Book Holiday Homes in Lenox

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Featured Holiday Homes in Lenox

Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington MA
The price is NZ$496 per night from 8 Feb to 9 Feb
NZ$496
8 Feb - 9 Feb
includes taxes & fees
Stay at this holiday home in Great Barrington. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Monument Mountain Reservation and Art et ...
Opens in a new windowPet Friendly Riverfront Home in Great Barrington
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
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
Amore Estate -  beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox MA
Stay at this family-friendly holiday home in Lenox. Enjoy private pools, laundry facilities and in-room jetted baths. Popular attractions Wood's Pond and Berkshire ...
Opens in a new windowAmore Estate - beautiful room with many places to explore and relax in.
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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$166
Highest Price
NZ$496
Popular accommodation
Pet Friendly Riverfront Home in Great Barrington, 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, Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!, Berkshire House Stay, Falls Reach In The Heart of Copake, Amore Estate - beautiful room with many places to explore and relax in.

Top trending hotels in Lenox

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$166 per night from 8 Mar to 9 Mar
NZ$166
8 Mar - 9 Mar
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
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$183 per night from 8 Feb to 9 Feb
NZ$183
8 Feb - 9 Feb
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
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$242 per night from 1 Mar to 2 Mar
NZ$242
1 Mar - 2 Mar
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
Save an average of 15% on thousands of hotels when you're signed in
Element Lenox Berkshires

Element Lenox Berkshires

3 out of 5
130 PITTSFIELD ROAD Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$262 per night from 22 Feb to 23 Feb
NZ$262
22 Feb - 23 Feb
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Kennedy Park and Pleasant Valley Wilderness ...
Opens in a new windowElement Lenox Berkshires
Don't see what you're looking for?
See all available properties in 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.