Lenox Vacations from $413

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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
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
8.6/10 Excellent! (1,862 reviews)
This is a great get away! Beautiful atmosphere and lots of variety of activities

Reviewed on Jul 17, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Save 100% on your flight
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
7.4/10 Good! (491 reviews)
The property was historic and very quaint and the common areas were nice. Coffee was good. For the price paid -carpet in halls & elevator needed replaced/woodwork repainted. Air conditioner was a window unit/room outdated.

Reviewed on Jul 14, 2025

Club Wyndham Bentley Brook

Club Wyndham Bentley Brook

3 out of 5
Save 100% on your flight
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
9.2/10 Wonderful! (530 reviews)
Really nice modern units and layout. Loved the car charger for our EV. We stayed in and cooked, as there were minimal food options in the area. Lovely stay and we will be back!

Reviewed on Jun 7, 2025

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 2
found 4 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
No reviews
DoubleTree by Hilton Schenectady Downtown

DoubleTree by Hilton Schenectady Downtown

4 out of 5
Seward Place
per person
Aug 28 - Sep 2
found 4 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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

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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 21 to Jul 22
$223 total
Jul 21 - Jul 22
Total includes taxes and fees
9/10 Wonderful! (636 reviews)
Beauty Berkshire stay
"This was one of my favorite hotels I have ever stayed in. The room and lounge/restaurant are beautiful. Rooms are super quiet, and the bed was incredibly comfortable. I am sure to return."

Reviewed on Jul 17, 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
$135 nightly
The price is $151 total per night from Jul 30 to Jul 31
$151 total
Jul 30 - Jul 31
Total includes taxes and fees
9/10 Wonderful! (1,014 reviews)
"Loved the Yankee Inn!"

Reviewed on Jul 14, 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
$180 nightly
The price is $202 total per night from Jul 22 to Jul 23
$202 total
Jul 22 - Jul 23
Total includes taxes and fees
8.6/10 Excellent! (440 reviews)
A wonderfully elegant inn
"Lovely, charming inn. Very clean and comfortable. I especially appreciated the quiet air conditioning split. Logan, who checked us in, was very warm and helpful. Some suggestions: a safety bar in the shower would be helpful to older guests, as would a rubber mat on the shower floor; tile is slippery. ..."

Reviewed on Jul 17, 2025

The Constance by the Lenox Collection
See all 1,421 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 $413 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.