Lanesborough Vacations from $571
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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.
Spacious Home in Troy
$571
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
4/10 (1 review)
First of all when we got there we weren't told where the parking area was . We had 5 people staying 3 nights. There were 3 bath mats, 3 bath towels & 2 washcloths. No hand towels. No kitchen towels. The shower head didn't work correctly. Dining area lights didn't work. Control panel on the washer/dryer was falling off. No place to put our clothes. The one dresser had stuff stored in it Master bed sheets had a cigerette burn. Half empty bottles of water laying around. But the worst part was when I did the dishes, all the water from the sink poured into the cupboard and flooded the floor. I cleaned it up & we looked to see if something needed tightening but it was more than that & when I messaged the host was told they would look at it. Nobody came.
Reviewed on May 25, 2026
Holiday Inn Club Vacations Oak 'n Spruce Resort
$614
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.2/10 Wonderful! (946 reviews)
The resort is fabulous, has everything a person could want, from swimming pools, workout areas, sauna, hot tub, shuffleboard, volleyball, miniature golf, etc., etc., laundry facilities.
THe staff is very nice, efficient, and helpful.
The units are a little old and we have had some difficulty with our washing machine. The biggest issue, actually, has been connectivity. We have had a great deal of trouble trying to make phone calls.
Have been here four times and plan to return again.
Reviewed on Aug 9, 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
$185 nightly
$207 total
Aug 31 - Sep 1
Total with taxes and fees
9.8/10 Exceptional! (289 reviews)
"Perfect place for 1-2 people to stay and use as home base while visiting the Berkshires."
Reviewed on Jul 26, 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$128 nightly
$143 total
Aug 31 - Sep 1
Total with taxes and fees
8.8/10 Excellent! (2,516 reviews)
"Great area...reasonable, very clean and cosy... Highly recommended"
Reviewed on Aug 9, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$158 nightly
$176 total
Aug 10 - Aug 11
Total with taxes and fees
9.2/10 Wonderful! (1,018 reviews)
"We attended a Tanglewood concert and needed a place to stay for 1 night. Booked 3 weeks out and many places were sold out. Hotel prices in the Berkshires are very high in the summer. Room was clean and nicely furnished. Only complaint was that the air conditioner was very loud, and we couldn't just ..."
Reviewed on Aug 9, 2026
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 $571 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.
