Elm Court (Lenox and Stockbridge, Massachusetts)

Wheatleigh is a historic country estate on West Hawthorne Road in Stockbridge, Massachusetts, United States. Built in 1893 to a design by Peabody and Stearns, it is one of the few surviving great Berkshire Cottages of the late 19th century, with grounds landscaped by Frederick Law Olmsted. Its estate now reduced to 22 acres (8.9 ha), Wheatleigh was listed on the National Register of Historic Places in 1982. It is now operated as a hotel.

The Mount (1902) is a country house in Lenox, Massachusetts, the home of noted American author Edith Wharton, who designed the house and its grounds and considered it her "first real home." The estate, located in The Berkshires, is open to the public. The property was declared a National Historic Landmark in 1971. Today, The Mount is a cultural center and historic house museum, welcoming over 50,000 visitors each year. Visitors can explore the property and learn about Edith Wharton by taking tours of the house and gardens and are invited to sit in and interact with the rooms without obstruction. Interpretive exhibits throughout the house explore Wharton and her servants’ lives, as well as her humanitarian efforts and literary legacy. The Mount also presents lectures, dramatic readings, theater, music, storytelling, workshops, outdoor sculptures, films, and literary panels with over 40 local partner organizations.

The Frelinghuysen Morris House and Studio is a historic house museum and former art studio in Lenox and Stockbridge, Massachusetts. The house and studio were home to American Abstract Artists George L.K. Morris and Suzy Frelinghuysen. The studio was built in Bauhaus style in 1930 by Morris and his friend George Sanderson. The house was added in 1941, designed by John Butler Swann. The house and studio were entered onto the National Register of Historic Places in 2016.The house contains furnishings and decorations unchanged since the couple's lifetime. The art collection includes cubist frescoes and paintings by Morris and Frelinghuysen, as well as works by Pablo Picasso, Juan Gris, Georges Braque, Joan Miró and Henri Matisse.

Shakespeare & Company is an American theatre company and venue complex located in Lenox, Massachusetts, in the Berkshires region of western Massachusetts. It was founded in 1978 by artistic director Tina Packer. The company performs plays by Shakespeare and new plays of "social and political significance", reaching over 75,000 patrons annually. It also conducts training programs for professional classical actors as well as education programs for elementary through high school students, the latter reaching over 50,000 students annually.

Lenox School was an Episcopal independent, college-preparatory boarding school for boys in grades nine through twelve in Lenox, Massachusetts, in the United States.

Spring Lawn is an historic home on Kemble Street in Lenox, Massachusetts. Built in 1904 for John Alexandre, the mansion is considered a unique blend of Beaux-Arts and Classical Revival styles. Spring Lawn was designed by Guy Lowell who was also the architect of the Museum of Fine Arts, Boston and the New York Supreme Court courthouse. The property has seen many uses over the years, including acting as the home of the National Music Foundation and Shakespeare & Company. Today, there are plans to convert the mansion and its surrounding property into a luxury resort.

Canyon Ranch operates two Destination spas and one retreat property in the United States. The two Canyon Ranch spa resorts are located in Tucson, Arizona, and Lenox, Massachusetts; its retreat property is located in Woodside, California. Canyon Ranch also operates Spa + Fitness locations with primarily day spa facilities. These are located at The Venetian and the Palazzo hotels in Las Vegas, and on cruise lines including Cunard Line, Regent Seven Seas, Oceania, and Celebrity.

The Windsor Mountain School was a private, co-ed boarding school for grades 9 through 12 located in Lenox, Massachusetts.

The Tanglewood Jazz Festival was a summer music festival, featuring contemporary jazz artists. In 2012, the event was cancelled. It was held every year on Friday, Saturday, and Sunday of Labor Day weekend, in Lenox, Massachusetts. The festival was held since the early 1990s, at Tanglewood, which is a beautiful outdoor festival grounds, and the summer home of the Boston Symphony Orchestra during June, July, and August, and given over to the jazz festival on the final weekend of the season. Friday night's concert by tradition featured Latin jazz music. Saturday afternoon usually featured pianist Marian McPartland and her guest, and also another concert as well. Saturday night usually featured the contemporary greats and is held in the main venue, known as the "shed". Sunday featured two concerts, one in the afternoon, and on in the evening, often featuring Dave Brubeck. Artists who appeared include Miles Davis, Diana Krall, Wynton Marsalis, Natalie Cole, Ahmad Jamal, Donal Fox, Nancy Wilson, Roy Haynes, Roy Hargrove, Jimmy Smith, Freddie Hubbard, Ray Charles, Hiromi Uehara, and many more. The festival is world-renowned and famous for its contributions to jazz culture.

The Foxhollow School was a private boarding school for girls. Founded by Aileen M. Farrell in 1930 on the Foxhollow Farm in Rhinebeck, New York. The school was moved to the Lenox, Massachusetts former estate of the Alfred Gwynne Vanderbilt family. The school expanded to the neighboring property, The Mount. Miss Farrell was a British citizen and Oxford University graduate, who never sought American citizenship. She led the school for forty years until 1970. The school closed in 1976 and the property became an inn. In 2017, it was announced the building would be converted to luxury apartments.Foxhollow School was one of several private secondary schools in the vicinity that occupied the properties of Gilded Age estates to close in the 1970s. These schools included Stockbridge School, Windsor Mountain School, Lenox School for Boys and Cranwell Preparatory School. The costs of maintaining these grand Berkshire Cottages and their sprawling grounds was one of the contributing causes of their closures.

Ventfort Hall Mansion and Gilded Age Museum is a historic, Jacobean-style mansion and museum located at 104 Walker Street, Lenox, Massachusetts. It is listed on the National Register of Historic Places. Visitors can tour the mansion and learn about the changes that occurred in American life, industry, and society during the late 19th-century period known as the Gilded Age.

Trinity Episcopal Church is an historic Episcopal church building at 88 Walker Street in Lenox, Massachusetts. Built in 1888 for a congregation organized in 1793, it is a prominent local example of Romanesque architecture, funded by Gilded Age summer congregants. The church was listed on the National Register of Historic Places in 1996.