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Featured Holiday Homes in Lanesborough

Peace and quiet on the lake

Peace and quiet on the lake

Becket MA
With a stay at this vacation home in Becket (Sherwood Forest), you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.
Opens in a new windowPeace and quiet on the lake
Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat

Great Barrington MA
The price is AU$443 per night from 17 May to 18 May
AU$443
17 May - 18 May
includes taxes & fees
Located in Great Barrington, this vacation home is on a river, a short 4-minute walk from Monument Mountain Reservation and within 1 minutes by car from Housatonic ...
Opens in a new windowCozy Riverside Berkshires Retreat
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Lanesborough MA
With a stay at this vacation home in Lanesborough, you'll be within a 10-minute drive of Crane Museum of Papermaking and Barrington Stage Company.
Opens in a new windowCozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
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Mid Century Modern  4 bedroom home with sweeping mountain views in Williamstown

Mid Century Modern 4 bedroom home with sweeping mountain views in Williamstown

Williamstown MA
Located in Williamstown, this vacation home is a 2-minute drive from Green Mountain National Forest and 7 minutes from Farm Museum.
Opens in a new windowMid Century Modern 4 bedroom home with sweeping mountain views in Williamstown
19th c. Barn in the Berkshires

19th c. Barn in the Berkshires

Cheshire MA
When you stay at this vacation home in Cheshire, you'll be in the mountains, within a 5-minute drive of St Mary's of the Assumption Church and Mount Greylock ...
Opens in a new window19th c. Barn in the Berkshires
Beautiful Estate: Week of  8/30 still open to enjoy pool, pond, trails & more!

Beautiful Estate: Week of 8/30 still open to enjoy pool, pond, trails & more!

Old Chatham NY
Located in Old Chatham, this vacation home is on a lake, within a 10-minute drive of Shaker Museum and Library and Valatie Free Library.
Opens in a new windowBeautiful Estate: Week of 8/30 still open to enjoy pool, pond, trails & more!
Charming Berkshire Retreat-Minutes to Williamstown

Charming Berkshire Retreat-Minutes to Williamstown

Williamstown MA
With a stay at this vacation home in Williamstown, you'll be within a 5-minute walk of Mount Greylock State Reservation and Green River Wildlife Management ...
Opens in a new windowCharming Berkshire Retreat-Minutes to Williamstown
3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome

3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome

Williamstown MA
A stay at this vacation home places you in the heart of Williamstown, steps from Lower Linear Park and 3 minutes by foot from Williams College.
Opens in a new window3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome
120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views

120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views

East Chatham NY
Located in East Chatham, this vacation home is within a 15-minute drive of Queechy Lake and New Lebanon Library.
Opens in a new window120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views
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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.

Lanesborough Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Lanesborough vacation homes are the perfect way for you to wing it.

Holiday houses in Lanesborough let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Lanesborough in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Lanesborough adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Lanesborough with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Lanesborough vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Lanesborough Holiday Homes essential information

Accommodation
294 Holiday Homes
Lowest Price
AU$150
Highest Price
AU$443
Popular accommodation
Peace and quiet on the lake, Cozy Riverside Berkshires Retreat, Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!, Mid Century Modern 4 bedroom home with sweeping mountain views in Williamstown, 19th c. Barn in the Berkshires, Beautiful Estate: Week of 8/30 still open to enjoy pool, pond, trails & more!, Charming Berkshire Retreat-Minutes to Williamstown, 3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome, 120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views

Top trending hotels in Lanesborough

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough MA
The price is AU$294 per night from 22 May to 23 May
AU$294
22 May - 23 May
includes taxes & fees
Located in Lanesborough, this guesthouse is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.
Opens in a new windowBerkshire Village Carriage House - Super Private!!
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is AU$168 per night from 24 May to 25 May
AU$168
24 May - 25 May
includes taxes & fees
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's ...
Opens in a new windowBerkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is AU$168 per night from 19 May to 20 May
AU$168
19 May - 20 May
includes taxes & fees
Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.
Opens in a new windowBerkshires Untold
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Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is AU$150 per night from 17 May to 18 May
AU$150
17 May - 18 May
includes taxes & fees
Located in Williamstown, Vacation Village in the Berkshires is a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain Coaster.
Opens in a new windowVacation Village in the Berkshires
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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.

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^Subject to availability and chosen travel dates.