Lenox Vacations

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Find the Best Lenox Vacation Packages

Lenox Hotel Deals

The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
NT$3,430
NT$3,831 total
Oct 27 - Oct 28
includes taxes & fees
9.2/10 Wonderful! (1,016 reviews)
"Nice room. Exceptionally clean. Great staff"

Reviewed on 2026/9/28

The Yankee Inn
Berkshires Untold

Berkshires Untold

194 Pittsfield Rd Lenox MA
NT$4,969
NT$5,551 total
Sep 30 - Oct 1
includes taxes & fees
9/10 Wonderful! (1,028 reviews)
"Amazing!"

Reviewed on 2026/9/28

Berkshires Untold
The Whitlock

The Whitlock

16 Church St Lenox MA
NT$4,646
NT$5,190 total
Oct 29 - Oct 30
includes taxes & fees
8.4/10 Very Good! (387 reviews)
"The hotel staff were very friendly and helpful. There is ample parking and the location in town is great for walking to shops and restaurants. This is a very nice property."

Reviewed on 2026/9/25

The Whitlock
See all 1,402 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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A large white mansion surrounded by dense green trees and a clear blue sky with clouds.

The Mount

9.4/10 (174 reviews)
Edith Wharton designed this 42-room mansion herself, showcasing her architectural vision alongside literary legacy. Explore elegant interiors and Italianate gardens while attending seasonal author events.
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A grassy field with a prominent tree and a small house in the distance.
Photo by Ed Gaffny

Wyndhurst Golf & Club

8.4/10 (46 reviews)
This historic 1926 golf course challenges players with tree-lined fairways and contoured greens against Berkshire mountain backdrops. Enjoy Wayne Stiles' classic design, then unwind at the elegant manor house.
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Shakespeare and Company

9.2/10 (76 reviews)
Experience world-class Shakespeare performances in the scenic Berkshires at one of America's largest Shakespeare festivals. Summer evening shows offer magical theatrical moments under the stars.
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Ventfort Hall Mansion and Gilded Age Museum

9.2/10 (65 reviews)
Explore the opulent 1893 Jacobean Revival mansion built for J.P. Morgan's sister during the Gilded Age. Immerse yourself in restored period rooms while enjoying Victorian teas or performances in authentic splendor.
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Lenox Library

9.0/10 (45 reviews)
The Lenox Library occupies a stately Greek Revival building, once the Berkshire County Courthouse. Browse Colonial manuscripts and rare first editions while admiring the beautifully restored 19th-century architecture.
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Lenox Mountain

10.0/10 (2 reviews)
Hike through verdant forests to Lenox Mountain's summit for panoramic views of the Berkshire valleys. Fall visitors are rewarded with a spectacular tapestry of autumn foliage colors.
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Kennedy Park

9.2/10 (86 reviews)
Kennedy Park's hardwood forests and carriage roads offer exceptional hiking and mountain biking trails. Explore scenic vistas during fall foliage when the landscape transforms into a vibrant natural spectacle.
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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 many days is enough for Lenox?
For a Lenox vacation, 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 vacation package to Lenox?
Lenox is a good vacation destination with attractions like The Mount among the many things to keep you busy. Whether you're traveling with the family or planning a trip with friends, a Lenox vacation 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 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.

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