Lanesborough, MA

Travel Guide

A tower with a green glass dome and intricate carvings.
A tall tower with a green dome and a pointed top, surrounded by trees and clouds.
A panoramic view of a town nestled in a valley surrounded by dense forests and rolling hills.
A paved path flanked by trees with autumn foliage, leading to a lakeside area with benches.
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough MA
$189 nightly
The price is $211 total per night from Oct 19 to Oct 20
$211 total
Oct 19 - Oct 20
Total with taxes and fees
Stay at this guesthouse in Lanesborough. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Jiminy Peak Mountain Resort and Pontoosuc ...
9.8/10 Exceptional! (298 reviews)
"This place is beautiful. Perfect for me very clean and quiet. Slept well bed very comfy."

Reviewed on Oct 12, 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
$128 nightly
The price is $143 total per night from Nov 1 to Nov 2
$143 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$115 nightly
The price is $128 total per night from Nov 15 to Nov 16
$128 total
Nov 15 - Nov 16
Total with taxes and fees
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,207 reviews)
"The bath tub and the wash basin had some water clogging"

Reviewed on Oct 15, 2026

Berkshire Mountain Lodge
See all 1,030 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.
Charming historic cottage on scenic road to Mt. Greylock

Charming historic cottage on scenic road to Mt. Greylock

Lanesboro MA
Stay at this cottage in Lanesborough. Enjoy free WiFi, a garden, and Netflix. Popular attractions Jiminy Peak Mountain Resort and Mount Greylock State Reservation ...
10/10 Exceptional! (124 reviews)
"This fall our trip brought us to the Berkshires. One of our reasons for choosing this property was the location to Mt. Greylock, which is literally up the road. Also the Ashuwillticook Rail Trail is just a couple miles from this property also. We liked the unique idea of staying at a nearly 200 year ..."

Reviewed on Oct 15, 2026

Charming historic cottage on scenic road to Mt. Greylock
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

Lanesborough MA
Stay at this vacation home in Lanesborough. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and Cheshire Reservoir ...
9.6/10 Exceptional! (85 reviews)
"Thank you Jill for a lovely stay. The house was very clean and had an abundance of amenities. We would highly recommend your property!"

Reviewed on Sep 30, 2026

Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
Vacation Village in the Berkshires
See all 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.

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

Frequently asked questions

Is Lanesborough worth visiting?
Lanesborough is worth visiting for its standout attractions, such as Skyline Country Club. Travelers can also explore a diverse food scene, with many local eateries offering North American dishes like burgers and steaks, alongside Italian favorites such as pasta and pizza.
When is the best time to visit Lanesborough?
The best time to visit Lanesborough is from May through September, when the climate is generally most pleasant for exploring. For travelers seeking fewer crowds and better value, the quieter months of November through February are a good option, offering a different experience with cooler weather.
What is a good itinerary length for Lanesborough?
A good itinerary length for Lanesborough is one day to enjoy the Skyline Country Club. For a longer visit, travelers might explore the area further and enjoy its North American, Italian, and Asian dining options.
What are the top things to do in and around Lanesborough?
In Lanesborough, travelers can visit the Skyline Country Club, a notable landmark and point of interest.
What cuisines can you find in Lanesborough?
In Lanesborough you can find Italian cuisine, featuring classic dishes like pasta, pizza, and lasagna. Travelers can also enjoy a range of North American favorites, diverse Asian specialties, broader European options, and fresh seafood dishes.
Can I book a refundable hotel in Lanesborough?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Lanesborough by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Lanesborough with Expedia?
Expedia makes it easier to plan your Lanesborough trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Lanesborough?
The best choice depends on your travel style. Hotels in Lanesborough can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Lanesborough trip on Expedia?
Once you've booked your Lanesborough trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Lanesborough trip?
Expedia offers customer support before, during, and after your Lanesborough trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Lanesborough?
If it's your first trip to Lanesborough, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Lanesborough hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Lanesborough hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Lanesborough

A waterfall cascading over rocks into a calm pool surrounded by autumn foliage.

Dalton

The Purple Pub with outdoor seating and autumn foliage.

Williamstown

A historic building with classical architecture, a traffic light, and a yellow taxi.

Pittsfield

A road lined with autumn-colored trees, a green house, and a mountain in the background.

Hancock

Explore a world of travel with Expedia