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22 Aug - 24 Aug
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12 Sept - 14 Sept
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Featured Cottages in Lanesborough

Charlemont Retreat on Chickley River w/ EV Charger
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Charlemont Retreat on Chickley River w/ EV Charger

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
Luxury Vacation Rental in the Berkshires!
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Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!
A-frame Cabin w/ Furnished Deck in Becket!
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A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
Spacious Historic Home in the Berkshires!
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Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
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Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

3.0 star property
6.0 out of 10, (1)
"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Terrace/patio

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay
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Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3.0 star property
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay
Cozy Stockbridge Cabin - Walk to Beach & Lake!
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Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property
2.0 out of 10, (1)
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Berkshire Hideaway w/ Fire Pit & Playground!
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Berkshire Hideaway w/ Fire Pit & Playground!

3.0 star property
Berkshire Hideaway w/ Fire Pit & Playground!
Stockbridge Home: Walk to Town Beach!
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Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!
Picturesque Cottage With Sunroom on Ashmere Lake!
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Picturesque Cottage With Sunroom on Ashmere Lake!

3.0 star property
Picturesque Cottage With Sunroom on Ashmere Lake!
Cozy Becket Cottage Escape w/ Lake Access!
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Cozy Becket Cottage Escape w/ Lake Access!

3.0 star property
Cozy Becket Cottage Escape w/ Lake Access!
Massachusetts Vacation Rental w/ Deck & Grill
4 bedrooms, desk, laptop workspace, bed sheets

Massachusetts Vacation Rental w/ Deck & Grill

3.0 star property
Massachusetts Vacation Rental w/ Deck & Grill
12-acre Vacation Rental in the Berkshires!
Property grounds

12-acre Vacation Rental in the Berkshires!

3.0 star property
12-acre Vacation Rental in the Berkshires!
Stockbridge Retreat w/ Pool & Hot Tub!
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Stockbridge Retreat w/ Pool & Hot Tub!

3.0 star property
Stockbridge Retreat w/ Pool & Hot Tub!
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Front of property

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

3.0 star property
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Woodland Zen by Avantstay Modern Design + Patio
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Woodland Zen by Avantstay Modern Design + Patio

3.0 star property
Woodland Zen by Avantstay Modern Design + Patio
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
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4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

3.0 star property
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
Elegant Pittsfield Home Near Downtown & Skiing!
Front of property

Elegant Pittsfield Home Near Downtown & Skiing!

3.0 star property
Elegant Pittsfield Home Near Downtown & Skiing!
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

Hotel On North

Hotel On North

10/10 Excellent
"This is a great hotel in a rather run down town. The staff was very helpful in providing us with everything we needed and gave us good recommendations in the town. The hotel is very creative and comfortable in how they used its space. We were very content, including our dog."
Whitney 3-night trip
Posted 2 days ago
Hotel On North

Frequently asked questions

How much do cottages in Lanesborough cost?
Cottages in Lanesborough range between and per night. These stays offer a chance to get in tune with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Lanesborough with Expedia?
Expedia has some excellent cottages in Lanesborough, so get ready for a memorable holiday close to nature. If you have a budget, select how much you'd like to spend and your preferred property star rating. Or, use our filters to search for cottages with free WiFi or a pool. We'll help you find a suitable place whatever your trip looks like.
How can I find cheap cottages in Lanesborough?
The best way to track down cheap cottages in Lanesborough is with Expedia's useful filter tool. Tailor your search results by amenities, star rating and budget to land excellent rates with only a few clicks.