Lanesborough Vacations from $400

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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 $587, price is now $400 per person
$400
per person
Dec 9 - Dec 16
found 24 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9/10 Wonderful! (702 reviews)
The kitchen was well equipped. The bed was very comfortable.

Reviewed on Oct 25, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,702, price is now $1,053 per person
$1,053
per person
Dec 9 - Dec 16
found 24 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9/10 Wonderful! (8 reviews)
Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay....

Reviewed on Oct 20, 2025

Gedney Farm

Gedney Farm

3.5 out of 5
Save 100% on your flight
Price was $1,179, price is now $737 per person
$737
per person
Dec 9 - Dec 16
found 24 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9.2/10 Wonderful! (130 reviews)
Gedney Farms is very quiet, peaceful and rustic. Your stay is in a converted barn with towering ceilings, hard wood floors, and rustic reused furniture with no TV phones or radios. Note some rooms require stair climbing on winding stairs with sections without rails or handholds. Some bathtubs are very high. It would be helpful to talk to the location about the room accommodations if mobility is an issue. The staff is very unobtrusive almost to the point of non existent. The breakfast was fresh and healthy with plain Greek yogurt, granola, fresh fruits, hard boiled eggs, muffins and bread to toast. The grounds are well tended but not fussy and offer beauty, peace and quiet. The location is an easy 30 minutes to Tanglewood and 15 minutes to Stockbridge. It is nearby Berkshire Botanical Gardens, Dr. Suess Museum, WEB DuBois statue and homestead, Norman Rockwell museum, Monument mountain, Housatonic river and many art stores, general stores, outdoor activities. This area is car dependent.

Reviewed on Aug 12, 2025

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Save 100% on your flight
Price was $678, price is now $451 per person
$451
per person
Dec 9 - Dec 16
found 24 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
8.6/10 Excellent! (2,062 reviews)
Check in was easy. Room was clean and well-stocked. Lay out for the double room was great. Pool was well-maintained. Game room was added benefit. Very nice stay.

Reviewed on Oct 24, 2025

Club Wyndham Bentley Brook

Club Wyndham Bentley Brook

3 out of 5
Save 100% on your flight
Price was $1,023, price is now $706 per person
$706
per person
Dec 9 - Dec 16
found 24 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9.2/10 Wonderful! (548 reviews)
Great property! So much to do with great views!

Reviewed on Sep 29, 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
$188 nightly
The price is $210 total per night from Oct 28 to Oct 29
$210 total
Oct 28 - Oct 29
Total with taxes and fees
9.6/10 Exceptional! (261 reviews)
What an ideal place to make home base for an extended weekend in the Berkshires with activities. Place is a gem in the woods but accessible to everything.

Reviewed on Sep 24, 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
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $125 total per night from Oct 30 to Oct 31
$125 total
Oct 30 - Oct 31
Total with taxes and fees
8.6/10 Excellent! (2,097 reviews)
Check in was easy. Room was clean and well-stocked. Lay out for the double room was great. Pool was well-maintained. Game room was added benefit. Very nice stay.

Reviewed on Oct 24, 2025

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $108 total per night from Nov 2 to Nov 3
$108 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (723 reviews)
We loved this place. Quiet, very clean,attractive. Loved that it had a kitchen area. Second story, sliding glass doors overlooked the fall foliage in the back of the building. Very peaceful..

Reviewed on Oct 22, 2025

Berkshire Mountain Lodge
See all 1,027 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 $400 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.