Lenox Vacations

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Find the Best Lenox Vacation Packages

Lenox Hotel Deals

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
The price is SAR 434 per night from Jun 17 to Jun 18
SAR 434
SAR 484 total
17 Jun - 18 Jun
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"Lovely staff!"

Reviewed on 31 May 2025

The Yankee, Trademark Collection by Wyndham
Berkshires Untold
Berkshires Untold
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is SAR 570 per night from Jun 15 to Jun 16
SAR 570
SAR 637 total
15 Jun - 16 Jun
includes taxes & fees
9/10 Wonderful! (600 reviews)
"Great spot for hitting hiking spots"

Reviewed on 27 May 2025

Berkshires Untold
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 SAR 557 per night from Jun 15 to Jun 16
SAR 557
SAR 622 total
15 Jun - 16 Jun
includes taxes & fees
8.6/10 Excellent! (412 reviews)
"Lovely old building. Cosy and picturesque. Wish I had know that my room was on the 3rd floor because it got hard climbing those stairs after a while. A clock in the room and some lights in the hallways would have been nice. Friendly, helpful staff. Comfortable parlor to hang out. Breakfast was ..."

Reviewed on 1 June 2025

The Constance by the Lenox Collection
See all 1,400 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 vacation package cost?
You can pick up a vacation package to this destination 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?
If you’re hoping to snag a cheap Lenox vacation 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 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. Choose when to travel: Check your calendar and get packing. Your favorite 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 accommodations 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 vacation package.

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