Winter on the Chesapeake

Plan your Winter on The Chesapeake Today!

Image courtesy of Albert Ewing.

Discover the best holiday deals, hotel packages, festive cocktails, special menus, and pop-up markets in Annapolis and Anne Arundel County this season.

Enjoy all the festive experiences our beautiful and magical region has to offer!

Wintry Days❄️

If you've ever been to Annapolis in the Winter, you'll know it's a magical experience where the chilly air is swirling off the festive and ambient reflective waters at City Dock, the aroma of hot cocoa topped with fluffy whipped cream wafting through the cobblestone streets, and festive decorations lighting up every corner! 

Annapolis and Anne Arundel County are sparkling with seasonal delights!

Capture and share your adventures with us on social media using #WinterOnTheChesapeake.

DEALS

Annapolis Holiday Market

Free Admission. Discover one of the region's fast fast-growing holiday markets from December 12th - December 15th. Filled with local and regional artisans, holiday foods, and entertainment. This event on the City Dock will put you in the holiday spirit.

Cozy Stays 🔥

Our region warmly welcomes you to a plethora of cozy stays to make the most of a magical winter on the Chesapeake getaway.

Cozy stays offer discounts that can't be beat, check out new lodging deals and places to stay this season.

DEALS

Courtyard Fort Meade BWI Business District

Enjoy 15% discount off retail rates plus 1,000 Marriott Bonvoy Points per stay at Courtyard Fort Meade, from November 1, 2024 - February 28, 2025!

Maritime Conference Center

For Inauguration Weekend, stay out of the fray at the Maritime Conference Center! only 5 minutes from BWI airport and the Amtrak/MARC train stations, for easier access to Washington.
Group rate for January 18-21 is $239 per night, up to 4 guests per room, including an amazing buffet breakfast. Breakfast area is large enough for all your guests to eat together at the same time! Free parking for guests and motor coaches. Free airport shuttle to BWI.

Winter Chills☃️

Bundle up at charming and festive events that give you those winter chills!

DEALS

Midnight Madness

Shop in downtown Annapolis on the first three Thursday nights in December. The streets are filled with entertainment, the shop windows are decorated, and inside the shops, you may find unique gifts for the holidays, sales, and refreshments late into the night. Arrive early and enjoy dinner and happy hours at the restaurants. Take a break as you stroll downtown and get your picture in Snowflake Alley, under a light canopy, or by the Christmas Tree.

Holiday Shopping 🛍️

Haul in the holidays with exclusive deals around Anne Arundel County to gift to loved ones. 

Twinkling Lights🌟

Get your cameras and flash ready for animated dazzling light displays by the Chesapeake Bay, Annapolis Town Center, City Dock, and more! 

A winter on the Chesapeake will be one holiday getaway you will always remember.

Looking for more things to do on your getaway? Read our latest blog of Things to Do This Holiday Season in Annapolis and Anne Arundel County and plan your stay today!