Lanesborough Trips (flight + hotel)

Photo by Caitlin Reese

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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 P6,184 per night from Aug 27 to Aug 28
P6,184
P7,534 total
Aug 27 - Aug 28
includes taxes & fees
8.6/10 Excellent! (1,936 reviews)
"The driveways and parking areas are in mediocre condition. The furniture is ok but not as good as in other timeshares we have visited and the kitchenette is functional but as complete as is desirable. However, on the positive side, the property is quiet and surroundings are scenic. It is located ..."

Reviewed on Aug 8, 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! (546 reviews)
"Incredible spacious suites"

Reviewed on Aug 6, 2025

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Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is P4,059 per night from Aug 24 to Aug 25
P4,059
P4,534 total
Aug 24 - Aug 25
includes taxes & fees
5.2/10 (763 reviews)
"This family is professional and kind. I left a $100 tip because I watched attend to her guests and her two Autistic sons as well as her elderly parent. Amazing"

Reviewed on Aug 2, 2025

FairBridge Inn Express
See all 1,014 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 many days is enough for Lanesborough?
The ideal length for your Lanesborough vacation 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 vacation package to Lanesborough?
Lanesborough offers everything you need for an amazing getaway. Get your Lanesborough vacation 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 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.