Easton, Maryland
Easton, Maryland

An Unforgettable St. Michaels Holiday Getaway

Have a joyous holiday escape at The Oaks Waterfront Hotel, your vacation destination for the perfect getaway. Relax in luxury at our premier accommodations far from the bustle of town, a serene waterfront stay with everything you need for a wonderful time here in St. Michaels. Make your seasonal stay all the more exciting with events both here at The Oaks Waterfront Hotel and in town! We’ve put together this handy guide to help you make the most of it with a Thanksgiving feast, fun Christmas events, and so much more to discover. Make our St. Michaels hotel your holiday home away from home and experience the natural beauty of winter in the Maryland countryside.

a spread of thanksgiving food at the oak

Thanksgiving at the Inn

Give thanks this year with us and sit down to a home-cooked Thanksgiving meal surrounded by the holiday warmth of The Oaks Waterfront Hotel. We’ve put together a delicious menu with all the classics like roasted turkey with gravy, homemade mashed potatoes, and green bean casserole, and enjoy a New England twist on a favorite with our oyster stuffing! Indulge in decadent pumpkin and pecan pies for dessert along with a refreshing glass of wine from the bar, the perfect way to end this special day. Make sure to call ahead for reservations as slots are limited, and we hope to see you soon!

women enjoying the sights during a winter vacation in Maryland

Christmas in St. Michaels

Shop for gifts and enjoy the festivities as snow gently falls in St. Michaels, home to the annual Christmas in St. Michaels. This charming holiday event is a must if you are visiting from December 8-10th, a recommendation we make every year that is an absolute delight to attend. It’s a packed weekend with so much to do, so we’ve laid out happenings by day so you can make sure to see everything on your list.


  • Stop by the Marketplace and Sweet Shoppe for delectable culinary delights and handcrafted goods from local artisans, a great way to support the community, find gifts for loved ones, and satisfy that sweet tooth! It’s open every day of the event and is a great place to start your adventures.
  • Every night you can explore gorgeously decorated homes lit up bright with lights and get into the holiday spirit while admiring the impressive decor. Christmas in St. Michael’s website will have listings of some of the best neighborhoods being added to the whole weekend, so make sure and check that out while you’re here for stunning seasonal sights!

Saturday – Sunday:

  • A Christmas dinner will be held on Saturday, so be sure to stop by and enjoy a delicious holiday meal if you end up staying out later enjoying all there is to do.
  • Make sure and set aside some time to see the Lighted Boat Parade and watch as contestants display their colorful crafts decked with glittering lights and more than just boughs of holly! An absolute must-see and one of Christmas in St. Michael’s most iconic events.
  • The Talbot Street Parade is a time-honored tradition, a classic holiday event with Santa, his elves, and tons of decorated floats and performances. Make sure and arrive early for a great vantage point as they’re sure to be taken up quickly!
  • One of the highlights of this weekend-long event, the Tour of Homes has its own separate ticket purchase, but the effort is well worth it. Admire gorgeously decorated countryside homes and feel the warmth of the holiday spirit as you walk by roaring fireplaces and take in the soothing scents of seasonal spices. Make sure and check the Christmas in St. Michael’s site for tickets and further information.
a couple christmas shopping in st. michaels

Midnight Madness

Shop till you drop at St. Michaels Midnight Madness and add some excitement to your holiday gift shopping. Stores are open later with snacks and refreshments as well as exclusive sales for that day only. Every purchase gives you a chance to win a gift basket, so cross off your list and you might get a little something more too! Stop by one of St. Michael’s excellent restaurants for a delicious dinner and soak in the atmosphere with live music and sparkling Christmas lights; a truly memorable evening out on the town.

a bottle of sparkling wine awaiting in a room

Stay in Comfort

You can return to The Oaks Waterfront Hotel every evening for rest and relaxation after a full day of holiday activities around town. Our luxury accommodations have everything you need for a great stay with king and queen beds and walk-in showers while our private cottages also include kitchens and beautiful waterfront views. Make your stay more tranquil with our exclusive Romance Package, the perfect way to slow down after all that gift shopping, with a bottle of wine, a chef-selected miniature pastry platter, and a gift certificate to Bistro St. Michaels Restaurant awaiting on arrival. We hope all this has helped you plan an amazing holiday retreat here in St. Michaels and wish you and yours a Merry Christmas and Happy New Year.

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