Blantyre

Discover the elegant romance of a bygone era at the legendary Blantyre Country Manor. Set amidst 110 manicured acres of lush grounds and rolling hills, the Tudor-style mansion offers modern furnishings with fairytale finishes, from grand fireplaces and chandeliers to luxuriant fabrics and linens. When staying at this Forbes Five-Star resort, be sure to sample champagne cocktails and speciality vintages at the Dom Perignon Champagne Salon, followed by the chef’s tasting menu at The Conservatory. End a decadent day in the property’s boutique spa.

Berkshire Elegant Country Inns

Choose from five beautiful New England inns – Applegate, Devonfield, Gateways, Inn at Stockbridge, and The Old Inn on the Green – all offering elegant accommodations in the charming country setting of Western Massachusetts. Begin a romantic Berkshire day with a gourmet breakfast by your in-room fireplace, then take a dip in the heated pool or explore one of many idyllic towns. Enjoy daily wine and cheese receptions and fine dining on or off the grounds. If spring wedding bells are in your future, consider tying the knot at one of these elegant destinations.

Kemble Inn

Perfect for proposals, honeymoons, and anniversaries, the Kemble Inn’s Lovers’ Getaway package offers indulgent accommodations for an amorous escape. Spoil your sweetie and yourself with a Superior or Deluxe King Room when you book two or more nights. In the morning, stroll downtown Lenox hand-in-hand with your sweetheart to enjoy fabulous shopping, delicious dining, and engaging art collections. End your day with a romantic dip your jacuzzi tub followed by a fireside glass of champagne. The Lovers’ Getaway package includes champagne, dining, and spa credits.

Wheatleigh

Book a luxuriantly romantic getaway at a nineteenth-century Italianate mansion nestled on 22 lush acres in the Berkshires. Located next to the legendary Tanglewood, Wheatleigh is the only Forbes Five-Star and Five Diamond resort in Massachusetts, so you and your lover are sure to delight in innovative multi-course menus and excellent personalized service. A full breakfast is offered each morning. During your stay, pamper yourselves with a massage, enjoy the beautiful property, or adventure into the surrounding Berkshires for a full day of fun and exploration.

Fairfield Inn & Suites

Book your upscale accommodations at Fairfield Inn & Suites, your home in the heart of the Berkshires. With convenient access to a myriad of arts, culture, and outdoor adventures, you and your darling will indulge in restful nights and invigorating days. A deluxe breakfast is included in your stay. During your visit, soak in the hot tub or heated pool, hit the slopes at Ski Butternut, or pursue the Norman Rockwell Museum. Fairfield’s friendly staff will happily recommend favorite picks for local dining, ensuring a romantic dinner for two or a picnic lunch for a Berkshire hike.

Hilton Garden Inn

Relax with your sweetheart at The Hilton Garden Inn in Lenox. Centrally located to everything the Berkshires has to offer, from ski resorts and hiking trails to music venues, theaters, and museums, your cozy nights will be complemented by full days of adventure. Bright, modern rooms, a fitness center, a heated pool, and a hot tub will ensure a relaxing and comfortable stay. Dine in to enjoy award-winning Pan-Asian cuisine at Jae’s Restaurant, or venture out to downtown Lenox, Pittsfield or Stockbridge for fine local fare.

Hampton Terrace Inn

Reignite that romantic spark surrounded by Gilded Age glamour at this historic bed and breakfast. Voted one of 25 top small hotels in the 2019 TripAdvisor Travelers’ Choice Awards, the Hampton Terrace Inn invites you to hide away in a deluxe King Suite Cottage for a dreamy stay in the Berkshires. Enjoy a private entrance, Jacuzzi tub, and cozy fireplace. Walk hand in hand from your front door to explore the charming village of Lenox where you’ll find award-winning restaurants, eclectic boutiques, theatre, and art galleries.

Rose and Goat Retreat

Relax and rejuvenate at the top of Florida Mountain at the Rose and Goat Retreat, a beautiful 50-acre estate looking east towards Vermont and New Hampshire. Boasting spectacular year-round views, the accommodations include an outdoor hot tub and fireplaces where you and your loved one can snuggle with a bottle of wine or cup of cocoa. Zip through the trees and kayak at Zoar Outdoor, hit the slopes at Berkshire East ski resort, or take in the art and concerts at MASS MoCA or The Clark – these and other attractions are just a short drive away. Great for couples or good friends looking for an amazing weekend getaway. Enjoy a one-of-a-kind experience you’ll never forget. 

9. Chesterwood

10. The Mount

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