Planning a trip or weekend getaway and looking for the coolest and BEST Airbnbs in Maryland? Well, look no further, as I’ve put together this amazing guide for top Maryland Airbnb vacation rentals across the state!
Baltimore and Annapolis are of course home to some stunning Airbnb rentals – and that’s no surprise, given that Baltimore, the “Charm City”’ has a history as a trade port, and is also the birthplace of the US national anthem.
Annapolis plays its own part in US history. Between 1783 and 1784 it was the capital of the country! If that’s not a reason for a history buff to visit, it’s hard to imagine anything more fascinating.
Maryland is well known for its relationship with crustacea. It has a state crustacean – the Blue Crab. Along with rockfish and oysters, blue crab is considered a Maryland culinary cannon. Just remember that in MD, crab is steamed, not boiled.
Beyond that, Maryland’s most famous geographical marking is the Chesapeake Bay, which essentially splits the state in two. It makes the Atlantic coastlines of Maryland bountiful and popular, competing with its rivers and lakes.
So expect to see lots of boat masts, jetties, rolling hills, marshland, and pine forests on your stay here. All from the comfort of your home base, hopefully in one of these amazing Maryland Airbnbs.
Airbnb Maryland: The Best Vacation Rentals & Cabins
In a hurry? Check out my shortlist of ‘quick picks’ for vacation homes in Maryland.
- Best Waterfront Rental in Maryland – Waterfront, Relax, Recharge, Getaway/Bird/Fish/Paddle/Beach/Stargaze, Screen, Porch
- Best Luxury Maryland Vacation House Rental – Waterfront estate with gorgeous pool, pier, 3 acres of entertainment!
- Best Cheap Maryland Rental – Diamond Head – Ocean View Condo w/ Pool, Elevator And Just Steps To The Beach
- Best Vacation Rental in Maryland for Artists – A Living Canvas
- Best MD Vacation Rental for Big Groups – Architect-designed home w/gourmet kitchen, 4 BRs
I’ve added some videos throughout this article. They provide some of the best insights and ideas for things to see and do while visiting Maryland.
Note: Due to the closure of the Airbnb Associates program, some of the properties listed have been changed to other booking platforms (which can have lower rates and less cleaning/service fees!
Top 16 Vacation Rentals & Airbnbs in Maryland
Heading to southern Maryland? Perhaps you’re looking to spend some time around the Chesapeake Bay area? Here’s my pick of the best vacation home rentals in Maryland.
Price: $230+ USD per night
Looking for a top Maryland vacation rental right on the waterfront? You’ll fall in love with this spacious three bedroom upmarket home off Tangier Sound of Deal Island. The modern family home features heating and cooling throughout the open and light-filled interiors, brand new king and queen sized beds, new hardwood floors and new appliances – just to name a few highlights! There’s also a big backyard. You’ll be staying right on the water, the ideal spot to go paddling, fishing, birdwatching, swimming or to simply soak up the sun. A number of great islands are a short distance away.
Guest Review: “We spent a week in the middle of August. Weather was very warm (mid 90’s every day). Property was just as described in the listing. Owners were there to greet us and show us around. Nice communication throughout the trip and arrival time. We really enjoyed having breakfast on the screened in porch and the house worked out great for our group of 4 women. Everyone had their own sleeping area and plenty of room. Plenty to see and do in the area if you are looking for a nice beach vacation. Even got to see the ponies on Chincoteague and Assateague Island however were not able to approach them as we thought. I would certainly recommend this property to anyone wanting to visit the area. The owners are terrific, we forgot something that was special to us and they took the time to mail it to us! Very nice treatment.” – Leah
2) Waterfront estate with gorgeous pool, pier, 3 acres of entertainment!
Price: $3000+ USD per night
This stunning family home in Herald Harbor is the perfect spot to treat your family to a luxury vacation. Located right on the waterfront, the upmarket home span a huge 4500 square feet and boasts highlights such as a large heated swimming pool with waterfalls, a large outdoor patio, fire pits, a large yard with lots of games, a pier and a sandy beach. Just nine miles from historic Annapolis, this fantastic home is the perfect summer stay to enjoy a relaxed waterfront lifestyle right by the city.
Guest Review: “There’s no doubt that water was the highlight of the week – from the beautiful pool and hot tub – to the kayaking, canoeing, paddle boat, & SUP boards – not to mention the excellent crabbing, we had all the water sport activity one could ask for. After the grandchildren (and adults) had their daily fill of all of the above there were plenty of indoor activities, even a movie or two, to make for full, fun and exciting days. Thanks Cindy and Dave for providing the perfect spot for a perfect vacation!” – Bill
3) Diamond Head – Ocean View Condo w/Pool, Elevator And Just Steps To The Beach!!
Location: Ocean City
Price: $50+ USD per night
Cheap as chips and nestled right on the beach in Ocean City, Maryland, this fantastic one bedroom condo is cute and compact and equipped with all you need for a five-star stay. The neat pad offers great ocean views from its balcony, and is located within a complex that features a swimming pool and an elevator, and is just minutes from the shops, restaurants and bars of Midtown Ocean City. If you’re traveling to the Maryland coast on a shoestring, this condo is for you.
Guest Review: “This was a wonderful place for my 2 teenagers and myself to get away for the weekend. The place was clean and comfy. The beach was right there! Sunsets over the bay and sun rises over the ocean. Both could be seen from the balcony. Couldn’t ask for more. Everything was so close we walked everywhere. We didn’t want to leave! Wishing I had booked a longer stay. Gloria was fantastic to deal with. We will be back.” – Andrea
4) Artsy, Historic Row House with Striking Harbor Views – Best Waterfront Rental in Maryland
Airbnb Plus: Yes
Price: $421+ USD per night
All three floors of this 1840s-constructed home ooze coziness and charm. The wooden floors and brickwork add a tidy but genuinely warm feel to the space. While it isn’t expansive and broad, it’s incredibly well laid-out, and easily accommodates 8 guests.
But the kicker is the top floor terrace, which offers a 360-degree view of the area, including the marina. There isn’t a better seat in the morning for your first cup of coffee. Grab one of those deck chairs and get to relaxing!
Guest Review: “My friends and I absolutely loved this place! It was absolutely beautiful, well within walking distance to everything and it made us feel like we were home away from home.”
5) Abington Farm—National Historic 1640s Home in Serene Setting – Best Countryside Maryland Vacation House Rental
Airbnb Plus: Yes
Price: $181+ USD per night
Head out to Maryland country. This huge ranch-style home offers rolling hills for views. Watch the horses in the nearby fields and they will watch you back, while wilder creatures like foxes and deer are not uncommon.
The outdoors is what you want to enjoy here, whether from the gorgeous patios or on the walks in the fields. Indoors, there’s an incredibly comfortable living space. I especially love the lofted second bedroom with its simplistic, minimalist approach.
Guest Review: “Just stunning! We will be back. Do yourself a favor, and book this place for a restful time away from home.”
6) Walk to Historic Annapolis from a Waterfront Apartment – Best Southern Maryland Rental
Airbnb Plus: Yes
Price: $400+ USD per night
Some living spaces just make you want to never leave. This one has the added bonus of nothing but boat masts for a view. And you can even step out onto the balcony for a closer look at that. But any living space that goes big and generous on windows, sunlight, and views is a winner.
Add in the exquisite dark hardwood floors, beautiful white color-scheme, and location close to the waterfront, and there’s very little to dislike about this outstanding MD Airbnb. As Southern Maryland vacation rentals go, this one’s top of the pile.
Guest Review: “The place is very bright and airy. It has beautiful wood floors. The location is great, overlooking the sailboats in the marina and easy walking distance to dining and downtown Annapolis.”
7) A Living Canvas – Best Vacation Rental in Maryland for Artists
Airbnb Plus: No
Price: $42+ USD per night
If your tastes go to the more artful side of life, this place is paradise. Everything about the space inspires creativity unbridled. The art on the walls (which themselves are often murals), the sunflowers adorning the living space, the colorful pieces and pillows scattered over the sofas.
The host even offers the use of her sewing machine and video games. Why not do a bit of stitching and leave your own token of appreciation? And because it’s a private room at a great value, it’s ideal for a solo traveler. Cats are welcome too!
Guest Review: “The best stay! I was here for a month and I booked with Amanda because the pictures were so beautiful. And the pictures don’t do it justice.”
8) Architect-designed home w/gourmet kitchen, 4 BRs – Best Maryland Airbnb for Large Groups
Airbnb Plus: No
Price: $725+ USD per night
Splash out a little for something truly unique and stylish, especially if it’s a big family reunion or large gathering. Eleven people can stay in this fabulous home in a fantastic setting. Start in the kitchen – it’s delightful finishes make you want to stay in it for your entire holiday.
The bathrooms are another highlight – the tubs look inviting, as do the walk-in showers. But there’s also the temptation to just walk around the quiet and friendly neighborhood. Stone paths, trees, and rest areas abound. This is a superb option for a big celebration.
Guest Review: “A++ What an amazing surprise this warm home delivered. Chickens coup outside, Ping pong, antique music players, room for everyone with separate areas, and a wonderful dining room for ten.”
9) Beautiful and Tranquil Carriage House
Airbnb Plus: Yes
Price: $358+ USD per night
The elegant living space is a perfect wake-up experience to prepare for what lies beyond the walls and windows. It’s primarily white which somehow accentuates whatever furniture is placed in it. Most of that is leather or wood-based, which, along with the high ceilings, immediately elevates the sense of luxury.
The 8 guests you can host here will love the interior. But they’ll also love the sounds and sights of the surrounding nature. This is a place you come to spend a few days in quiet relaxation. Between books and cooking for self-care, you’ll have no shortage of activities. And there’s always a walk in the woods to rejuvenate your soul.
Guest Review: “This was our 3rd stay in the beautiful carriage house. We always feel so at home. There is plenty of room for my son, his wife, and young son to visit us. It is a home away from home for us when we visit Annapolis.”
10) Fun Apartment w/a Kitchenette and a Parking Space
Airbnb Plus: No
Price: $75+ USD per night
If you like to keep it simple, and you happen to be a sports fan, you’ll fit right in here. This guest suite is within walking distance of The Avenue which is a famous row of restaurants, bars, and shops. There’s a small games room down the stairs, and a fun set of vintage video games to enjoy as well.
Sports types will love the walls, upon which there’s a fair selection of memorabilia. There’s a ton of movies to watch as well, in case you’re not up for a visit to a local bar. You may receive a courtesy visit from the upstairs cat, which is always a great sign. They don’t bring biscuits, though.
Guest Review: “Fun club basement 1-bedroom apartment with lots of great movies, games, music, and Nintendo! The parking space in the back is really convenient. Would stay again.”
11) Affordable Furnished Luxury Townhouse near Stadiums
Airbnb Plus: No
Price: $109+ USD per night
This townhouse is recently-renovated and offers an interesting mix of functional and classic decor. It even has a small yard area to enjoy a bit of fresh air or a meal. Upstairs, the walk-in closet in the main room offers more space than most will need.
Location-wise, you’ll be close to Federal Hill and M&T Bank Stadium, which are popular landmarks for visitors and locals alike. In the other direction, there’s the tranquil scenery of Carroll Park to explore.
Guest Review: “Couldn’t find one thing to complain about if I tried. Great location, clean, comfy, and stylish. we were very happy with Carls place”
12) Wright’s Cottage- No cleaning fees! Pets! River!
Airbnb Plus: No
Price: $113+ USD per night
Just ten minutes from downtown Annapolis is a cute cottage nestled on a small acreage. Just a stone’s throw from the South River, it’s quiet enough to be a wonderful, peaceful getaway from the hustle and bustle of the city.
Get a feel for real cottage living. The space is cozy, comfy, and somewhat romantic. There’s a fabulous gazebo on the grounds you can use, and if you’re keen to see the river, there’s a small jetty to explore.
Guest Review: “We loved our stay in Annapolis! This place has everything you need and even had the firewood set up for us upon arrival. It was clean and a great location!”
13) Butchers Hill/Baltimore. Clean, Cozy, and Private!
Airbnb Plus: No
Price: $99+ USD per night
This studio apartment is close to many bars and restaurants, so you’ll have no shortage of places to dine and explore. It also has a kitchenette, should you choose to eat something light at home. But the main appeal here is Patterson Park, where you’ll always find something going on, whether it be an event, live music, or just people having fun.
The apartment itself is as pretty as can be. A large king bed overlooks a comfy living space. There’s a brick fireplace to help during the cold seasons, and plenty of large windows to let the light in. This space is superb value.
Guest Review: “The studio was so warm and comfy. I loved the fireplace, surround sound, the workspace, the views from the windows… John’s a gracious host and very responsive.”
14) Urban Eden
Airbnb Plus: No
Price: $185+ USD per night
Unusual for Baltimore, this location feels peaceful and calm. The house is at the end of a street, with access to the Stony Run Trail and more. It’s a home with character, appropriate for its age. And the furniture inside also reflects a collection of different eras, colors, and styles.
The house even comes with its own wildlife – you may get to feed the turtle! And the piano in the hall and vintage writer’s desk upstairs just add a wonderfully genuine touch. There’s a personal feel in every room, from the pink girls’ room to the old-style window seat on the third floor.
15) Beautiful Home in Roland Park
Airbnb Plus: No
Price: $242+ USD per night
What’s better than a fireplace? Two fireplaces! There’s one in the living room, and another in the dining room of this first-floor home. The beamed ceiling adds to the warm construction, and it’s worth noting the gigantic windows looking out into the woods nearby.
In keeping with the vintage feel of the house, there’s less of an emphasis to engage with modern media here. Although you have the best of modern facilities in the kitchen and bathrooms, a holiday here is more suited to a book, a glass of wine, and a great chat with your companions.
Guest Review: “Mary’s home is absolutely magical. I don’t have the architectural vocabulary to describe the house, but it was like stepping into the 1900s (with the benefit of 2020 appliances, AC, etc.) The neighborhood has the feel of a fairy tale. ”
16) Riverslie Estate on the Miles River
Airbnb Plus: No
Price: $819+ USD per night
Built in the 1840s, this updated charmer is an absolute gem of a find. The sunsets here are epic, as are the tolling gardens. Most elegant of all are the living spaces, though. This space boasts a classically designed sofa as well as a gorgeous wooden dining room table. And there’s a separate family room for TV time.
The outdoor sofas on the deck invite long lazy afternoons with a good book. That’s when you’re not sitting at the brunch table under the umbrella. From here, you could easily choose the shops and charms of either Easton or St Michaels, two shoreline towns with wonderful visitor potential.
Guest Review: “This is a unique, beautiful, 150-year-old home overlooking the Miles River. It offers spectacular views across the River to a large island, quiet paddling, and boating, herons hanging out on the dock, fancy restaurants a few minutes away in Easton or St. Michaels and nearby crabs fresh off the boat. A true vacation.”
Am I Missing Any Vacation Home Rentals in Maryland Worth Mentioning?
That’s my list of amazing Airbnb Maryland options. If you know of any more great vacation homes for rent in Maryland, please let me know! You can reach out via email or my social media. I’m looking forward to hearing from you.
Other Recommended Reading
If you’re looking at other options for your getaway, take a look at this list of awesome Airbnb options in the US.
- 15 Coolest & Best Airbnb Asheville Rentals in North Carolina
- The 20 Coolest & best Airbnbs in Michigan for an Epic Great Lakes Getaway
- The 22 Coolest & Best Airbnbs In Hawaii For The Ultimate Vacation Experience
- The 17 Coolest & Best Airbnbs In Miami For The Ultimate Beach Getaway
- The 17 BEST Airbnbs In Las Vegas For All Budgets & Travelers
- The 17 Coolest & Best Airbnbs In Oahu For An Amazing Hawaii Vacation
- The 18 Coolest & best Airbnbs in Colorado for a Rocky Mountain Getaway
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- 19 Incredible Airbnbs Along The Oregon Coast: Cannon Beach & Beyond
- 17 Stunning Airbnbs In Tampa For The Ultimate Florida Getaway
- The 18 Coolest & best Airbnbs in Dallas, Texas – Airbnb Dallas Guide
- Top 20 Coolest Airbnbs In Philadelphia, Pennsylvania
Final Thoughts on Maryland Airbnbs
Airbnb offerings in the state of Maryland range from the historical to the urban. Many put you in close proximity to water, harbors, jetties, and boats. Others give you access to parks, walkways, and the best of nature.
Why not consider one of these amazing vacation rentals in MD we’ve highlighted above? And if you do, let me know what your experience was.