Lenox Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Lenox Vacation

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 vacation packages are calling your name. Make your trip to Lenox even more fun by going sightseeing. Tanglewood Music Center, 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, organizing a tailored Lenox vacation is a walk in the park with Expedia.

Ready to book your vacation to Lenox?

 

Choose your dates

Lenox Hotel Deals

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 CA $163 per night from Nov 20 to Nov 21
CA $163
CA $182 total
Nov 20 - Nov 21
includes taxes & fees
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 CA $150 per night from Dec 6 to Dec 7
CA $150
CA $167 total
Dec 6 - Dec 7
includes taxes & fees
9/10 Wonderful! (1,071 reviews)
"A beautiful relaxing vibe! The gathering area is comfortable with a full variety of, games, food. The lighting brings. Alm to the day"

Reviewed on Nov 11, 2026

Berkshires Untold
The Whitlock

The Whitlock

2 out of 5
16 Church St Lenox MA
The price is CA $150 per night from Dec 1 to Dec 2
CA $150
CA $168 total
Dec 1 - Dec 2
includes taxes & fees
8.4/10 Very good! (420 reviews)
"The room was clean, parking was easy, shower & bed were great. We had a 'cozy queen' and it was very small, no closet, but adequate for a one-night stay. We were disappointed that the restaurant, advertised to be open for breakfast, and the salsa bar, later in the day, were both closed."

Reviewed on Nov 13, 2026

The Whitlock
See all 1,384 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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)
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.
See properties

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 travelling 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 many days is enough for Lenox?
You can visit all the major attractions in Lenox in a few days, including the must-see The Mount. If you're looking for a longer Lenox vacation, look at what kind of excursions and activities are available close by.
Is it worth booking a vacation package to Lenox?
It's no wonder a Lenox vacation is on the must-do list of many travellers. Leading attractions like The Mount are just the beginning of things to see and do here.
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," "Traveller 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 travelling 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.

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