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Vacation Rentals & House Rentals in Maryland

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1,105 house rentals

AAH Chalet

Oakland house

5 bedrooms / 3 bathrooms / sleeps 12

“Ahh Chalet” Raileys Mountain Lake Rental was great as usual. Very easy check in and check out process. We had two issues at the begining of the week and all it took was one phone call and they were resolved that same day aAH Chalet was a great lakefront home located close to all activities. The house was furnished beautifully and the kitchen was very well stocked. There were plenty of extra pillows and blankets. The outdoor fire pit, private dock and hot tub were all big hits with all three families that stayed. Renting our boat from Bill Marina was an extremly easy process because aHH Chalet was in walking distance to pick up and drop off the boat. The location was great. Some may not like being directly in the middle of everything but it worked out great considering we had five teenage girls with us. They were able to walk to the Lakeside Creamery and Popcorn Factory every evening and we made morning walks to arrowhead market. It was in close driving distance to the Wisp, Funland and restaurants. There were three families that stayed at aHH Chalet and we all enjoyed it. Staying lakefront and near everything was great. I highly recommend aHH Chalet!

Price per night from

$280

Tranquil Dreams

Oakland house

4 bedrooms / 3 bathrooms / sleeps 10

“Fun Stay” Many amenities (toilet paper, cleaning supplies, grilling materials, camping gear) were already provided when we arrived, making for a nice, care-free vacation. Beautiful location. Wonderful living space. Billiards table, fire pit, and hot-tub a great addition. Some of the beds were a little uncomfortable.

Price per night from

$166

Cozy Cumberland Cabin in the Allegheny Mountains!

Cresaptown log cabin

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$113

Steps to the Slopes

McHenry house

4 bedrooms / 4 bathrooms / sleeps 12

“Enjoyable and relaxing family Thanksgiving setting” House has great features ... large open greatroom/kitchen/dining area, however 'heating' was an issue; 4 large bed rooms, each with full bath. Very convient to ski slopes!

Price per night from

$258

Traditions on the Lake

McHenry house

5 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$334

Arrowhead #26

Oakland condo

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$145

Rocky Knoll II

McHenry house

4 bedrooms / 3 bathrooms / sleeps 12

“Fun time, great views, good location” Nice cabin, views are great. Could use some maintenance work and updating.

Price per night from

$180

Tall Castle

McHenry house

4 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$292

Deer Pass

Oakland house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$292

Hemlock Chalet

Oakland house

3 bedrooms / 2 bathrooms / sleeps 10

“Great cabin, clean and beautiful!” The Hemlock Chalet was a wonderful place to relax and enjoy Deep Creek. Though it is a bit of drive to the mountain, the cabin was clean, beautifully decorated, and spacious. My friends and I had a blast.

Price per night from

$182

Wispering Ridge

Oakland house

2 bedrooms / 3 bathrooms / sleeps 6

“Great location, great view” The townhome was spotless. We love to cook and the kitchen was well equipped. Linens were provided and that was a great help. Location just off 219 but we had a great view of Deep Creek Lake. Only problem for elderly guest were the steps from the parking lot to reach the front door.

Price per night from

$132

Deep Creek Village #07

McHenry house

2 bedrooms / 2 bathrooms / sleeps 8

“We rang in the new year with friends in a winter wonderland!” We had a fabulous time ringing in the New Year with friends. The snow fell all weekend and the skiing was great. We rented two townhomes in Deep Creek Village which was a super location since there was a large group of adults and teenagers that were able to come and go to the slopes as they pleased. The townhomes were spacious, well stocked and clean. Our coffee maker broke while we were there and the rental office had one at the place within a couple of hours. We also enjoyed the hot tub! It was a wonderful way to spend the holiday!

Price per night from

$149

Annapolis Home w/ Deck & Whitehall Bay Access

Cape Saint Claire house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$235

Ski Harbor #21

McHenry house

3 bedrooms / 3 bathrooms / sleeps 8

“Good overall” Overall a good value. The Cable was out when we arrived (no TV and no internet). We called. It was fixed the next day. The grill gas tank was empty. Other than that, our stay was very enjoyable. Friendly staff at the office, good environment. We would return.

Price per night from

$132

Cambridge Colonial Home, Walk to Town & Waterfront

Cambridge house

3 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$268

WISPering Timbers

McHenry house

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$297

Owl Cabin

Oakland log cabin

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$251

Nice! 2 BR, Coastal Cottage Condo, Walk To Beach, Restaurants!

Ocean City condo

2 bedrooms / 1 bathroom / sleeps 6

“loved it” Very nice place in a great location. Quiet neighborhood, can see people walking their dogs and jogging. Harris Teeter and Food Lion less than 5 minutes away along with a CVS. Beds are very comfy and were able to relax with a family of 8. Parking is very convenient with 6 available spots. House is clean and well kept. Harpoon Hannah's is few minutes away. I would definitely rent this again.

Responds fast! avg. 35 minutes

Price per night from

$149

Immaculate Waterfront Town Home

Ocean City villa

3 bedrooms / 3 bathrooms / sleeps 10

“My Birthday Vacation” We had such an amazing time here in Ocean City, the villa we stayed in was amazing, will definitely be back

Price per night from

$317

Best kept secret by the bay (Entire House)

Fishing Creek house

3 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$197

Wilderness Walk

McHenry house

7 bedrooms / 5 bathrooms / sleeps 18

“Fantastic” The service was fantastic. The house was laid out nice and good views.They need to upgrade the hot water heater not enough hot water.The location is perfect and the amenities are good.We liked the quietness of the house best and the hot water least.

Price per night from

$362

Mystic Cove

McHenry house

6 bedrooms / 6 bathrooms / sleeps 16

“Great Location - Spacious House” Plenty of room for our extended family of nine. Best part? The kids put on their gear and walked to the ski lift!

Price per night from

$434

Old World Charm, Immaculate Potomac River Woodland Cottage, Polite Pets OK

Piney Point house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$288

Cedar Shores Villa #16

McHenry house

5 bedrooms / 4 bathrooms / sleeps 12

“Comfort and convenience” Our extended family of 6 adults and 2 children loved the layout and decor. The children loved the bunk beds and their parents conveniently stayed in the neighboring bedroom in the privacy of the lowest level. They also had their own family room for the kids to watch TV. The remaining adults enjoyed having 2 master bedrooms and the tasteful decor. This house was very clean and provided everything we needed for a weekend stay. We would definitely recommend Railey for rentals as they had such a selection of properties to choose from as well as exceptional customer service.

Price per night from

$188

Dreamer's Overlook

McHenry house

4 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$229

Linwood

Oakland house

3 bedrooms / 2 bathrooms / sleeps 8

“Rental for wedding party” Plenty of space, nice locations, big patio and deck

Price per night from

$145

SUNsational

Swanton house

4 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$200

Direct Oceanfront ON The Beach ~ A SPECIAL 2BD/2BA ~ Private 4 Season Balcony!

Ocean City condo

2 bedrooms / 2 bathrooms / sleeps 6

“All Superlatives!” Clean. Comfortable. Quiet. Well-supplied. Wonderful ocean view from balcony and bedroom. Easy access to beach. Smooth "registration" system. Convenient to restaurants, shops, entertainment. We loved it!

Responds fast! avg. 1 hour 58 minutes

Price per night from

$126

Big Sky

McHenry house

5 bedrooms / 5 bathrooms / sleeps 14

“had a Damm good time” I have been comeing to Deep Creek for the last four years,and I will keep coming,I have time to relax, have fun, eat good, and enjoy my family and friends. thanks Deep Creek see you next year

Price per night from

$322

It's 5 O'Clock Somewhere

Oakland house

5 bedrooms / 5 bathrooms / sleeps 14

“beautiful weekend” our group has rented this home several times and it is always very clean. we rent this home because we look for 5 couples to have their own private bedroom & bath & it is difficult to find very many homes that met our needs w/ queen &/or king beds for five couples. the locate is nice & the hot tub is under the deck for cover in bad weather.the view is nice & we would rent again.

Price per night from

$267

Deep Creek Village #12

McHenry house

2 bedrooms / 3 bathrooms / sleeps 8

“Perfect Winter Ski&Board Vacation” Everything we needed for an exceptional winter ski & snowboard vacation. Home was very clean & fully equipped. We loved being able to walk right to the slopes and then lounge in the hot tub under the stars. The gas fireplace kept us warm and relaxed between mountain ventures. Railey even gave us DVD rentals! We will be back!

Price per night from

$95

Bright Beginnings

McHenry condo

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$150

5 BR - AWESOME lake views, pool, billiards, tennis & hot tub on Wisp Mountain!

McHenry house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$435

ambience

McHenry house

5 bedrooms / 6 bathrooms / sleeps 14

“Excellent home and location” This is a great house. Nicely furnished. Nice kitchen. The weber grill was fine but it would be nice to have a gas grill. The cleaning service did a nice job. Overall we had a great experience. The house is centrally located but it is on a busy place on the water.

Price per night from

$235

Wind & Water

McHenry house

4 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$215

Independent cozy unit with private entrance

Bethesda house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$114

Beautiful Day

McHenry house

5 bedrooms / 3 bathrooms / sleeps 14

“Fun Time at Wisp” The house was very nice, however, I misunderstood the description online and thought the house was ski in/ski out. I believe the online description is a little misleading.

Price per night from

$161

Home on the Ridge

Oakland house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$141

Viewing 38 of 1,105
rentals in Maryland

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About Maryland

Maryland's balmy coastal weather, close proximity to the nation's capital and phenomenal beaches make it an excellent place to enjoy a vacation. This small mid-coastal state is home to one of America's most beautiful bays, Chesapeake Bay. Maryland is nicknamed "America in miniature" because it offers a little of everything: urban charm, mountains, rolling plains and grasslands, crystal-clear coastal waters and a rich history. The state is also famous for its food; no vacation to Maryland is complete without sampling the fresh seafood, especially the delectable crab cakes.

Some of the many attractions and destinations in the state include:

  • Baltimore: A vibrant city on the Chesapeake Bay, Baltimore bustles with excitement and glimpses into America's storied history. Scenic Annapolis is also worth checking out if you want to take in a broader sampling of the state's urban style.
  • Chesapeake Bay: Spanning beyond Baltimore, Maryland's famous bay is a world unto itself, with outstanding fishing, swimming and sightseeing. Spectacular sunsets are a daily occurrence making Chesapeake Bay a perfect romantic getaway for couples.
  • Antietam Battlefield: The site of the single bloodiest battle in Civil War history, the Antietam Battlefield was the setting for the first Civil War battle fought in the North.
  • The Appalachian Trail: Even though the Appalachian Trail only meanders through 40 miles of Maryland, it's among the most beautiful and scenic stretches on the entire route.
  • Assateague Island National Seashore: Perhaps the most unique of the many Maryland National Parks, Assateague Island National Seashore is a barrier island that hosts an astonishing range of flora and fauna, including rare birds and wild ponies.

Summer is the perfect time to visit Maryland as Ocean City makes a perfect place for a family vacation. Annapolis' City Dock, which has remained virtually unchanged for a century, has summertime concerts by the shores of the Chesapeake. During the summer, you can also visit Maryland campgrounds and bring the family to one of the many water parks in Maryland.

For your accommodations, why not get a beach house if you're staying along the coast or a condo to better enjoy all the sights and sounds of the city? Vacation rentals offer more room and privacy than hotels and come complete with all the comforts of home.

Maryland is also close to two of the eastern United States' most storied and popular cities: Philadelphia and Washington, DC. Both are an easy day trip from just about anywhere in the state and offer a more complete glimpse into the vibrant culture of this important corner of the country.

If you want to explore more of the area surrounding Delaware, remember that Philadelphia is only about 20 miles from downtown Wilmington. One of America's most historic and popular cities, Philadelphia makes an ideal day trip for those staying in Delaware.

Top Destination reviews

Large Home with Assateague Island Views near Ocean City, Berlin and Frontierland
Lovely home with amazing views and pet friendly

We loved our stay at this home in Assateague. The house was big and plentiful for our family and fur babies. The kitchen was well stocked with the essentials. We enjoyed the use of the hot tub, the huge windows with amazing views and the ease of checking in. The fenced in yard was a huge plus for us as we have a dog with disabilities who does not walk on a leash well. Thank you for opening your home to us and we looking forward to staying again sometime soon!see more
Cozy Cumberland Cabin in the Allegheny Mountains!
Super Cozy Cabin, insulated and secluded, yet so close to civilization.

Unfortunately the weather did not really cooperate, it was foggy, rainy, and generally dreary...however...I found plenty of things to do anyway! Nature is at the doorstep, but civilization is just a few minutes away. Elegantly decorated in a hunting cabin theme, I passed the hours cooking, reading, and, during breaks in the weather, exploring outside and around the cabin, and also at Rocky Gap State Park only 20 minutes away, and in Hagerstown, a little under an hour away. Overall, a great experience. The Cabin is clean and well kept, and somehow can sleep up to 6!see more
Reach 4 the Beach! Regency Place, OCMD - Weekends Available in May!
Beautiful Place

Reach For The Beach was a beautiful clean place to stay. The balcony does not look directly at another large building like the others do. The beach was literally 4 min walk from the building! Everything was very close and the hostess is extremely responsive and helpful! You will not be disappointed if you go with this place!see more
Best kept secret by the bay (Entire House)
Perfect Vacation Getaway

The house is beautiful, complete with any amenity you could ask for. Private dock was easily accessible. Close by to a nature preserve we spent a lot of time in. We were looking for a nice vacation spot where we could maintain distance from the crowds with the pandemic going on and this was perfect. There were no crowds anywhere, the locals were friendly, and the scenery was gorgeous. 10/10see more
Oceanscape 403
WGA

Great spot, ocean side. Clean & spacious. Def bring soap, dish detergent, trash bags & paper towels. … see more
Scenic Serenity
Not perfect, but pretty close!

Let’s get the cons out of the way. 1. All of the knives need to be thrown away. I couldn’t get through a tomato. 2. There was no broom or mop. We had to buy them from the Walmart that was about 10 minutes away. 3. The shower heads need to be updated. 4. A previous family had left a bag of trash in the boiler room. We found it as we were cleaning up. A surprise. I e-mailed about an Iron/ironing board and was told that there was none, but there actually was in the laundry room. Also, there is a very powerful grill outside. Favorite amenities. 1. The jacuzzi is updated and has Bluetooth built in for music. 2. The fire pit is spectacular and there was enough fire wood provided to enjoy it for hours. 3. We got into the 20s some nights, so the wood burning fireplace downstairs and the gas fireplace upstairs were very welcome. 4. A beautiful view of the lake is unobstructed from every floor and is a minute walk from the house. The occasion. We have 2 friends with a birthday on the same day. To be safe, we all invited our quarantine bubble of people to celebrate in Deep Creek. On the first night, we had a welcome cocktail hour. The house is an acoustic dream, so I brought one large JBL Bluetooth speaker to place on the top floor next to the overhang. We could hear music everywhere. There are space enough options for 14 people play games, eat together, and have conversations. On the second day, we went horseback riding at the ranch that’s 5 minutes away. That evening, we had a costume party because it was Halloween. I set up a pipe and drape to take pictures in the pool room. Everyone seemed to love that. We also had trophies made to honor different categories of costumes. On Sunday, we had a birthday brunch. Everyone dressed in their day party attire. We made sangria and mimosas and had so much food! I had a special backdrop for pictures on Sunday. After cleanup, we sat by the fireplace, then had a pajama party/ karaoke night contest on the top floor. I brought karaoke mics for the occasion. At midnight, we did an official birthday toast and everyone was able to get to bed shortly after for checkout the next day. The house is perfect for all of these events. Quiet time is 11pm, so we made sure to adhere to all of the rules. Trash was taken out daily. We will definitely be using this house again.see more

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