Lenox Vacations from $401

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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.

The Latest Lenox vacation packages

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Save 100% on your flight
per person
Sep 13 - Sep 20
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
8.6/10 Excellent! (1,862 reviews)
I loved the pool for the kids, it a quiet place

Reviewed on Jul 13, 2025

DoubleTree by Hilton Schenectady Downtown

DoubleTree by Hilton Schenectady Downtown

4 out of 5
Seward Place
Save 100% on your flight
per person
Sep 13 - Sep 20
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
8.4/10 Very Good! (664 reviews)
Hotel was beautiful. The room was clean and maintenance crew kept it clean.

Reviewed on Jul 12, 2025

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
8.2/10 Very Good! (1,005 reviews)
The property was clean and the staff very pleasant, but the key card often stopped working. Also, the doors didn’t close easily (or securely) so we had to keep making sure we secured it after ourselves.

Reviewed on Jul 13, 2025

Brook Bound Inn

Brook Bound Inn

2 out of 5
Save 100% on your flight
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9.4/10 Exceptional! (10 reviews)
Forget-me-not by Avantstay Bold Lakefront Escape

Forget-me-not by Avantstay Bold Lakefront Escape

3 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
No reviews
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Discover the most popular places to visit in Lenox

A road near Tanglewood. Driving through the Berkshires is never a disappointing #roadtrip

Tanglewood Music Center

5/5(150 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
Bye fall

Pleasant Valley Wilderness Sanctuary

Explore the great outdoors at Pleasant Valley Wilderness Sanctuary, a lovely green space in Lenox. Wander the lakeside in this family-friendly area.

Pleasant Valley Wilderness Sanctuary

The Mount

5/5(37 reviews)

You can spend an afternoon studying the exhibits at The Mount during your trip to Lenox. While you're in the area, stroll along the lakeside.

The Mount

Lenox Hotel Deals

Berkshires Untold
Berkshires Untold
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $223 total per night from Jul 15 to Jul 16
$223 total
Jul 15 - Jul 16
Total includes taxes and fees
9/10 Wonderful! (632 reviews)
"I’ve stayed at this property several times including before it changed management. We have always enjoyed everything about it. My only strong suggestion is that there is better signage out by the highway. You do not see the hotel or the sign until you get very close to the turn and it is a very busy ..."

Reviewed on Jul 10, 2025

Berkshires Untold
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $141 total per night from Jul 24 to Jul 25
$141 total
Jul 24 - Jul 25
Total includes taxes and fees
9/10 Wonderful! (1,011 reviews)
Great location for Tanglewood
"Friendly staff, clean rooms and a very nice breakfast buffet. Staff went out f their way to help locate and ship two items that I had left behind."

Reviewed on Jul 10, 2025

The Yankee, Trademark Collection by Wyndham
The Constance by the Lenox Collection
The Constance by the Lenox Collection
3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
$167 nightly
The price is $187 total per night from Jul 15 to Jul 16
$187 total
Jul 15 - Jul 16
Total includes taxes and fees
8.6/10 Excellent! (433 reviews)
"Very convenient and walkable to downtown Lenox, plus there's a free EV charger at the property. The inn is old but charming -- i.e., the library with its wood paneling, its out-of-tune grand piano, and the orange upholstered furniture; definitely feels like staying at an inn during a different age! ..."

Reviewed on Jul 9, 2025

The Constance by the Lenox Collection
See all 1,422 properties in Lenox
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.

Find the Best Lenox Vacation Packages

Lenox Essential Information

Language
English
Currency
U.S dollars
Population
1,700
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Norman Rockwell Museum, Ski Butternut and Bousquet Ski Area

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Frequently asked questions

How much does a Lenox vacation package cost?
You can pick up a vacation package to this destination from $401 on Expedia. But how much your vacation to Lenox costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Lenox?
You can typically find reduced prices and better availability in October, November and December. Check out our cheap Lenox vacation packages and you could land some great off-season discounts.
How many days is enough for Lenox?
You can easily see all the main attractions in Lenox in a few days, including the popular The Mount. If you're after a longer Lenox vacation, look at which kind of activities and excursions are available nearby.
Is it worth booking a vacation package to Lenox?
Lenox is a good vacation destination with attractions like Tanglewood Music Center among the many things to keep you entertained. Whether you're traveling with the family or getting away with friends, a Lenox vacation promises a good time for everyone.
How to find the best Lenox package deals?
Use Expedia's filters to find some fabulous Lenox package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Lenox package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Lenox vacation as a package?
You can enjoy significant savings on your Lenox getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to view some great hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Lenox?
If you're planning an impromptu Lenox getaway, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Lenox?

  1. Pick the ideal time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to visit Lenox.
  2. Set your budget: Consider expenses like flights, transportation and food when calculating how much to save for your trip to Lenox. Then, select a property that matches your budget, whether that's an affordable stay or a more upscale retreat.
  3. Use Expedia's trip planning tool to explore Lenox: Research every part of your trip to Lenox with this handy planner. Invite your friends and family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Decide your trip length: Think about how long you'd like to spend exploring Lenox. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
  5. Bundle your airfare and accommodations: Once you've settled on your trip dates and duration, lock in the perfect Lenox vacation package for you.
  6. Book any activities or day trips: Now to the fun part --- locking in everything you want to do and see. Browse some of the exciting things to do in Lenox and book your tickets early to save time (and maybe some spending money too!).

Does Expedia offer Book Now, Pay Later Lenox vacation packages?
Set off on your perfect trip to Lenox with help from our Book Now, Pay Later vacations. There's no need to save like crazy or wait until your next payday --- we've teamed up with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily budget for your trip and snap up bargains before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.