Historical 18th-Century Inn with Candlelit Restaurant

With whitewashed clapboard exteriors and graceful front porches overlooking sweeping rural landscaping and overgrown meadows, The Old Inn on the Green looks like an idyllic setting written for a historical novel rather than a real place. Once a stagecoach relay, the inn's main building has been located in this quiet stretch of Massachusetts's Berkshire Hills since 1760, and honey-colored wooden floorboards, antiques, and period pieces nod to its origins. But while staying immersed in its past, the inn has leapt to the culinary present through its intimate restaurant, which earned a Best in the Berkshires rating from Zagat and was called "one of the finest dining destinations in the area, and arguably in the northeast" by Travel + Leisure.

Inside The Old Inn on the Green's candlelit dining room, chef and inn co-owner Peter Platt bases his seasonal American fare around ingredients sourced from area farmers. A four-course dinner for two, included in this deal, sates appetites with dishes such as slow-braised Angus short ribs and seared Maine diver scallops. In the morning, the cooks craft omelets made from local barnyard eggs and Vermont cob-smoked ham served alongside buttermilk pancakes sweetened by local maple syrup.

Eleven faithfully restored bedrooms are available between the main building and the separate Thayer House, which contains a little library and two large shared living rooms. Each guest room is different—most have fireplaces, some have claw-foot tubs, and some have cardboard cutouts of Thomas Jefferson—but all feature authentic antiques arranged to evoke the 1800s.

New Marlborough, Massachusetts: Cultural History in the Midst of the Berkshire Hills

A peaceful, rural town in the lower Berkshire Hills about 120 miles from Boston, New Marlborough is surrounded on all sides by state forests, which host fishing, hiking, mountain biking, and other activities. After a day exploring the outdoors, one could easily spend some time exploring the area's cultural history as well, starting at Herman Melville's Arrowhead, the home where he penned Moby Dick. Melville's study, piazza, and original fireplace are on display, as is the barn where he and The Scarlet Letter author Nathaniel Hawthorne met to discuss their writings and a shared love for Doritos. In nearby Stockbridge, the Norman Rockwell Museum displays a massive collection of paintings and drawings from the famous Saturday Evening Post artist, including the well-known Christmas Homecoming and Girl Reading the Post.