Lanesborough Vacations from $206

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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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Save 100% on your flight
Price was $291, price is now $206 per person
$206
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
9/10 Wonderful! (756 reviews)
This place is so peaceful and the staff is always helpful

Reviewed on Dec 9, 2025

Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Save 100% on your flight
Price was $372, price is now $236 per person
$236
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
9.2/10 Wonderful! (218 reviews)
The place was fantastic in every way, clean, great service, beautiful location and close to everything you want to do in and around Saratoga Springs. I will book this beautiful spot again!

Reviewed on Dec 1, 2025

The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Stockade Historic District
Price was $757, price is now $500 per person
$500
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
Everything about our stay was perfect! The lady at check-in was super friendly, the room was extremely clean and modern. Definitely recommend The Landing!

Reviewed on Nov 23, 2025

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Save 100% on your flight
Price was $716, price is now $474 per person
$474
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
8.8/10 Excellent! (3 reviews)
This was a very cool new hotel. Easy walk into the cute town of Hudson. They are still working out some kinks, we didn’t have hot water but staff was very understanding and offered us

Reviewed on Dec 9, 2025

The Clocktower Hotel at Century House, an Ascend Collection Hotel

The Clocktower Hotel at Century House, an Ascend Collection Hotel

2.5 out of 5
Price was $471, price is now $362 per person
$362
per person
Jan 15 - Jan 19
found 2 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
8.4/10 Very Good! (1,004 reviews)
Everything was great except we stayed 4 nights and never once was our room cleaned or towels refreshed.

Reviewed on Dec 7, 2025

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Discover the most popular places to visit in Lanesborough

Mount Greylock State Reservation Visitor Center

5/5(4 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.

Mount Greylock State Reservation Visitor Center

Lanesborough Hotel Deals

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough MA
$188 nightly
The price is $210 total per night from Dec 10 to Dec 11
$210 total
Dec 10 - Dec 11
Total with taxes and fees
9.6/10 Exceptional! (268 reviews)
Just a beautiful, and very clean/organized place. With several teas/coffees & different brewing options/..dishes/pots/pans/mugs available. Many lighting options, as well as surround sound throughout the Carriage House. Expert carpentry, creative wood-work pieces, and nice tree paintings. Many clear ...

Reviewed on Nov 4, 2025

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
$126 nightly
The price is $141 total per night from Dec 14 to Dec 15
$141 total
Dec 14 - Dec 15
Total with taxes and fees
8.6/10 Excellent! (2,166 reviews)
Clean spacious toom

Reviewed on Dec 6, 2025

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
Fully refundable
$107 nightly
The price is $120 total per night from Dec 20 to Dec 21
$120 total
Dec 20 - Dec 21
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
I don’t have a single complaint about this hotel! Everything was perfect! Staff was great, parking was easy, everything was clean! My family and I will definitely be staying here again in the future!

Reviewed on Dec 5, 2025

Hotel Downstreet, an Ascend Collection Hotel
See all 1,007 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 $206 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.