Lanesborough Vacations from $516
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Your Lanesborough Vacation
The adventure-filled city of Lanesborough is calling. Delve into everything from its highlights to its hidden gems with a Lanesborough vacation package that's customized to you. If a sightseeing tour is part of the program during your trip to Lanesborough, look around popular attractions like Jiminy Peak Mountain Resort, Colonial Theater and Berkshire Museum. Whoever you're taking time off with and whatever you want to spend, your ultimate Lanesborough vacation is just a few clicks away with Expedia.
The Latest Lanesborough vacation packages
Price found within the past 48 hours. Click for updated prices.
Hideaway Inn Lenox
$516
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
7.6/10 Good! (50 reviews)
Easy check in, but a bit different since there is no staff to help check in. Had to find things on your own, but that was not difficult. Outside furniture could use and upgrade as our friends almost fell through the chair. But is was wonderful being able to sit outside, have appetizers, and play a game or just relax. All other guests we ran into were nice. I would return.
Reviewed on Sep 18, 2026
Urban Cowboy Lodge
$880
per person
Dec 3 - Dec 6
found 10 hours ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
9.4/10 Exceptional! (255 reviews)
Food not great for the money loud funk music played at dinner very disappointing paid 52 for a steak all fat breakfast not great we chose to eat elsewhere. The grounds well maintained
Reviewed on Sep 15, 2026
The Old Catskill Game Farm Inn
$2,721
per person
Dec 3 - Dec 6
found 10 hours ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
9.8/10 Exceptional! (35 reviews)
Everything was amazing. Shawn was awesome. He greeted you when we came in. It's definitely experiences. All I can say we had a great time. A little quirky.Amazing history set on 200 acres closed down zoo
Reviewed on Sep 21, 2026
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View all tripsStay near popular Lanesborough attractions
Mount Greylock State Reservation Visitor Center
10.0/10 (16 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.
Lanesborough Hotel Deals
Berkshire Village Carriage House - Super Private!!
Lanesborough MA
$179 nightly
$200 total
Sep 22 - Sep 23
Total with taxes and fees
9.8/10 Exceptional! (295 reviews)
"We were looking for a private, quiet, one bedroom cottage that was close to Tanglewood and this property was perfect. It was clean, updated, with cool little window seats to read from. The surrounding forest and gardens were lovely. Next time we will stay longer!"
Reviewed on Sep 3, 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$122 nightly
$136 total
Sep 22 - Sep 23
Total with taxes and fees
8.8/10 Excellent! (2,665 reviews)
"Excelente A+, lo recomiendo"
Reviewed on Sep 20, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$108 nightly
$120 total
Oct 21 - Oct 22
Total with taxes and fees
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.
Find the Best Lanesborough Vacation Packages
Lanesborough Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 3,000 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Jiminy Peak Mountain Resort, Bousquet Ski Area and Shakespeare and Company |
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Frequently asked questions
How much does a Lanesborough vacation package cost?
You can pick up a vacation package to this popular destination from $516 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?
November, December and January are great times to search for cheap Lanesborough vacation packages. Choosing to travel in less busy months means you can typically find better prices on hotels and flights.
How many days is enough for Lanesborough?
Typically, a handful of days is enough to tick off the top sights during your Lanesborough vacation. However, if you want to have time to relax or take day tours, think about extending your trip.
Is it worth booking a vacation package to Lanesborough?
It's easy to see why a Lanesborough vacation is on the to-do list of many travelers. Top attractions like Mount Greylock State Reservation Visitor Center are just the start of things to keep you busy here.
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?
- Choose when to travel: Check your calendar and get packing. Your preferred time of year and the activities on offer will also help you decide when to escape to Lanesborough.
- Budget wisely: As well as the cost of your accommodations, you'll need to factor in other expenses. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that could arise during your trip to Lanesborough.
- Organize your Lanesborough escape with our trip planning tool: Look for and book hotels and things to do all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Lanesborough together.
- Set the duration of your trip: Start by listing all the attractions and activities you'd like to experience in Lanesborough. Then, estimate how long you'll need for each, including any travel time.
- Bundle your accommodations and airfare: Once you've nailed down your travel dates and duration, lock in the perfect Lanesborough vacation package for you.
- Add on excursions and experiences: Have a look at our dedicated travel guide to find some fun things to do in Lanesborough. Book tickets or make reservations before you go to save time and skip the hassle of trying to find activities when you arrive.
Does Expedia offer Book Now, Pay Later Lanesborough vacation packages?
If you're like us, you love exploring new places but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Lanesborough break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
