Lanesborough Vacations from $272

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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.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $346, price is now $272 per person
$272
per person
Sep 5 - Sep 7
found 7 hours ago
Roundtrip flight included
Nashville (BNA) to Albany (ALB)
8.8/10 Excellent! (2,411 reviews)

Hill Farm Inn

Hill Farm Inn

4 out of 5
Price was $811, price is now $619 per person
$619
per person
Aug 15 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Albany (ALB)
9.6/10 Exceptional! (176 reviews)
Best part: Breakfast and the views. Communication and follow through were not what I was hoping for. We reported fire ants being at the door on the first night. Received an email saying they would have a service person address it. Next morning the ants made their way into the room. I notified staff the next morning, in person, and was assured it was taken care of. We had ants the entire time, which because more and more of a problem, as one might expect. Additionally, we paid $300 at the Inn for various fees and I believe for cleaning. However, house keeping is not included. I cannot wrap my mind around paying premium prices for lodging and trash takeout/towels refreshed being an even further additional charge. We quickly blew through our rags and hand towels wiping ants up with soapy water. In our 5 day stay, we never had fresh towels and we took our own trash out. I just have to stop short at calling this hospitality. It's akin to a VRBO. But at a VRBO I could wash laundry and have a fridge. I don't know that we would choose this location again. I also cannot fathom hosting customers and knowing they have fire ants in their room and now personally following up with them regarding the issue.

Reviewed on Apr 23, 2026

South Shire

South Shire

4 out of 5
Price was $759, price is now $587 per person
$587
per person
Aug 15 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Albany (ALB)
9.2/10 Wonderful! (127 reviews)
South Shire is a quaint Victorian Inn on Elm Street within walking distance to the center of Bennington, VT. The Inn has a family feel and elegance. We traveled as a couple. It was easy to get to sites and enjoy fine restaurants. The Inn is in keeping with the feel of strength of the Bennington community, as a place for artists, musicians, and people's expression generally to thrive. We enjoyed our stay and would recommend South Shire.

Reviewed on Jun 18, 2026

Ambler Hotel

Ambler Hotel

2 out of 5
Save 100% on your flight
Price was $1,181, price is now $932 per person
$932
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
7/10 Good! (12 reviews)
The place is great. The location is perfect.

Reviewed on Jul 11, 2026

The Yankee Inn

The Yankee Inn

2.5 out of 5
Price was $416, price is now $336 per person
$336
per person
Sep 5 - Sep 7
found 7 hours ago
Roundtrip flight included
Nashville (BNA) to Albany (ALB)
9.2/10 Wonderful! (1,011 reviews)
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Reviewed on Jul 12, 2026

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Stay 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.
See properties

Lanesborough Hotel Deals

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough MA
$240 nightly
The price is $268 total per night from Jul 15 to Jul 16
$268 total
Jul 15 - Jul 16
Total with taxes and fees
9.8/10 Exceptional! (287 reviews)
"Sweet, spotless accomodation, very well- maintained. Loved the window seats and walks through the expansive property. We did not meet or communicate much with our host, but everything worked as described. We would definitely recommend."

Reviewed on Jul 7, 2026

Berkshire Village Carriage House - Super Private!!
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$145 nightly
The price is $162 total per night from Jul 15 to Jul 16
$162 total
Jul 15 - Jul 16
Total with taxes and fees
Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
$170 nightly
The price is $190 total per night from Jul 21 to Jul 22
$190 total
Jul 21 - Jul 22
Total with taxes and fees
8.8/10 Excellent! (1,009 reviews)
"Property and hotel was very clean. The staff was pleasant and helpful."

Reviewed on Jul 14, 2026

Hotel Downstreet, an Ascend Collection Hotel
See all 1,020 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.

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 $272 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. Bundle your accommodations and airfare: Once you've nailed down your travel dates and duration, lock in the perfect Lanesborough vacation package for you.
  6. 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.