Book Holiday Homes in Lenox

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Featured Holiday Homes in Lenox

Spacious Home nestled along the Blackberry River in Northwest CT

Spacious Home nestled along the Blackberry River in Northwest CT

East Canaan
Book a stay at this family-friendly vacation home in East Canaan. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Beckley Furnace ...
Spacious Home nestled along the Blackberry River in Northwest CT
Contemporary Berkshire Home with Views of Taconic Golf Course

Contemporary Berkshire Home with Views of Taconic Golf Course

Williamstown
Stay at this vacation home in Williamstown. Enjoy a garden, laundry facilities, and patios. Popular attractions Williams College Taconic Golf Course and Lunder ...
Contemporary Berkshire Home with Views of Taconic Golf Course
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 laundry facilities. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
Peace and quiet on the lake
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Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

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

Stockbridge
Book a stay at this family-friendly vacation home in West Stockbridge. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Tanglewood Music ...
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
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.
Deluxe Queen Room with 2 Queen Beds

Deluxe Queen Room with 2 Queen Beds

2 out of 5
Lee
The price is NZ$223 per night from 1 Sept to 2 Sept
NZ$223
1 Sept - 2 Sept
includes taxes & fees
Stay at this vacation home in Lee. Enjoy laundry facilities, cable/satellite TV service, and air conditioning. Popular attractions Tanglewood Music Center and ...
Deluxe Queen Room with 2 Queen Beds
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 laundry facilities, in-room jetted tubs, and an in-room coffeemaker. Popular attractions Lake Mansfield ...
Spectacular views and close to Great Barrington.
Taconic Hideaway – Swimming, BBQ Pit, Hiking

Taconic Hideaway – Swimming, BBQ Pit, Hiking

2 out of 5
Copake
Stay at this vacation home in Copake. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Copake Town Park and Copake Lake are located ...
Taconic Hideaway – Swimming, BBQ Pit, Hiking
Falls Reach In The Heart of Copake

Falls Reach In The Heart of Copake

Copake Falls
Stay at this vacation home in Copake Falls. Enjoy a garden, laundry facilities, and an in-room coffeemaker. Popular attractions Copake Town Park and Bash Bish ...
Falls 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
487 Holiday Homes
Lowest Price
NZ$148
Highest Price
NZ$301
Popular accommodation
Spacious Home nestled along the Blackberry River in Northwest CT, Contemporary Berkshire Home with Views of Taconic Golf Course, Peace and quiet on the lake, Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. , Deluxe Queen Room with 2 Queen Beds, Spectacular views and close to Great Barrington., Taconic Hideaway – Swimming, BBQ Pit, Hiking, Falls Reach In The Heart of Copake

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$301 per night from 1 Sept to 2 Sept
NZ$301
1 Sept - 2 Sept
includes taxes & fees
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 ...
Berkshires 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$251 per night from 8 Sept to 9 Sept
NZ$251
8 Sept - 9 Sept
includes taxes & fees
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
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$148 per night from 2 Sept to 3 Sept
NZ$148
2 Sept - 3 Sept
includes taxes & fees
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Howard Johnson by Wyndham Lenox
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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$269 per night from 2 Sept to 3 Sept
NZ$269
2 Sept - 3 Sept
includes taxes & fees
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
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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.