The Coolest Airbnbs In Maryland: Top Vacation Rentals In 2021
Here are the best Airbnbs in Maryland by category, taking into account unique amenities, trip types, and budgets. The next sections will cover each listing in more detail, as well as other cool vacation rentals youll want to check out.
Stay at this unique Airbnb in Maryland and youll fully enter vacation mode. This cozy vintage cabin in Middletown is decked out with all the amenities youll need for a perfect stay, including rustic cabin décor, expansive porches, propane fireplace, BBQ grill, bikes, kayaks, ski equipment, fishing rods, golf clubs, and more.
This Maryland vacation rental is just steps from Middletowns lively restaurant scene, and you will also be a stones throw away from several shops and parks. A little further down the road are some local wineries, breweries, and hiking trails. Theres so much to see in this part of MD, that a short stay is simply not enough.
Screen & Projector 2 20 Foot Screen
$200 a day.
This fantastic item is one of our most popular rental products and is available to rent. This item is loved by all of our customers for its great quality, but also for its unbeatable price. Want to watch a movie, why not outside? Having a community movie night, set up inside a gym or community center. Too cold outside, set up in the garage or barn. The kids will love it matter of fact were sure youll love it.
This package comes with the screen, projector, a stand for the projector and speaker kit. All you need to do is add a device for the video.
Waterfront Maryland Rental Overlooking The Bohemia River
Location: Earleville, Maryland
Rates from: $529 per night
Accommodates: 16 guests
If youre interested in finding the perfect Airbnb in Maryland for large groups, youre looking at it!
This stunning waterfront home has plenty of space for entertainment and fun. Theres an outdoor swimming pool, hot tub, 5 TVs, fireplaces, Adirondack chairs, and basically every other modern amenity imaginable. Wake up every morning with a cup of coffee as you look out on the cove, and youll see why this is one of the best Airbnbs in Maryland for large groups!
Read Also: Ducky Bob’s Party Rentals Dallas
Live In The Heart Of Chevy Chase
Chevy Chase is a friendly, close-knit community once named the best suburb of the National Capital. Enjoy wide open green spaces, peace, quiet and respite from the tourism of D.C. With an abundance of locally owned shops and markets, family-owned restaurants and cafes, Chevy Chase combines small-town ambiance with D.C. charm.
Charming Cabin On Deep Creek Lake One Of The Most Romantic Airbnb Lake Houses In Maryland

Location: Oakland, Maryland
Rates from: $200 per night
Accommodates: 8 guests
Looking for a romantic retreat on Marylands most beautiful lake? This charming Maryland cabin will amaze you.
The woodsy charm, lake views, expansive deck, and hot tub make this the perfect place to relax and unwind. Wake up every morning with breakfast on the dock, curl up by the fire with some smores, and rejuvenate in the hot tub. It wont be long until you see this place for what it is: one of the most romantic vacation rentals in all Maryland!
You May Like: Decorations For Anniversary Parties Ideas
Bar And Bat Mitzvah Receptions
The Rock Creek Mansion is a unique, private venue for Bar and Bat Mitzvah receptions. The circular driveway provides a convenient spot for guest drop off and pick up. Parents can then head into Bethesda for a meal or movie while their children party! Rental clients can greet guests in the foyer, with the adults moving into the lounge for the cocktail hour, and the children going into the ballroom for dancing and games.
The L Shaped ballroom allows for adults to be seated in one section, the children on the other side and the dancing in the center without an actual divider. This way the older adults can be partly separated from the music. The spacious ballroom allows for a variety of creative seating arrangements, especially for the children. Festive decorations can be hung from the ceiling to enhance the theme. The side entrance allows for easy load in of musical equipment, casino tables, a photo booth and/or couches.
The outdoor patio can provide an additional cocktail space or can be used for a smoothie station. It can be tented for an additional fee. This area can provide a green screen area.
For daytime events, the lawn provides space for field day games and/or a moon bounce.
Whether the theme is a night club, casino event, Hollywood movie night, beach party, sports event, camping or field day parties, The Rock Creek Mansion is an ideal location with an easy flow.
All the Best, RAMEEZ
BONNIE & PAUL, Happy couple
Historical Sites In Maryland
23,000 men were wounded, killed, or went missing on September 17th, 1862 in the bloodiest battle of Civil War which only lasted for a single day. The site of this historical battle is called the Antietam National Battlefield. To learn more about the battle, pay a visit to the visitor center.
The Baltimore and Ohio Railroad Museum gives you a glimpse of the important railroad history of the United States. Designated as a National Historic Landmark, this museum gives you a chance to see, touch and explore some of Americas most important railroad collections. It is located in the old Mount Clare Station as well as the roundhouse next to it.
You May Like: Skechers Women’s Parties Mate Oxford Shoe
The Log House At Sugarloaf Mountain
Location: Dickerson, Maryland
Rates from: $735 per night
Accommodates: 15 guests
Looking for a large group getaway in Maryland? Dont miss this gorgeous log cabin home at Sugarloaf Mountain.
This one-of-a-kind vacation rental has it all. Its a solar-powered eco house, offering top notch amenities including a large deck, chefs kitchen, 3 gas fireplaces, heated floors, washer and dryer, custom furniture, game room, and so much more.
If youre looking to get off the grid with your large family or group of friends, this luxury home will amaze you.
Life In The Heart Of Chevy Chase
Enjoy your suburb-in-the-city lifestyle in this unique D.C. neighborhood. Youre a 10-minute walk from Whole Foods where you can appreciate tree-lined streets and flowered walkways. Live 10-minutes from the popular Friendship Heights and Connecticut Avenue enjoy a bite with friends, browse local shops, or take in the sounds of music at one of the many piano lounges and cafes.
Read Also: Couples Matching Outfits For Party
Wedding Venue Prices In Maryland
Venue cost depends on space availability and services offered . Most venues in Maryland hold only one wedding party at a time. Marylands four main regions offer similar prices across the board. Location costs alone range from $3,001-$5,001 in Maryland.
Here is another cost to be prepared for: taxes and service fees. When you start looking at venues, you need to remember that there are state-allowed taxes that tack on surprising increases to your bill. In Maryland, the sales tax is now 6.0 percent . One positive about having your wedding in this state is that individual counties and cities are not allowed to tack on their own personal tax as well. As for service fees, they are more loosely based on the desires of each specific venue. This charge is usually around 20 percent of your venue costs.
The 10 Most Instagrammable Places In Maryland
1. The Graffiti Alley
This creative space is a wonderful riot of art and colors, and a photographers delight. The only legal graffiti art space in Baltimore, the alley features changing work by street artists.
2. Sugarloaf Mountain
This landform in Barnesville makes the perfect backdrop for hiking or romantic pictures. There is a beautiful vineyard at the base, yet another Instagram-worthy location.
3. Sandy State Point Park
Visit the Sandy State Point Park armed with your camera for the scenic beach areas and spectacular views of the Chesapeake Bay. The Bay Bridge also makes for lovely pictures.
4. Rawlings Conservatory
Go for a photo shoot at the Rawlings Conservatory, which boasts a stunning glass façade on the exterior, a sprawling garden with colorful tulips, and greenhouses full of blooming plants.
5. Assateague Island
Magnificent wild ponies run free on the pristine beach and play in the blue waters at Assateague Island in Berlin, which makes for a breathtaking sight to be captured.
6. Visionary Art Museum
If quirky and colorful is your style, the American Visionary Art Museum is just the place to be. This popular spot is full of sculptures and eclectic artworks.
7. Cylburn Arboretum
Instagram pictures of Japanese maples at the Cylburn Arboretum, and watch the number of likes multiply. No wonder that these trees are a favorite for wedding pictures.
8. Swallow Falls State Park
9. Annapolis Rock
10. Ocean City Maryland Boardwalk
Read Also: What To Wear To Housewarming Party
May The Forest Be With You One Of The Best Cabin Rentals In Maryland
Location: Oakland, Maryland
Rates from: $268 per night
Accommodates: 8 guests
Experience the ultimate mountain vacation from this magical Airbnb cabin in Western Maryland. Its located near Deep Creek, one of the coolest parts of MD, and also not far from Wisp Ski Resort.
Spend your days hiking, skiing, or doing watersports on the lake. And at night, retreat to this gorgeous cabin rental with all the comforts of home. Soak in the Jacuzzi, curl up by the wood fireplace with a cup of tea, and youll quickly see why this is among the most romantic Airbnbs in Maryland.
Ocean City Maryland Vacation Rental On The Water

Location: Ocean City, Maryland
Rates from: $126 per night
Accommodates: 10 guests
Live the life at this gorgeous Ocean City vacation rental in Maryland that touches the ocean. Its equipped with its own private dock, kayaks, pool, tennis courts, expansive deck, dedicated work space, and high-speed internet.
In addition to all of the typical Maryland beach house amenities youd expect to find, theres also a new outdoor movie experience at the property, which makes for the best staycation ever. Go fishing off the dock and swimming or boating in the water. Then, retreat to this cozy house for rent in Maryland, filled with 1,248 sq. ft. of living space. I truly cant imagine a better Maryland vacation rental for large families!
Read Also: Bachelor Party In San Diego
Mountain Myst A Top Airbnb In The Blue Ridge Mountains Of Maryland
Location: Boonsboro, Maryland
Rates from: $290 per night
Accommodates: 8 guests
Experience the Blue Ridge Mountains in style from this luxury cabin in Maryland. Its just an hour from Washington DC, but feels worlds apart in this idyllic wilderness setting.
Wake up every morning with a cup of coffee as you sit on the porch and take in the stunning views of the forest. You wont have to put in much effort to see dear and wild turkey wandering the property. There are lots of state parks, wineries, restaurants, and other attractions in the area, but after stepping foot inside this rustic home, you wont want to leave!
Is this one of the best-value vacation rentals in Maryland? Absolutely!
Faqs When Booking A Vacation Rental In Maryland
What are the most popular vacation rental destinations in Maryland?
Based on KAYAK vacation rental searches, the most popular destination is Swanton . The next most popular destinations are Frostburg and Newark . Searches for vacation rentals in Friendsville , Suitland and Denton are also popular.
How much is a vacation rental in Maryland for tonight?
In the last 72 hours, users have found Maryland vacation rentals for tonight for as low as $109.
Recommended Reading: Best Catering For Birthday Party
Exclusive Md Vacation Rental In Upscale Chevy Chase A Beautiful Maryland Home For Rent
Location: Chevy Chase, Maryland
Rates from: $315 per night
Accommodates: 6 guests
This classic Maryland home for rent in Chevy Chase offers a luxury getaway like no other. Its located in a prestigious neighborhood with plenty of space and low traffic.
Spend your days relaxing in these bright elegant rooms, all professionally designed. Read a book in the study or garden room. Spend quality time with family and friends from the large brick patio. In addition to being one of the best Maryland vacation rentals, its also among the top pet-friendly Airbnbs in the area!
Tree Top Bliss The Best Airbnb Treehouse In Maryland
Location: Ocean Pines, Maryland
Rates from: $295 per night
Accommodates: 6 guests
Looking to experience the magic of a golden a-frame cabin? Look no further.
Step inside this unique chalet in Maryland and youll feel like youve transported yourself halfway across the US. This beautiful and cozy Airbnb in Maryland is decked out with all the modern amenities youll need for a comfortable stay, including a hot tub. Its also dog-friendly, which is a huge plus, as youll have plenty to explore nearby in Deep Creek State Park.
Its got the rustic vibe of the accommodations youll find in New England, with the charm of this region of Maryland. I cant imagine a better way to spend a few days in western Maryland!
Recommended Reading: 70s Party Outfits For Ladies
The 5 Best Seafood Restaurants In Maryland
Crabs are an indispensable part of Maryland cuisine and the Steamed Crabs are worth a try. Instead of boiling crabs, Marylanders are known for steaming blue crabs which are then doused with Old Bay seasoning. You can also order crab cakes made from bread crumbs, egg, crab meat, mayo and Old Bay.
1. Jimmy’s Famous Seafood
The legendary Jimmy’s Famous Seafood in Baltimore is known for its steamed crabs, crab cakes, and lobster. Go for the famous seafood UFO to feast on a platter of crab cake, shrimp salad, a crabby mac ball, and fried shrimp with oysters.
2. Faidley Seafood
Another Baltimore favorite, Faidley Seafood, is considered to have some of the best crab cakes in the entire state. The standing-only space is filled with patrons enjoying the award-winning, Maryland-style crab cakes and other fresh seafood.
3. Jerry’s Place
Located in Prince Frederick, Jerry’s Place serves the freshest seafood in a welcoming, homely setting. Popular items on their menu include all the crab delicacies, fried oysters, scallops, and Icelandic Haddock.
4. Shark on the Harbor
An upscale ambiance with harbor views, organic meals, and the freshest of seafood is what makes Shark on the Harbor is a well-known name in Ocean City. Favorites on their all-natural menu include the crab dip, shark bites, and fishermans stew.
5. O’Leary’s Seafood
A Maryland Vacation Rental Is Your Home Away From Home
Located in the Mid-Atlantic region, Maryland is one of the original 13 colonies of the United States. Water lovers are in for a treat because the Potomac River, the Atlantic Ocean and Chesapeake Bay are all nearby, while outdoor enthusiasts can enjoy various skiing, hiking, and camping opportunities.
With a vacation home, you can accommodate your entire family without having to pay for extra rooms like in a hotel. There is a wide variety of vacation rentals available throughout Maryland. Baltimore offers row houses, while Ocean City is known for its condo rentals.
Accommodations can be selected based on various criteria. Above, you can see the number of rentals that offer a specific amenity in Maryland. Many vacation rentals in Maryland include “Internet” or “TV,” which makes it a great vacation destination if you need internet access during your vacation or you never miss an episode of your favorite show. You can even compare and find properties if you love sweating the stress away in saunas or if you want a rental with a jacuzzi .
Recommended Reading: 40th Birthday Party Favor Ideas
Redwall Castle An Ornate House To Rent In Maryland
Location: Boyds, Maryland
Rates from: $495 per night
Accommodates: 10 guests
This Airbnb castle in Maryland is nothing short of extraordinary. Its located near Washington D.C., but it feels worlds apart with its royal castle flair and secluded location.
This is easily one of the most unique houses to rent in Maryland due its historic castle design and large size. Its comprised of a main house and carriage house, with 5 bedrooms and 4.5 bathrooms along in the main home. Be sure to utilize the open wood firepits on the property, and explore the 6 acres of land for outdoor activities. With its unique fixtures and amenities and high-class residential area, its no wonder this is among the best vacation rentals in Maryland.
Annapolis Row House A Recently Renovated Vacation Rental In Maryland

Location: Annapolis, Maryland
Rates from: $133 per night
Accommodates: 6 guests
Stay at this and youll be in for a treat. This nautically themed home is located close to the Naval Academy. It offers a charming front porch, interior millwork, and luxurious bathrooms and kitchen.
If youre looking to stay at a beautiful house to rent in Maryland, this accommodation in historic Annapolis has got you covered. I cant imagine a better VRBO Maryland than this one.
Read Also: Cheap Party Bus For Rent
Weddings In The Heart Of Bethesda
The Rock Creek Mansion offers the feel of a private home with a ballroom and outdoor patio. A couple can plan for an outdoor component, including a ceremony on the lawn and cocktails on the patio, with a sizable ballroom in the event of inclement weather.
The Rock Creek Mansion foyer offers an elegant staircase ideal for bridal party pictures. The newly upgraded lounge provides an intimate gathering space for cocktails. The mantle is ideal for displaying personal photographs and decorations. Couples can play a personal video or slideshow on the flat screen tv, located above the built-in bar. The fireplace makes this space cozy during winter months.
The spacious ballroom allows for full seating all in one room. Lots of windows create a bright daytime space, and the new chandeliers can be dimmed during evening events. The ballroom can be set in a variety of configurations. The mansion beige padded chairs are included with the rental. If a client chooses to rent different chairs, the house chairs will be stored.
During warm months, guests can enjoy the new outdoor patio overlooking the spacious lawn. This can be an ideal spot for a satellite bar and overflow seating. It can also provide a spot for a cigar area. This can be tented for an additional fee to insure use of the space.
A House Manager is present from the set up to the end of the clean up of each event.
All the Best, RAMEEZ
BONNIE & PAUL, Happy couple