Lenox Holidays
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Lenox Holiday
Our pick of the best Lenox Hotel Deals
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
NZ$226
22 Sept - 23 Sept
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"The room was very clean with a nice bathroom and close to Tanglewood!"
Reviewed on 20 Sept 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
NZ$273
28 Sept - 29 Sept
includes taxes & fees
9/10 Wonderful! (1,019 reviews)
"Hello it was husband and I anniversary and our stay was wonderful the ambience decorations was top-tier. Our room was clean. Temperature was perfect fireplace was really cozy. The only negative thing I would say was the food and the hotel was overpriced and the taste was underwhelming."
Reviewed on 19 Sept 2026
The Whitlock
16 Church St Lenox MA
NZ$271
22 Sept - 23 Sept
includes taxes & fees
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
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.
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.
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.
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.
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.
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.
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.
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.
Frequently asked questions
How much does a Lenox holiday package cost?
You can pick up a holiday package to this destination on Expedia. But how much your holiday 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 holiday 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 holiday, 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 holiday package to Lenox?
Lenox is a good holiday destination with attractions like The Mount among the many things to keep you busy. Whether you're travelling with the family or planning a trip with friends, a Lenox holiday 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 holiday package as early as possible.
Is it cheaper to book a Lenox holiday as a package?
You can enjoy significant savings on your Lenox getaway by booking a tailored holiday package. Click on the "Package" heading, then enter your destination and travel dates to view some great hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday 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?
- Choose when to travel: Check your calendar and get packing. Your favourite season and the type of activities available will also help you decide when to escape to Lenox.
- Work out your budget: Ensure you have enough money to cover everything from meals and transportation to flights and activities. Your accommodation will likely be the largest expense during your trip to Lenox.
- 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.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a tailored Lenox holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
