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Featured Cottages in Lanesborough

Property grounds
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (94)
"I adored my stay at The Stone School. Rich and Cheryl were terrific hosts who had great suggestions for food and things to do. And the whole experience was easy to navigate. Excellent marks for cleanliness, comfort, ease of parking, quiet & solitude, quaintness, local pleasures. I found it perfect for myself and it would also be ideal for a couple (or perhaps a couple with one or two young children.) The bathroom is on the first floor with a modern sink and vanity; everything looks brand...
Charming historic cottage on scenic road to Mt. Greylock
Property grounds
Cozy Cottage in the Woods
10.0 out of 10, Exceptional, (1)
"I have nothing but great things to say about our stay! Our hosts were great and very welcoming. The property was beautiful and our cottage as well. We will most definitely be back! Thank you!"
Cozy Cottage in the Woods
Outdoor pool
Cozy cottage with pool, walking distance to lake
10.0 out of 10, Exceptional, (11)
"Very clean property with nice amenities near beautiful lake. Beds were comfortable owner very helpful with anything you might need"
Cozy cottage with pool, walking distance to lake
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Fridge, microwave, oven, stovetop
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (20)
"the property was very well maintain, the host put alot of very personal and special touches inside the house.i have stayed in alot of houses over the years, but this one the host made you feel right at home."
Cozy Berkshire cottage with fireplace.
Beach nearby, sun-loungers
Morgan House on Crooked Lake
10.0 out of 10, Exceptional, (6)
"Beautiful home on water. Perfect place to have family gatherings! Looking forward to another visit. Best area for pizza, too! ( Kay’s)"
Morgan House on Crooked Lake
Property grounds
Beachwood Cottage
10.0 out of 10, Exceptional, (1)
"Second time staying at the property. Comfortable, low key cabin. Access to private beach a big plus. Near Lenox, Stockbridge and Tanglewood."
Beachwood Cottage
Fridge, microwave, oven, stovetop
Caretaker's Cottage: 20 minutes to Tanglewood
10.0 out of 10, Exceptional, (3)
"Excellent home, beautiful views, no issues."
Caretaker's Cottage: 20 minutes to Tanglewood
Interior
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
3.5 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Interior
Spacious Historic Home in the Berkshires!
3.0 star property
Spacious Historic Home in the Berkshires!
Interior
Charlemont Retreat on Chickley River w/ EV Charger
3.5 star property
Charlemont Retreat on Chickley River w/ EV Charger
Property grounds
Cottage in the Clouds With Mountain Views
10.0 out of 10, Exceptional, (1)
"A sanctuary for writers and astronomers! Exquisite cottage and surroundings. Short hop to all that goes on in the Berkshires. You won't want to leave!"
Cottage in the Clouds With Mountain Views
Interior
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
3.0 star property
10.0 out of 10, Exceptional, (1)
"The host was so kind and helpful. I will definitely cime abck here. "
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
View from property
Picturesque Cottage with Sunroom on Ashmere Lake!
9.6 out of 10, Exceptional, (17)
"It was perfect for me and my close friends. We enjoyed the lake each day and all remarked that the beds were very comfortable. Wish we could have stayed longer."
Picturesque Cottage with Sunroom on Ashmere Lake!
Property grounds
Berkshires - Charming Lakefront Cottage
10.0 out of 10, Exceptional, (1)
"We stayed for a week at Stacy and Bob's place. Communication was excellent ahead of time. The house was incredibly clean upon arrival and everything was just as listed. They even went above and beyond with a wonderful welcome basket. They even had a small first aid/medicine kit, "just in case." We truly enjoyed their place."
Berkshires - Charming Lakefront Cottage
Private kitchen
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Interior
Peaceful Family Home w/ Fire Pit & Large Yard
3.5 star property
Peaceful Family Home w/ Fire Pit & Large Yard
Exterior
Cozy Berkshires Cottage w/ 11 Private Acres!
Cozy Berkshires Cottage w/ 11 Private Acres!
Terrace/patio
Peaceful Seasonal lake front cottage with view of Burden Lake
10.0 out of 10, Exceptional, (2)
"We had a great weekend stay at this beautiful lake house. The house is perfectly located directly on Burden Lake. The inside of the house was very clean and spacious with a nice nautical theme to it. The outside was equally as beautiful equipped with all the amenities to have an amazing outdoor weekend and a beautiful view of the lake. Kendra was an amazing host. She was very easy to contact with any questions and responded quickly to any concerns. Thank you for a great stay Kendra!"
Peaceful Seasonal lake front cottage with view of Burden Lake
Exterior
Black Bear Mountain Cottage
Black Bear Mountain Cottage
Interior
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
3.5 star property
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Don't see what you're looking for?
See all available 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.

Other property types in Lanesborough

Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (203)
"Very clean, tastefully decorated place perfect for our weekend getaway for two. Enjoyed the reading nooks and kitchen amenities, comfortable bed and peacefulness of this carriage house!"
Berkshire Village Carriage House - Super Private!!
Terrace/patio
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, (64)
"This is the 2nd time we've stayed here and loved it again. This has become our go to place to stay for our Berkshires adventures. Clean, comfortable, beautiful, private (the garden center was not open while we were there in Feb.), and great location!"
Hearts Desire is a furnished whole house in a small, colorful garden center.
Property grounds
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (94)
"I adored my stay at The Stone School. Rich and Cheryl were terrific hosts who had great suggestions for food and things to do. And the whole experience was easy to navigate. Excellent marks for cleanliness, comfort, ease of parking, quiet & solitude, quaintness, local pleasures. I found it perfect for myself and it would also be ideal for a couple (or perhaps a couple with one or two young children.) The bathroom is on the first floor with a modern sink and vanity; everything looks brand...
Charming historic cottage on scenic road to Mt. Greylock
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.

Lanesborough Cottages information

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Cottages
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Frequently asked questions

How much do cottages in Lanesborough cost?
Prices for cottages in Lanesborough range between and per night. Whatever your budget, you’re sure to find an ideal place to relax and reconnect with nature. This price was 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.
What is there to do in Lanesborough near my cottage?
You’ll find loads of fun things to put on your itinerary in Lanesborough. You won’t want to miss top attractions like Jiminy Peak Mountain Resort, Bousquet Ski Area and Pittsfield State Forest. Berkshire Museum, Colonial Theatre and Barrington Stage Company are other must-see’s.

Recent Reviews in Lanesborough
Expedia verified reviews