The best Airbnbs in Maryland range from treehouse and cabin rentals to luxury lake houses and vacation rentals on the ocean. From group trips and family reunions to romantic retreats in the woods, there’s truly something for everyone in this slice of the East Coast. If you’re dreaming of a relaxing getaway, just wait until you see these Maryland vacation rentals on Airbnb and VRBO.
From the big cities on the Chesapeake Bay to quaint towns, beach destinations, and nature spots, Maryland is one of the best states to visit in the US. Maryland has got a unique mix of rural and city destinations, each offering some incredible vacation rentals. These stays provide a safer and more local experience than traditional hotels, which make them especially appealing during these COVID times. And what better way to experience the best of this Mid-Atlantic state than by staying in a beautiful Maryland vacation rental?
This article covers the top lodging in Maryland, including Airbnbs, VRBOs, and cabins for rent in Maryland. Whether you’re looking for a romantic nature getaway or a modern space for a large group, keep reading. Here, we’ve ranked the best Airbnbs in Maryland, which include places like Ocean City, Annapolis, the Chesapeake Bay, Deep Creek Lake, Baltimore, Assateague Island, Frederick, and more. Now, let’s go explore the beautiful state of Maryland!
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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 you’ll want to check out.
Top Airbnb in Maryland: Sunset Breezes – a Quiet Retreat
Best Luxury Rental Maryland: Annapolis Sunset Escape
Top Romantic Airbnb in Maryland: Charming Cabin on Deep Creek Lake
Best Maryland Airbnb for Large Groups: Waterfront Retreat with a Pool
Best Cheap Airbnb Maryland: Penthouse in Ocean City MD
Coolest Treehouse Airbnb in Maryland: Tree Top Bliss
Best Cabin Rental Maryland: A-Frame Cabin with a Hot Tub
Top Airbnb Maryland with Pool: Saint Michael’s 6 Acre Home with Pool
Best Beach House Rental Maryland: Waterfront Home with Private Beach
Most Unique Airbnb in Maryland: Luxury Boat Yacht for Rent
20 Top Airbnbs in Maryland
If cabins, treehouses, beach houses, and luxury vacation rentals in Maryland sound good to you, get excited! Below are some of the most unique stays in Maryland that you should add to your bucket list:
1. House to Rent in Maryland with Indoor Hot Tub and
Location: Oakland, Maryland
Rates from: $252 per night
Accommodates: 10 guests
Bring the whole family along the enjoy this cozy log house for rent in Maryland. It’s nestled in the mountains with luxurious decor and amenities.
Take full advantage of the indoor hot tub, covered porch swing, fireplace with fire wood, and cozy cabin furniture. If you’re looking to get away from the hustle and bustle of the city, I can’t imagine a better vacation rental in Maryland than this home in Oakland.
2. Charming Vintage Cabin in the Heart of Middletown, Maryland
Location: Middletown, Maryland
Rates from: $110 per night
Accommodates: 2 guests
Stay at this unique Airbnb in Maryland and you’ll fully enter vacation mode. This cozy vintage cabin in Middletown is decked out with all the amenities you’ll 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 Middletown’s lively restaurant scene, and you will also be a stone’s throw away from several shops and parks. A little further down the road are some local wineries, breweries, and hiking trails. There’s so much to see in this part of MD, that a short stay is simply not enough.
3. 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. It’s 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 you’d expect to find, there’s 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 can’t imagine a better Maryland vacation rental for large families!
4. 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. It’s 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 won’t 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 won’t want to leave!
Is this one of the best-value vacation rentals in Maryland? Absolutely!
5. Beautiful Waterfront Home near Annapolis
Location: Arnold, Maryland
Rates from: $897 per night
Accommodates: 12 guests
Looking for the ultimate getaway in Maryland? This luxury waterfront home has got you covered. It’s decked out with a private pool, pier, boathouse, and all the modern fixtures you’ll need for an amazing stay. Three private bedrooms open directly to the pool – not a bad set up! I truly can’t imagine a prettier lake house rental in Maryland.
With so much luxury and personality, it’s no wonder this is one of the best Airbnbs in Maryland!
Read next: Coolest Rentals with Private Pools
6. Unique Maryland Vacation Rental on the Water
Location: Cambridge, Maryland
Rates from: $295 per night
Accommodates: 8 guests
This is one of the best-value Airbnbs in Maryland, hands down. Nestled on the water, this unique Maryland rental is in the perfect location, within reach of Cambridge, Blackwater Refuge, and Ocean City. Take advantage of the kayaks or relax on one of the hammocks by the pier or fire pit. It won’t be long until you experience the allure of this beautiful property.
It’s one of the most tranquil and peaceful spaces imaginable, which is why it deserves to be mentioned among the top Airbnbs in MD!
7. 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 Maryland’s 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 s’mores, and rejuvenate in the hot tub. It won’t be long until you see this place for what it is: one of the most romantic vacation rentals in all Maryland!
8. Waterfront Maryland Rental Overlooking the Bohemia River
Location: Earleville, Maryland
Rates from: $529 per night
Accommodates: 16 guests
If you’re interested in finding the perfect Airbnb in Maryland for large groups, you’re looking at it!
This stunning waterfront home has plenty of space for entertainment and fun. There’s 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 you’ll see why this is one of the best Airbnbs in Maryland for large groups!
9. 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. It’s 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 you’ll quickly see why this is among the most romantic Airbnbs in Maryland.
10. Penthouse in Ocean City MD – One of the Best Beach House Rentals in Maryland
Location: Ocean City, Maryland
Rates from: $89 per night
Accommodates: 10 guests
Is this one of the best Airbnbs in Maryland? Absolutely!
Experience Ocean City in style from this budget-friendly penthouse with unobstructed views of the sea.
This condo is perched on the 8th floor, where you’ll get to wake up every morning to the smell and sounds of the ocean. The private balcony is over 150 sq. feet, but you can also take in the sweeping vistas from the sun deck and rooftop pool. There’s also a sauna here, which rounds up everything you’ll possibly need for the perfect beach vacation in Maryland.
11. 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? Don’t miss this gorgeous log cabin home at Sugarloaf Mountain.
This one-of-a-kind vacation rental has it all. It’s a solar-powered eco house, offering top notch amenities including a large deck, chef’s kitchen, 3 gas fireplaces, heated floors, washer and dryer, custom furniture, game room, and so much more.
If you’re looking to get off the grid with your large family or group of friends, this luxury home will amaze you.
12. Tree Top Bliss – The best Airbnb treehouse in Maryland
Location: Ocean Pines, Maryland
Rates from: $295 per night
Accommodates: 6 guests
Experience a home nestled in the trees from this unique Airbnb treehouse in Maryland.
This Maryland vacation rental is equipped with everything you’ll need for a fun and memorable stay. There’s a rooftop deck and screened-in porch where you can soak in the magic of this property. It’s also within close reach to the beach. What more could you want in a top Maryland Airbnb rental?
Watch next: Best Tree House Stays in the US
13. A-Frame Cabin Rental in Maryland with Hot Tub
Location: Swanton, Maryland
Rates from: $175 per night
Accommodates: 8 guests
Looking to experience the magic of a golden a-frame cabin? Look no further.
Step inside this unique chalet in Maryland and you’ll feel like you’ve transported yourself halfway across the US. This beautiful and cozy Airbnb in Maryland is decked out with all the modern amenities you’ll need for a comfortable stay, including a hot tub. It’s also dog-friendly, which is a huge plus, as you’ll have plenty to explore nearby in Deep Creek State Park.
It’s got the rustic vibe of the accommodations you’ll find in New England, with the charm of this region of Maryland. I can’t imagine a better way to spend a few days in western Maryland!
14. Annapolis Row House – A Recently Renovated Vacation Rental in Maryland
Location: Annapolis, Maryland
Rates from: $133 per night
Accommodates: 6 guests
Stay at this Maryland vacation rental in Annapolis and you’ll 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 you’re looking to stay at a beautiful house to rent in Maryland, this accommodation in historic Annapolis has got you covered. I can’t imagine a better VRBO Maryland than this one.
15. Saint Michael’s 6 Acre Waterfront Home – One of the best Airbnbs in Maryland with a Pool
Location: Saint Michaels, Maryland
Rates from: $697 per night
Accommodates: 8 guests
This 3,000 sq. ft. home has to be one of the most beautiful Airbnbs in Maryland. It’s nestled on over 5 acres of waterfront property, all with breathtaking views and modern amenities, including an in-ground pool.
This Airbnb is just a 5-minute bike ride from historic downtown Saint Michaels, making it the perfect location to explore the surrounding area. Though once you step foot on this beautiful property, you likely won’t want to leave!
16. 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. It’s 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, it’s also among the top pet-friendly Airbnbs in the area!
17. Waterfront Vacation Rental in Maryland with Private Beach – A Top Maryland Beach House for Large Groups
Location: Ridge, Maryland
Rates from: $541 per night
Accommodates: 12 guests
Soak in the best views of the Chesapeake Bay from this amazing Airbnb rental in Maryland. This 3,000 sq. ft. beach house is elegant and peaceful, making it the perfect vacation retreat for family/friends.
Go kayaking from the private beach or play bocce while cooking up a delicious meal from the charcoal grill. There’s definitely something for everyone here.
Escape the hustle and bustle of Maryland’s biggest cities by staying at this beautiful beach house Airbnb overlooking the Bay! In addition to being among the best Airbnbs in Maryland, it’s also one of the top long term rentals in the US.
Read next: Coolest Monthly Rentals in America
18. Art Filled Garden Home – Among the Top Maryland Houses for Rent by Owner
Location: Bethesda, Maryland
Rates from: $129 per night
Accommodates: 10 guests
Looking for a budget friendly stay in MD? This garden accommodation is one of the best Maryland houses for rent by owner.
Bring your family/friends along to enjoy this peaceful and quiet VRBO Maryland, close to DC, but distant enough to feel secluded. This vacation rental in MD is just steps from Rock Creek Park’s hiking and biking trails. Enjoy the garden patio, decked out with a hammock and lounge chairs. If you’re looking to reconnect with nature’s harmony, this house for rent in Central Maryland is the ideal home base.
19. Redwall Castle – An Ornate House to Rent in Maryland (Near DC)
Location: Boyds, Maryland
Rates from: $495 per night
Accommodates: 10 guests
This Airbnb castle in Maryland is nothing short of extraordinary. It’s 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. It’s 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, it’s no wonder this is among the best vacation rentals in Maryland.
20. Luxury Motor Yacht – Unique Maryland Airbnb
Location: Edgewater, Maryland
Rates from: $989 per night
Accommodates: 10 guests
This luxury yacht is easily one of the most unique Airbnbs in Maryland. It’s 78 feet long and offers 4 staterooms for large groups (i.e., bachelor parties). There are two decks onboard with a Jacuzzi and BBQ grill, perfect for soaking in the amazing views. What more could you want in a top Airbnb in Maryland?
Read next: Coolest Overnight Houseboat Rentals
Best Places to Stay in Maryland
Still undecided on where you want to stay in Maryland? Here are my favorite cities, towns, and nature areas where I recommend staying:
– Top Cities and Towns: Annapolis, Baltimore, Bethesda, Oakland, Ocean City, Rockville, Silver Spring, Washington D.C.
– Best Cabins and Campgrounds: Deep Creek Lake
– Coolest State Parks: Patapsco Valley State Park
Coolest Airbnbs in Maryland: From rustic nature getaways to lake and beach house rentals!
Have you ever stayed in a unique Airbnb vacation rental in the state of Maryland? Definitely let me know! As I’m always looking to add to this list of the best Airbnbs in MD!
Considering other outdoor destinations? Here are some ideas:
– Top Airbnb Rentals in Vermont
– Best Places to Stay in Jackson Hole, WY
– Unique Accommodations in Colorado
– Coolest Places in the Berkshires MA
– Top Vacation Rentals in New Hampshire’s White Mountains
– Most Unique Stays throughout New England
