Lenox Holidays

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Lenox Holiday

Our pick of the best 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 NZ$197 per night from 20 Nov to 21 Nov
NZ$197
per night
20 Nov - 21 Nov
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 NZ$243 per night from 29 Nov to 30 Nov
NZ$243
per night
29 Nov - 30 Nov
Berkshires Untold
The Whitlock

The Whitlock

2 out of 5
16 Church St Lenox MA
The price is NZ$231 per night from 12 Nov to 13 Nov
NZ$231
per night
12 Nov - 13 Nov
8.4/10 Very good! (414 reviews)
"The Whitlock provided just the right vibe for a friends fall vacation. We loved the coffee and tea downstairs, and even though the room did not have a fridge, the staff was very helpful about letting us use a community fridge. The rooms were clean and an appropriate size for a cozy vacation. The ..."

Reviewed on 3 Nov 2026

The Whitlock
See all 1,380 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.
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Frequently asked questions

How much does a Lenox holiday package cost?
You can pick up a holiday package to this destination on Expedia. But how much your holiday 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?
If you're hoping to snag a cheap Lenox holiday package, consider planning a trip in January, March and April. You're likely to find better rates on hotels and flights during these quieter months — perfect for a budget-friendly break.
How many days is enough for Lenox?
For a Lenox holiday, a handful of days will be enough to explore the top spots. Make sure to check out The Mount — it's one of the major attractions in this destination. If you want more adventure, think about basing yourself here and setting off on some day trips from Lenox.
Is it worth booking a holiday package to Lenox?
Lenox is a good holiday destination with attractions like The Mount among the many things to keep you busy. Whether you're travelling with the family or planning a trip with friends, a Lenox holiday 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 holiday package as early as possible.
Is it cheaper to book a Lenox holiday as a package?
You can enjoy significant savings on your Lenox getaway by booking a tailored holiday package. Click on the "Package" heading, then enter your destination and travel dates to view some great hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday 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. Choose when to travel: Check your calendar and get packing. Your favourite season and the type of activities available will also help you decide when to escape to Lenox.
  2. Work out your budget: Ensure you have enough money to cover everything from meals and transportation to flights and activities. Your accommodation will likely be the largest expense during your trip to Lenox.
  3. Decide how long to go away for: Now that you're up to speed on Lenox, you can figure out the ideal length of your break. Create a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a tailored Lenox holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.