different websites to find the best deal — our Price Match Guarantee ensures you’ll always score the lowest possible price, and our professional customer service experts are available round-the-clock.
Can I save money on my The Berkshires car rental if I combine it with a hotel or flight?
Absolutely. And our The Berkshires vacation packages will help you do it. With only a few clicks you can save cash and time by bundling your bookings. Collect the keys to your rental car and feel the freedom of the open road. Searching for things to do? Throw some tours or experiences into your package and make savings on those too.
What is the best time of year to go to The Berkshires?
are the months when most travelers visit, while are typically less busy. If you’re traveling with a limited budget, you’d be better off if you visit during . is regarded as the costliest time of year to come here.
Which airport is best for The Berkshires?
Hartford, CT (BDL-Bradley Intl.) is often the first choice for many people visiting the region. But depending on your itinerary, Albany, NY (ALB-Albany Intl.) or Hartford, CT (HFD-Hartford - Brainard) could suit you better.
What is there to do in The Berkshires?
A visit to The Berkshires isn’t complete without stopping at Jiminy Peak Mountain Resort. Ensure this popular sight is right at the top of your itinerary.
Can I go on vacation to The Berkshires at this time?
Our team has the local know-how to ensure your travel dreams come true, so before booking a ticket to The Berkshires, look over our Covid-19 Travel Advisor. Here you’ll find all the current info about quarantine policies, travel restrictions and other useful advice.