One of The Barrington’s eight suites, all of which are 500+ square feet.
297 North St., Pittsfield, Mass.
Rates begin at $259/night in September and $179/night beginning Oct. 13
Opened June 1 of this year, Hotel on North comprises a pair of 1880s buildings in downtown Pittsfield that are on the National Register of Historic Places. Mixing 19th-century and industrial chic motifs, this 45-room boutique hotel offers exceptional attention from its staff and the best location in the Berkshires, with all other Berkshire County towns and attractions within a 30 to 40 minute radius. Furnished with locally crafted furniture and décor, the spacious hotel features all of the amenities you’d expect from a more urban hotel, such as 24/7 valet parking, a fitness center, gift shop, art gallery, bar, lounge, restaurant (Eat + Drink on North), and late-night room service.
281 Main St, Great Barrington, Mass.
Rates begin at $235/night
Opened in 2014, The Barrington offers the personal touch of a B&B with the convenience of hotel accommodations. The boutique property is located on the third floor of a building right on Main Street, making it the only accommodations residing in the walkable part of downtown Great Barrington—putting the town’s myriad shops, bars, restaurants, and theaters literally steps away from your oh-so-comfy queen-size poster bed. The property’s eight salon-suites also feature flat-screen TVs, Keurig coffee makers, refrigerators, separate sitting areas, and spacious bathrooms with walk-in showers. In the morning, you have a choice of a made-to-order breakfast delivered to your room or credit toward breakfast at a restaurant in town.
The lobby at The Gateways Inn recalls its private mansion past.
51 Walker St, Lenox, Massachusetts
Rates begin at $170 per night, with a two-night minimum from June to October
Located in the heart of Lenox, this 11-room bed and breakfast perfectly blends old-world charm and elegance with modern-day luxury. The former Procter mansion features sleigh beds (complete with a teddy bear), fireplaces, plush robes, coffee makers, and mini-refrigerators. Innkeepers Michele and Eiran Gazit will even stock your refrigerator with breakfast should you need to leave in the morning before breakfast is served. The restaurant at The Gateways Inn offers delicious Mediterranean seasonal cuisine.and The Lounge features live music, and serves late-night fare. The bar has an impressive selection of whiskies.
The foliage typically peaks in the northern Berkshires (above Pittsfield) during the first week of October and in the southern Berkshires during the second week. While Route 7 is the main corridor, Route 8, which runs mostly parallel to it, is less developed and more scenic.
The Berkshire Botanical Gardens in Stockbridge hosts the Berkshires’ annual Harvest Festival on its grounds. With more than 10,000 attendees annually, it is one of the country’s largest and longest-running harvest festivals. This year’s event will be held Oct. 10 and 11.