Wheatleigh

Elm Court is a former Vanderbilt mansion located on Old Stockbridge Road, straddling the town line between Lenox and Stockbridge, Massachusetts. It is listed on the National Register of Historic Places and until July 2012 was owned and operated as a hotel by descendants of the original owners. Elm Court was built as the Berkshire summer home of William Douglas Sloane and Emily Thorn Vanderbilt, a member of the wealthy American Vanderbilt family. Designed by premier architectural firm Peabody and Stearns, with gardens and landscape design by Frederick Law Olmsted, Elm Court is the largest Shingle style house in the United States, with 106 rooms.

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.

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.

Tanglewood is a music venue and festival in the towns of Lenox and Stockbridge in the Berkshire Hills of western Massachusetts. It has been the summer home of the Boston Symphony Orchestra since 1937. Tanglewood is also home to three music schools: the Tanglewood Music Center, Tanglewood Learning Center, and the Boston University Tanglewood Institute. Besides classical music, Tanglewood hosts the Festival of Contemporary Music, jazz and popular artists, concerts, and frequent appearances by James Taylor, John Williams, and the Boston Pops Orchestra.

The Tanglewood Music Festival is a music festival held every summer on the Tanglewood estate in Stockbridge and Lenox in the Berkshire Hills in western Massachusetts.The festival consists of a series of concerts, including symphonic music, chamber music, choral music, musical theater, contemporary music, jazz, and pop music. The Boston Symphony Orchestra is in residence at the festival, but many of the concerts are put on by other groups. It is one of the premier music festivals in the United States and one of the top in the world.

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.

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

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

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.

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.

The Tanglewood Music Center is an annual summer music academy in Lenox, Massachusetts, United States, in which emerging professional musicians participate in performances, master classes and workshops. The center operates as a part of the Tanglewood Music Festival, an outdoor concert series and the summer home of the Boston Symphony Orchestra (BSO).

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.