Book Holiday Homes in Lenox

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Featured Holiday Homes in Lenox

Private Lake House in the Berkshires

Private Lake House in the Berkshires

Hinsdale
Located in Hinsdale, this vacation home is on a lake, within a 15-minute drive of Bas Ridge Golf Course and Crane Museum of Papermaking.
Private Lake House in the Berkshires
Hearts Desire is a furnished whole house in a small, colorful garden center.

Hearts Desire is a furnished whole house in a small, colorful garden center.

Lanesborough
With a stay at this vacation home in Lanesborough, you'll be on a lake, within a 10-minute drive of Jiminy Peak Mountain Resort and Mount Greylock State ...
Hearts Desire is a furnished whole house in a small, colorful garden center.
Cozy Retreat on Copake Lake in our Charming Home

Cozy Retreat on Copake Lake in our Charming Home

Copake Lake
With a stay at this vacation home in Copake Lake, you'll be next to a golf course, just steps from Copake Lake and a 3-minute drive from Mosquito Island.
Cozy Retreat on Copake Lake in our Charming Home
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Peaceful Retreat Compound 10 Minutes to Great Barrington!

Peaceful Retreat Compound 10 Minutes to Great Barrington!

Great Barrington
The price is AU$2,049 per night from 17 Jun to 18 Jun
AU$2,049
per night
17 Jun - 18 Jun
When you stay at this vacation home in Great Barrington, you'll be within a 10-minute drive of Catamount Ski Area and Catamount Aerial Adventure Park.
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Tranquil 3-BR Waterfront Retreat

Tranquil 3-BR Waterfront Retreat

Becket
Located in Becket, this vacation home is on the waterfront, within a 5-minute drive of Pyramid Lake and Jacob's Pillow.
Tranquil 3-BR Waterfront Retreat
 Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!

Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!

Craryville
Located in Craryville, this vacation home is in a rural location, within a 10-minute drive of Hillsdale Town Hall and Copake Lake.
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Craryville
The price is AU$512 per night from 30 Jun to 1 Jul
AU$512
per night
30 Jun - 1 Jul
With a stay at this vacation home in Copake Lake, you'll be within a 5-minute drive of Copake Lake and Mosquito Island.
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

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

Lee
With a stay at this vacation home in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Greenock Country Club.
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

Adams
A stay at this vacation home places you in the heart of Adams, steps from Mount Greylock State Reservation and 7 minutes by foot from East Hoosac Quaker ...
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
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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.

Lenox 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 Lenox vacation homes are the perfect way for you to wing it.

Holiday houses in Lenox 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 Lenox 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 Lenox adventures, obvs.

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

Lenox Holiday Homes essential information

Accommodation
369 Holiday Homes
Lowest Price
AU$150
Highest Price
AU$2,049
Popular accommodation
Private Lake House in the Berkshires , Hearts Desire is a furnished whole house in a small, colorful garden center., Cozy Retreat on Copake Lake in our Charming Home, Peaceful Retreat Compound 10 Minutes to Great Barrington!, Tranquil 3-BR Waterfront Retreat, Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!, COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!, Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!, Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

Top trending hotels in Lenox

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 AU$201 per night from 16 Jun to 17 Jun
AU$201
per night
16 Jun - 17 Jun
With a stay at Life House Berkshires in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Kennedy Park.
Life House Berkshires
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 AU$228 per night from 26 Jun to 27 Jun
AU$228
per night
26 Jun - 27 Jun
Located in Lenox, The Yankee, Trademark Collection by Wyndham is on the Strip, a 4-minute drive from Bousquet Ski Area and 7 minutes from Shakespeare and ...
The Yankee, Trademark Collection by Wyndham
The Lenox Collection

The Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
The price is AU$165 per night from 16 Jun to 17 Jun
AU$165
per night
16 Jun - 17 Jun
With a stay at The Lenox Collection in Lenox, you'll be within a 5-minute drive of Tanglewood Music Center and Lenox Library.
The Lenox Collection
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Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$150 per night from 16 Jun to 17 Jun
AU$150
per night
16 Jun - 17 Jun
With a stay at Howard Johnson by Wyndham Lenox in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Guido's Marketplace.
Howard Johnson by Wyndham Lenox
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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.