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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.
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.
Exterior View - Hotel on North - Pittsfield, MA
Hotel on North

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

Boutique Berkshires hotel will ensure your couple-time is all you wish it to be

The Hotel on North has a singular sense of what makes a romantic atmosphere: inviting, individually appointed rooms; impeccable service; great spaces for relaxing; and proximity to countless couples activities. Oh, and the historic building, with its exposed brick, tin ceilings, art gallery and comfy atrium, plays its part, too. Ask about a room with a gas fireplace, or seek out the Library Suite with its panoramic mountain views and claw-foot tub. (And don’t forget to inquire about in-room spa services.) Each of the 45 rooms feature original art, pillowtop mattresses and luxurious linens. Nearby activities range from great skiing, hiking and biking to gardens and museums perfect for strolling, arts venues and fun shopping and dining.
King Suite 500x250 - Deerfield Inn - Deerfield, MA
Deerfield Inn

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

Experience the romance of an earlier time at this charming historic inn

Check in to the Deerfield Inn and prepare to travel back to a more romantic time. The inn, on a picturesque tree-lined street amid 19th- and 20th-century homes, opened its doors in 1884, and that charm of earlier days is still evident in its antique-appointed rooms and suites (all with chamois robes and comfy reading chairs; the King Suite has a gas-burning fireplace) and romantic dining inside by a fire or on the patio at Champney’s Restaurant & Tavern. The Romance Package includes wine, chocolates, flowers and robes to take home. Or, just add a room enhancement, like champagne, chocolate-covered strawberries or a massage, when you make your reservation. Please visit our website to see current COVID policies.
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.
Romantic Dining 500x250 - Berkshires Visitors Bureau - Photo Credit Red Lion Inn
The Berkshires of Western MA

Find Wintery Romance in the Berkshires

Travel & Leisure named the Berkshires one of America’s most romantic winter destinations: “With open roads, small towns, and classic red barns, the Berkshires deliver all the dreamlike wintery romance of New England, as immortalized by singer James Taylor.” Reconnect with your sweetheart through the shared exhilaration of a downhill ski slope or during a cross-country trek through enchanting, snowy woods. Delight in cultural attractions, shop unique boutiques, or book a date at a world-class spa (many offer couples packages). After a full day, satisfy your inner foodie with a fresh, farm-to-table meal and craft cocktails, then share a bottle of wine by an open fire. Learn more at Berkshires.org or follow “Visit the Berkshires of Western Massachusetts” on Facebook.
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.
Ponds at Foxhollow Exterior Lenox MA
Ponds at Foxhollow

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

Romance is in the Berkshires air at this stunning 223-acre resort estate

Your romantic getaway begins at the Ponds at Foxhollow – and you might not want to leave. This scenic, 223-acre resort nestled in the heart of the Berkshires has breathtaking vistas wherever you look, plus 48 units with Jacuzzis, fireplaces and decks overlooking the picturesque pond. Go cross-country skiing, or hiking, or take a canoe for two out on the pond. Relax in the indoor and outdoor pools, hot tub or sauna, or play a little tennis, practice on the putting green or try a little shuffleboard or bocce – all without leaving the property. Or just enjoy some time together reading in the beautiful fireplaced library. The beautiful Berkshires region is known for its many romantic restaurants, walks, and cultural venues.