When you plan a Valentine’s Day getaway in Maryland, you can look forward to walking hand-in-hand with your loved one on the beach, as well as embarking on cruises along Chesapeake Bay at twilight. Whether you want to go on a couple’s hike or experience unforgettable dinners, staying at a Maryland vacation rental puts you within driving distance of the most popular Valentine’s Day activities. Check out the top getaway locations in the state, as well as where to go in Baltimore, Annapolis, and other top cities and towns to celebrate the holiday of love.
1. Annapolis
Start off your vacation with an invigorating Valentine’s 5K (to work off those future chocolate calories) at the Kinder Farm Park. With the Kinder Farmhouse open to the public, this option also works well if you have kids. Stick with the outdoors theme at the Quiet Waters Park to ice skate hand-in-hand. Show your kids you love them with a Valentine’s Day party at My Gym. Your kids get to make their own personalized valentines, play games, dance to music, and eat cupcakes. Head over to Whole Foods for some Valentine’s Day cookie decorating or to the library for love-themed activities. After taking the kids home, head over to Studio 111 Theater for a production by the Annapolis Shakespeare Company. Wrap up your night with some easy listening at 49 West, a club with live jazz, dinner, and drinks. Some other top dining options include Carroll’s Creek — with a romantic fireplace and view of the water — and Harvest Wood Grill and Tap. Instead of just passively receiving your meal, cook together at Simply Sienna Dishes’ Couples Date Night activity. Singles don’t have to spend this holiday alone, either. The Haunted Pub Crawl of Historic Annapolis is surprisingly popular, allowing you plenty of opportunities to meet other people while having a blast.
Find vacation rentals in Annapolis
2. Baltimore
Get the whole family involved with the holiday of love while you’re in Baltimore. Kick things off with a Family Valentine’s Dance Party at the Port Discovery Children’s Museum. There are games, music, dancing, and food. Next, head over to the Maryland Science Center for Paper Circuits and Pop Up Cards Workshop, because a Valentine’s Day card that buzzes and lights up is the best kind. Treat the kids to some red velvet pancakes for brunch. Once they’re worn out, go out with your significant other for romantic dining at Bluegrass Tavern, Cunningham’s, Fleet Street Kitchen, or Pazo depending on what you’re looking for. Bluegrass Tavern is all about the Southern comfort food and chocolate mousse dessert, while Fleet Street Kitchen enhances the mood with hanging chandeliers, four-course meals, and background music. Up the romance factor at Red Maple or Anastasia, low-key lounges with soft light, champagne, and chocolate-covered strawberries. If you want to spice up your night, learn about love from the animals at the Maryland Zoo. This Sex at the Zoo event has music, hors-d’oeuvres, and dancing.
Find vacation rentals in Baltimore
Find the perfect Maryland vacation rental on Tripping.com. Tripping.com is the world's #1 vacation rental search engine with over 10 million properties!
3. Savage
Savage is a town that lies about halfway between Baltimore and Washington D.C. This is the place to get a vacation rental if you want uninterrupted time with your sweetheart and some green space to roam. Savage’s Terrapin Adventures has a special Valentine’s Day event in which you can get your adrenaline pumping together…on a zip line or ropes course. There’s even a giant swing and Terrapin Flyer.
Find vacation rentals near Savage
4. Columbia
Columbia’s Central Branch Library really gets into the holiday spirit with Valentine Craft Creations for kids. These crafts aren’t just paper either, but bracelets and keychains. You might find yourself the recipient of a special child-made bracelet that says “I love you.” Valentine’s Day is not just about love, but ways to express that love in chocolate and jewelry, which is why Valentine’s Chocolate and Jewelry Show is the perfect place to go. Its location in the Historic Oakland Manor provides a romantic atmosphere, while the shopping options and spa services are the gifts to your valentine that shows your devotion. Afterwards, head to the Valentine’s Day Truffle Making and Wine Tasting at the Robinson Nature Center.
Find vacation rentals in Columbia
5. Bethesda
You might not often get the opportunity to go out as a couple for dancing, so take advantage of your stay in Bethesda to cut a rug at the annual Valentine’s Day Dance at Dance Bethesda. If your skills aren’t up to snuff, enroll in a dancing class instead. Food’s another big Valentine’s Day deal, and there’s plenty of it from the three-course Valentine’s Day dinner at Lebanese Tavern to the four-course chef-tasting menu and champagne toast at Cesco Osteria. With Washington D.C. bordering Bethesda on the south, head to the capital of the country for a dinner cruise on the Potomac River, Cupid’s Bar Crawl, DC Metro Chocolate Tours, or the Spy Museum’s Valentine’s Day Event.
Find vacation rentals in Bethesda
6. Jarrettsville
If Savage isn’t remote enough for you, head to northern Maryland to Jarrettsville. This small town is nestled amid rolling farmland, trees and the Rocks State Park. Explore nature on the guided Sweetheart Hike to the King and Queen Seat at Rocks State Park. Listen to the local legends about the King and Queen Seats, and then take a picture there when you reach them to commemorate your experience. Afterwards, warm up with a romantic dinner at Enotria Restaurant and Grill or Madonna Seafood Restaurant.
Find vacation rentals in Jarrettsville
7. Ocean City
There’s just something magical about walking hand-in-hand barefoot on a beach at twilight that speaks to the romantic soul, which makes knowing where to go in Ocean City for your special night a breeze. Before this, though, stop at the Captain’s Table or Adolfo’s for some good food. The Captain’s Table is all about the seafood, so oysters are on the menu along with crab cakes and filet mignon. Adolfo’s, an Italian eatery, offers a Valentine’s Day package with appetizers, entrees, dessert, and drinks included.
Find vacation rentals in Ocean City
Ready to go? Check out these amazing Maryland vacation rentals on Tripping.com.