Lenox Vacation Packages 2025/2026 from $494

Lenox flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Vacation Village in the Berkshires

$494

per person

Feb 14 - Feb 17

found 20 hours ago

Roundtrip non-stop flight included

San Jose (SJC) to Albany (ALB)

This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Hotel Brookmere & Arbor Spa

$499

per person

Feb 14 - Feb 17

found 20 hours ago

Roundtrip non-stop flight included

San Jose (SJC) to Albany (ALB)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 4 conference rooms, along with free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.

South Shire

$566

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

San Juan (SJU) to Albany (ALB)

A restaurant and a bar/lounge are featured at this inn. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, luggage storage, and concierge services are also on offer.

Aspen At Manchester

$761

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

San Juan (SJU) to Albany (ALB)

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and a lobby fireplace are also on offer.

The Manchester View

$610

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

San Juan (SJU) to Albany (ALB)

A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.

Top Lenox hotels deals

Berkshires Untold

194 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$103 nightly

$115 total

Nov 30 - Dec 1

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

461 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$62 nightly

$70 total

Dec 7 - Dec 8

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

Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$136 total

Dec 24 - Dec 25

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.

Hampton Inn & Suites Berkshires-Lenox

445 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$111 nightly

$124 total

Dec 7 - Dec 8

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

462 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$79 nightly

$88 total

Nov 30 - Dec 1

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

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

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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

5/5(150 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.

Pleasant Valley Wilderness Sanctuary

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

The Mount

5/5(37 reviews)

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.

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 $494. 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.