Foxhollow School

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.

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.

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.

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.

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.

Beaupré Creative Arts Center was an American summer camp for girls, located in Berkshire County, Massachusetts. The camp, which ran from 1955 to 1980, focused mainly on theater, dance, and art. The Beaupré property was sold in 1982 to the Berkshire Theatre Festival.

Blantyre is one of the grand Berkshire "cottages" put up during the Gilded Age in Western Massachusetts. Built in 1902 by Robert Paterson, a wealthy New York City businessman, it is named for his mother's ancestral home in Scotland.

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.

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.

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.