Deals on vacations and trips to Lenox

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Lenox flight + hotel vacation packages

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The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,126, price is now $943 per person
$943
per person
Dec 7 - Dec 11
found 13 hours ago
Roundtrip flight included
Great Falls (GTF) to Albany (ALB)
A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.
Courtyard by Marriott Lake George

Courtyard by Marriott Lake George

3 out of 5
Price was $965, price is now $964 per person
$964
per person
Dec 29 - Jan 3
found 6 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Albany (ALB)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $1,378, price is now $1,055 per person
$1,055
per person
Dec 7 - Dec 11
found 13 hours ago
Roundtrip flight included
Great Falls (GTF) to Albany (ALB)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a picnic area are also on offer.
Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater Sunny Pond

Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater Sunny Pond

3 out of 5
Save 100% on your flight
Price was $7,614, price is now $6,087 per person
$6,087
per person
Dec 7 - Dec 11
found 2 hours ago
Roundtrip flight included
Great Falls (GTF) to Albany (ALB)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
Secluded Berkshires Estate + Private Pond/pool,theater, Gym Sunny Pond

Secluded Berkshires Estate + Private Pond/pool,theater, Gym Sunny Pond

3 out of 5
Save 100% on your flight
Price was $7,294, price is now $5,843 per person
$5,843
per person
Dec 7 - Dec 11
found 2 hours ago
Roundtrip flight included
Great Falls (GTF) to Albany (ALB)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.

Top Lenox hotels deals

Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $98 total per night
$98 total
Nov 2 - Nov 3
Total with taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and express check-in are also on offer.
Pet friendly
Parking included
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
$134 nightly
The price is $150 total per night
$150 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
$111 nightly
The price is $124 total per night
$124 total
Nov 13 - Nov 14
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $88 total per night
$88 total
Oct 19 - Oct 20
Total with taxes and fees
An outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A garden and express check-out are also provided.
Pool
Parking included
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA
Get rates
This condo resort features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the outdoor tennis court and conveniences like a 24-hour front desk and laundry facilities.
Pool
Hot Tub
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3 out of 5
70 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $142 total per night
$142 total
Nov 9 - Nov 10
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Parking included
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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.

Popular places to visit

A road near Tanglewood. Driving through the Berkshires is never a disappointing #roadtrip

Tanglewood Music Center

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.

Tanglewood Music Center
Bye fall

Pleasant Valley Wilderness Sanctuary

Explore the great outdoors at Pleasant Valley Wilderness Sanctuary, a lovely green space in Lenox. Wander the lakeside in this quaint area.

Pleasant Valley Wilderness Sanctuary

The Mount

You can spend an afternoon studying the exhibits at The Mount during your trip to Lenox. While you're in the area, stroll along the lakeside.

The Mount

Frequently asked questions

How much are vacation packages to Lenox?
Travelocity has package deals to Lenox, including hotels and flights, starting from as low as $943. With all that extra money, you could purchase some cool tours or perhaps even add some extra nights to your vacation.
How long should my Lenox vacation be?
Most sightseers vacation in Lenox for an average of 2 nights. That being said, traveling is all about checking out new things and creating memories — why not book a few more nights to do just that?
Where can I get the best vacation package deals for Lenox?
There are excellent Lenox package deals to be scored with Travelocity. Did you know we partner with 400 airlines and 1,000,000 worldwide properties? Remember this the next time you're ready to check another destination off your bucket list.
Why should I purchase my Lenox vacation package via Travelocity?
From incredible destinations to fun experiences, we have everything you need to satisfy your wanderlust. Our 24/7 support will also ensure you're being taken care of before, during and after your trip. And don't panic if you spot a cheaper price on your reservation, we'll match it. That's our Price Match Guarantee.
Can I save on my Lenox car rental if I book it with hotels and flights?
With a Lenox vacation package, you can bundle your flight, hotel and car bookings and save tons. If you're in the mood to explore the best of this fabulous area, why not make a beeline for Times Square? This well-known sight is 120 mi from Lenox. With your own wheels, you'll be there in no time.
Which airport is best for Lenox?
There's a good chance you'll touch down at Bradley Intl. Airport (BDL), which is 45 mi southeast of inner Lenox. Albany Intl. Airport (ALB) (40 mi away from central Lenox) and Hartford, CT (HFD-Hartford - Brainard) (55 mi away from central Lenox) are other choices.
What is there to do in Lenox?
You'll notice a certain kind of magic as you roam the streets of Lenox. The Mount and Ventfort Hall Mansion and Gilded Age Museum are just a couple of attractions that lure visitors to this fantastic city, so add them to your itinerary.
Where should I stay when visiting Lenox?
If you're after someplace comfortable to spend your nights, check out the The Yankee, Trademark Collection by Wyndham. It's the top choice for many visitors.

Photos of local treasures

Browse Lenox vacation photos for more inspiration

Lenox which includes an administrative buidling
Lenox showing fall colors
Lenox which includes signage and autumn leaves
Lenox featuring autumn leaves
Lenox which includes a park and autumn leaves

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