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Top Holiday Rentals in Lenox

Restored 1881 Farm House

Restored 1881 Farm House

76 E Dugway Rd, Lenox, MA
Situated in Lenox, this holiday home is within 3 miles (5 km) of Ventfort Hall Mansion and Gilded Age Museum, Pleasant Valley Wilderness Sanctuary and Frelinghuysen ...
4.8/5Exceptional! (28 reviews)
Exactly the getaway we needed
"We had a great time at this property. The kitchen layout is great and the bathtubs were so relaxing to use! The deck right off the kitchen was perfect for our pre-schooler to play on her own. Lots of great trails nearby too. The hosts were super responsive to all of our questions and made everything ..."

Reviewed on 11 Apr 2021

Restored 1881 Farm House
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

225 Pittsfield Road, Lenox, MA
Located in the heart of Lenox, this holiday home is within 3 miles (5 km) of Pleasant Valley Wilderness Sanctuary, Kennedy Park and Arrowhead Museum. Ventfort ...
4.6/5Exceptional! (13 reviews)
Perfect accommodations
"The house was very clean when we entered. It was a perfect set up with plenty of space. The furniture was inviting and the bedding was so comfy! Even though the house was located on a busy road, it was barely noticeable. I was worried when we pulled up. Working with the owner was a breeze! Mary was ..."

Reviewed on 15 Mar 2021

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Lenox Lake House

Lenox Lake House

13 Sargent Brook Rd, Lenox, MA
Situated on the waterfront, this holiday home is 0.7 mi (1.2 km) from The Mount and within 3 miles (5 km) of Shakespeare and Company and Ventfort Hall Mansion ...
5/5Exceptional! (1 review)
Lake house
"The house was in a great location for all that we did while in the Berkshires. It was nice and quiet and very clean. We had a lovely stay!"

Reviewed on 24 Apr 2021

Lenox Lake House
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Very Private Setting, yet Walk to Town

Very Private Setting, yet Walk to Town

41 Cliffwood Street, Lenox, MA
Situated in Lenox, this holiday home is 0.3 mi (0.5 km) from Lenox Library and 1.7 mi (2.8 km) from Tanglewood Music Center. Ventfort Hall Mansion and Gilded ...
5/5Exceptional! (1 review)
Lovely Berkshires retreat
"We loved our stay in this comfortable cottage, tucked away down along driveway far from the street. The house was very clean, the kitchen was well-equipped, and the heated floors in the bathroom were a surprisingly nice touch. The kids loved playing in the huge yard. The owner was very responsive, ..."

Reviewed on 6 May 2021

Very Private Setting, yet Walk to Town
One Bedroom Luxury Cottage at Blantyre, Relais & Châteaux

One Bedroom Luxury Cottage at Blantyre, Relais & Châteaux

16 Blantyre Rd, Lenox, MA
Located in the heart of Lenox, this historic cottage is within 3 miles (5 km) of Wood's Pond, The Mount and Ventfort Hall Mansion and Gilded Age Museum. Berkshire ...
One Bedroom Luxury Cottage at Blantyre, Relais & Châteaux
Private Guest House in Dtwn Lenox, Walk to Dining!

Private Guest House in Dtwn Lenox, Walk to Dining!

59 Walker Street, Lenox, MA
Located in the heart of Lenox, this holiday home is 0.2 mi (0.3 km) from Lenox Library and 1.4 mi (2.3 km) from Tanglewood Music Center. Ventfort Hall Mansion ...
4.4/5Wonderful! (7 reviews)
The house is nicer than the listing portrayed it. Very comfortable in all aspects.
"Great location. Very comfortable, simple and clean. Great for our family of 4. We will be back for any of our Berkshire adventures."

Reviewed on 15 Mar 2021

Private Guest House in Dtwn Lenox, Walk to Dining!
Two Bedroom Luxury Cottage at Blantyre, Relais & Châteaux

Two Bedroom Luxury Cottage at Blantyre, Relais & Châteaux

16 Blantyre Rd, Lenox, MA
Located in the heart of Lenox, this historic cottage is within 3 miles (5 km) of Wood's Pond, The Mount and Ventfort Hall Mansion and Gilded Age Museum. Berkshire ...
Two Bedroom Luxury Cottage at Blantyre, Relais & Châteaux
Two Bedroom Luxury Cottage at Blantyre, Relais & Châteaux

Two Bedroom Luxury Cottage at Blantyre, Relais & Châteaux

16 Blantyre Rd, Lenox, MA
Located in the heart of Lenox, this historic cottage is within 3 miles (5 km) of Wood's Pond, The Mount and Ventfort Hall Mansion and Gilded Age Museum. Berkshire ...
Two Bedroom Luxury Cottage at Blantyre, Relais & Châteaux
Garfield Guest House in the Office Complex

Garfield Guest House in the Office Complex

208 Main St, Lee, MA
The price is £92 per night from 22 May to 22 May
Situated in Lee, this apartment building is within a 5-minute walk of Animagic Museum of Animation and Lee Library. Greenock Country Club and Lee Prime Outlets ...
4.5/5Wonderful! (23 reviews)
Overnight stay
"We had a nice overnight visit in Lee. Jeff’s place was very conveniently located to the town."

Reviewed on 22 Apr 2021

Garfield Guest House in the Office Complex
Honeysuckle Rose Cottage

Honeysuckle Rose Cottage

173 Barker Rd, Pittsfield, MA
Situated in Pittsfield, this holiday home is within 2 miles (3 km) of Colonial Theater, Berkshire Museum and Berkshire Athenaeum. Canoe Meadows Wildlife Sanctuary ...
4.5/5Wonderful! (2 reviews)
Quaint and Beautiful Little Cottage
"We loved staying here! It was quaint and relaxing, just what we wanted. Despite the age of the cottage the heaters throughout kept us nice and warm. We were cozy the whole time. Some great books to read on the shelves and the TV was set up with streaming services and cable. Not a far drive from trails ..."

Reviewed on 11 Mar 2021

Honeysuckle Rose Cottage
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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.

Other types of properties in Lenox you may be interested in

Hampton Inn & Suites Berkshires Lenox

Hampton Inn & Suites Berkshires Lenox

2.5 out of 5
445 Pittsfield Rd, Lenox, MA
Free cancellationReserve now, pay when you stay
The price is £79 per night from 26 May to 26 May
Hampton Inn & Suites Berkshires Lenox
Seven Hills Inn

Seven Hills Inn

4 out of 5
40 Plunkett Street, Lenox, MA
Free cancellationReserve now, pay when you stay
The price is £94 per night from 16 May to 16 May
Seven Hills Inn
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.