Lenox Vacations

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    Save up to SARĀ 5,400 when you book a flight and hotel together*

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Find the Best Lenox Vacation Packages

Lenox Hotel Deals

The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is SARĀ 672 per night from Jul 19 to Jul 20
SARĀ 672
SARĀ 751 total
19 Jul - 20 Jul
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"I still suffer from bed bugs bite and mosquito, we were placed in the old room, old carpet and smelly room. The staff were nice and the cleaners too. I just wish we could have stayed in the main building."

Reviewed on 15 July 2026

The Yankee Inn
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is SARĀ 700 per night from Jul 30 to Jul 31
SARĀ 700
SARĀ 782 total
30 Jul - 31 Jul
includes taxes & fees
9/10 Wonderful! (1,020 reviews)
"The rooms were very small, the fridge in the room was not working there was no microwave in the entire property, we couldn't heat up our toddler food."

Reviewed on 16 July 2026

Berkshires Untold
The Whitlock

The Whitlock

2 out of 5
16 Church St Lenox MA
The price is SARĀ 653 per night from Jul 30 to Jul 31
SARĀ 653
SARĀ 729 total
30 Jul - 31 Jul
includes taxes & fees
8.4/10 Very Good! (330 reviews)
"Canā€™t beat the location. Hotel has a lot of character and great outdoor space."

Reviewed on 15 July 2026

The Whitlock
See all 1,396 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.

Stay near popular Lenox attractions

A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.

Tanglewood Music Center

9.6/10 (457 reviews)
Tanglewood enchants as the summer home of the Boston Symphony Orchestra, set in the picturesque Berkshire Hills. Enjoy world-class performances while picnicking on the expansive lawns as the sun sets over the mountains.
See properties

Frequently asked questions

How much does a Lenox vacation package cost?
You'll find cheap prices on Expedia for your Lenox getaway. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Lenox costs.
What are the cheapest months to go to Lenox?
If you'd like to snag a cheap Lenox vacation package, consider traveling in January, March and April. You'll generally find better rates on hotels and airfares during these quieter months ā€” ideal for a budget-friendly break.
How to find the best Lenox package deals?
Finding a cheap Lenox package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, apply a couple of filters and see what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Lenox package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Lenox vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component separately. And you'll still get the freedom to create a tailored Lenox vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Lenox?
If you've got your Lenox travel dates finalized, book early to bag some incredible deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Lenox?

  1. Choose when to travel: Check your diary and pack your bags. Your preferred season and the type of activities on offer will also help you decide when to vacation in Lenox.
  2. Plan your budget wisely: In addition to the cost of your hotel, you'll need to consider other expenses too. These include food, transportation and flights. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Lenox.
  3. Decide how many days away: Start by compiling a list of the activities and sights you want to experience in Lenox. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a tailored Lenox vacation package.