Lenox Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Lenox

The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
The price is 3.300.570 ₫ per night from 30 Jun to 1 Jul
3.300.570 ₫
3.686.684 ₫ total
30 Jun - 1 Jul
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Nice place to stay. Good breakfast."

Reviewed on 23 Jun 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
The price is 4.040.317 ₫ per night from 25 Jun to 26 Jun
4.040.317 ₫
4.512.875 ₫ total
25 Jun - 26 Jun
includes taxes & fees
8.6/10 Excellent! (420 reviews)
"Very good"

Reviewed on 22 Jun 2025

The Constance by the Lenox Collection
Berkshires Untold
Berkshires Untold
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
9/10 Wonderful! (611 reviews)
"Good Attentive Staff with Good Comfortable Room."

Reviewed on 22 Jun 2025

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Berkshires Untold
See all 1,412 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.

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.

Popular places to visit

Pleasant Valley Wilderness Sanctuary

Pleasant Valley Wilderness Sanctuary

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

Pleasant Valley Wilderness Sanctuary

Shakespeare and Company

You can make plans for a show at Shakespeare and Company during your trip to Lenox. While you're in the area, stroll along the lakeside.

Shakespeare and Company

Ventfort Hall Mansion and Gilded Age Museum

You can spend an afternoon browsing the exhibits at Ventfort Hall Mansion and Gilded Age Museum during your trip to Lenox. Wander the lakeside in this family-friendly area.

Ventfort Hall Mansion and Gilded Age Museum