Lanesborough Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Caitlin Reese

Top hotels in Lanesborough

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is 2.845.757 ₫ per night from 27 Aug to 28 Aug
2.845.757 ₫
3.466.915 ₫ total
27 Aug - 28 Aug
includes taxes & fees
8.6/10 Excellent! (1,948 reviews)
"Very nice"

Reviewed on 15 Aug 2025

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (571 reviews)
"Shower/tub side in accessible room was extremely high fyi."

Reviewed on 17 Aug 2025

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Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is 4.200.257 ₫ per night from 18 Aug to 19 Aug
4.200.257 ₫
4.691.688 ₫ total
18 Aug - 19 Aug
includes taxes & fees
9/10 Wonderful! (679 reviews)
Upscale Motel
"Lovely reception area and comfortable room. I would describe the place as an upscale motel. Do not count on dining here. Choices are limited and neither my husband nor I enjoyed what we ordered. ."

Reviewed on 16 Aug 2025

Berkshires Untold
See all 1,013 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.

Popular places to visit

Mount Greylock State Reservation Visitor Center

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

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

Frequently asked questions

How much does a Lanesborough holiday package cost?
You can pick up a holiday package to this popular destination on Expedia. However, how much your holiday 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 holiday packages. Bear in mind that public holidays and major local events can impact prices, so do your research before booking.
How many days is enough for Lanesborough?
The ideal length for your Lanesborough holiday depends on what you'd like to do. Generally, a few days to a week will give you plenty of time to go to all the major sights and discover some hidden treasures along the way.
Is it worth booking a holiday package to Lanesborough?
Lanesborough offers everything you need for an amazing getaway. Get your Lanesborough holiday off to a flying start by exploring popular attractions like Skyline Country Club.
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 holiday package as soon as possible.
Is it cheaper to book a Lanesborough holiday as a package?
You can enjoy significant savings on your next Lanesborough getaway by booking a personalised holiday package. Check the "Package" heading, then select your travel dates and destination to view some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Lanesborough?
If you've got your Lanesborough holiday 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, favourite 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 accommodation: Once you've settled on your travel dates and duration, lock in the ideal Lanesborough holiday package for you.