Lanesborough Vacations

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Photo by Caitlin Reese

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Find the Best Lanesborough Vacation Packages

Lanesborough Hotel Deals

Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
Lanesborough
9.6/10 Exceptional! (245 reviews)
Great stay
"Stayed there in March - cozy and private. Was a perfect stay while visiting the area with my partner. Communication with host was excellent. Couldn't have been better!"

Reviewed on 15 May 2025

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Berkshire Village Carriage House - Super Private!!
Charming historic cottage on scenic road to Mt. Greylock
Charming historic cottage on scenic road to Mt. Greylock
Lanesboro
9.8/10 Exceptional! (93 reviews)
Quaint little cottage
"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"

Reviewed on 10 February 2025

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Charming historic cottage on scenic road to Mt. Greylock
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is SAR 437 per night from Jun 17 to Jun 18
SAR 437
SAR 488 total
includes taxes & fees
17 Jun - 18 Jun
9/10 Wonderful! (1,002 reviews)
"Lovely staff!"

Reviewed on 31 May 2025

The Yankee, Trademark Collection by Wyndham
See all 1,001 properties in Lanesborough
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.

Frequently asked questions

How much does a Lanesborough vacation package cost?
You can pick up a vacation package to this popular destination on Expedia. However, how much your vacation to Lanesborough costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Lanesborough?
Plan your trip for the shoulder or low season and you’re likely to find cheap Lanesborough vacation packages. Bear in mind that public holidays and major local events can impact prices, so do your research before booking.
How to find the best Lanesborough package deals?
Use Expedia’s filters to find some terrific Lanesborough package deals. When you start your search, just set your maximum budget and then sort the results by “Price: low to high.” If you’re looking to save, plan your adventure for midweek, or search for Lanesborough package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it’s typically best to book your vacation package as soon as possible.
Is it cheaper to book a Lanesborough vacation as a package?
You can enjoy significant savings on your next Lanesborough getaway by booking a personalized vacation package. Check the “Package” heading, then select your travel dates and destination to view some great flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Lanesborough?
If you’ve got your Lanesborough vacation dates finalized, book as early as you can to bag some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Lanesborough?

  1. Pick the perfect time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to go to Lanesborough.
  2. Set your budget: Factor in costs such as flights, meals and transportation when working out how much to save for your trip to Lanesborough. Then, select a property that fits your budget, whether that’s a low-cost stay or a more upscale getaway.
  3. Work out your trip length: Think about how much time you want to spend discovering Lanesborough. Plan your days so you can get to all the attractions and activities you’re interested in without rushing.
  4. Bundle your airfare and accommodations: Once you’ve settled on your travel dates and duration, lock in the ideal Lanesborough vacation package for you.

Discover the most popular places to visit in Lanesborough

Mount Greylock State Reservation Visitor Center

5/5(4 reviews)

Enjoy the mountain views and explore Mount Greylock State Reservation Visitor Center, a lovely green space in Lanesborough. You can seek out the ski slopes in this quaint area.

Mount Greylock State Reservation Visitor Center

Skyline Country Club

5/5(1 review)

Play a round of golf in Lanesborough at Skyline Country Club, and enjoy other activities such as skiing. Discover the entertainment venues in this family-friendly area, or seek out its hiking trails.

Skyline Country Club