These 8 Romantic Getaways in the Berkshires are the Perfect Escape

One of the most historic hotels in New England, this charming inn in Stockbridge has been hosting guests since before the American Revolution. Its classic New England style is evident as soon as you cross the threshold: antiques, chintz, china, and pewter occupy seemingly every nook and cranny of its lounges and guest rooms. After enjoying classic New England cuisine in the main dining room or the wood-paneled Widow Bingham’s Tavern (think creamy clam chowder, chicken pot pie, or Prince Edward Island mussels), head downstairs to the Lion’s Den—the inn’s underground pub—where you can listen to live music seven nights a week.

Sister property to the Red Lion Inn, the Porches Inn in North Adams offers modern accommodations in seven renovated Victorian buildings. Its location right across the river from Mass MoCA makes it ideal for culture vultures who made the pilgrimage to see the mill-turned-museum's incredible wall drawings by Sol Lewitt and massive installations by German sculptor Anselm Kiefer. The creativity continues inside the inn, which has an artist-in-residence program, vintage plates, and paint-by-number artwork. In summer, you can hike nearby Mount Greylock, the highest mountain in Massachusetts.

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The highlight of this Gilded Age resort, built around a historic Tudor-style mansion, is dining at the award-winning restaurant Wyndhurst at the Mansion. There, American classics are served in an elegant dining room with panoramic views of the Berkshires from the Rose Terrace. Rooms and suites are done up in a classic style, with some suites boasting fireplaces, marble bathrooms, and four-poster beds. Relax at the spa—one of the largest in the northeast—then venture out into the charming town of Lenox, where you can visit the Mount (Edith Wharton’s estate) and attend concerts by the Boston Symphony Orchestra at Tanglewood.

This historic B&B in Lenox has played host to literary luminaries including Pulitzer Prize-winning poets, so it’s no wonder you’ll find a cozy library. The design is very granny chic, with antique furniture, dainty floral wallpaper, and doilies aplenty in the individually decorated rooms. In winter, you can warm up by the fire, while in summer the pool is the perfect place to take a dip. Yogis can take private lessons on the property or enroll in classes at the nearby Kripalu Center for Yoga & Health.

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Housed on the sprawling estate built in 1902 for Gilded Age millionaire Robert Patterson, this gorgeous hotel outside Lenox recently received a multi-million-dollar renovation and was reborn as a Relais & Châteaux property. Named for the Scottish estate where Patterson’s mother was raised, it resembles a Scottish glen with ivy-clad brick walls, mullioned windows, slate-roofed turrets, and bucolic gardens. Luxury seekers will love the Dom Pérignon salon—the first such year-round lounge in the U.S.—and foodies should be sure to make a reservation for the chef’s tasting menu for a romantic dinner.

Guests of this charming inn in Stockbridge rave about the warm welcome from innkeepers Lisa and Jeff, who prepare a homemade breakfast every morning and will make your stay extra special with chilled champagne and fresh-cut flowers upon request. Individually decorated rooms are spread out among a main house, cottage suites, and four barn suites, which feature whirlpool Jacuzzis. Bonus: the location puts you within easy reach of nearby hiking trails, the Norman Rockwell Museum, and other Berkshires attractions.

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Want to play Gatsby for a weekend? This grand estate, built in 1893, was a wedding present for a Gilded Age tycoon's daughter. The Florentine Renaissance-style mansion sits on 22 acres of grounds designed by Frederick Law Olmstead (the man behind New York’s Central Park). Now a member of Leading Hotels of the World, the intimate property has just 19 rooms and suites, a heated outdoor pool, tennis court, sculpture garden, and three restaurants and bars including The Portico by Jeffrey Thompson, an elegant fine dining restaurant in an enclosed glass colonnade with just eight tables.

This award-winning B&B was originally built as the summer cottage for Harley Proctor of Proctor & Gamble fame. The 11 rooms are all individually designed—some have fireplaces and hardwood floors; others come with antiques and marble bathrooms. After dinner (the restaurant serves contemporary American fare in a laid-back atmosphere), pull up a stool at the custom-built mahogany bar and listen to live jazz in the lounge. Looking to take in the fresh mountain air? The Gateways is within striking distance of Mount in Lenox and the Hancock Shaker Village in nearby Pittsfield.