Lenox Vacation Packages 2025/2026 from $503

Lenox flight + hotel vacation packages

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

Pocketbook Hotel and Bath

Save 100% on your flight

$503

per person

Oct 31 - Nov 3

found 22 hours ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

A full-service spa and a restaurant are featured at this hotel. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. A coffee shop is provided and the front desk is staffed around-the-clock.

Prospect Berkshires

Save 100% on your flight

$538

per person

Oct 31 - Nov 3

found 22 hours ago

Roundtrip flight included

Orlando (MCO) 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.

The Landing Hotel at Rivers Casino & Resort

Stockade Historic District

$733

per person

Nov 24 - Dec 1

found 1 day ago

Roundtrip non-stop flight included

Portland (PDX) to Albany (ALB)

This smoke-free hotel features a casino and 5 restaurants. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference center. Free self parking is free for guests, and you can enjoy a meal in one of the 2 coffee shops/cafes.

Gedney Farm

$617

per person

Nov 10 - Nov 14

found 11 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Albany (ALB)

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace, a garden, and a communal living room are also on offer.

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

Save 100% on your flight

$3,926

per person

Oct 31 - Nov 3

found 22 hours ago

Roundtrip flight included

Orlando (MCO) 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

194 Pittsfield Rd, Lenox, MA

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$134 total

Sep 25 - Sep 26

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

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd, Routes 7 and 20, Lenox, MA

Free Cancellation

Reserve now, pay when you stay

$79 nightly

$88 total

Sep 23 - Sep 24

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 Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd, Lenox, MA

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$122 total

Oct 1 - Oct 2

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

445 Pittsfield Rd, Lenox, MA

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$151 total

Sep 28 - Sep 29

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

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

Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd, Lenox, MA

Free Cancellation

Reserve now, pay when you stay

$161 nightly

$180 total

Sep 29 - Sep 30

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.

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

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 $503. 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.