Lanesborough Vacations from $556

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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.
Countryside Inn

Countryside Inn

2.5 out of 5
Price was $683, price is now $556 per person
$556
per person
Jun 17 - Jun 24
found 8 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
7.6/10 Good! (337 reviews)
Rooms Clean Planty of Parking

Reviewed on May 14, 2026

Secluded Estate Optional Guest House, Pond, Playroom, Gym & Theater Sunny Pond by Avantstay

Secluded Estate Optional Guest House, Pond, Playroom, Gym & Theater Sunny Pond by Avantstay

3 out of 5
Save 100% on your flight
Price was $3,253, price is now $2,482 per person
$2,482
per person
Jul 29 - Jul 31
just found
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
No reviews
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $1,092, price is now $837 per person
$837
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
8.6/10 Excellent! (141 reviews)
Expedia stated the front desk is open until midnight, but when I arrived at 8:05pm the door to the registration bldg was locked.i located a mailbox marked “late check ins” where I found a key card that was only good for one of my two nights. It snowed 2-3” during my 2-day stay, but the sidewalks to my building were never shoveled. Room was extremely clean but quite outdated. Bathroom tiles were cracked with pieces missing along the exterior wall, allowing very cold air in. Price was good for my short stay - unfortunately I didn’t have time to use the clubhouse amenities.

Reviewed on Jan 7, 2026

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $887, price is now $680 per person
$680
per person
Jul 29 - Jul 31
just found
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
9.2/10 Wonderful! (1,003 reviews)
Lovely Inn , comfy bed and suite. The breakfast was delicious…especially enjoyed the frittata, fresh baked sweet breads, and latte. Appreciated the fireplace and cognac nightcap served on on a cool April evening ,coming back from a delicious dinner in Lenox. Kool speak easy style bar, good vibes!

Reviewed on May 1, 2026

Gedney Farm

Gedney Farm

3.5 out of 5
Price was $685, price is now $558 per person
$558
per person
Jul 29 - Jul 31
just found
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
9.4/10 Exceptional! (136 reviews)
My wife and I chose Gedney Farms at the last minute to enjoy a quick escape from the city. The staff was friendly and welcoming. The checkin and checkout experience was seamless. The room had a truly rustic charm, and clean and orderly. In the morning we took a nice walk on the grounds. For a quick and relaxing getaway, Gedney Farms is a great choice.

Reviewed on Nov 2, 2025

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Discover the most popular places to visit in Lanesborough

Mount Greylock State Reservation Visitor Center

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
$187 nightly
The price is $209 total per night from May 22 to May 23
$209 total
May 22 - May 23
Total with taxes and fees
9.8/10 Exceptional! (277 reviews)
Beautiful “New England” layout and area!!!

Reviewed on Mar 9, 2026

Berkshire Village Carriage House - Super Private!!
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $124 total per night from May 27 to May 28
$124 total
May 27 - May 28
Total with taxes and fees
9/10 Wonderful! (932 reviews)
Loved this place - and would probably come. again. My only issue is that check-out is at 10:00 am. I had friends staying there who were not checking out, so I was able to linger in their suite. I imagine that I could have eaten breakfast in the large sunny open lounge on the first floor - if this ...

Reviewed on May 14, 2026

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
$119 nightly
The price is $133 total per night from May 21 to May 22
$133 total
May 21 - May 22
Total with taxes and fees
9/10 Wonderful! (942 reviews)
Great experience

Reviewed on May 13, 2026

Berkshires Untold
See all 1,031 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 $556 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.