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Our top choices for Lanesborough vacation homes
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
$335 nightly
The price is $374
Jan 5 - Jan 6, 2026
Total with taxes and fees
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, DineSherwood Forest
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
James D.
$351 nightly
The price is $392
Jan 5 - Jan 6, 2026
Total with taxes and fees
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
Tristan e.
$316 nightly
The price is $339
Dec 23 - Dec 24
Total with taxes and fees
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Historic Berkshires Home Near Tanglewood, Trails & WineriesLebanon Springs
8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
Kaye S.
$329 nightly
The price is $368
Jan 8 - Jan 9, 2026
Total with taxes and fees
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont RetreatBennington
8.6 out of 10, Excellent, (34)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
Malika R.
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
Ann C.
$442 nightly
The price is $494
Jan 3 - Jan 4, 2026
Total with taxes and fees
Near Tanglewood: Historic Summer Retreat
Near Tanglewood: Historic Summer RetreatNew Lebanon
9.4 out of 10, Exceptional, (23)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
Paul S.
$474 nightly
The price is $531
Dec 27 - Dec 28
Total with taxes and fees
Riverbend Berkshire East Basecamp - 3 bedrooms available
Riverbend Berkshire East Basecamp - 3 bedrooms availableCharlemont
$377 nightly
The price is $421
Dec 23 - Dec 24
Total with taxes and fees
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.
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Top Lanesborough Hotel Reviews
Holiday Inn & Suites Pittsfield-Berkshires by IHG
10/10 Excellent
Find out more about Lanesborough
Lanesborough Vacation Homes information
Number of reviews | 204 |
|---|---|
Accommodation | 295 Vacation Homes |
Lowest Price | $283 |
Highest Price | $1,049 |
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