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Berkshires and Pioneer Valley welcome romantic vacationers

Massachusetts > Western Mass. > Resorts and Luxury > Romantic Getaways
The historic Berkshire Mountains and the Pioneer Valley are in the western end of Massachusetts. Year-round attractions include skiing at Butternut ski area, art museums around North Adams and Stockbridge, live summer music at Tanglewood, and much more. Visitors enjoying a romantic getaway -- for a weekend or longer -- have a choice of luxurious hotels and resorts. The rural nature of the region also lends itself to small, cozy bed and breakfast inns.
Ponds at Foxhollow Exterior Lenox MA
Ponds at Foxhollow

Route 7 Lenox, MA, 01240 Phone: 413-637-1469

A Berkshire’s hideaway for you and the love of your life

Nestle in to this cozy and secluded resort framed by towering pine and 223 acres of breathtaking scenery. Inventor/Industrialist George Westinghouse built a late 19th century cottage on this land for his wife, Marguerite. Today you can rent a one or two bedroom condominium with master bathroom and Jacuzzi, a fully equipped kitchen, fireplace, living and dining areas, a deck overlooking the pond, and entertainment tech for whatever your needs may be. There are indoor and outdoor pools, an exercise room with hot tub and sauna, tennis, rowboats and canoes, and trails for walking hand in hand. The magnificent Berkshire’s offer a lover’s paradise of historic sites, old inns and taverns, great food, art, music and more. Don’t miss a moment.
King Suite 500x250 - Deerfield Inn - Deerfield, MA
Deerfield Inn

81 Old Main Street Deerfield, MA, 01342 Phone: 413-774-5587

A Romantic Getaway set in an Historic Village

It’s easy to see why New England is often called “the romantic heart” of America with places like this classic, historic inn. Set on a street with a landmark pedigree, there is more than enough romance to forge the perfect getaway: cozy rooms with private bath and chamois robes, a convivial tavern with a mahogany dining bar, craft beers, inviting seating, and warming fireplaces. Enjoy classic favorites with a contemporary twist and local, seasonal produce. Don’t leave town and discover the treasure trove that is Deerfield with museums, 18th and 19th-century homes open to the public, colonial burying ground, and other attractions. Stay in for a couple’s massage in the Relaxing Room. Head out in any direction and you’ll find nearby towns and villages just made for lovers. Check out the KISS special.
Fireplace Suite - Devonfield Inn - Lee, MA
Devonfield Bed & Breakfast

85 Stockbridge Road Lee, MA, 01238 Phone: 413-243-3298 Toll-Free: 800-644-0880

Imagine your time together in a charming inn in the oh-so-romantic Berkshires

A luxurious, antiques-appointed room with a canopy bed, whirlpool tub, wood-burning fireplace, complimentary cognac and chocolates. Breakfast in a dining room or porch overlooking 32 peaceful acres of Berkshire beauty while classical music plays in the background. A dip in a heated pool. A massage in your room – or under the birches. If it all sounds romantic, imagine all this and more taking place in a stately English country home, Devonfield Bed & Breakfast, where impeccable service is still the order of the day. Located in the heart of the Berkshires, the historic 1800 inn is convenient to great theater, museums, galleries, music, shopping and an eclectic array of restaurants to make your special couple time even more memorable.
Romantic Dining 500x250 - Berkshires Visitors Bureau - Photo Credit Red Lion Inn
The Berkshires of Western MA

Find Wintery Romance in the Berkshires

As stated by Travel & Leisure in their America’s Most Romantic Winter Destinations, “With open roads, small towns, and classic red barns, the Berkshires deliver all the dreamlike wintry romance of New England, as immortalized by singer James Taylor. Couples can find alone time as they snowshoe and cross-country through mountain trails, explore Norman Rockwell–esque Stockbridge, and enjoy candlelit dinners at inviting lodge.” You can get cozy in front of a fireplace in a cozy New England inn or get rejuvenated together at a world-class spa (many with couples packages). Be sure to end your day over a delicious farm fresh meal cooked to perfection by one of our great local chefs. To learn more visit us at berkshires.org or find us on Facebook at "Visit the Berkshires of Western Massachusetts".
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Corner Room Fireplace 500x250 - Blantyre Hotel Restaurant & Spa - Lenox, MA
Blantyre Hotel, Restaurant & Spa

16 Blantyre Road Lenox, MA, 01240 Phone: 413-637-3556 Toll-Free: 844-881-0104

Romance is in the Berkshires air at this luxurious Gilded Age hotel

If you have ever wanted to slip back in time, to the luxurious and carefree Gilded Age, you need look no further than the Berkshires and the romantic Blantyre hotel. As you drive up to the estate, on 110 acres of rolling lawns, gardens and meadows, the Main House’s ivy-covered walls and Tudor-style turrets will make you feel like you’ve stepped into a castle. Inside, everywhere you look are period pieces, glittering chandeliers, fabric-covered walls and fireplaces. Whether your room is an elegant suite in the Main House, a loft suite in the charming Carriage House or a separate, secluded cottage, you will feel pampered. Gourmet dining, an exquisite spa and lots of places to just snuggle up and talk, are all part of the Blantyre experience.

Visit our sister properties - Ocean House Resort - Weekapaug Inn - Watch Hill Inn
Exterior View - Hotel on North - Pittsfield, MA
Hotel on North

297 North Street Pittsfield, MA, 01201 Phone: 413-358-4741

A boutique hotel that combines Victorian elegance with a modern vibe

People have been coming to the Berkshires for 200 years for its natural wonders, high culture, and restful beauty. The names Lenox, Tanglewood, Rockwell, The Clark, and The Mount signal a vacation of historic and fresh pleasures. The Hotel on North, in downtown Pittsfield, offers chic hospitality in a restored menswear store. The hotel’s signature lounging sofa greets you with notice that you will find older beauty, like brick walls and tin ceilings, along with modern services like WiFi, rooms with fireplaces, and a great casual restaurant and bar. As you head for your room be sure to check out the antique birdcage elevator - while it’s no longer in operation, it's a great piece of our heritage. A short drive takes you to museums, live theater, and mountain vistas.
Cranwell Spa and Golf Resort Romantic Getaways Lenox MA
Cranwell Spa and Golf Resort

Route 20 - Lee Road Lenox, MA, 01240 Phone: 800-272-6935

Beauty of the Berkshires beckons travelers seeking romance

The beauty and romance of the Berkshires beckon travelers to the Cranwell Resort, high on its hilltop in Lenox, home to 380 acres and the kind of views that take your breath away, four seasons of the year. Book one of 18 rooms in the resort’s Carriage House, which brings back the glory of the original 1890s building with its tower, gables and cantilevered floors. Settle into luxury queen- or king-sized bedding. Enjoy the resort’s indoor pool, historic golf course and fitness center (the spa and mansion are on hiatus until the summer), sip cocktails in the tavern, stroll hand in hand through the resort grounds or take a trip into charming Lenox to shop or dine.
Queen Room - Red Lion Inn - Stockbridge, MA
Red Lion Inn

30 Main Street Stockbridge, MA, 01262 Phone: 413-298-5545

Romance is in the air at famed Stockbridge inn

No one is more passionate about creating romantic ambiance than the staff at the historic Red Lion Inn. With the Berkshires as a backdrop, the gorgeous Stockbridge inn positively radiates romance. From the antique-filled guest rooms with feather duvets to the flower-filled courtyard, the inn offers all you need for an intimate getaway. Dine in the splendid main dining room or tavern, catch some live entertainment at the Lion’s Den, or arrange for private dining in the Plumb Room. Don a plush bathrobe and sneak down to the heated outdoor pool and hot tub or get a massage at the Seven Salon Spa. And don’t forget to ask for champagne and chocolate-covered strawberries for your room when you make your reservation.
Wine & Rose Petals - Oak & Spruce Resort - Holiday Inn Club Vacations - South Lee, MA
Holiday Inn Club Vacations Oak & Spruce Resort

190 Meadow Street South Lee, MA, 01260 Phone: Toll-Free: 866-454-5101

Romantic Escape in the Beautiful Berkshire Mountains

Romance is in the air at Holiday Inn Club Vacations® Oak n’ Spruce Resort in the heart of the Berkshire Mountains. The resort features everything needed for an intimate getaway, from a spacious villa with a dining area perfect for a candlelit dinner with a special someone to a welcoming private patio/balcony for champagne and a late-night dessert. Guests can also enjoy each other’s company the onsite bar, while savoring a cocktail or other specialty drink. Plus, there’s a host of activities for couples to enjoy including indoor/outdoor pools, a mini golf course, movie theater and more. And for those wanting to explore nature together, there’s nearby hiking and biking paths along the Appalachian Trail.