Lenox Holidays

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Your Lenox Holiday

There's loads to like about Lenox, from its cultural experiences to its spectacular views. When you're ready to say hi to this interesting city, our Lenox holiday packages are calling your name. Make your trip to Lenox even more fun by going sightseeing. Tanglewood Music Centre, National Shrine of the Divine Mercy and Lee Premium Outlets are some of the major attractions you'll want to explore. No matter your travel plans or budget, organising a tailored Lenox holiday is a walk in the park with Expedia.

Lenox Essential Information

Language
English
Currency
U.S dollars
Population
1,700
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Norman Rockwell Museum, Ski Butternut and Bousquet Ski Area

Top hotels in Lenox

The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
£130
14 Sept - 15 Sept
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"It was very convenient for an overnight with pool and close to downtown. Affordable. I stayed in the annex so no noise from other guests!"

Reviewed on 14 Aug 2026

The Yankee Inn
Berkshires Untold

Berkshires Untold

194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
£108
8 Sept - 9 Sept
includes taxes & fees
Berkshires Untold
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
£65
31 Aug - 1 Sept
includes taxes & fees
7.6/10 Good! (894 reviews)
"Great hotel for a reasonable price. The only drawback is that they didn’t offer shampoos and body wash like most hotels but otherwise a great value."

Reviewed on 14 Aug 2026

Howard Johnson by Wyndham Lenox
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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.
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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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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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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 splendour.
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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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Lenox Mountain

10.0/10 (2 reviews)
Hike through verdant forests to Lenox Mountain's summit for panoramic views of the Berkshire valleys. Autumn visitors are rewarded with a spectacular tapestry of autumn foliage colours.
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Frequently asked questions

Why should I book my Lenox holiday with Expedia?
Choose Expedia to plan your next escape with ease, all in the same place. Our insider tip for scoring an unbeatable deal on a Lenox getaway? Bundle your hotel, flights and/or car hire into a package holiday. Then throw in some exciting tours and activities. Many bookings also include flexible cancellation policies, so there's no need to stress if you have to switch up your travel agenda. Round-the-clock assistance with amending and cancelling your trip is on-hand via our Customer Service Portal link.
When is the best time of year to holiday in Lenox?
Enjoy sightseeing but don't like huge crowds? Organise your Lenox trip for October, November and December. Typically, it's much quieter than in February, May and July. Organise your visit to Lenox according to what type of adventure you're looking for. January is the coolest month, when daytime temperatures average -5ºC. In July, the warmest period, you can expect averages of 21ºC during the day.
What is the top hotel for my holiday in Lenox?
Offering plenty of amenities and a cosy place to relax between adventures, Boston Park Plaza will make the ideal base for your Lenox escape.
How do I get a cheap holiday to Lenox?
Bundle your flights and hotels with Expedia to save on your next big adventure. With more than 400 airlines and 321,000 hotel options across the globe, your Lenox holiday can be customised exactly to suit your travel style. With all that extra cash, why not add a few fun tours and experiences? It's an easy way to unlock even more savings. That dream holiday to Lenox is closer than you thought! Learn more about how you can save money on your next holiday when you book a flight and hotel together with Expedia.
What should I do on my Lenox holiday?
With popular attractions like Tanglewood Music Centre and National Shrine of the Divine Mercy, a holiday in Lenox promises lots of fun things to do and see. Norman Rockwell Museum and Lee Prime Outlets are two other sights worth discovering.
What is the best area to stay in when on holiday in Lenox?
There's so much to do in Lenox, so stay close to its attractions and treat yourself to more time sightseeing. Tanglewood Music Centre is one place to add to your itinerary.
Do I need a visa for my Lenox holiday?
Official government websites are the best source of information on visa requirements, application procedures and any supporting documentation. Your nationality and reason for your visit, whether it be for holidays or business, will determine if you need a visa for Lenox. Also double-check that your passport is up to date and has a minimum of six months validity remaining beyond the date of your intended return. Finalise all your travel planning well in advance to avoid any last-minute surprises.
What should I wear on my Lenox holiday?
Do some research into the types of clothing people in Lenox wear, and maybe even look up social media fashion pages for inspiration. Aim to create a versatile wardrobe filled with pieces that suit your destination and show off your unique sense of style. Daytime temperatures in January, Lenox's coolest month, average -5ºC. July marks this city's warmest month when average temperatures reach 21ºC. Our top tip? Take the guesswork out of what to pack and check the weather forecast.
What does an Expedia Lenox holiday include?
Select from any combination of hotels, flights and hire cars. Once you've made your booking, add the fun stuff like experiences and activities. Want to pick your fare class? That's easily done too. The choice is all yours when it comes to planning your ideal Lenox getaway. Private holiday homes and condos are a few of the most highly sought-after property types in Lenox. No matter your group size or holiday style, you can rely on Expedia for the flexibility to personalise your next big adventure.
Does Expedia offer Book Now, Pay Later Lenox holidays?
Yes, we do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply pick the payment plan that suits best during checkout and take the stress out of budgeting for your next trip. Be sure to bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:
  • Pay monthly holidays: Klarna offers convenient monthly payment plans that work for all types of budgets, so you can take that well-deserved holiday now.
  • No-deposit holidays: Hitting the "book now" button is easier with this payment plan. With no upfront fee for your getaway, you can Book Now, Pay Later and get on your way.
Can I choose my airline with a Lenox Expedia holiday?
Expedia has access to more than 400 partner airlines globally, so you sure can! Just choose the carrier that suits you and craft the perfect Lenox escape.

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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. Flight-inclusive packages are ATOL protected.