Guides

Are you and your partner looking to get away for a special weekend? If you’re searching for the best winter getaways for couples, look no further than the Berkshires! The Berkshires are filled with romantic stays and fun and exciting activities that will satisfy any lifestyle. When love is in the air, Zeitcaster cares! Follow this guide for the perfect weekend for two!

Where to Stay: Best Winter Getaways For Couples

First things first. For your special getaway, you need special accommodations. You have plenty of options for places to stay in the Berkshires, but if you are looking for romance, then we recommend a cozy stay at one of the area’s Inns. Here are our top choices:

Chambery Inn: Located in Lee, Chambery Inn offers the most spacious lodging in the area with 500 sq ft rooms and 13 ft ceilings. Rooms include gas fireplaces and jetted whirlpool tubs. (We recommend the FireSpa Suite.) Enjoy a romantic in- room couple’s massage and breakfast in bed!

Devonfield Inn: Also located in Lee, Devonfield Inn will customize any romantic package for you. If you tell the owners what the occasion is, they will go out of the way to make sure it’s memorable. You can also choose from a variety of enhancements such as having a bottle of champagne, an artisanal cheese tray or a floral bouquet be waiting for you in your room.

Inn at Stockbridge: Make this bed and breakfast your weekend retreat. Choose from a selection of special add-ons to make your stay even better. Enhancements include an in-room fondue tray, champagne or wine, and flowers. The Inn also offers elopement and wedding packages if happily ever after is on your mind!

The Red Lion Inn: Afternoon tea, anyone? If you stay here, you can experience the elegance of a formal tea party. The Red Lion is over 200 years old with a storied past. Each room is unique and will afford you the privacy and luxury you and your honey are looking for. Head downstairs to the Lion’s Den at night to catch one of their amazing musical performances.

The Williams Inn: If staying in a farmhouse-style guestroom suits your taste, then make this Williamstown Inn your home base. Choose one of their suites, enjoy a breakfast for two, and get ready for an enchanting stay.

Weekend Itinerary: Best Winter Getaways For Couples

After you check into your room, and unwind, how will your winter wonderland weekend begin? Zeitcaster can do the planning for you!

Friday night: Make a dinner reservation at Mazzeo’s Italian restaurant over the Lenox line in Pittsfield. Afterwards, head to Doctor Sax House for a late-night cocktail.

Saturday morning: Grab some pastries for breakfast at Patisserie Lenox. They make homemade French delicacies that are the sweetest way to begin your day. Wash them down with a nice steaming cup of gourmet coffee, and you will be fueled to begin your busy day.

Even though it’s winter, don’t be afraid to get outside! Hit the slopes at Bousquet or go tubing for a couple of hours. If being out in the cold isn’t your cup of tea, then head north to Mass MoCa Contemporary Art Museum. They have a rotating collection of exhibits that are always worth checking out.

For lunch, treat yourself to an Indian feast at Mint in Lee. Served with warm naan, you won’t be disappointed. Afterwards, head to Main St and find some vintage treasures at Finders Keepers. You never know what you will find at this eclectic little shop.

From there, enjoy a scenic drive down to Great Barrington and lace up your bowling shoes at The Cove. Spend an hour or two getting your competition on before heading to downtown Great Barrington. Plan on walking around the main and side streets, checking out all of the trendy little shops. There are plenty of coffee shops around if you want to get out of the cold and warm up.

By this time, you will want to drive to South Egremont and have dinner at the newly opened Hilltown Pies. They make delicious brick oven pizzas, and you can see the masterpieces crafted from the open kitchen. Saturday night is the perfect night to go to the Egremont Barn, which is right down the street from Hilltown Pies. The “Barn” is a fantastic venue for live music and for ending the evening with a nightcap.

Sunday: The best place to have brunch in the Berkshires is Rose’s in Lee. The staff are incredibly friendly, and the portions are generous. It tends to get packed on the weekends, though, so you may have to wait for a table. It is worth it!

Since this is your last day in the Berkshires, treat yourself to a couples massage at either Miraval Berkshires Resort and Spa or Canyon Ranch, and be refreshed and recharged for your trip back home.