Book Holiday Homes in Lenox

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Featured Holiday Homes in Lenox

Peace and quiet on the lake

Peace and quiet on the lake

Becket MA
With a stay at this vacation home in Becket (Sherwood Forest), you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.
Opens in a new windowPeace and quiet on the lake
Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat

Great Barrington MA
The price is AU$442 per night from 25 May to 26 May
AU$442
25 May - 26 May
includes taxes & fees
Located in Great Barrington, this vacation home is on a river, a short 4-minute walk from Monument Mountain Reservation and within 1 minutes by car from Housatonic ...
Opens in a new windowCozy Riverside Berkshires Retreat
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
With a stay at this vacation home in Lanesborough, you'll be within a 10-minute drive of Crane Museum of Papermaking and Barrington Stage Company.
Opens in a new windowCozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
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Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!

Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!

Austerlitz NY
Located in Hillsdale, this vacation home is in the mountains, within a 15-minute drive of Hillsdale Town Hall and Ebenezer II Gifts and Antiques.
Opens in a new windowRenovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham NY
The price is AU$445 per night from 14 May to 15 May
AU$445
14 May - 15 May
includes taxes & fees
Located in Chatham, this vacation home is a 5-minute drive from The Mac-Haydn Theatre and 8 minutes from Hudson Chatham Winery.
Opens in a new windowPet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay

Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay

East Chatham NY
Located in East Chatham, this vacation home is in the mountains, within a 15-minute drive of Queechy Lake and The Mac-Haydn Theatre.
Opens in a new windowSecluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay
Charming Berkshire Retreat-Minutes to Williamstown

Charming Berkshire Retreat-Minutes to Williamstown

Williamstown MA
With a stay at this vacation home in Williamstown, you'll be within a 5-minute walk of Mount Greylock State Reservation and Green River Wildlife Management ...
Opens in a new windowCharming Berkshire Retreat-Minutes to Williamstown
Contemporary Berkshire Home with Views of Taconic Golf Course

Contemporary Berkshire Home with Views of Taconic Golf Course

Williamstown MA
Located in Williamstown, this vacation home is within a 5-minute drive of Williams College Taconic Golf Course and Williams College.
Opens in a new windowContemporary Berkshire Home with Views of Taconic Golf Course
19th c. Barn in the Berkshires

19th c. Barn in the Berkshires

Cheshire MA
When you stay at this vacation home in Cheshire, you'll be in the mountains, within a 5-minute drive of St Mary's of the Assumption Church and Mount Greylock ...
Opens in a new window19th c. Barn in the Berkshires
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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
438 Holiday Homes
Lowest Price
AU$137
Highest Price
AU$445
Popular accommodation
Peace and quiet on the lake, Cozy Riverside Berkshires Retreat, Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!, Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires! , Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight., Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay, Charming Berkshire Retreat-Minutes to Williamstown, Contemporary Berkshire Home with Views of Taconic Golf Course, 19th c. Barn in the Berkshires

Top trending hotels in Lenox

Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
The price is AU$154 per night from 25 May to 26 May
AU$154
25 May - 26 May
includes taxes & fees
Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.
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 AU$184 per night from 25 May to 26 May
AU$184
25 May - 26 May
includes taxes & fees
Located in Lenox, Hampton Inn & Suites Berkshires-Lenox is in a rural location, within a 5-minute drive of Guido's Marketplace and Kennedy Park.
Opens in a new windowHampton Inn & Suites Berkshires-Lenox
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
The price is AU$137 per night from 14 May to 15 May
AU$137
14 May - 15 May
includes taxes & fees
Located in Lenox, The Yankee Inn is a 4-minute drive from Bousquet Ski Area and 8 minutes from The Mount.
Opens in a new windowThe Yankee Inn
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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 AU$239 per night from 28 May to 29 May
AU$239
28 May - 29 May
includes taxes & fees
Located in Lenox, Courtyard by Marriott Lenox Berkshires is a 1-minute drive from Kennedy Park and 6 minutes from The Mount.
Opens in a new windowCourtyard by Marriott Lenox Berkshires
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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.

Top Picks

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^Subject to availability and chosen travel dates.