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Cabins in Maryland

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Houses in Maryland

Top guest favorite
A scenic view of a sunset over the water, with a silhouette of a person kayaking. Adjacent, a cozy seating area is set up around a fire pit, surrounded by trees. In the foreground, a table with wine and glasses is shaded by a red umbrella, beside a hot tub.
Home in Dameron
5 out of 5 average rating, 110 reviews

Peace Point - Waterfront, Secluded, Home w/hot tub

MichelleRating, 5 stars2 weeks ago
We visited Southern Maryland for a family wedding. The property is beautiful and peaceful. Beds are comfy, house comfy, and they thought of the little things like : a full sized ironing board & Iron, beach towels, good soaps, and all you need for s’mores!Their welcome handbook was very detailed. Our only regret was that we could not spend more time on the property itself (because of family events). Would have loved to use the kayaks and the fire pit. My brother did use hot tub. Great stay! Highly recommend
Guest favorite
The exterior of the cottage is depicted, showcasing a beige wood-clad wall with a white door leading inside. A charcoal grill is positioned nearby on a concrete patio, surrounded by natural stone and greenery. The view includes trees and the landscape beyond.
Home in Clear Spring
4.9 out of 5 average rating, 106 reviews

Cozy Creek House W/Hot Tub by Whitetail

JessicaRating, 5 stars2 days ago
We enjoyed our stay at Michael’s place, and it had everything we needed, along with good communication. The hot tub was a nice touch!
Top guest favorite
The modern two-story cottage is set against a backdrop of lush greenery, featuring a well-manicured lawn and vibrant flower beds. Elevated views of the waterfront are visible in the distance, while a stone pathway leads to the front entrance adorned with wooden double doors.
Home in Shady Side
5 out of 5 average rating, 168 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

SusanRating, 5 stars2 weeks ago
Immaculate and well-appointed home with gorgeous water views. Evan has thought of every amenity and then some. His guidebook is thorough and helpful in explaining the home and area. Our stay was beyond enjoyable and comfortable. The outside was just as welcoming. The lawn is lush and landscaping beautiful. Would highly recommend- a complete 10/10!
Guest favorite
A wooden pathway leads to a relaxing outdoor space adorned with lush green grasses and a large umbrella. The Chesapeake Bay is visible in the distance, providing a serene backdrop. A flagpole with an American flag is positioned nearby, adding to the coastal ambiance.
Home in Annapolis
4.9 out of 5 average rating, 203 reviews

Country House on the Bay

MayaRating, 5 stars2 weeks ago
A wonderful stay at Stephen's place for our son's USNA commissioning. Although he lives in the 2nd floor, he was very respectful of our space - we hardly knew that he was there. He was very responsive when you needed him and helped us to host a gathering of friends and family to celebrate at his beautiful home on the water. Highly recommend.
Top guest favorite
A serene waterfront view is captured at sunset, highlighting the calm water and a colorful sky filled with clouds. Several chairs are arranged near the water's edge, framed by lush trees and grassy areas.
Home in Perryville
4.99 out of 5 average rating, 122 reviews

Upper Chesapeake Getaway

BetsyRating, 5 stars1 day ago
This is a beautiful home in a serene setting. Although there was plenty of boat traffic it was I. The distance and not noisy at all. The home is furnished simply but there are many more amenities than most airbnbs including children’s equipment and toys! The host readily honored a special request! The pictures are not clear about the water access. It is not a beach, but a stairway. We still spent much time at the water’s edge, and sitting in those great Adirondack chairs!!
Top guest favorite
The exterior of a modern two-story home is visible, showcasing a gray facade with white trim. A two-car garage is present, alongside a well-maintained lawn. Soft lighting illuminates the front entrance, while a pathway leads to the porch. A peaceful neighborhood setting is suggested by the surrounding trees.
Home in Silver Spring
4.99 out of 5 average rating, 250 reviews

Rare New Build Home w/Hot Tub, Fire pit, Game Room

SummerRating, 5 stars5 days ago
Eric’s place is wonderful in a very quaint neighborhood! Communication with Eric was excellent. The home is very comfortable and accommodating for families and large groups visiting. We were in town checking out the DC sites and the proximity from the home to the Glenmont Metro was close and easy. The kitchen is well equipped with just about every appliance or cooking utensil you could need to whip up a meal. There’s two washer and dryers and plenty of towels which is really convenient for large groups. The backyard hot tub was nice for relaxing especially after a 20,000 step day exploring DC (phew!) I would most definitely recommend this home and host!
Top guest favorite
A single-story house is shown with blue siding and white trim, featuring a prominent brick chimney and a welcoming pink door. Large windows provide ample natural light. A grassy area surrounds the home, with trees adding greenery in the background.
Home in Piney Point
5 out of 5 average rating, 108 reviews

Living on Island Time

AmberRating, 5 stars3 weeks ago
We’ve stayed in several Airbnb’s and this one is our favorite! The house is absolutely beautiful inside. You really only need to bring clothes. Melissa has every toiletry and kitchen equipment available and then some! The beds are very comfortable. The pier and views are perfect! Highly recommend Island Time!!
Top guest favorite
A hot tub is situated under a pergola adorned with string lights, offering a relaxing spot to enjoy open views of lush greenery and distant hills. Potted plants flank the area, enhancing the serene outdoor ambiance. The deck provides a spacious layout for guests.
Home in Sharpsburg
4.95 out of 5 average rating, 153 reviews

Steps to Winery & Battlefield-Pvt Acre w/ Hot Tub!

MelodyRating, 5 stars1 week ago
This house was absolutely perfect and if you are coming for the Civil War history, this is the place to stay! Not enough focus is on just how close this house is in relation to the Antietam Battlefield and the walking trails. The house was absolutely spotless and well laid out. The hot tub was a perfect way to rest and recover from our miles of hikes. Captain Benders Tavern is only about 3 minutes away in town and has a nice menu and food was delicious! And Harpers Ferry is only about a 25 minute drive. Just a word of advice, if you are planning on hiking, bring tick spray and as soon as you get back to the house, put your clothes in the dryer on high for 10 or 20 minutes and do a good body check. We brought SEVERAL ticks home with us... Yuck!

Lake cabins in Maryland

Guest favorite
Cabin in Saint Michaels
4.99 out of 5 average rating, 110 reviews

True St. Michaels 6 Acre Waterfront w/heated pool

SheriRating, 5 stars1 month ago
Great place for a getaway! St. Michael’s is a wonderful town and so easy to get to from this lovely place! Was perfect location for our family ladies trip- plenty of space and just a quick trip down town to the shops and restaurants! - I think we’ll be back!
Guest favorite
An open-concept living area features a cozy seating arrangement with a dark leather couch and a light-colored sectional. A beautiful wooden canoe hangs from the ceiling, adding a unique touch. Natural light floods in from large windows, highlighting the stone fireplace and modern kitchen.
Cabin in McHenry
4.97 out of 5 average rating, 136 reviews

Mad Men Lake House*LAKEFRONT*Fam&Dog Friendly*OUTDOOR MOVIE EXPERIENCE*HOT TUB*1.8mi to WISP*WORK SPACES*wood CRIB!

CindyRating, 5 stars3 days ago
We had a fabulous week at the mad men house. There were plenty of places to get some personal quiet time and the sleeping arrangements were perfect for our group. Stay here again if we return to deep Creek Lake.
Guest favorite
The hot tub is positioned on a spacious deck, offering views of the surrounding mountains and lush greenery. A gas grill is nearby, and a fire pit with seating is visible, creating an inviting atmosphere for outdoor relaxation.
Cabin in McHenry
4.98 out of 5 average rating, 130 reviews

Sunsets~LAKE access~Dock~Game ROOM~Hot Tub~Dogs OK

HeatherRating, 5 stars3 weeks ago
This house was perfect for our family vacation. Beautiful home with plenty a space for 10 adults. Location was close to the things we wanted to do. Highly recommend staying here.
Superhost
A charming cabin is nestled among tall trees, showcasing a front porch with steps leading down to a floating dock. A red umbrella provides shade over a picnic table, while outdoor seating is arranged nearby, offering a serene view of the surrounding nature.
Cabin in Dickerson
4.93 out of 5 average rating, 40 reviews

River Island

AlyssaRating, 5 stars1 day ago
Such a nice off the grid spot with access to great food and restaurants within a short drive, the location was very peaceful and had one of the cleanest portable restrooms I’ve ever used.
Superhost
A screened-in porch features wooden walls and ceiling, allowing natural light to filter in through multiple large windows. A rustic rocking chair is positioned on the wooden flooring, offering a comfortable space to relax and enjoy the view of the surrounding forest.
Cabin in Oakland
4.79 out of 5 average rating, 81 reviews

~Cabin on a Mountain Sanctuary w/pond

JunkoRating, 5 stars4 months ago
We loved staying at this cabin! The hosts were super responsive and super friendly. The property is beautiful and we enjoyed walking around in the snow. The cabin was super cozy and clean, we loved the wall decorations and art. The kitchen was great and had nearly everything we needed. There is no regular oven but the large toaster oven worked perfectly for a small tart. Would definitely stay here again!
Guest favorite
A rustic cabin exterior is showcased, featuring a curved corrugated metal roof and weathered wood siding. A small porch is adorned with two light-colored chairs and a table, providing a space to relax outdoors. Surrounding trees add to the serene, natural environment.
Cabin in McHenry
5 out of 5 average rating, 13 reviews

Kaya Cabin on Deep Creek Lake

JamesRating, 5 stars1 month ago
Blue moon rising was nothing short of amazing. I couldn’t recommend it enough. It was peaceful and beautiful. Exactly what we were looking for!
Top guest favorite
A hot tub is positioned on a covered deck, designed for relaxation amidst a serene winter landscape. Wooden beams and a ceiling enhance the rustic charm, while large windows offer views of snowy trees outside. Soft lighting is provided by string lights overhead.
Cabin in Oakland
5 out of 5 average rating, 42 reviews

“Treehouse feel” *Pet*HotTub*Walk to lake*Fire pit

VanceRating, 5 stars2 days ago
Cozy cabin with an amazing host
Guest favorite
A wooden dock extends into a calm body of water, reflecting the blue sky and surrounding trees. The serene scene is framed by lush green foliage, enhancing the tranquil atmosphere of the creek.
Cabin in Worton
4.96 out of 5 average rating, 91 reviews

Cabin on the Creek ~ Kayaks and Fire Pit

RachelRating, 5 stars2 weeks ago
We loved being in the woods and right by the river. Access to kayaks was a big draw. The home was comfortable and had everything we needed. We also loved being just a quick drive to Chestertown.

Vacation rentals in Maryland

Top guest favorite
Treehouse in McHenry
5 out of 5 average rating, 113 reviews

Bird's Eye View

EmilyRating, 5 stars1 week ago
We absolutely loved our stay at Bird’s Eye View for a long weekend. Honestly, I wish we could’ve stayed here longer. It’s peaceful, secluded, and beautiful. Mike was quick to respond and always offering his help if we needed anything. We would absolutely stay here again.
Guest favorite
A modern kitchen features a stylish mosaic mural of an octopus, contributing a unique artistic touch. Stainless steel appliances are complemented by granite countertops and dark cabinetry. A large window provides natural light, highlighting the intricate tile work and the welcoming atmosphere of the space.
Guesthouse in Glen Burnie
4.93 out of 5 average rating, 342 reviews

The Crab House - a Private, Waterfront Guest House

TasharaRating, 5 stars2 weeks ago
The pictures do this place no justice whatsoever. It was absolutely beautiful and very homey.
Top guest favorite
Tiny home in Saint Inigoes
4.98 out of 5 average rating, 347 reviews

Historic St.Mary's City at the Lazy Bear Cottage

BrandonRating, 5 stars5 days ago
The place was great! I had success fishing with some worms! I caught probably 10-15 small red drum I believe! It was located in a great area! All the other towns were about 20-30 minutes away. I would recommend this place 100 times over
Top guest favorite
Two houseboats are positioned side by side on a boat lift, reflected in calm waters. The structure features a combination of wooden and grey exteriors, large windows, and porches. Lush trees and the warm hues of sunset provide a serene backdrop.
Houseboat in Solomons
4.98 out of 5 average rating, 102 reviews

Good Vibe Villa, Tiny houseboat

MayRating, 5 stars1 week ago
We had a great time! We would definitely stay here again and are recommending this place for couples who want to get away for a quick weekend! Staying on the water was so beautiful. We got up every morning with the sunrise. Thank you for hosting us!
Guest favorite
Cottage in Charlestown
4.94 out of 5 average rating, 175 reviews

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

RichRating, 5 stars2 weeks ago
This place was amazing and such an awesome find for our trip. Host was super communicative, and the place matched the description. Would have loved to stayed longer. Fun time kayaking, hot tub, fire pit and the place had everything we could imagine. The restaurants were great too
Top guest favorite
An inviting living space features a comfortable sofa and a wall-mounted television. A modern kitchen area includes dark cabinetry and light furnishings, while large glass doors lead to a covered deck with scenic water views. Natural light enhances the airy atmosphere.
Houseboat in Kent Narrows
4.97 out of 5 average rating, 150 reviews

Cass-N-Reel Luxury Houseboat

ZacharyRating, 5 stars1 week ago
Place was exactly as described and Kirby was very responsive when I had any questions. Highly recommend!
Top guest favorite
Guesthouse in Stevensville
4.99 out of 5 average rating, 277 reviews

Waterfront Getaway - View of bay from your bed

AndresRating, 5 stars2 weeks ago
We had such a peaceful and memorable stay at Andy’s place. From the moment we arrived, Andy was incredibly welcoming, we could genuinely feel the warmth and care. He even brought us breakfast and made sure we had everything we needed. Even though the weather was a bit gloomy at first, we had a great time relaxing indoors with the ping pong table and enjoying the beautiful waterfront view right from our bed. The sunset was absolutely breathtaking. One of our favorite moments was walking to the dock and spotting a bald eagle through the binoculars provided, such a special experience! The pool area looked so serene; although it was too cold for us to go in this time, we’re already hoping to come back in warmer weather to enjoy it fully. This trip was the perfect way to unwind after my wife’s graduation, and it made us so happy to see that even our dog felt right at home. Thank you, Andy, for creating such a thoughtful and relaxing retreat. We hope to return soon
Guest favorite
A charming cottage sits at the water's edge, surrounded by lush greenery. A wooden staircase leads down from an elevated deck to the sandy beach. Two blue chairs are positioned on the deck, inviting relaxation as the sun sets in the background.
Cottage in Leonardtown
4.96 out of 5 average rating, 190 reviews

Beach Front and 'Perfectly Placed'

MichaelRating, 5 stars1 week ago
Perfectly Placed was everything we had hoped it would be! We were celebrating our 15th wedding anniversary and wanted something peaceful and relaxing, this was all of that and more ♥️ We are looking to come back as a family.

Your guide to Maryland

Welcome to Maryland

Maryland’s 3,190 miles of shoreline and long riverfronts shape its natural appeal with sandy stretches and stellar sunrises. Charming old towns boast beautiful views and relaxing beaches as well as a healthy dose of American history, be it the origins of the national anthem or the Battle of Antietam. Though Annapolis is the state’s political capital, Baltimore is much larger, and both take many cultural and political cues from being a part of the National Capital Region and their proximity to Washington D.C. Many of the state’s claims to fame come from Chesapeake Bay, the water that nearly splits the eastern part of Maryland in two. From there we get the famed Maryland crab and other seafood that drive the local cuisine; the naval and civilian boating culture of Annapolis; and, of course, the scenic byways that weave across the water.


The best time to stay in a vacation rental in Maryland

Most of Maryland experiences four classic seasons, with chilly, snowy winters and hot, humid summers. At the Chesapeake Bay beaches, the hot, humid summers are more tolerable, making it a big draw for people looking to cool off on their vacation. But for most of the state, late spring and early fall bring the most comfortable weather. Spring in Maryland brings out the blooms, and various cherry blossom and garden events lure visitors to admire the bright colors, while fall shows its own red, orange, and brown hues. Though western Maryland stays cooler year-round, the higher elevations receive more snow in winter, which attracts snowshoers and other winter sports enthusiasts. But even the eastern part of the state can see significant snowfall, resulting in cold, icy conditions that are best suited for exploring indoor attractions.


Top things to do in Maryland

Cambridge

The small Eastern Shore town of Cambridge merges many of Maryland’s most iconic features. You can get a taste of history — it’s one of the oldest colonial towns in the country, just 15 minutes from the Harriet Tubman Underground Railroad Visitor Center — as well as a taste of the local seafood at the many crab restaurants overlooking Chesapeake Bay as you wander the boardwalk, or at Sailwinds Park.

Baltimore Inner Harbor

The focal point of Maryland’s largest city, this historic seaport and repurposed industrial area holds a slew of history and tons of museums. The National Aquarium, Port Discovery Children’s Museum, and the Reginald F. Lewis Museum of Maryland African American History and Culture will keep you busy all day, along with the area’s many restaurants and bars.

Assateague Island National Seashore

The peaceful, sandy beaches and windswept salt marshes of this 37-mile barrier island on Maryland’s far eastern Atlantic shores would be enough to make it an ideal destination. But it’s the beautiful herd of wild horses for which it’s most famous.

Destinations to explore

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