Luxury Long Stay Rentals in Massachusetts

River Song

• 10 guests

• 5 bedrooms

Dalton, Berkshire County

It’s no wonder why a multitude of actors, composers, and artists have hideaways in the Berkshires. This classic Berkshires home, originally built as a schoolhouse in 1866, is steeped in history and rural charm.

Long Point

• 8 guests

• 4 bedrooms

Noyack, Southampton

Set within an acre of lush green grounds, this seriously charming home is just a twenty-minute drive from the centre of Sag Harbour - undoubtedly one of New York State's best-kept secrets. This centuries-old seaside village may be known as one of the most family-friendly places in the Hamptons, but its strictly adults-only activities include a visit to the nearby Wölffer Estate vineyards to sample their famed rosé cider.

Victorian Gingerbread

• 6 guests

• 4 bedrooms

Oak Bluffs, Dukes County

Built in 1871, this picture-perfect cottage has been beautifully renovated while retaining the most important elements of its original design. We're talking wood panelling, timber beams, and arched windows and doors.