Once you find the right place to stay for your vacation, it feels like striking gold. Let's be honest - choosing the perfect place to rest your head at night or have downtime during the day can shift the dynamics of your trip! This is why we created an ultimate guide to some of the best places to stay in Maryland the next time you're heading east. Some travelers start with where to stay in Maryland in terms of the city - Baltimore, Ocean Springs, and Annapolis. There is so much to see! But also, once you narrow down where you're going, you want to find the right accommodation in Maryland to suit your needs. Whether you're choosing an inn with delightful guest rooms to relax or want free Wi-Fi, a fitness center, and hot tubs, we have you covered with the best places to stay in Maryland.
Best Affordable Places to Stay in Maryland
Let’s kick things off with some affordable vacation rentals in Maryland. This is a perfect way to save money on where to stay and instead put it into activities and excursions. Choosing more affordable accommodations doesn’t mean sacrificing things like having an indoor pool or fireplaces. It just means that you aren’t breaking the bank by putting all your hard-earned vacation funds into the rental cost. Choosing one of these affordable accommodations allows you to have a fabulous getaway in Maryland.
1. Renovated Condo, Thayerville
- Location: Thayerville, MD
- Size: 1 bedroom, 1 bathroom (Sleeps 4)
- Price: $136/night
- Amenities: Free Wi-Fi wood fireplace, Deep Creek Lake views, furnished deck
- Ratings: 4.2
This delightful newly renovated condo in Thayerville has everything you need for an affordable overnight getaway in Maryland. You will have full views of the stunning Deep Creek Lake, plus a cozy fireplace inside, perfect for those chilly winter nights.
2. Calvert Cliffs Cottage, Calvert County
- Location: Calvert County, MD
- Size: 4 bedrooms, 2 bathrooms (Sleeps 8)
- Price: $180/night
- Amenities: Full bath, free Wi-Fi, washer and dryer, big backyard
- Ratings: 4.9
The Calvert Cliffs Cottage sleeps up to eight people without breaking the bank. There are four bedrooms and two bathrooms, which means plenty of space for the whole family. Plus, it doesn’t hurt that you’re situated in a quiet country setting with proximity to Calvert Cliffs State Park. Fossil hunting, anyone?
3. The Canal House at Taylors Landing, Sharpsburg
- Location: Sharpsburg, MD
- Size: 2 bedrooms, 1.5 bathrooms (Sleeps 4)
- Price: $166/night
- Amenities: Canal view, Wi-Fi, A/C, heating, gas fireplace, fire pit, private backyard
- Ratings: 4.99
The Canal House at Taylors Landing is a 1790 historic log cabin that's been remodeled into one of the most unique vacation rentals in Maryland. Located by the Chesapeake & Ohio Canal Historic National Park and close to the Antietam Battlefield, this historic home is surrounded by historic attractions. The Canal House offers a warm and inviting space with a wraparound porch perfect for sitting, relaxing, and taking in views of the C&O Canal. What are you waiting for? Book your stay today!
Best Places to Stay in Maryland for Families
Nothing beats a vacation that is dedicated solely to family time. Finding where to stay in Maryland for the whole brood can take some time, especially if your family is bigger than most. You have to factor in things like location, plus things for the kids to do! Here are some rentals in Maryland with on-site activities and loads to do.
4. Waterfront Riverhouse, Calvert County
- Location: Calvert County, MD
- Size: 3 bedrooms, 2 bathrooms (Sleeps 6)
- Price: $310/night
- Amenities: River access, private beach, farm setting, new kitchen, outdoor deck, paddle boards, kayaks
- Ratings: 5
It’s completely justified that this waterfront country house in Maryland has a perfect 5-star rating. With an exceptional setting on the Patuxent River, families can sit on the outdoor patio taking in all the sights and sounds. There are kayaks and paddle boards to keep the kids busy during the day. Did we forget to mention the house has its own beach?
5. Family-Friendly Lakehouse, Garrett County
- Location: Garrett County, MD
- Size: 4 bedrooms, 2 bathrooms (Sleeps 11)
- Price: $262/night
- Amenities: Lake access, dock, deck, views, hot tub, front deck
- Ratings: 4.4
You can fit the entire gang in this family-friendly lakefront home that sleeps up to 11 people comfortably. There is much to love about this house, from the extending deck into the water to your own private hot tub. This rental getaway is great not just for the kids but for the parents, too!
6. Beachy Maryland A-Frame, Scotland
- Location: Scotland, MD
- Size: 3 bedrooms, 2 bathrooms (Sleeps 8)
- Price: $170/night
- Amenities: Wi-Fi, washer/dryer, beach access, waterfront, fireplace, fire pit
- Ratings: 5
Located on the Chesapeake Bay and close to Point Lookout State Park, this Beachy Maryland A-Frame is a wonderfully unique Airbnb in Maryland for a getaway. Two bedrooms have queen beds while the third bedroom has a queen bed and bunk beds, kids and adults will love the space in the home. The interior is light and airy with views of the bay. Head outdoors, and you can walk to the beach and the bay or hang out in the yard by the fire pit. What a wonderful place for a getaway!
Best Romantic Places to Stay in Maryland for Couples
Ahh, alone time. It’s become coveted for many couples looking to take a quick getaway in Maryland without the kids. A family vacation is fun, but sometimes you need quality time with your significant other to reconnect. Sure, you could head to the Four Seasons, but what if we showed you a few charming spots in Maryland that are also incredibly romantic?
7. Overlook On Dun's Cove, Sherwood
- Location: Sherwood, MD
- Size: 2 bedrooms, 2 bathrooms (Sleeps 4)
- Price: $290/night
- Amenities: Free Wi-Fi, air conditioning, Fireplace, and a washer and dryer
- Ratings: 5.0
Are you searching for a peaceful getaway on the Eastern Shore? Overlook on Dun's Cove is the perfect choice. This custom-built vacation home is on nearly three private wooded acres and is only minutes from St. Michaels, Easton, and Tilghman. Plus, with the deep water pier, you can easily access the water and enjoy all sorts of fun activities. Additionally, this rental property has HDTV with Netflix, a modern home office with high-speed Wi-Fi and cable internet access, and a cozy wood-burning fireplace. A wrap-around deck, outdoor stainless gas grill, and all-weather patio furniture make hosting outdoor gatherings a breeze.
8. Beachy Oceanfront Condo, Ocean City
- Location: Ocean City, MD
- Size: 1 bedroom, 1 bathroom (Sleeps 5)
- Price: $260/night
- Amenities: Free Wi-Fi, air conditioning, and a washer and dryer
- Ratings: 4.6
Are you looking for a serene and romantic escape to Ocean City? This oceanfront condo on the second floor is the perfect place for you. Start your day with a cup of coffee while enjoying the stunning view of the ocean from the balcony. And when you're ready to venture out, you'll find a variety of shops, restaurants, and attractions within walking distance. This one-bedroom condo has a fully equipped kitchen, a standalone island with barstool seating, and a washer and dryer. The rental also provides four beach chairs, two boogie boards, and a beach umbrella in the storage locker. Make your Ocean City memories today and stay at the Beachy Oceanfront Condo.
9. Cass-Away A Luxury Houseboat, Grasonville
- Location: Grasonville, MD
- Size: 2 bedrooms, 2 bathrooms (Sleeps 4)
- Price: $225/night
- Amenities: Bay views, TV with Netflix/Hulu, dock, rooftop deck
- Ratings: 4.99
Located within the Kent Narrows is this unique Airbnb in Maryland. This houseboat offers plenty of amenities for a luxurious romantic getaway on the water. Spend time indoors watching TV or staring out the window at the water. Or, better yet, sit out on the dock or the rooftop deck where you can get a birds'-eye view of the gorgeous surroundings. I don't know about you but this seems like a wonderful getaway for an anniversary!
Best Places to Stay in Baltimore
Baltimore, Maryland, is one of the most popular cities within the state and a great place to explore on your next weekend getaway. There is much to see and do here, from indulging in the local history to tasting all the delicious coastal cuisines. Located on the state's eastern shore, Baltimore is a great place for historians and those looking to get a taste of city life. Enjoy Downtown Baltimore with these fascinating accommodations.
10. Charmed Brick Townhouse, Baltimore
- Location: Baltimore, MD
- Size: 2 bedrooms, 3 bathrooms (Sleeps 4)
- Price: $196/night
- Amenities: Perfect location, outdoor sitting area, family-friendly, free Wi-Fi, towels provided
- Ratings: 5.0
Enjoy the city life when you visit this charming brick townhouse in Baltimore. With a loft-like feel, you’ll fit right into the cityscape. Indulge yourself in the exposed brick and exposed ductwork. This multi-level home has history and style. Relax at night on the rooftop patio and take in all the sights and sounds of the city.
11. Baltimore Retreat, Cylburn
- Location: Baltimore, MD
- Size: 3 bedrooms, 3 bathrooms (Sleeps 8)
- Price: $182/night
- Amenities: Close to Downtown, fire pit, Smart TV, free Wi-Fi, newly remodeled, keyless entry
- Ratings: 4.4
A charming bungalow rental in Baltimore makes for the perfect overnight getaway, especially once you see all this accommodation has to offer. Just a few miles from Downtown Baltimore, you’ll be close enough to the city to explore but far away to relax and unwind. This adorable home is tastefully furnished, stylish, and upgraded with new technological amenities.
12. Rooftop Deck Downtown Townhome, Baltimore
- Location: Baltimore, MD
- Size: 2 bedrooms, 2 bathrooms (Sleeps 6)
- Price: $250/night
- Amenities: Free Wi-Fi, air conditioning, pet-friendly, and a washer and dryer
- Ratings: 5.0
Stay at the Rooftop Deck Downtown Townhome, and you'll be in a prime location on the most sought-after streets in Pigtown Baltimore! This neighborhood is known for being safe, quiet, and family-friendly, making it a perfect place to call home. You'll love the convenience of being within walking distance from the Baltimore Ravens and Orioles stadiums and many shops along Washington Blvd. The two-bedroom townhome also has a rooftop deck, a game room, and a fully equipped kitchen.
13. Industrial/Lux Brick Home w/Rooftop Skyline Views, Fells Point, Baltimore
- Location: Baltimore, MD
- Size: 3 bedrooms, 4 bathrooms (Sleeps 8)
- Price: $328/night
- Amenities: Free Wi-Fi, city skyline view, HDTV, outdoor dining area, and a washer and dryer
- Ratings: 5.0
One of the best Airbnbs in Maryland must be this industrial-style home in Fells Point, my favorite part of Baltimore! This two-floor row home has so many stunning architectural details including exposed brick walls and a rooftop deck where you can take in city views. While you can cook in the gourmet kitchen, you'll be within walking distance of restaurants as well as coffee shops, bars, and shops.
Best Places to Stay in Ocean City
A beach vacation getaway in Maryland, anyone? If you’ve forgotten that Maryland is a coastal state, we’re here to remind you of these incredible rental properties. Ditch the hotels with indoor pools, and take in all the best natural beauty beachside. You can make this a family-friendly vacation to the ocean or cozy up on top of the Marriott for a romantic weekend away. Either way, Ocean City has it all.
14. Luxury Boardwalk Stay, Ocean City
- Location: Ocean City, MD
- Size: 2 bedrooms, 2 bathrooms (Sleeps 8)
- Price: $150/night
- Amenities: Hot tub, indoor pool, top floor views, oceanfront
- Ratings: 4.9
Nothing offers a better way to see all Ocean City has to offer than at the top of a beachfront Marriott hotel. If you’re a tried-and-true traveler who loves hotels, this is your overnight stay. This 1,400-square-foot condo sits on the top floor of the Marriott Courtyard. Not only will you have access to the year-round hot tub and indoor pool, but you’ll also be a stone’s throw away from the ocean! It doesn’t get much better than that.
15. Renovated Ocean Block Gem, North Ocean City
- Location: Ocean City, MD
- Size: 5 bedrooms, 3 bathrooms (Sleeps 15)
- Price: $316/night
- Amenities: Foosball, ocean block, deck, BBQ grill, blender, free Wi-Fi, game room, free parking, easy access to the beach
- Ratings: 5.0
Imagine renting an ocean block getaway in Ocean City that can fit all of your friends and family members. This North Ocean City two-story gem features 2,500 square feet of space and enough room to sleep 15 people comfortably. You’ll have beach access when you stay here, plus games, foosball, patio seating, and so much more.
16. Ocean City Beachfront Condo, Ocean City
- Location: Ocean City, MD
- Size: 1 bedroom, 2 bathrooms (Sleeps 6)
- Price: $190/night
- Amenities: Air conditioning, free Wi-Fi, outdoor swimming pool, and a washer and dryer
- Ratings: 4.8
Stay steps away from the beach and oceanfront, and book a night or two at Ocean City Beachfront Condo. The outdoor balcony is like a cozy second living room where you can relax and unwind while listening to the waves. Inside, the unit boasts updated furnishings and fantastic decor. The fully equipped kitchen has stainless steel appliances and granite countertops where you can whip up delicious meals. There's even a washer and dryer in the unit for your convenience. And if you need to stay connected, there's Wi-Fi available for streaming or working from home.
17. Home Beach Resort, Ocean City
- Location: Ocean City, MD
- Size: 3 bedrooms, 2 bathrooms (Sleeps 8)
- Price: $260/night
- Amenities: Bay view, air conditioning, electric fireplace, free Wi-Fi, outdoor swimming pool, and a washer and dryer
- Ratings: 4.93
An Airbnb Guest Favorite, the Home Beach Resort is a condo that's just 5 minutes walking distance to the boardwalk, Ocean City beach, and everything else you could hope for in town. This unit offers views of the bay from many parts of the house. You'll absolutely love the space here and its convenient location!
Which of these incredible vacation rentals in Maryland is your favorite? Share with us your top choices in the comments section! Or, if you know the best places to stay in Maryland from your own personal experience, we'd love to have you shout those out, too.
And if you're interested in exploring more of the Old Line State on foot, a great resource for finding trails in Maryland is AllTrails!
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