Berkshires and Pioneer Valley welcome romantic vacationers

There’s a sense of time-traveling, back to a more relaxed era, when you check in to the Red Lion Inn, the historic inn on the picture-postcard Main Street of Stockbridge village. Everything feels romantic, from your sunlit inn room with a canopy bed and luxurious linens to the candlelight-and-chandelier atmosphere of the elegant dining room or the cozy intimacy of a table for two in the rustic tavern. Go for a late afternoon swim in the outdoor heated pool, dine al fresco in a flower-filled courtyard and toast each other with a glass of wine as your rock together on the inn’s welcoming porch. Catch an evening concert at Tanglewood or go gallery hopping or antiquing in the morning.

Visit our sister properties - Briarcliff - Porches Inn

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.

Bring your sweetie to the Berkshires for an unforgettable fall adventure. You can snuggle up by a crackling fire with a bottle of wine at a cozy inn, or book a luxurious stay for two—complete with spa offerings—at a world-renowned resort. Hand in hand, you can experience fantastic fall foliage on scenic hikes or drives, or while dining outdoors by a fire pit. Toast your time together with a craft cocktail over farm fresh fare designed by an expert local chef, and be sure to order dessert or pick up sweets to savor from our chocolate shops or patisseries. Whether you visit to unwind or let loose, the romantic Berkshires in fall is sure to delight. Book today.

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.

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 hot tubs, 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.