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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Lenox holiday homes

Smart TV, books

Holiday Home in Lee

Sun Filled Lenox Retreat - Minutes to Tanglewood!
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 HK$1,403
HK$3,588 total
includes taxes & fees
27 Jan - 28 Jan
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Fridge, microwave, oven, stovetop

Holiday Home in Lee

Spacious 5-bedroom house in charming Lee with WiFi
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 HK$3,704
HK$6,715 total
includes taxes & fees
12 Feb - 13 Feb
Spacious 5-bedroom house in charming Lee with WiFi
Smart TV, books

Holiday Home in Sherwood Forest

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
9.6 out of 10, Exceptional, (10 reviews)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is HK$1,249
HK$2,954 total
includes taxes & fees
21 Jan - 22 Jan
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Fridge, microwave, oven, stovetop

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26 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 HK$1,137
HK$1,949 total
includes taxes & fees
26 Jan - 27 Jan
Home in Great Barrington
Exterior

Holiday Home in New Lebanon

Near Tanglewood: Historic Summer Retreat
9.2 out of 10, Wonderful, (25 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is HK$933
HK$2,748 total
includes taxes & fees
1 Feb - 2 Feb
Near Tanglewood: Historic Summer Retreat
Exterior detail

Holiday Home in Pittsfield

3-bedroom house in beautiful Berkshires, close to amenities!
The price is HK$1,668
HK$2,656 total
includes taxes & fees
17 Feb - 18 Feb
3-bedroom house in beautiful Berkshires, close to amenities!
Interior

Holiday Home in Housatonic

Sweet Cozy Victorian in Housatonic. Close to everything.
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 HK$1,053
HK$2,090 total
includes taxes & fees
1 Feb - 2 Feb
Sweet Cozy Victorian in Housatonic. Close to everything.
Fridge, microwave, stovetop, dishwasher

Holiday Home in Stephentown

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
2.0 star property
8.0 out of 10, Very good, (1 review)
"excellent communication with property manager."
United States
Nancy H.
The price is HK$1,364
HK$4,332 total
includes taxes & fees
21 Jan - 22 Jan
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Interior

Holiday Home in Spencertown

Suite 3 - Quiet and private accommodations in a country setting.
10.0 out of 10, Exceptional, (1 review)
"Fantastic place to stay!"
United States
James
The price is HK$1,661
HK$2,122 total
includes taxes & fees
25 Jan - 26 Jan
Suite 3 - Quiet and private accommodations in a country setting.
Interior

Holiday Home in Lebanon Springs

Historic Berkshires Home Near Tanglewood, Trails & Wineries
9.0 out of 10, Wonderful, (21 reviews)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
The price is HK$1,123
HK$2,986 total
includes taxes & fees
21 Jan - 22 Jan
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Property grounds

Holiday Home in Chatham

Renovated house. Built in 1890s. No neighbors in sight.
2.0 star property
The price is HK$1,364
HK$2,375 total
includes taxes & fees
25 Jan - 26 Jan
Renovated house. Built in 1890s. No neighbors in sight.
Interior

Holiday Home in Great Barrington

Family Ski Getaway in the Berkshires
9.2 out of 10, Wonderful, (7 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,579
HK$2,321 total
includes taxes & fees
3 Feb - 4 Feb
Family Ski Getaway in the Berkshires
TV, fireplace, printers

Holiday Home in Great Barrington

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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 HK$4,435
HK$10,388 total
includes taxes & fees
21 Jan - 22 Jan
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
TV, fireplace

Holiday Home in Old Chatham

Artists’ Hideaway in Old Chatham
The price is HK$1,258
HK$4,002 total
includes taxes & fees
21 Jan - 22 Jan
Artists’ Hideaway in Old Chatham
Outdoor dining

Holiday Home in Pittsfield

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 star property
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 HK$2,098
HK$3,850 total
includes taxes & fees
28 Jan - 29 Jan
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Exterior

Holiday Home in Stockbridge

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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 HK$2,331
HK$5,069 total
includes taxes & fees
3 Feb - 4 Feb
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Outdoor dining

Holiday Home in Hancock

Hancock Village Inn Near Jiminy Peak
10.0 out of 10, Exceptional, (16 reviews)
"Great place for a family reunion. Lots of bedrooms and bathrooms. Kitchen is large & well equipped"
United States
Veronica and Mark W.
The price is HK$4,904
HK$8,958 total
includes taxes & fees
21 Jan - 22 Jan
Hancock Village Inn Near Jiminy Peak
Property grounds

Holiday Home in Niverville

The Lakeshore House
10.0 out of 10, Exceptional, (1 review)
"Excellent stay!"
United States
KEITARO A.
The price is HK$3,781
HK$6,252 total
includes taxes & fees
3 Feb - 4 Feb
The Lakeshore House
Pool

Holiday Home in Hancock

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
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 HK$2,518
HK$4,868 total
includes taxes & fees
12 Feb - 13 Feb
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
A heated pool

Holiday Home in Hancock

Comfortable Berkshires retreat on mtn resort, SISO
9.0 out of 10, Wonderful, (7 reviews)
"Kind and responsive host."
United States
Javier
The price is HK$2,511
HK$5,711 total
includes taxes & fees
21 Jan - 22 Jan
Comfortable Berkshires retreat on mtn resort, SISO
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The hotel is very nice and clean. From the moment we checked in to check out, we had an amazing time. "
Gina 1-night trip
Posted 16 hours ago
The Yankee, Trademark Collection by Wyndham

Find out more about Lenox

Lenox Vacation Homes information

Number of reviews
230
Accommodation
431 Vacation Homes
Lowest Price
HK$1,949
Highest Price
HK$10,388

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