A town hall with a central dome and columns, surrounded by trees and people.

Holiday Homes in Lenox

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Lenox holiday homes

A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

1. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
Stylish Mid-century Modern Berkshires Cape
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

2. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is €187
includes taxes & fees
24 Sept - 25 Sept
NEW RENO - Chalet-style farm loft near Tanglewood
A flat landscape with a clear sky and distant hills.

3. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is €625
includes taxes & fees
28 Sept - 29 Sept
Ellie’s Overlook, best view in the Berkshires!
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

4. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (26 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is €281
includes taxes & fees
25 Sept - 26 Sept
Riverside Retreat in the Berkshires
A spacious living room with a dining area, a kitchen, and a large window.

5. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is €216
includes taxes & fees
29 Sept - 30 Sept
1800s Carriage house in Berkshires / Hudson Valley
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

6. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very good, (1 review)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is €256
includes taxes & fees
27 Sept - 28 Sept
Real Estate: Therapy - Lake, Laundry, Love it
A white two-story house with a porch, surrounded by trees and a hill.

7. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is €384
includes taxes & fees
5 Oct - 6 Oct
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

8. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is €313
includes taxes & fees
30 Sept - 1 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

9. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is €288
includes taxes & fees
24 Sept - 25 Sept
Home in Great Barrington
A hot tub with a string of lights above it, set against a dark night sky.

10. 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, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is €340
includes taxes & fees
29 Sept - 30 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

11. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is €496
includes taxes & fees
24 Sept - 25 Sept
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

12. 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, (40 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveller
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

13. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is €501
includes taxes & fees
28 Sept - 29 Sept
Treetop Hideaway in Tyringham

14. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is €476
includes taxes & fees
24 Sept - 25 Sept
Comfortable Berkshires retreat on mtn resort, SISO
A camping setup with a metal chair and a table by a river in a forest.

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (15 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is €301
includes taxes & fees
21 Oct - 22 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A wooden deck with a table and chairs, surrounded by a white railing.

16. 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
8.4 out of 10, Very good, (10 reviews)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is €443
includes taxes & fees
20 Oct - 21 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A modern building with a wooden deck and a door.

17. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is €507
includes taxes & fees
24 Sept - 25 Sept
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A spacious room with a wooden ceiling, large windows, and a chandelier.

18. Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful weekend spot"
United States
Michael T.
Luxury Barn Retreat — All-Season Escape Awaits!
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

19. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (7 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveller
The price is €473
includes taxes & fees
29 Sept - 30 Sept
NEW RENO Historic Creamery in Berkshires w/hot tub
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Lenox Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Kudos to the welcoming and attentive staff. Fast check-in, clean suite, convenient laundry room, quiet area, and less than a 10 minute drive to Tanglewood and restaurants. Hot tub was unavailable but the beverage machine at the lobby was very much appreciated."
L 2-night trip
Posted 1 hour ago
Berkshire Mountain Lodge

Find out more about Lenox

Lenox Holiday Homes information

Number of reviews
189
Accommodation
415 Holiday Homes
Lowest Price
€187
Highest Price
€507