Guests can choose from an array of intimate proposal experiences, coordinated by Bonita Wilson, Main Street’s “Proposal Concierge.” Ideas include a cozy proposal in rocking chairs on the porch at the Red Lion Inn, private time with champagne at the outdoor fire pit at Porches at MASS MoCA or a private dinner in the iconic vintage birdcage or new Library Suite at Hotel on North. 

Soon-to-be engaged couples can book one of the following “Leap into Love in the Berkshires” packages below. For more information on “Leap into Love in the Berkshires”, please visit http://www.mainstreethospitalitygroup.com/#!leap-into-love-in-the-berkshires/ca63.

Another idea is to "Snuggle Up" at Red Lion Inn in Stockbridge, MA. The historic Red Lion Inn has been welcoming guests for over two centuries, now with 125 guests rooms (some with in-suite fireplaces), four restaurants and a year-round heated pool.

• Overnight accommodations 
• Dinner for two
• Breakfast the following morning
• Rates start at $345 (Sunday through Thursday), $415 (Fridays and Saturdays), including all taxes and meal gratuities
• Offer subject to availability. Blackout dates may apply

We also love the "Date Night on North" at the new Hotel on North, Pittsfield, MA

Hotel on North opened its doors in summer 2015 and is located in the heart of the Berkshires just minutes away from some of the area's leading cultural institutions. Named one of Architectural Digest’s “Favorite New American Hotels” of 2015, the hotel's modern design, contemporary decor and inventive cuisine is ideal for hip urbanites on a quick getaway.

• Overnight accommodations
• Continental breakfast for two
• One three course dinner for two at Eat with oyster amuse
• Champagne and strawberries and cream in-room upon arrival
• Rates start at $380 weekdays, $405 weekends, including all taxes and meal gratuities 
• Offer available now through March 31, 2016

"Date Night" at Porches Inn at MASS MoCA in North Adams, MA

Located one block from MASS MoCA, one of the country's largest contemporary art museums, Porches Inn has become a destination for art-loving couples. 

• Overnight accommodations
• Two tickets to MASS MoCA
• Dinner for two at one of the area's restaurants (excluding beverages and gratuity) 
• A bottle of wine
• Continental breakfast 
• Rates start at $305, per night (Sunday to Thursday), $349 per night (Friday and Saturday)
• Offer available now through May 19, 2016, based on availability. Not available during holidays.