Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Lanesborough Vacations

Pack those stellar shades. We have Lanesborough vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Lanesborough – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Lanesborough vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Lanesborough

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Lanesborough vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Lanesborough well.

Top Hotel Deals

See all 135 Hotels in Lanesborough
The Weathervane Motel

The Weathervane Motel

475 South Main St. Route 7, Lanesborough
2.5 out of 5.0

Situated in Lanesborough, this motel is within 6 mi (10 km) of Berkshire Athenaeum, Mount Greylock State Reservation Visitor Center, and Berkshire Museum. Crane ...

$44

$44
Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Hancock
3.0 out of 5.0

Situated in Hancock, this condo building is 5.8 mi (9.3 km) from Mount Greylock State Reservation Visitor Center and within 12 mi (20 km) of Waubeeka Golf Links ...

$105

$105
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

37 Corey Rd, Hancock
3.5 out of 5.0

Located in the mountains, this Hancock condo resort offering ski-in/ski-out access is 6.1 mi (9.8 km) from Mount Greylock State Reservation Visitor Center and ...

$159

$159
Yankee Inn

Yankee Inn

461 Pittsfield Rd, Lenox
3.0 out of 5.0

Located in the heart of Lenox, this hotel is 0.5 mi (0.9 km) from Kennedy Park and within 3 mi (5 km) of Pleasant Valley Wilderness Sanctuary and Arrowhead Museum. ...

$80

$80
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd, Lenox
3.5 out of 5.0

Situated in Lenox, this hotel is within 2 mi (3 km) of Kennedy Park, Lenox Library, and Pleasant Valley Wilderness Sanctuary. Ventfort Hall Mansion and Gilded ...

$116

$116
Hampton Inn & Suites Berkshires Lenox

Hampton Inn & Suites Berkshires Lenox

445 Pittsfield Rd, Lenox
3.0 out of 5.0

Situated in a rural location, this hotel is within 2 mi (3 km) of Arrowhead Museum, Kennedy Park, and Bousquet Ski Area. Pleasant Valley Wilderness Sanctuary ...

$101

$101
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield
3.0 out of 5.0

Located in the heart of Pittsfield, this hotel is 1.7 mi (2.8 km) from Hancock Shaker Village and 2.9 mi (4.7 km) from Bousquet Ski Area. Colonial Theater and ...

$82

$82
The Red Lion Inn

The Red Lion Inn

30 Main Street, Stockbridge
4.0 out of 5.0

This family-friendly Stockbridge hotel is located in the historical district, within a 15-minute walk of Mission House, Berkshire Theatre Festival, and Naumkeag. ...

$136

$136
Crowne Plaza Pittsfield-Berkshires

Crowne Plaza Pittsfield-Berkshires

1 West St, Pittsfield
4.0 out of 5.0

Located in the heart of Pittsfield, this hotel is within a 5-minute walk of Berkshire Museum, Colonial Theater, and Berkshire Athenaeum. Canoe Meadows Wildlife ...

$90

$90
Holiday Inn Berkshires

Holiday Inn Berkshires

40 Main St, North Adams
3.5 out of 5.0

Located in the heart of North Adams, this hotel is within a 10-minute walk of Mass MoCA, North Adams Public Library, and Western Gateway Heritage State Park. ...

$99

$99