Book Holiday Homes in Lanesborough

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Featured Holiday Homes in Lanesborough

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is NZ$391 per night from 16 Apr to 17 Apr
NZ$391
includes taxes & fees
16 Apr - 17 Apr
Stay at this vacation home in Lanesborough. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Jiminy Peak Mountain Resort and Crane ...
Berkshire Village Carriage House - Super Private!!
Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

Hancock
The price is NZ$1,813 per night from 4 Apr to 5 Apr
NZ$1,813
includes taxes & fees
4 Apr - 5 Apr
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy a pool table, in-room washers/dryers, and an in-room coffeemaker. Popular attractions ...
Hancock Village Inn at Jiminy Peak
Peace and quiet on the lake

Peace and quiet on the lake

Becket
Stay at this vacation home in Becket. Enjoy free WiFi, a garden, and patios. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry are located ...
Peace and quiet on the lake
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Heart of Lenox Walk to Town Cozy Cottage!

Heart of Lenox Walk to Town Cozy Cottage!

Lenox
Stay at this vacation home in Lenox. Enjoy free WiFi, a garden, and in-room washers/dryers. Popular attractions Tanglewood Music Center and The Bookstore are ...
Heart of Lenox Walk to Town Cozy Cottage!
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Richmond
Book a stay at this family-friendly vacation home in Richmond. Enjoy a garden, patios, and in-room jetted tubs. Popular attractions Tanglewood Music Center and ...
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Mountain Blossom Retreat by Evergreen Home

Mountain Blossom Retreat by Evergreen Home

Lanesborough
Stay at this vacation home in Lanesborough. Enjoy private pools, a fitness center, and a garden. Popular attractions Jiminy Peak Mountain Resort and Mount Greylock ...
Mountain Blossom Retreat by Evergreen Home
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Lee
Stay at this vacation home in Lee. Enjoy free WiFi, a garden, and patios. Popular attractions Tanglewood Music Center and Greenock Country Club are located ...
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Quintessential 6-BR Berkshires Lodge

Quintessential 6-BR Berkshires Lodge

Becket
Stay at this vacation home in Becket. Enjoy private pools, a garden, and patios. Popular attractions Jacob's Pillow and Pyramid Lake are located nearby.
Quintessential 6-BR Berkshires Lodge
Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat

New Lebanon
The price is NZ$590 per night from 6 Apr to 7 Apr
NZ$590
includes taxes & fees
6 Apr - 7 Apr
Stay at this vacation home in New Lebanon. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Shatford Memorial Park and New Lebanon Library ...
Near Tanglewood: Historic Summer Retreat
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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
292 Holiday Homes
Lowest Price
NZ$173
Highest Price
NZ$1,813
Popular accommodation
Berkshire Village Carriage House - Super Private!!, Hancock Village Inn at Jiminy Peak, Peace and quiet on the lake, Heart of Lenox Walk to Town Cozy Cottage!, Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!, Mountain Blossom Retreat by Evergreen Home, Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!, Quintessential 6-BR Berkshires Lodge, Near Tanglewood: Historic Summer Retreat

Top trending hotels in Lanesborough

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is NZ$391 per night from 16 Apr to 17 Apr
NZ$391
includes taxes & fees
16 Apr - 17 Apr
Stay at this vacation home in Lanesborough. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Jiminy Peak Mountain Resort and Crane ...
Berkshire Village Carriage House - Super Private!!
Charming historic cottage on scenic road to Mt. Greylock

Charming historic cottage on scenic road to Mt. Greylock

Lanesboro
Stay at this cottage in Lanesborough. Enjoy free WiFi, a garden, and Netflix. Popular attractions Jiminy Peak Mountain Resort and Mount Greylock State Reservation ...
Charming historic cottage on scenic road to Mt. Greylock
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$189 per night from 16 Apr to 17 Apr
NZ$189
includes taxes & fees
16 Apr - 17 Apr
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
Life House Berkshires
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The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$173 per night from 10 Apr to 11 Apr
NZ$173
includes taxes & fees
10 Apr - 11 Apr
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
The Yankee, Trademark Collection by Wyndham
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See all available properties in Lanesborough
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.