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
AED 389
AED 435 total
1 Nov - 2 Nov
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
"Gave my jacuzzi room, that I paid extra for, away to the wrong person because we had the same first name."

Reviewed on 4 October 2026

The Yankee Inn
Berkshires Untold

Berkshires Untold

194 Pittsfield Rd Lenox MA
AED 484
AED 540 total
1 Nov - 2 Nov
includes taxes & fees
Berkshires Untold
The Whitlock

The Whitlock

16 Church St Lenox MA
AED 468
AED 523 total
2 Nov - 3 Nov
includes taxes & fees
The Whitlock
See all 1,369 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'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 — 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.

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