Easton, Maryland
Easton, Maryland

The Best Romantic Winter Weekend Getaways in Maryland

Escape the hustle and bustle of the big city and retreat to a winter hideaway, your home-away-from-home for holiday fun and so much more. Here at The Oaks, we know how hectic this time of year can be, but what if it didn’t have to be? Take a romantic winter weekend getaway in Maryland, and escape for a time that is all your own in St. Michaels. Named one of the Top 10 Best Small Coastal Towns in America by USA Today, St. Michaels is a picturesque harbor on Maryland’s Eastern Shore. You can curl up by the fireplace and stay warm after a long day of winter activities, with delicious food, and plenty of ways to rest and rejuvenate. Read on for your guide to an amazing weekend getaway, that way you can spend less time planning and more time enjoying everything our little corner of the world has to offer.

a couple christmas shopping in st. michaels

Explore & Enjoy the Eastern Shore Together

The area surrounding the inn is simply gorgeous, a fantastic place to take in the sights during this wonderful season. Have a romantic stroll by the waterfront hand-in-hand with your beloved, find gifts for friends and family, or grab a special treat for yourself in town and shop till you drop! There are plenty of stores to choose from, with everything from local goods and fine clothing to specialty Christmas crafts. Relax back at the inn with a glass of wine in hand and a good book, or make conversation with fellow guests and enjoy the calming atmosphere, the perfect way to end a full day of Eastern Shore adventures.

a couple having fun in the snow near the oaks

Embrace Adventure Outdoors

There are plenty of ways to enjoy the great outdoors in St. Michaels, even if the weather gets a little chilly! Make sure to bring warm clothes and a camera, because the serene beauty of Maryland is unmatched during this season, the vibrant colors of fall giving way to a gentle canvas of white as the snow gently falls. Venture forth on foot or take a complimentary bike and explore over 30 miles of trails that wind their way throughout the area, with convenient access to nearby shops, restaurants, and local attractions. While you’re out and about make sure and keep an eye out for seasonal wildlife, especially birds, that live here during this time of year.

man pouring wine at a winery near The Oaks

Sip & Savor at Top Local Spots

Get a taste of local flavor at the best restaurants in and around St. Michaels with a wide variety of cuisine to suit any palate. Whether you’re in the mood for an upscale dinner out or a casual lunch in between activities, we’ve got it all! Unique eateries like Ava’s Pizzeria & Wine Bar offer the best of both worlds, while Chesapeake Landing is just the ticket for those craving delicious seafood at their extensive buffet! For a romantic date night, there’s no better recommendation than Bistro St. Michaels, a local staple for nearly three decades. Now owned and operated by the renowned Chef Stewart, the food is simply unmatched, a culinary experience you’re sure to remember long after the plates have been cleared. One of their most iconic attractions is their open kitchen, and if you’d like, you can sit at the bar and watch the kitchen staff cook your meal right in front of you!

While you can always enjoy a drink from our onsite bar, we also recommend some nearby wineries and breweries for lovers of liquid libations. The historic St. Michaels Winery makes excellent wines and offers tastings every Thursday – Sunday with private tours available on request. In the mood for an ice-cold brew? Eastern Shore Brewing pours a fantastic pint; refreshing and tasty award-winning beers that are sure to wow with tons of local flavor. They’re the oldest brewery on Maryland’s Eastern Shore and it shows, with a dedication to their craft honed over a decade of brewing expertise.

young woman getting a massage at the oaks

Treat Yourselves to Pampering

Make your weekend getaway extra special and treat yourself and your partner to a soothing Spa Retreat Package for unparalleled relaxation. There’s no need to let the cold weather make those muscles stiff when you can enjoy a 60-minute massage for two at our onsite spa. Our professional masseuse will help make those muscle aches disappear and leave you feeling refreshed and rejuvenated. In addition, a bottle of sparkling wine and an artisanal cheese plate will be waiting in your room upon arrival, the perfect way to start your stay and unwind after hectic holiday shopping.

Sink Into Luxurious Accommodations

Our historic waterfront property is just the place to be during the busy winter season, a cozy hideaway where you can have a romantic stay in luxurious accommodations. Choose from our deluxe rooms, suites, or full-size cottages, and make your stay your own. All feature plush king and queen beds, tub/shower combos, or walk-in showers, and many feature stunning views of the water! Customize your experience with unique add-ons to enhance your stay and indulge in goodies like chocolate-covered strawberries or a gourmet pastry platter. Treat your lover to a dozen roses, a bottle of red or white wine, or a savory charcuterie board for an unforgettable romantic winter weekend getaway to St. Michaels, MD. Make us your holiday escape, a bastion of calm amidst an ever-busy Christmas season, and give yourself the stay you deserve at The Oaks.

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Front lawn of The Oaks Waterfront Hotel in Easton, MD