Book Holiday Homes in Lenox

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Featured Holiday Homes in Lenox

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires

Great Barrington MA
The price is NZ$517 per night from 22 Dec to 23 Dec
NZ$517
22 Dec - 23 Dec
includes taxes & fees
Stay at this holiday home in Great Barrington. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Monument Mountain Reservation and Art et ...
Opens in a new windowFamily Ski Getaway in the Berkshires
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge MA
Stay at this family-friendly holiday home in West Stockbridge. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Stockbridge Bowl and Berkshire ...
Opens in a new windowLocation!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
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
Stay at this holiday home in Lanesborough. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Jiminy Peak Mountain Resort and Crane Museum ...
Opens in a new windowCozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
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Peace and quiet on the lake

Peace and quiet on the lake

Becket MA
Stay at this holiday home in Becket. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
Opens in a new windowPeace and quiet on the lake
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield MA
Stay at this family-friendly holiday home in Pittsfield. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and ...
Opens in a new windowBeautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Wildlife Lakeside Cottage
beautiful views, amazing wildlife, great location

Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

Lanesborough MA
Stay at this holiday home in Lanesborough. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Jiminy Peak Mountain Resort and Crane Museum ...
Opens in a new windowWildlife Lakeside Cottage beautiful views, amazing wildlife, great location
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

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

Lee MA
Stay at this holiday home in Lee. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Greenock Country Club and Lee Library are located ...
Opens in a new windowCordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Berkshire House Stay

Berkshire House Stay

Lee MA
Stay at this holiday home in Lee. Enjoy laundry facilities, an in-room coffee maker and in-room fireplaces. Popular attractions Greenock Country Club and Lee ...
Opens in a new windowBerkshire House Stay
Falls Reach In The Heart of Copake

Falls Reach In The Heart of Copake

Copake Falls NY
Stay at this holiday home in Copake Falls. Enjoy a garden, laundry facilities and an in-room coffee maker. Popular attractions Copake Town Park and Bash Bish ...
Opens in a new windowFalls Reach In The Heart of Copake
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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
431 Holiday Homes
Lowest Price
NZ$147
Highest Price
NZ$517
Popular accommodation
Family Ski Getaway in the Berkshires, Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!, Peace and quiet on the lake, Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location, Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!, Berkshire House Stay, Falls Reach In The Heart of Copake

Top trending hotels in Lenox

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$147 per night from 4 Jan to 5 Jan
NZ$147
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
Opens in a new windowThe Yankee, Trademark Collection by Wyndham
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$213 per night from 22 Dec to 23 Dec
NZ$213
22 Dec - 23 Dec
includes taxes & fees
Stay at this lodge in Lenox. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowBerkshires Untold
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$203 per night from 4 Jan to 5 Jan
NZ$203
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their ...
Opens in a new windowHampton Inn & Suites Berkshires-Lenox
Save an average of 15% on thousands of hotels when you're signed in
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3 out of 5
70 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$270 per night from 23 Dec to 24 Dec
NZ$270
23 Dec - 24 Dec
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff in their reviews. ...
Opens in a new windowCourtyard by Marriott Lenox Berkshires
Don't see what you're looking for?
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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.