Lenox Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Lenox Vacation
There's loads to like about Lenox, from its cultural experiences to its spectacular views. When you're ready to say hi to this interesting city, our Lenox vacation packages are calling your name. Make your trip to Lenox even more fun by going sightseeing. Tanglewood Music Center, National Shrine of the Divine Mercy and Lee Premium Outlets are some of the major attractions you'll want to explore. No matter your travel plans or budget, organizing a tailored Lenox vacation is a walk in the park with Expedia.
Top Lenox Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
Price was CA $612, price is now CA $506 per person
CA $506
per person
Aug 31 - Sep 3
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (2,396 reviews)
Have stayed multiple times. Staff is friendly, always working to make the resort clean and enjoyable! Love the rooms. Very relaxing environment.
Reviewed on Jun 23, 2026
Berkshire Mountain Lodge
Price was CA $632, price is now CA $524 per person
CA $524
per person
Aug 31 - Sep 3
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (980 reviews)
Property very well maintained, everything you would need for an extended stay, we stayed one night for a show at Tanglewood(20” away) The rooms have microwave, fridge, dishes, dishwasher,etc. everything you would need to eat in. Also pool, hot tub, exercise and movies at night in a great room. Helpful staff, great price for a great room( separate dining area, living area, bedroom and huge bathroom!!!!!) extra clean woukd def go back
Reviewed on Jun 21, 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Price was CA $743, price is now CA $621 per person
CA $621
per person
Aug 31 - Sep 3
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (910 reviews)
Mini golf was amazing, as was having access to shuffleboard, cornhole and more. And the arcade was great, too, we went back many times! Room was clean and nice with it's own balcony and the resort was calm and quiet.
Reviewed on Jun 19, 2026
Best Western Plus Berkshire Hills Inn & Suites
Price was CA $634, price is now CA $545 per person
CA $545
per person
Aug 31 - Sep 3
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
8.6/10 Excellent! (1,001 reviews)
The towels and bedding were very nice and the bed was comfortable. There was ample, close parking. However, the sink drain was slow. There was no body wash in the shower. The refrigerator noise was so loud we had to unplug it while we slept. The breakfast was poor (no fruit or meat) and the eggs & biscuits and gravy were barely warm. I would not recommend this hotel.
Reviewed on Jun 17, 2026
The Yankee Inn
Price was CA $693, price is now CA $597 per person
CA $597
per person
Aug 31 - Sep 3
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (1,016 reviews)
I had an excellent experience with the Yankee Inn. The room was updated and the house keeping was excellent. The location was good and the staff was very nice. The breakfast was very good. I would definitely recommend staying here.
Reviewed on Jun 23, 2026
Lenox Hotel Deals
The Yankee Inn
461 Pittsfield Rd Lenox MA
The price is CA $203 per night from Jul 7 to Jul 8
CA $203
CA $226 total
Jul 7 - Jul 8
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"I had an excellent experience with the Yankee Inn. The room was updated and the house keeping was excellent. The location was good and the staff was very nice. The breakfast was very good. I would definitely recommend staying here."
Reviewed on Jun 23, 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
The price is CA $233 per night from Jul 7 to Jul 8
CA $233
CA $261 total
Jul 7 - Jul 8
includes taxes & fees
Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd Lenox MA
The price is CA $225 per night from Jun 29 to Jun 30
CA $225
CA $251 total
Jun 29 - Jun 30
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"The breakfast was excellent. Lots of items."
Reviewed on Jun 18, 2026
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.
Discover the most popular places to visit in Lenox
Ventfort Hall Mansion and Gilded Age Museum
You can spend an afternoon exploring the galleries in Ventfort Hall Mansion and Gilded Age Museum during your travels in Lenox. Wander the lakeside in this family-friendly area.
Lenox Library
Lenox Library is just one of the places to see in Lenox, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's gardens or attend a sporting event.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
