Search Vacation Homes in Lenox

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Lenox vacation homes

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 reviews)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is AED 661
AED 1,690 total
includes taxes & fees
11 Feb - 12 Feb
Sun Filled Lenox Retreat - Minutes to Tanglewood!

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 AED 1,745
AED 3,163 total
includes taxes & fees
9 Mar - 10 Mar
Spacious 5-bedroom house in charming Lee with WiFi

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.8 out of 10, Exceptional, (11 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is AED 588
AED 1,449 total
includes taxes & fees
11 Feb - 12 Feb
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
10.0 out of 10, Exceptional, (3 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 AED 496
AED 985 total
includes taxes & fees
11 Feb - 12 Feb
Sweet Cozy Victorian in Housatonic. Close to everything.

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is AED 441
AED 1,246 total
includes taxes & fees
5 Mar - 6 Mar
Near Tanglewood: Historic Summer Retreat

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (27 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is AED 657
AED 1,071 total
includes taxes & fees
25 Feb - 26 Feb
Home in Great Barrington

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is AED 566
AED 1,448 total
includes taxes & fees
2 Mar - 3 Mar
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.2 out of 10, Wonderful, (9 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AED 744
AED 1,093 total
includes taxes & fees
11 Feb - 12 Feb
Family Ski Getaway in the Berkshires

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
8.0 out of 10, Very Good, (1 review)
"excellent communication with property manager."
United States
Nancy H.
The price is AED 643
AED 2,041 total
includes taxes & fees
11 Feb - 12 Feb
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is AED 681
AED 1,150 total
includes taxes & fees
23 Feb - 24 Feb
3-bedroom house in beautiful Berkshires, close to amenities!

Renovated house. Built in 1890s. No neighbors in sight.

Renovated house. Built in 1890s. No neighbors in sight.
Chatham
The price is AED 643
AED 1,140 total
includes taxes & fees
11 Feb - 12 Feb
Renovated house. Built in 1890s. No neighbors in sight.

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 AED 1,249
AED 2,158 total
includes taxes & fees
11 Feb - 12 Feb
Cozy. Clean. Free bagel shop. 3 Fireplaces.

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, (3 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 AED 2,079
AED 4,879 total
includes taxes & fees
11 Feb - 12 Feb
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (16 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AED 3,853
AED 6,148 total
includes taxes & fees
13 Mar - 14 Mar
Hancock Village Inn Near Jiminy Peak

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is AED 593
AED 1,885 total
includes taxes & fees
11 Feb - 12 Feb
Artists’ Hideaway in Old Chatham

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
9.4 out of 10, Exceptional, (26 reviews)
"Nice large kitchen and yard, walking distance to downtown, friendly neighborhood- we enjoyed our stay! "
United States
Deb W.
The price is AED 1,047
AED 1,924 total
includes taxes & fees
1 Mar - 2 Mar
Great Barrington Get Away

The Lakeshore House

The Lakeshore House
Niverville
10.0 out of 10, Exceptional, (1 review)
"Excellent stay!"
United States
KEITARO A.
The price is AED 1,781
AED 2,945 total
includes taxes & fees
11 Feb - 12 Feb
The Lakeshore House

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, (33 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is AED 1,098
AED 2,388 total
includes taxes & fees
11 Feb - 12 Feb
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (72 reviews)
"Howie was a great host, very responsive and accommodating. If we find ourselves in the area in the future , will def try to stay here again "
United States
jon e.
The price is AED 1,164
AED 2,269 total
includes taxes & fees
12 Feb - 13 Feb
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.

Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.
Becket
The price is AED 1,230
AED 2,261 total
includes taxes & fees
23 Feb - 24 Feb
Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Lenox Hotel Reviews

Explore a world of travel with Expedia