Top 10 Vacation Rentals In Maryland, USA - Updated 2024

Bettina
Bettina 
Updated
| 6 min read

Maryland, known for its picturesque bodies of water and mountain ranges, is home to one of the United States’ major seaports - Baltimore. Also an integral part of American history, this state is popular for being the birthplace of the national anthem of the United States. If you want to be close to nature, you can visit Swallow Falls State Park and enjoy the sight of Muddy Creek Falls, the tallest free-falling waterfalls in Maryland. For a fun way to see the area, you can go on a scenic bike ride or a boat ride in Chesapeake and Ohio Canal National Historical Park, once a famous waterway for transporting coal and crops to markets. For a memorable trip, book accommodation near the state’s top attractions. Discover the top vacation rentals in Maryland, USA.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 12, 2024.

1. Homey two-bedroom cabin with beautiful Chesapeake Bay view, Port Republic (from USD 375)

Enjoy the smell of hot coffee and the beautiful view of the sunrise every morning on this cabin’s furnished deck. Cook delicious food in the fully equipped kitchen then spend quality time with your loved ones in the dining room, which features stunning views of Chesapeake Bay. The living room has a La-Z-Boy, perfect for when you want to just sit back and relax after a busy day.

Central air conditioning and heating facilities ensure that you are comfortable in any weather. For added warmth during the winter, snuggle close to the fireplace in the living room. This homey two-bedroom cabin can fit up to five guests, a great choice for a small group of travelers looking for a relaxing getaway.

Stayed at this property?
Port Republic, Maryland, United States
cabin 5 Guests 2 Bedrooms 2 Bathrooms

Top guest reviews
Amenities & Room:
the house is primarily one huge room with the huge tivo-tv adorning the mantle
the cabin was also incredibly cozy and comfortable
the navy cabin is charming and comfortable
Cleanliness:
the house was clean and well equipped
Host:
owner was very helpful & had great suggestions
the owner was accommodating and easy to communicate with
brett was a very responsive and attentive owner and usually answered questions within minutes
brett is an amazing host for this wonderful rustic basically perfect (for us) chesapeake bay property
brett could not have been more helpful
Location:
brett’s cabin is comfy and the location is great
its a wonderful place for a quiet and relaxing family vacation with a small private beach right below
the neighborhood was quiet and neighbors were friendly
quiet neighborhood with mostly friendly neighbors although be prepared to adhere to a number of rules
plenty of places to order takeout from if you don’t feel like cooking
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

2. Cozy one-bedroom apartment for three guests, Fells Point (from USD 128)

Delve into Baltimore’s rich culture and history when you stay in this one-bedroom apartment located in Fells Point, the city’s first deepwater port. There are nearby restaurants, pubs, and tourist spots that you can explore, so you are sure to enjoy your time here.

After a long day outdoors, take a rest in this property that is well-decorated with wooden furniture and floors, giving it a cozy and warm ambiance. Prepare yourself a good meal in the kitchen as it has a small refrigerator, microwave, and electric stove. Planning to travel with friends? Worry not as the rental can host three guests.

Stayed at this property?
141 reviews   Wifi Available
Apartment 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3
Minimum Nights: 2
Refund Policy :

Top guest reviews
Amenities & Room:
The apartment was very well stocked with everything you would need toiletries pans
The apartment had all features as listed and was in a good neighborhood as several other reviewers mentioned
THAT IS IN THE WHOLE TOWN EVERYONE
I'm on crutches and this unit was perfect for me only a few steps up to the front door and everything on one level inside
Beautiful place ; clean and comfortable; walkable to Little Italy Fells Point and Inner Harbor
Cleanliness:
The apartment was very clean
The apartment itself was quaint and very clean
It had everything we needed Every space of the home was used wisely and it is decorated very well
The apartment was very clean and had lots of charm Bathroom and kitchen were well stocked with essentials
Host:
John was responsive to any questions we had
Mr Morgan was very easy to work with and was quick to return calls when I had questions about the rental
The owner was very responsive with correspondence
BUT THEY REALLY MADE US FEEL WELCOME
We couldn't be more pleased and John was very quick to answer any questions we had prior to our
Location:
Perfect location within walking distance to many restaurants and bars Easy to get to other fun sightseeing activities like the aquarium and science center
Great neighborhood; convenient to Canton
The location is also ideal access to many things and great restaurants
Parking was not really a problem at all
THEY ARE A TRUE ASSET TO THE NEIBORHOOD
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

3. Private two-bedroom cottage with hot tub, Sharpsburg (from USD 347)

Looking for a spacious rental where you can relax and have fun? This two-bedroom cottage is a great choice. Located in a 4-ac (1.6-ha) private property, it features a lot of areas where you can unwind, enjoy stunning views of lush greenery, and hang out with your loved ones.

For a calming afternoon with the best outdoor views, take a dip in the hot tub on the deck. If you are visiting during the cold season, you can sit by the fire pit while drinking a cup of hot chocolate for a relaxing night. The roomy living area is also a good place to relax when you want to stay indoors.

Stayed at this property?
126 reviews   Wifi Available
cottage 6 Guests 3 Bedrooms 1 Bathroom

Accommodates: 6
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
bedding was very comfortable and slept yeah 5 of us and two dogs comfortably
Cleanliness:
everything was clean and exactly as expected
the house was clean and well stocked and so comfortable
extremely clean and comfortable it had everything we needed and then some
Host:
great property fun little house good host
Location:
we loved the hot tub and the location is great so close to hiking/biking and sheperdstown
we really enjoyed the location of this property as well as the amenities
the location is great for the c&o tow path which we took walks on a couple of times
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

4. Fully furnished four-bedroom house with sunroom, Chester (from USD 395)

Going on a long summer getaway with your family and looking for a place to stay? This four-bedroom house, which can easily host eight guests, is a good fit. The host requires guests to book a minimum of seven nights during the summer. With lots of amenities, outdoor spaces, and nearby attractions, you might just want to stay longer.

The rental features a sunroom, which is a great spot when you want some alone time. The beautiful view of Cox Creek also offers a relaxing ambiance. All bedrooms have a window to ensure that you receive plenty of natural light. You can even host a lovely dinner for your friends while you’re here as it features a charcoal grill and gas grill on the patio.

Stayed at this property?
97 reviews   Wifi Available
House 8 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 8
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
very nice house comfortable for 7 ages 13-90 yo
lots of room great view very convenient location
just a lovely comfortable house
the living room and sitting rooms are very nice
the property is very comfortable and has all the conveniences to allow a relaxing stay
Cleanliness:
house is plenty big and clean
quiet comfortable clean all with a great view
at the same time while the interior decor was a bit dated everything was very comfortable and clean
Host:
host was vet helpful
the owners make you feel as welcome as a family member
harry and scott were super hosts
Location:
centrally located with many nice locations in driving distance
the restaurants and shops are close by and very good
this house is gorgeous clean well-equipped and located in such a serene location
the area has a country feel but is close to a food store and some great restaurants
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

5. Vista Country Home, Carroll County (from USD 325)

Located in a peaceful and private neighborhood, Vista Country Home is ideal for travelers who want to stay in a quiet area but do not want to miss what Carroll County has to offer. This three-bedroom house is near tourist spots, shopping sites, and numerous dining options, so looking for something to do will be the least of your worries.

If you are visiting during the winter, you can use the gas fireplace in the living room and lounge on the sofa for a relaxing night. Preparing a delicious home-cooked meal will not be a problem, as the house has a fully equipped kitchen. For a memorable dining experience, have dinner on the gazebo with your loved ones and enjoy beautiful views of lush green trees and a fountain.

Stayed at this property?
110 reviews   Wifi Available
chateau / country house 9 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 9
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
the house is very comfortable and met or exceeded all our expectations
the house was large very comfortable and furnished with all the amenities needed to make the stay enjoyable
my husband and i were in love with the patio and how spacious the kitchen was
lovely setting thoughtful touches everywhere fully stocked kitchen comfortable beds and lots of walking paths
it’s serene seclusion and beautifully appointed rooms offered the perfect setting for cook outs conversation walkabouts and relaxation
Cleanliness:
the house was spotless and very comfortable
highly recommended and very clean and nicely decorated
the last guest left the stove dirty but the owner came to clean it as well as possible
vista is exactly as described very clean and comfortable too
the house is lovely and was spotless
Host:
the owner was very responsive and timely
they are friendly generous hosts
the hosts were great as well
the owners were very courteous quick to answer inquiries and eager to help
our hosts were communicative and pleasant
Location:
the location is beautiful and hard to beat
this location is beautiful and truly amazing to behold
the family trip to gettysburg national military park was amazing
for quiet comfortable relaxation the spot was ideal
friendly hosts close proximity to historic gettysburg serene and peaceful
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

6. Family-friendly house for 10 guests, Thurmont (from USD 220)

Travelers whose itinerary includes a lot of outdoor adventures will have the best time here. Located at the foot of Catoctin Mountain Park, this four-bedroom house is near swimming, boating, and hiking sites. If you want to explore the area in a more fun way, you can use the bicycles that are available in the rental.

A great choice for a big group of travelers, this house can accommodate 10 guests. Kids can enjoy books, toys, and games here. A washer and dryer is provided to make sure that you have enough clean clothes during your stay.

Stayed at this property?
Thurmont, md, United States
PRIVATE VACATION HOME 10 Guests 4 Bedrooms 2 Bathrooms

Top guest reviews
Amenities & Room:
comfortable bed and house furnishings
a well equipped kitchen comfy beds soft chairs and a deck where we enjoyed dining outside
it is well stocked with plenty of kitchenware linens etc that make for an easy and comfortable stay
neat house w/a grill and nice kitchen
Cleanliness:
the house is clean and cozy
plenty of room and very clean
Host:
the host was responsive and easy to work with
as hosts bill and chris were great to work with
Location:
a wonderful place to stay with family
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

7. Conveniently located posh cottage for eight guests, Ballenger Creek (from USD 210)

Easily accessible from I-70, I-270, and Route 340, this four-bedroom cottage is perfect for guests who want an easy time exploring the area. This 2,000-sq. ft. (185.8-sqm) rental, which is located on a private 4-ac (1.6-ha) land, has posh and spacious bedrooms to ensure a restful stay.

Tastefully decorated common areas offer modern appliances and home-like conveniences to make your visit comfortable. If you prefer to eat a freshly cooked meal, the fully equipped kitchen can help you achieve this. Cleaning up will not be a problem, as there is a dishwasher available. All rooms have plush bedding and pillows to help you achieve a good night’s sleep.

Stayed at this property?
Frederick, MD, US
8 Guests 4 Bedrooms 1 Bathroom
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

8. Charming three-bedroom cottage with garden, Lochearn (from USD 131)

This quaint and charming house is a good choice if you are going on a trip with your family. It has 3 bedrooms, 2.5 baths, and can accommodate 5 guests. Travelers with children will have the best time here as it has a fenced backyard, which is a great spot for kids to play in and enjoy the sun and fresh air.

If you want to spend some quality time with your loved ones outdoors, head on to the nearby playground and disc golf course. After exploring, you can relax on the patio while enjoying a refreshing beverage and the beautiful view of the garden. A game night in the fully furnished basement is also a great idea for building memorable moments with your family.

Stayed at this property?
125 reviews   Wifi Available
House 5 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 5
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
nice to see the upgrades that they continue to make including the new roku tv and carpet
it would have been nice to know about the space heaters and family room upfront
we always feel comfortable in this neighborhood and the house fits all of our needs
Cleanliness:
clean cozy and welcoming
the house was clean and very nicely appointed
it was clean and set up with every thing we needed
the house is immaculately clean and super comfy cozy
very nice clean house in a great neighborhood
Host:
the owner was very responsive and helpful
rachel and bill are wonderful hosts and i recommend this house without reservation
the owners were great to work with
the owners make sure that the property is well maintain
the owner was very responsive pleasant and attentive to our needs
Location:
the park near the house is very cute
great location to explore the mid-atlantic region
perfect location close to lacrosse tournament fields
nice quiet neighborhood in a good location for our needs
we enjoyed walking in the neighborhood and park
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

9. The Beachwood Cottage, Mayo (from USD 326)

The Beachwood Cottage provides plenty of spaces where you can relax and have fun with your loved ones. It has three bedrooms with six beds so everyone can be comfortable. A living room with a lot of seating is a good spot when you want to catch up on your favorite TV shows.

Want some fresh air? The furnished deck offers calming views of nature. You can also enjoy a delicious meal and a bottle of beer with your loved ones, as there is a built-in bar and grill available. If you want to unwind before heading to bed, the bathtub in the upstairs bathroom is a great place to relax.

Stayed at this property?
145 reviews   Wifi Available
cottage 11 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 11
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Cleanliness:
very clean and comfortable
quiet clean and well-equipped
great communication and everything was so clean the view was beautiful
could not have asked for a more relaxing well decorated and sparkling clean place to stay
very clean well stocked and quiet but close to activities and restaurants
Host:
the hosts were just fantastic
hosts were available and responsive
owners very responsive and friendly
hosts next door ready to help but respecting your privacy
the hosts were easily accessible and friendly
Location:
excellent location and cozy house
easy trip from dc and close to annapolis
the property and location were perfect
it is very close to beautiful parks
great property beautiful location and very responsive owners
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

10. Stylish three-bedroom house with private deck, Annapolis

This well-lit three-bedroom house will welcome you in its many well-appointed spaces. Its crisp white walls, perfectly complemented by blue furniture and decorations make this rental a perfect place for travelers who are looking for stylish accommodations to stay in.

With a newly remodeled kitchen, any guest who loves to cook will have the best time here. You can lounge on the large sofa in the living room if you want to just sit back and relax while watching TV. There is also a private deck that has outdoor furniture. If you want to bond with your loved ones while enjoying the outdoors, this is a great spot for that purpose.

Stayed at this property?
208 reviews   Wifi Available
House 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
Parking was an ease with the pass provided
we had everything we needed in the well-stocked kitchen
The property is well appointed with comfortable modern conveniences in an older home
We had a comfortable 4 night stay for 4 adults in historic Annapolis
Very cozy & comfortable home Highly recommend
Cleanliness:
The home was very clean and Meghan (property manager)
Very comfortable & nicely furnished- had everything that I needed Clean & Megan
The property manager was very accessible and lovely (as indicated through her helpful texts in response to our queries)
The house had everything we needed and the five of us (all adults) were very comfortable
Host:
was so helpful and gracious
Perfect location Very responsive and helpful home owner
left me some helpful tips about the CVS basically being a "mini mart" - very good salads there
We had the best vacation
We had high hopes but were disappointed
Location:
Great location: just around corner from neighborhood park walk to town and to
but the times we did eat at the house
Perfect location that is indeed walking distance from DTA and USNA Quaint street with really nice neighbors too
I have never slept better
Upstairs bath a little small but not a deal breaker
Read more reviews
Oops, this listing is currently inactive. Check out these alternative properties in the same location.
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

Enjoy a historic trip with your loved ones in Maryland

With lots of historic attractions and amazing sceneries, travelers of all ages will have something to enjoy here. For a great trip, book one of the top vacation rentals in Maryland, USA mentioned above.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

History


Get Trip101 in your inbox

Unsubscribe in one click. See our Privacy Policy for more information on how we use your data

Bettina is a Behavioral Science graduate with a versatile background spanning human resources, management, sales, and marketing. Her love for travel matches her passion for coffee and wine. She...Read more

 Want to contribute as a Local Expert?
Explore Maryland
x
Good things are meant to be shared!
Back to top
Visited any of these places? Click this button to activate our "Add a Tip" feature to share your experience.