One of our friends told us he was psyched about an upcoming trip to the Berkshires, but not keen on staying at a country inn. “I think I’m allergic to gingham and frills,” he said.
Oh, you sweet, clueless man! One of the many delights of a getaway to the Berkshires is the sheer variety of lodgings. Sure, there are country inns galore, but there are also Scandi-style lakeside cabins, a converted Victorian millworkers’ row house, a Gilded Age gardener’s cottage, a mid-century modern guest house in the woodlands, a glamping resort (recently reviewed in these pages) and a historic hotel that’s been called one of the most haunted hotels in America. And that isn’t a complete list. Here’s a sampling.
Gilded Age gardener’s cottage: Ventfort Hall, Lenox
History buffs, take note: A cute-as-a-button, circa 1893 brick cottage was built on the estate of financier J.P. Morgan’s sister, Sarah, for landscape and garden architect John Huss. In private hands for decades, the cottage is once again part of the Ventfort Hall estate and is available for short-term rental. (Ventfort Hall is a 22-bedroom Jacobean-Revival mansion, now operating as a house museum.)
The gardener’s residence has two bedrooms and 1.5 baths, a kitchen, and a scullery. Period furnishings dominate (we love the clawfoot tub), but count on modern amenities like air conditioning and a washer-dryer. Downtown Lenox is within walking distance, and the rental includes four tickets to the Mansion at Ventfort Hall. From $400. 104 Walker St., Lenox. 413-637-3206, https://gildedage.org/pages/gardeners-cottage
Outstanding in their field: Guest House at Field Farm, Williamstown
What would you not expect to find in the middle of 320 acres of conservation land? How about a stylish circa 1948 house filled with Bauhaus-style furnishings and adorned with period artwork and outdoor sculptures. Managed by The Trustees of Reservations as a bed and breakfast, this six-room house is mid-century chic. Outdoors, it’s all woodlands, wetlands, and meadows, with views of Mount Greylock. Also on the property: The Folly at Field Farm, a private three-bedroom, two-bath, pinwheel-shaped guest cottage designed in 1965 by noted modernist architect Ulrich Franzen, complete with more influential artwork and period furnishings — think built-in sunken seating areas and hand-placed wood panels all overlooking a wildlife pond. “You feel like you’re on the set of ‘Mad Men,’” one guest said.
Explore 4 miles of hiking and unofficial Nordic ski trails by day, but plan to make tracks to local restaurants; there’s no full-service eatery on property. However, guests of the inn receive a home-cooked breakfast. Open year-round, the inn accepts kids over age 12 only and requires a two-night minimum stay. Guest house from $269; Folly from $649. 554 Sloan Road, Williamstown. 413-458-3135, https://fieldfarm.org/
Ghostly goings-on: Red Lion Inn, Stockbridge
In 2025, Vogue named the Red Lion Inn as one of the 25 most-haunted hotels in America. The innkeepers are fine with that. Mysterious happenings are par for the course here. Opened in 1773 as a small tavern, “the inn has a lively and rich history,” says Tim Eustis, director of catering sales & wine director, and ghosts are simply a part of that. “We’re stewards of the ghosts.”
Room 301 is Spooky Central, with guests reporting a gentleman wearing a top hat, a young girl carrying flowers, and more spectral sightings. But a former housekeeper has said that the entire fourth floor of the main inn is a haunted hub of activity. It’s easy to see why dearly departed guests would be loath to depart, given the lively vibe of this inn, with its Main Street location, bustling lobby, and coveted rocking chairs on the front porch. The guest list includes five US presidents, plus singers Bob Dylan and Post Malone. Main inn suites from $321; village house rooms from $194. 30 Main St., Stockbridge. 413-298-5545, www.redlioninn.com
Art-lover’s pick: The Porches Inn at Mass MoCA, North Adams
Six Victorian-style row houses built for millworkers in the 19th century have been reimagined as The Porches Inn, a 57-room boutique hotel. They’ve been restored, of course, and no two rooms are alike. The property opened in 2001 — the 25th anniversary was celebrated in August — and was a catalyst for the North Adams cultural revival. Mass MoCA is directly across from the hotel, and Porches is home to Studio 9, a sustainable, state-of-the-art recording and performance venue with artist residencies. A new annex offers 10 minimalist rooms without TVs or phones. All guests have access to a Finnish-style sauna, outdoor hot tub, and four-season outdoor pool. Head to the lobby bar for cocktails and a full breakfast. (Breakfast is included in the $20 per night amenity fee.) If you’re looking for artistic inspiration (or just a cool base for exploring Mass MoCA, the Clark Art Institute, the Williams College Museum of Art, and other Berkshires treasures, don’t sleep on this one. From $198 plus a $20 nightly amenity fee. 231 River St., North Adams. 413-664-0400. https://porches.com
Best transformation ever: Prospect Berkshires, Egremont
We never saw this one back in the day, when it was an RV park, but we can only imagine it looked wildly different back then. Now, Prospect Berkshires is a cool colony of 49 Amish-made “nature cabins” made with wood, stone, and glass that fit in seamlessly with the grassy hillside and knoll fronting Prospect Lake.
Opened in June 2025, this place has a Nordic resort look and a pastoral vibe that makes relaxation easy-peasy. For fun, there’s a seasonal swimming pool (the resort is open year-round), tennis, paddleboards, kayaks, and a lakeside sauna. Some cabins sit on the lake, or are on a hillside with views of the lake, while others sit in a grassy knoll. Nine “bunk hideaways” share a restroom. Firepits and hammocks dot the property, and even folks who aren’t staying show up for dinner at the Cliff House for locally-sourced fare. From $400 (includes breakfast for weekday stays). 50 Prospect Lake Road, Egremont. 413-528-5005, www.prospectberkshires.com
As for James Taylor, he and his wife, Kim Smedvig, live in Washington, Mass., in central Berkshire County. Nice guy though he is, he’d probably rather you not show up at their doorstep. Pay your respects at Tanglewood next July Fourth (not officially announced, but here’s hoping!).
For information: https://berkshires.org.
Diane Bair and Pamela Wright can be reached at bairwright@gmail.com