Holiday Homes in Lenox

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Our top choices for Lenox holiday homes

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is €733
includes taxes & fees
10 May - 11 May
Spacious 5-bedroom house in charming Lee with WiFi

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Very nice cabin, responsive host."
United States
Nick R.
The price is €352
includes taxes & fees
3 Jun - 4 Jun
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is €322
includes taxes & fees
10 May - 11 May
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (31 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is €275
includes taxes & fees
4 May - 5 May
Home in Great Barrington

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (24 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is €376
includes taxes & fees
4 May - 5 May
North Getaway Cottage

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Great location and nice size house for a family of 5. We had a couple hiccups but the host responded quickly and handled things promptly. "
United States
Jennifer L.
The price is €268
includes taxes & fees
4 May - 5 May
Cozy Riverside Berkshires Retreat

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.8 out of 10, Excellent, (8 reviews)
"Kind and responsive host."
United States
Javier
The price is €465
includes taxes & fees
4 May - 5 May
Comfortable Berkshires retreat on mtn resort, SISO

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is €257
includes taxes & fees
27 May - 28 May
Real Estate: Therapy - Lake, Laundry, Love it

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is €425
includes taxes & fees
6 May - 7 May
Cheerful 3-bedroom cottage with woodstove

Modern Victorian Walk to Main Street

Modern Victorian Walk to Main Street
Great Barrington
10.0 out of 10, Exceptional, (26 reviews)
"The house and location both perfect for a girls weekend away! "
United States
karen b.
The price is €646
includes taxes & fees
10 May - 11 May
Modern Victorian Walk to Main Street

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (36 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is €620
includes taxes & fees
4 May - 5 May
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is €418
includes taxes & fees
4 May - 5 May
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is €475
includes taxes & fees
5 May - 6 May
Treetop Hideaway in Tyringham

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is €1,132
includes taxes & fees
4 May - 5 May
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (6 reviews)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is €228
includes taxes & fees
4 May - 5 May
Sweet Cozy Victorian in Housatonic. Close to everything.

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.4 out of 10, Exceptional, (3 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is €266
includes taxes & fees
4 May - 5 May
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.4 out of 10, Exceptional, (3 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is €462
includes taxes & fees
2 Jun - 3 Jun
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is €450
includes taxes & fees
4 May - 5 May
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (19 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
Hancock Village Inn Near Jiminy Peak

Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK

Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK
Hillsdale
10.0 out of 10, Exceptional, (128 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is €505
includes taxes & fees
17 May - 18 May
Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK
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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Top Lenox Hotel Reviews

Find out more about Lenox

Lenox Holiday Homes information

Number of reviews
375
Accommodation
438 Holiday Homes
Lowest Price
€228
Highest Price
€1,132