Lenox Vacation Packages 2025/2026 from $624

Lenox flight + hotel vacation packages

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

Prospect Berkshires

Save 100% on your flight

$624

per person

Oct 17 - Oct 20

found 16 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 Equinox Golf Resort & Spa

Save 100% on your flight

$1,186

per person

Oct 12 - Oct 18

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Albany (ALB)

This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.

The Dewey

Save 100% on your flight

$734

per person

Oct 17 - Oct 20

found 16 hours ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

The Cornell Inn, Lenox & The Berkshires

Save 100% on your flight

$1,285

per person

Oct 9 - Oct 12

found 9 hours ago

Roundtrip flight included

Charlotte (CLT) 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.

Brook Bound Inn

Save 100% on your flight

$910

per person

Oct 12 - Oct 18

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Albany (ALB)

A seasonal outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A garden, a lobby fireplace, and a communal living room are also on offer.

Top Lenox hotels deals

Berkshires Untold

194 Pittsfield Rd, Lenox, MA

Free Cancellation

Reserve now, pay when you stay

$178 nightly

$199 total

Sep 3 - Sep 4

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 3 - Sep 4

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

$125 nightly

$140 total

Sep 21 - Sep 22

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and 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

$144 nightly

$160 total

Sep 8 - Sep 9

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 Constance by the Lenox Collection

11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA

$165 nightly

$184 total

Sep 15 - Sep 16

Total with taxes and fees

A gym, free self parking, and concierge services are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A library, express check-out, and wedding services are also on offer.

Breakfast included

Pet friendly

Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd, Lenox, MA

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$170 total

Sep 4 - Sep 5

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 $624. 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.