Lenox Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AEDĀ 5,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 AEDĀ 555 per night from Jul 9 to Jul 10
AEDĀ 555
AEDĀ 620 total
9 Jul - 10 Jul
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
"Great location with easy parking Excellent cleaning staff. Done promptly and right. Very helpful front desk staff."

Reviewed on 7 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 AEDĀ 685 per night from Jul 13 to Jul 14
AEDĀ 685
AEDĀ 765 total
13 Jul - 14 Jul
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Great ā€œmotelā€ close to Lenox and Tanglewood! Nice rooms, nicely decorated. Vibrant restaurant/bar in lobby. Nice outdoor seating with a band playing. Small but good menu."

Reviewed on 4 July 2026

Berkshires Untold
The Whitlock

The Whitlock

2 out of 5
16 Church St Lenox MA
The price is AEDĀ 569 per night from Jul 15 to Jul 16
AEDĀ 569
AEDĀ 636 total
15 Jul - 16 Jul
includes taxes & fees
8.4/10 Very Good! (323 reviews)
"Be careful - this property charges your credit card for the stay when you check in online, after youā€™ve already paid Expedia. It is very difficult to reach a responsible individual/manager to resolve the billing dispute, and they havenā€™t been responsive to Expedia either."

Reviewed on 8 July 2026

The Whitlock
See all 1,399 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.