Roland Park vacation rentals

We found 15 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Roland Park that are perfect for your trip. Whether you're staying in a vacation rental with family, friends, or just your furry companion, you'll have the best amenities for spending time at your home away from home, which might include a fireplace and a washer and dryer. You'll be able to choose a rental that has what everyone needs, including options that are accessible or non-smoking.

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Find out more about Roland Park

Why visit Roland Park

  • Charming Neighborhoods: Explore the picturesque streets of Roland Park, ideal for romantic strolls or family outings.
  • Outdoor Activities: Enjoy urban parks and scenic ridge gardens, perfect for relaxation and recreation.
  • Cultural Experiences: Visit local art museums and experience the vibrant community atmosphere.
  • Stunning Views: Check out Greenspring Overlook for breathtaking views of the surrounding area.
  • Comfortable Accommodations: Choose from a variety of vacation rentals, including cozy cottages and modern apartments.

Popular types of accommodation around Roland Park

Planning a getaway to Roland Park? Discover the charm of this vibrant community with a range of vacation rentals perfect for your stay. From houses to cozy cottages and modern apartments, including the popular Roland Ridge Apartments and Marylander Apartment Homes, you’ll find the ideal space to relax. Enjoy top-notch amenities and comfortable accommodations, including spacious bedroom homes, to make your visit truly memorable.

  • Houses: The top choice for visitors to Roland Park, offering spacious accommodations perfect for families or groups.
  • Apartments: A popular option for couples or solo travelers, providing the comfort of home in a convenient location.
  • Cottages: These quaint retreats offer a cozy and charming atmosphere for a relaxing getaway.
  • Condos: A great choice for those seeking modern amenities and community features during their stay.
  • Villas: Luxurious accommodations that provide an upscale experience with ample space and privacy.**

Top attractions near Roland Park

Roland Park in Baltimore offers a delightful mix of outdoor activities and cultural experiences perfect for families and city explorers. Visitors can enjoy attractions like the local art museum, urban parks, and the medical center. Notable spots include Roland Avenue and Roland Park Elementary, providing a charming environment for both relaxation and exploration. Whether you're seeking culture or family fun, Roland Park has something for everyone to enjoy.

  • Pimlico Race Course: Experience the thrill of horse racing at this historic venue, renowned for the Preakness Stakes. Located 2 miles from Roland Park, it offers a vibrant atmosphere filled with sports excitement and a chance to witness the skill of elite jockeys and horses.
  • Baltimore Museum of Art: Just 2 miles away, this art museum boasts an impressive collection, including works by Matisse and Picasso. Its cultural ambiance invites you to explore diverse exhibitions and enjoy free admission.
  • Lyric Opera House: Located 3 miles from Roland Park, this elegant arts center hosts a variety of performances, from operas to concerts, showcasing exceptional talent in a stunning architectural setting.

Things to do recommended for couples

Explore the charming streets of Roland Park hand-in-hand, then enjoy a cozy dinner at a local bistro. For a romantic touch, take a leisurely stroll through the picturesque gardens and relax at a nearby park while soaking in the beautiful surroundings together.

Things to do recommended for families

Families visiting Roland Park can enjoy a delightful day at the Maryland Zoo, where kids can explore animal exhibits and interactive areas. Nearby, the Baltimore Museum of Art offers engaging family programs, making it a perfect blend of fun and culture for everyone.

Things to do recommended for groups

Explore the charming streets of Roland Park, enjoy a guided tour of the Baltimore Museum of Art, or gather for a picnic at Wyman Park. Don't miss the chance to savor local cuisine at nearby restaurants for a true taste of Baltimore.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Roland Park

If you’re traveling with a group, family, or pets, or if you’re interested in extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Roland Park with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Roland Park with young kids: Traveling with young children can present its challenges. It’s important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Roland Park: For many families, a vacation wouldn't be the same without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Roland Park: If you’re in search of vacation rentals that offer great deals for month-long stays, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria.

Where to stay near Roland Park

Discover the charm of Roland Park, Baltimore, where outdoor adventures meet family-friendly fun. Explore its picturesque ridge gardens and delightful neighborhoods, perfect for a romantic stroll or a family outing. Nearby Greenspring Overlook offers stunning views, while the urban atmosphere invites you to experience local culture and history. With affordable housing options and a welcoming vibe, Roland Park is an ideal base to explore the rich tapestry of Baltimore and its enchanting surroundings.

  • Baltimore: As the largest city in Maryland, Baltimore is a vibrant hub of culture, history, and entertainment. Located in close proximity to Roland Park, the city offers a diverse range of experiences for travelers. Whether you're interested in exploring educational institutions, attending music concerts, or indulging in shopping, Baltimore has it all. Key attractions include the iconic sports stadiums, bustling marinas, and event venues that host various conferences and gatherings. Enjoy a stroll along the Inner Harbor or visit the renowned National Aquarium for a day of family fun.
  • Evergreen: Nestled just 0.4 miles from Roland Park, Evergreen is a charming neighborhood that provides a delightful escape into nature and outdoor activities. This area is perfect for families and those seeking a city-themed experience. Evergreen offers recreational spaces, shopping centers, and educational venues that cater to various interests. Visitors can explore local landmarks such as historic universities, picturesque islands, and the beautiful national state park, making it a great spot for outdoor adventures and leisurely walks.
  • Keswick: Located 0.5 miles from Roland Park, Keswick is a peaceful neighborhood that seamlessly blends family-friendly activities with outdoor enjoyment. This area is enriched with educational opportunities and shopping centers that invite exploration. Visitors can unwind in the lush urban parks, visit historic sites, and enjoy the vibrant atmosphere of local shopping malls. Keswick’s inviting ambiance and proximity to nature make it an ideal destination for families looking to experience the best of city life while enjoying the outdoors.

Best time to go to Roland Park

If you're planning a trip to Roland Park, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in March to April and September, while off-peak times, like August and October to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January33.8°F (1.0°C)Light RainMostly SunnyAverageSlightly Low
February36.1°F (2.3°C)Light RainMostly SunnyAverageSlightly Low
March43.7°F (6.5°C)Light RainMostly SunnySlightly HighSlightly Low
April54.3°F (12.4°C)Light RainMostly SunnySlightly HighAverage
May63.9°F (17.7°C)Light RainMostly SunnyAverageSlightly High
June72.5°F (22.5°C)Light RainMostly SunnyAverageAverage
July78.1°F (25.6°C)Light RainMostly SunnyAverageSlightly High
August76.1°F (24.5°C)Light RainMostly SunnySlightly LowSlightly High
September69.8°F (21.0°C)Light RainMostly SunnySlightly HighAverage
October58.8°F (14.9°C)Light RainMostly SunnySlightly LowAverage
November46.8°F (8.2°C)Light RainMostly SunnySlightly LowAverage
December39.4°F (4.1°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is a breeze

Are you hoping to save on your next adventure? Flexibility with your travel dates can really pay off, as prices often change. Additionally, if you opt for a longer stay, you’re likely to enjoy significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers you a user-friendly platform to plan new trips, resume your previous ones, or manage your travel arrangements. Here, you can easily find the properties you've saved or booked, organized under Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Roland Park?
In Roland Park, apartments are the most popular vacation rental choice, with several available throughout the charming neighborhood. These apartments typically offer modern amenities, including fully equipped kitchens, comfortable living areas, and often attractive views of the surrounding area. The neighborhood is known for its beautiful tree-lined streets and proximity to parks, making it a pleasant environment for travelers.
How much does it cost to rent a vacation home in Roland Park?
Prices for vacation rentals in Roland Park vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Roland Park to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Roland Park vacation house rentals?
You can find great discounts on house rentals in Roland Park on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Roland Park?
In Roland Park, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, as well as coffee and tea makers for a morning pick-me-up. Many rentals also accommodate pets, welcoming dogs and cats, making them suitable for travelers who want to bring their furry friends along. Onsite parking is another common feature, providing convenience for those traveling by car. Additionally, some properties come with blenders, superb for whipping up smoothies or other blended drinks.
Are there any Roland Park vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Roland Park with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I book pet-friendly vacation rentals in Roland Park?
In Roland Park, travelers can find several pet-friendly vacation rentals that cater to those looking to enjoy the area with their furry companions. Many of these rentals are situated in charming neighborhoods, offering amenities such as spacious backyards, modern kitchens, and cozy living areas. Some properties may also include features like fenced-in yards, making them especially accommodating for pets.

The neighborhood itself is known for its beautiful tree-lined streets and close proximity to parks, providing ample opportunities for walks and outdoor play. Nearby, places like the Roland Park Community Center and various green spaces offer pet-friendly environments, adding to the appeal for those traveling with pets.
Can I find long-stay vacation rentals in Roland Park?
A long-stay vacation rental in Roland Park is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Roland Park for a vacation rental?
April is the most popular time to visit Roland Park, as it falls within the peak season from March to May. During this vibrant spring period, travelers flock to the area to enjoy the blooming gardens and pleasant temperatures, typically ranging from the mid-40s to the low 70s Fahrenheit. This is an ideal time for outdoor activities, including leisurely strolls in the picturesque parks and scenic picnics by the water.

As the flowers begin to bloom, visitors can experience firsthand the local culture by exploring historic sites and indulging in the culinary delights offered by nearby restaurants. The atmosphere is lively, with various events and activities that cater to those seeking both adventure and relaxation.

For those looking for a more budget-friendly option, consider visiting in October. This month, while quieter than the spring, showcases the stunning fall foliage and offers a unique charm of its own, great for cozy getaways and reflective nature walks.

Ultimately, the best time to book your vacation rental in Roland Park depends on your preference for a bustling spring adventure or a tranquil autumn escape.
Are there any remote work vacation rentals in Roland Park?
In Roland Park, Maryland, there are several vacation rentals available that cater to remote work needs. This charming neighborhood is known for its picturesque streets and historic architecture, providing a serene backdrop for those looking to balance work and leisure. Many rentals in the area offer essential amenities such as reliable Wi-Fi, allowing for seamless connectivity during work hours.

Travelers can expect comfortable living spaces with dedicated work areas, as well as fully equipped kitchens for easy meal preparation. The peaceful environment of Roland Park is ideal for productivity, while the nearby parks and local attractions provide opportunities for relaxation and recreation during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Roland Park vacation rental?
Book your Roland Park vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Roland Park, Maryland, United States of America?
In Roland Park, visitors can enjoy a charming mix of historic architecture and beautiful green spaces. One of the top attractions is the Roland Park Shopping Plaza, which features a variety of local shops, cafes, and restaurants, making it a great spot for leisurely strolls and dining. The neighborhood is also home to the picturesque Roland Park Historic District, known for its stunning homes and tree-lined streets that reflect the area's rich history.

Nearby, the Baltimore Museum of Art offers a fantastic collection of art and hosts various events throughout the year, providing a cultural experience just a short drive away. Additionally, the beautiful Druid Hill Park is within reach, offering expansive lawns, walking trails, and the Maryland Zoo, which can be superb for outdoor activities and family outings.
Can I change or cancel my Roland Park home rental booking on Vrbo?
To find Roland Park vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Roland Park vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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