Book Holiday Homes in Lenox

January 2025

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Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Lenox

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is NZ$410 per night from 14 Jan to 15 Jan
NZ$410
includes taxes & fees
14 Jan - 15 Jan
Stay at this vacation home in Lanesborough. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Crane Museum of Papermaking and Crane ...
Berkshire Village Carriage House - Super Private!!
Spectacular views and close to Great Barrington.

Spectacular views and close to Great Barrington.

Great Barrington
Stay at this vacation home in Great Barrington. Enjoy in-room jetted tubs, an in-room coffeemaker, and in-room fireplaces. Popular attractions Lake Mansfield ...
Spectacular views and close to Great Barrington.
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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Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Ghent
Book a stay at this family-friendly vacation home in Ghent. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Hudson Chatham Winery and ...
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Beautiful Berkshire Farm House on 160+ Acres

Beautiful Berkshire Farm House on 160+ Acres

Great Barrington
Stay at this vacation home in Great Barrington. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Catamount Aerial Adventure Park and ...
Beautiful Berkshire Farm House on 160+ Acres
Berkshires Lakefront Retreat

Berkshires Lakefront Retreat

Becket
Book a stay at this family-friendly vacation home in Becket. Enjoy free WiFi, a pool table, and patios. Popular attractions Pyramid Lake and Becket Land Trust ...
Berkshires Lakefront Retreat
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

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

Craryville
Stay at this vacation home in Copake Lake. Enjoy air conditioning. Popular attractions Copake Lake and Mosquito Island are located nearby.
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

Hillsdale
Book a stay at this family-friendly vacation home in Hillsdale. Enjoy free WiFi, a garden, and patios. Popular attractions High Falls Trail and Community Library ...
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Berkshire Ashmere Lake lodging. Quiet  room, Fantastic sunsets.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale
Stay at this vacation home in Hinsdale. Enjoy a garden, patios, and in-room jetted tubs. Popular attractions Bas Ridge Golf Course and Wahconah Falls State Park ...
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
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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
362 Holiday Homes
Lowest Price
NZ$178
Highest Price
NZ$410
Popular accommodation
Berkshire Village Carriage House - Super Private!!, Spectacular views and close to Great Barrington., Peace and quiet on the lake, Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna, Beautiful Berkshire Farm House on 160+ Acres, Berkshires Lakefront Retreat , COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!, Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons., Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

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 NZ$178 per night from 26 Jan to 27 Jan
NZ$178
includes taxes & fees
26 Jan - 27 Jan
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
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$207 per night from 21 Jan to 22 Jan
NZ$207
includes taxes & fees
21 Jan - 22 Jan
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
The Constance, The Whitlock, & The Dewey By The Lenox Collection

The Constance, The Whitlock, & The Dewey By The Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
The price is NZ$252 per night from 22 Jan to 23 Jan
NZ$252
includes taxes & fees
22 Jan - 23 Jan
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
The Constance, The Whitlock, & The Dewey By The Lenox Collection
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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$255 per night from 21 Jan to 22 Jan
NZ$255
includes taxes & fees
21 Jan - 22 Jan
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 helpful staff ...
Hampton Inn & Suites Berkshires-Lenox
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.