Book Holiday Homes in Lenox

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Featured Holiday Homes in Lenox

Deluxe Queen Room with 2 Queen Beds

Deluxe Queen Room with 2 Queen Beds

2 out of 5
Lee
With a stay at this vacation home in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Deluxe Queen Room with 2 Queen Beds
Charming Berkshires Retreat – Minutes to Williamstown

Charming Berkshires Retreat – Minutes to Williamstown

Williamstown
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 ...
Charming Berkshires Retreat – Minutes to Williamstown
4 Mi to Great Barrington: Berkshires Retreat!

4 Mi to Great Barrington: Berkshires Retreat!

Sheffield
Located in Great Barrington, this vacation home is a 3-minute drive from Housatonic River and 6 minutes from Thom Reed UFO Monument Park.
4 Mi to Great Barrington: Berkshires Retreat!
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Large Barn styled vacation home that fits groups with space to spare.

Large Barn styled vacation home that fits groups with space to spare.

Craryville
With a stay at this vacation home in Copake Lake, you'll be on the waterfront, just a 1-minute walk from Copake Lake and 13 minutes by foot from Mosquito ...
Large Barn styled vacation home that fits groups with space to spare.
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Valatie
Located in Valatie, this vacation home is on the waterfront, a 1-minute drive from Kinderhook Lake and 6 minutes from Valatie Family Care.
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Stay Lakeside This Summer!

Stay Lakeside This Summer!

Great Barrington
Located in Great Barrington, this vacation home is on the waterfront, within a 10-minute drive of Art et Industrie and Housatonic River.
Stay Lakeside This Summer!
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Cummington
With a stay at this vacation home in Cummington, you'll be on the waterfront, and 8.1 mi (13 km) from Swift River and 8.3 mi (13.3 km) from Westfield River.
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

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

Stockbridge
With a stay at this vacation home in West Stockbridge, you'll be within a 5-minute drive of Tanglewood Music Center and Stockbridge Bowl.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Spectacular views and close to Great Barrington.

Spectacular views and close to Great Barrington.

Great Barrington
Located in Great Barrington, this vacation home is within a 5-minute drive of Housatonic River and Housatonic River Walk.
Spectacular views and close to Great Barrington.
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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
482 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Deluxe Queen Room with 2 Queen Beds, Charming Berkshires Retreat – Minutes to Williamstown, 4 Mi to Great Barrington: Berkshires Retreat!, Large Barn styled vacation home that fits groups with space to spare. , Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!, Stay Lakeside This Summer!, Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft, Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Spectacular views and close to Great Barrington.

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
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
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.
Berkshires Untold
The Constance by the Lenox Collection

The Constance by the Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
With a stay at The Constance by the Lenox Collection in Lenox, you'll be within a 5-minute drive of Tanglewood Music Center and Lenox Library.
The Constance 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
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.
Hampton Inn & Suites Berkshires-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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