Deals on vacations and trips to Lanesborough

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Price found within the past 48 hours. Click for updated prices.
Gedney Farm

Gedney Farm

3.5 out of 5
Price was $682, price is now $474 per person
$474
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace, a garden, and a communal living room are also on offer.
Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,061, price is now $669 per person
$669
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a picnic area are also on offer.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $771, price is now $558 per person
$558
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.
Wilder House Berkshires

Wilder House Berkshires

2 out of 5
Price was $818, price is now $624 per person
$624
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
This bed & breakfast features free self parking and a garden. Free cooked-to-order breakfast is served. A lobby fireplace, a communal living room, and a picnic area are also on offer.
Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was $703, price is now $552 per person
$552
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Albany (ALB)
A 24-hour gym, free self parking, and laundry facilities are featured at this lodge. WiFi in public areas is free. A business center, a terrace, and a picnic area are also on offer.

Top Lanesborough hotels deals

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough MA
$189 nightly
The price is $211 total per night
$211 total
Dec 8 - Dec 9
Total with taxes and fees
This guesthouse includes a garden and barbecue grills.
Free WiFi
Air conditioning
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$111 nightly
The price is $124 total per night
$124 total
Dec 7 - Dec 8
Total with taxes and fees
This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
Pool
Parking included
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $120 total per night
$120 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$186 nightly
The price is $208 total per night
$208 total
Dec 9 - Dec 10
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking, a coffee shop, and a terrace are also offered.
Pet friendly
Parking included
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$92 nightly
The price is $103 total per night
$103 total
Dec 12 - Dec 13
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $127 total per night
$127 total
Dec 7 - Dec 8
Total with taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and express check-in are also on offer.
Pet friendly
Parking included
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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.

Popular places to visit

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

Skyline Country Club

5/5(1 review)

Play a round of golf in Lanesborough at Skyline Country Club, and enjoy other activities such as skiing. Discover the entertainment venues in this family-friendly area, or seek out its hiking trails.

Skyline Country Club

Frequently asked questions

How much are vacation packages to Lanesborough?
With vacation packages available from as low as $474, you won't need to drain your bank balance to visit Lanesborough. Travelocity can help. Bundle hotels, flights and tours into a package and score impressive discounts. The more you book, the greater the savings.
How long should my Lanesborough vacation be?
The majority of travelers spend around 3 nights in Lanesborough, but how long you stay is totally up to you. If you're eager to discover all the exciting things this destination has waiting for you, why not hang around for a bit longer?
Where can I get the best vacation package deals for Lanesborough?
There are awesome Lanesborough package deals to be scored with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties around the globe? Keep this in mind the next time you're ready to check another place off the old bucket list.
Why should I book my Lanesborough vacation bundle with Travelocity?
We take the stress out of travel planning. Whether you're after a new destination to discover or want to ensure you get the best deal around, we're here to assist. Our 24/7 customer care, quality service and Price Match Guarantee mean you can book with confidence.
Can I save on my Lanesborough car rental if I bundle it with a hotel or flight?
With a Lanesborough vacation package, you can combine your hotel, car and flight bookings and save tons. If you're in the mood to see the best of this fabulous city, why not make a beeline for Fenway Park? This must-see attraction is 110 mi from Lanesborough. With your own wheels, you'll be there in a flash.
Which airport is best for Lanesborough?
Bradley Intl. Airport (BDL) is 50 mi from the city center and is the beginning point for many fun adventures. Alternatively, Albany Intl. Airport (ALB) is 35 mi away from central Lanesborough and Hartford, CT (HFD-Hartford - Brainard) is 60 mi away from central Lanesborough.
What is there to do in Lanesborough?
You'll find some excellent photo opportunities at Skyline Country Club, one of the most well-known attractions in Lanesborough. There's a lot more to discover around this exciting city, so give yourself enough time to explore some lesser-known gems.
Where should I stay when visiting Lanesborough?
Many travelers opt to stay at the 6-BR Country Estate 14-Min. To Jiminy Peak. It's sure to be a great base for your Lanesborough escape.

Photos of local treasures

Browse Lanesborough vacation photos for more inspiration

Photo by Caitlin Reese
Photo by Caitlin Reese
Photo by Chris Addams
Photo by Chris Addams