Lenox Holidays from £4,263

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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.

Top Lenox Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was £4,514, price is now £4,263 per person
£4,263
per person
28 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LON) to Albany (ALB)
8.6/10 Excellent! (143 reviews)
Quiet property. Convenient location.

Reviewed on 2 Aug 2026

Forget-me-not by Avantstay Bold Lakefront Escape

Forget-me-not by Avantstay Bold Lakefront Escape

3 out of 5
Price was £5,949, price is now £5,440 per person
£5,440
per person
28 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LON) to Albany (ALB)
No reviews

Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

3 out of 5
Price was £5,656, price is now £5,221 per person
£5,221
per person
28 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LON) to Albany (ALB)
No reviews

Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was £4,979, price is now £4,668 per person
£4,668
per person
28 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LON) to Albany (ALB)
9.8/10 Exceptional! (38 reviews)
Once I got the cabin I expected it was an amazing stay. Right on the water as shown on the website. I look forward to my next stay.

Reviewed on 1 Aug 2026

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3 out of 5
Price was £5,041, price is now £4,746 per person
£4,746
per person
28 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LON) to Albany (ALB)
10/10 Exceptional! (1 review)
What a charming home! The bathrooms and bedrooms were updated beautifully. The downstairs was updated enough while keeping the character.

Reviewed on 14 Jan 2026

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

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is £145 per night from 20 Aug to 21 Aug
£145
20 Aug - 21 Aug
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
"This was our fourth year in a row staying at the Inn. They have a new sitting area outside with a gas fire pit, very nice. The pool is always very well maintained. We like to stay in the older section room away from the main building, the beds are comfortable and the room is basic but clean and nice. ..."

Reviewed on 5 Aug 2026

The Yankee Inn
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is £122 per night from 1 Sept to 2 Sept
£122
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (1,014 reviews)
"Lovely property, imaginative and we. Well-maintained. Food was very good but somewhat overpriced. Staffing was a bit scant. No cash on the property so it was difficult to change a bill and provide an accurate tip for housekeeping."

Reviewed on 4 Aug 2026

Berkshires Untold
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is £66 per night from 1 Sept to 2 Sept
£66
1 Sept - 2 Sept
includes taxes & fees
7.6/10 Good! (892 reviews)
"Parking"

Reviewed on 2 Aug 2026

Howard Johnson by Wyndham Lenox
See all 1,380 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.
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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.
See properties

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.