The Best Hotels to Book Near Tanglewood, Massachusetts

Where will you disappear to at Wheatleigh? The masterfully-landscaped grounds, complete with tucked-away, heated outdoor pool? Your grown-up guest room, with hill views, a large soaking tub, and decorated with art and antiques? Or perhaps the exclusive Portico restaurant, which serves up multi-course French gastronomy, and is reserved for only eight tables at a time? Or maybe you’ll want to hide away in the impressively-stocked wine cellar for a private tasting session? Wherever you end up, you’ll feel in a world of your own.

If the mountain views, roaring fireplace and four-posted bed of suite 204 at this Gilded Age mansion were satisfactory enough for 21st President Chester Arthur, we feel confident in saying they’ll tick your boxes, too. Elsewhere, the 1920’s Hollywood-themed suite 203 will wow you with its gold accents and white-on-white decor. Too fussy? The contemporary velvet headboard, heated marble bathroom floors and cowhide rug in suite 205 relaxes the vibe a bit. Whatever your mood, there’s a suit to fit here.

Does scheduled relaxation sound like an oxymoron to you? It did to us too, but put trust in Canyon Ranch to create an itinerary revolving around wellness and renewal, and you’ll reap the benefits. As early as 7:00 AM, morning walks transition into outdoor meditation, archery, and pickleball, punctuated by healthy, seasonal food. By the time activities wrap just after sunset, turn into your plush guest room for the best night’s sleep you’ve ever had.

If you’re a fan of historical chintz, the Birchwood Inn, with its matching wallpaper-and-drapes combos, is a must. Once a 17th-century tavern, it has period charm on tap throughout – from log-burning fireplaces to tea served in bone china crockery. Immerse yourself in more of the Lenox of yesterday with a visit to the Ventfort Hall Museum and Gilded Age Museum, Edith Warton’s Home, or the Berkshire Scenic Railway Museum.

33 Main delivers a luxury, local experience in Lenox, curated by owner Annie Selke, who’s called the Berkshires home since childhood. From the grand Aster room, which features the same handmade mattresses that the Swedish Royal Court sleeps on, to the Main Street views and all-natural bath products in the Stockbridge, each guest room has been individually curated with style and charm. If you love the look, you can take it home with a stop at Selke’s shop across the street.

While it’s not exactly the sound of silence you’ll find at Granville House, there is a soundtrack of tranquility that flows throughout the grounds. The collection of vinyl in the music room offers a front-row seat to relaxation, though the library, parlor, and fireside sitting room are equally chill and a little quieter. Trade the hum of the vinyl spinning for the crackling of the firepit in the backyard or pop in your earbuds and drift into a bath in your room’s soaking tub.

If the carriage house at The Inn at Kenmore Hall strikes a chord with your musical soul, perhaps it’s because the notes of Leonard Bernstein still linger throughout the rooms. Curl up in the cozy alcove or on the private porch and listen to the music in your head. Breakfast is served in the main house’s dining room, but use your cottage’s custom-built kitchenette when you want to brew a cup, turn the radio up, and fill every corner of the cottage with Bernstein’s music once more.