Lanesborough Vacations from $775

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Price was $962, price is now $775 per person
$775
per person
Sep 17 - Sep 20
found 1 hour ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Albany (ALB)
8.6/10 Excellent! (141 reviews)
I had not visited the Ponds for 30 years. It has not gracefully aged. Condo unit has not been updated since it was built in the early 70s and it shows. Drafty and slightly damaged doors, slow drains in the bathrooms, furniture and rugs that show damage and age, and a clubhouse in need of updating. Front desk staff not very friendly or useful, odd because they don’t have a lot of foot traffic this time of the season. There are other similar facilities in the area that might be worth exploring versus this tired old place.

Reviewed on Feb 9, 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 $4,587, price is now $3,400 per person
$3,400
per person
Sep 17 - Sep 20
found 1 hour ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Albany (ALB)
No reviews

Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay

Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay

3 out of 5
Save 100% on your flight
Price was $4,635, price is now $3,602 per person
$3,602
per person
Sep 17 - Sep 20
found 1 hour ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Albany (ALB)
No reviews

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,339, price is now $1,062 per person
$1,062
per person
Sep 17 - Sep 20
found 1 hour ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Albany (ALB)
9.2/10 Wonderful! (1,003 reviews)
Staff was helpful and friendly. Breakfast was amazing. The grounds are so beautiful . There were a number of lovely places inside and out for sitting and relaxing. We loved the welcome drink and a bottle of wine ( choice of red or white) to have in our room. We enjoyed it on our balcony with its lovely views of the main house and the yard. Unfortunately we couldn’t attend the cognac tasting as we were busy. I would love to come to the Cornell again-and again!

Reviewed on Jun 26, 2026

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3 out of 5
Price was $1,479, price is now $1,177 per person
$1,177
per person
Sep 17 - Sep 20
found 1 hour ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Albany (ALB)
10/10 Exceptional! (1 review)
Such a beautiful time was spent here with my family for my nephews graduation from university at Albany. We feed the birds, played family games, got in the hot tub.

Reviewed on May 23, 2026

Don't see what you're looking for?
See all available trips from Columbus to Lanesborough
View all trips

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
$239 nightly
The price is $267 total per night from Jul 2 to Jul 3
$267 total
Jul 2 - Jul 3
Total with taxes and fees
9.8/10 Exceptional! (285 reviews)
"Terrific cottage on the Ashuwillticook Trail near Cheshire Lake! This cottage is tucked away among acres and acres of woodlands with miles of hiking trails. The Ashuwillticook Trail is .5 mi from the door. As a runner, that was a bonus for me. The cottage is well-appointed with a comfortable bed, ..."

Reviewed on Jun 20, 2026

Berkshire Village Carriage House - Super Private!!
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
$159 nightly
The price is $178 total per night from Jul 6 to Jul 7
$178 total
Jul 6 - Jul 7
Total with taxes and fees
9.2/10 Wonderful! (1,011 reviews)
"The friendly atmosphere coming from the staff."

Reviewed on Jun 30, 2026

The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$139 nightly
The price is $156 total per night from Jul 6 to Jul 7
$156 total
Jul 6 - Jul 7
Total with taxes and fees
8.8/10 Excellent! (2,412 reviews)
"Staff was super friendly, splash pad was being renovated so that wasn’t available m.. we had fun but hate that check in is so late and check out so early!"

Reviewed on Jun 30, 2026

Vacation Village in the Berkshires
See all 1,015 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Lanesborough vacation package cost?
You can pick up a vacation package to this popular destination from $775 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.