Vacation rentals in Woodlawn

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Top-rated vacation rentals in Woodlawn

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost
A single-story house features a welcoming entrance with a front door framed by simple step railings. A spacious driveway leads to the home, and a newly fenced backyard is visible to the left, surrounded by well-maintained grass and brick pathways.
Home in Catonsville
4.84 out of 5 average rating, 155 reviews

Delightful 4-Bed Whole House with Easy Parking

Newly relisted! Centrally located next to route 40 & 695 Beltway. House newly furnished. Huge park & soccer field within 5 mins, for dogs & to play. 5 mins drive to Starbucks, Chick-fil-A, Walmart, Applebees, Safeway, Enterprise, Lotte, Home Depot, Lowe's. Plenty of local restaurants & bars on Frederick Rd. Easy commute to BWI, B'moreCity, Hopkins, Ellicot & Columbia. Train for DC commute is 10 mins drive to Halethorpe. Previously only basement listed, guests loved it, now listing whole house.

Top guest favorite
A living area features a light grey sofa facing a large window that invites natural light. Two woven chairs are positioned nearby, and a stone fireplace adds a touch of warmth to the space. Modern light fixtures are installed on the walls.
Home in Catonsville
4.95 out of 5 average rating, 149 reviews

Tudor Home

Enjoy your stay in this cozy, newly remodeled Tudor home in a historic and architecturally eclectic neighborhood in Catonsville, MD! You’ll be close to everything but far enough to enjoy a relaxing trip. The home features Four bedrooms, two full baths, a fully stocked kitchen, a full basement, and 18ft ceilings on the main level. You will enjoy 65, 42, and 32-inch smart TV's throughout the home. In addition, a private upstairs main suite with King size bed, sofa seating area, and workstation.

Guest favorite
An eclectic studio apartment displays a spacious bed and a patterned throw atop it. Sunlight filters through tall windows, reflecting off decorative wall art. A piano and a book-filled shelving unit add character, while plants bring life to the room's corners.
Apartment in Union Square
4.91 out of 5 average rating, 851 reviews

South-Facing Studio Overlooking Union Square Park

Pick out tunes on the refurbished 1910 piano or classical guitar of this eclectically furnished studio apartment, elegantly lit by tall windows under high ceilings overlooking lovely Union Square Park in downtown Baltimore. The residential area is a mile from the inner harbor/ stadium and street parking is easy. Nearby, enjoy walking in the park, dinner at Rooted or even see a puppet show. A well-stocked library offers great reading and the kitchenette has coffee, tea, and a light breakfast.

Top guest favorite
A classic brick Colonial house is surrounded by well-maintained gardens and lush greenery. Large trees provide shade over the front lawn, which features manicured bushes and young saplings, contributing to the inviting exterior of the home.
Guest suite in Catonsville
4.94 out of 5 average rating, 559 reviews

Rollingside: Two-Room Guest Suite

Two-room guest suite with private entrance located in picturesque Catonsville, MD on a pre-Colonial road originally used for rolling tobacco to the harbor. Downtown Baltimore is 20 minutes away, BWI airport and Amtrak station 15 minutes, and our street is located on a bus route. Beautiful 3.5 mile walk to historic Ellicott City and an hour from Washington, D.C. Individuals and families with children are welcome, but the Airbnb member renting the property must be over the age of 25.

Superhost
The kitchen features sleek, modern appliances and a spacious island with bar seating. Light-colored cabinetry surrounds the area, complemented by a decorative plant centerpiece on the dining table. Natural light enters through a nearby window, creating a welcoming atmosphere.
Home in Baltimore
4.84 out of 5 average rating, 81 reviews

Charming 3BR House in Historic Neighborhood

You will feel right at home in this charming house located in Historic Dickeyville, known for it's garden club and cobble stone roads. The house sits on the edge of the community with a small front and back yard. Newly remodeled kitchen hosts sleek appliances and bar seating at the peninsula. Family room is extremely welcoming with an extra large, stylish sectional sofa. Upstairs you will find 3 bedrooms, 2 full baths and a bonus office/lounge space. We look forward to hosting you!

Top guest favorite
An open layout is showcased with a spacious living area, featuring a comfortable sectional sofa and a coffee table. A smart TV is positioned on a stand, while a dining set is visible in the background. Natural light filters through the windows, illuminating the space.
Guest suite in Randallstown
4.99 out of 5 average rating, 141 reviews

Private Efficiency Suite ~ King Bed ~ Baltimore Co

Welcome to Hickory Roots Hideaway! A cozy yet spacious 750 sq ft efficiency guest suite situated on our picturesque 4 acre homestead! Great Wi-Fi and amenities make this a perfect getaway even if work and virtual school must continue. Enjoy a relaxing stay - you are welcome to explore our garden, shoot some hoops in our basketball court, or get to know our adorable farm animals! We are conveniently located with easy access to I-70, I-795, and just 30 minutes from downtown Baltimore!

Top guest favorite
Home in Woodlawn
5 out of 5 average rating, 19 reviews

Luxury Home w/ Deck/Loft & Skyline Views near Balt

Perched on a gentle hill in Woodlawn, Maryland, this newly built 4-bedroom Townhome offers sweeping views, open spaces, and the perfect balance between privacy and togetherness. The home unfolds across several floors, creating a natural rhythm for family living, friend groups,Unwind upstairs in one of the two luxurious master suites, while the others laugh and play in the open 3rd loft, complete with a balcony overlooking the skyscape. From this height, the sunsets are magic

Guest favorite
A spacious living area features a large sectional sofa and two accent chairs positioned around a low table. A decorative area rug enhances the floor space, while large windows allow natural light to brighten the room. Modern furnishings and a stylish lamp add to the welcoming ambiance.
Home in Catonsville
4.92 out of 5 average rating, 37 reviews

3 Bed, 2 Bath in quiet Catonsville neighborhood

Enjoy your stay in this sun-soaked, cozy house nestled in a quiet neighborhood just outside of downtown Baltimore. Recently renovated (2024) and decorated with modern touches, this 3 bedroom, 2 bathroom home offers two living spaces that boast a large sectional, sofa and loveseat. Only 20 mins from Inner Harbor and close to numerous restaurants, shops and major roadways. PLEASE NOTE: The owner of this property does not allow events of any kind. No prom send offs allowed.

Top guest favorite
The living area features a textured gray couch adorned with colorful pillows, complemented by a wooden armchair. A coffee table sits at the center, showcasing a decorative bowl. In the background, a fully equipped kitchen is visible, along with a dining area featuring tall stools.
Home in Ellicott City
4.94 out of 5 average rating, 112 reviews

Historic Hillside Cottage

Experience the charm of an 1800s home styled with modern amenities. This historic cottage is steps away from all that Historic Ellicott City has to offer. Spend the day exploring Main Street lined with restaurants and small businesses or go for a walk, hike, bike ride or swim in nearby Patapsco State Park. Perfect for guests in town for weddings, concerts or those that love history and nature. Centrally located with easy access to Columbia, Baltimore & Washington D.C.

Top guest favorite
A historic stone house features a welcoming front porch with white railings, flanked by lush greenery and blooming flowers. The American flag adds a charming touch. A gently sloping landscape guides the eye towards the two-story structure, surrounded by natural beauty.
Home in Ellicott City
4.97 out of 5 average rating, 86 reviews

Historic Riverside Cottage

Its prime location in the Granite Hill area of Oella offers the charm of Old Ellicott City's shops and restaurants within walking distance. With river views and quick access to the hiking and mountain biking trails of Patapsco State Park, it blends nature’s beauty with urban comforts. It is also close to Merriweather Post Pavilion for easy access to concerts and events. The historical essence of the 1809-built house is preserved through a comprehensive 2023 renovation.

Top guest favorite
Guesthouse in Owings Mills
4.96 out of 5 average rating, 137 reviews

The Garden Studio

Thoughtfully appointed 1 bedroom guesthouse in beautiful Greenspring Valley. Enjoy quiet quarters on an acre of private residential property within 5 minutes of the Baltimore beltway & restaurants, grocers, gas, and services. Close to Stevenson University (2 mi), Towson University (7 mi), convenient to other colleges & universities in the area; and 11 mi to the Inner Harbor. Host available in main house as needed.

Guest favorite
A two-story home built into the hillside is framed by lush greenery. A wooden porch, supported by stone pillars, features a railing and an American flag. The exterior showcases a mix of siding and stone, with large front windows allowing natural light into the interior.
Home in Ellicott City
4.82 out of 5 average rating, 143 reviews

Mello-Ray River House

Historic 3BR, 2BA colonial on Frederick Rd—once the main route from Baltimore to Ellicott City. Built on a foundation dating to the late 1700s, the current structure has stood since 1875. Overlooks the Patapsco River and the B&O Railroad, the first in the nation. Features hardwood floors, modern kitchen, central air, and fenced patio. Walk to shops, parks, and the historic district.

Popular amenities for Woodlawn vacation rentals

When is the best time to visit Woodlawn?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Woodlawn?

    Woodlawn has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Woodlawn?

    Experience the best of Woodlawn with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Woodlawn?

    Four-legged friends are welcome in Woodlawn. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there house rentals with a dedicated workspace in Woodlawn?

    Yes! Work meets play with ease at over 10 house rentals in Woodlawn featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Woodlawn?

    Make yourself at home in Woodlawn by choosing from our most frequently booked neighborhoods. We have over 180 vacation rentals in Chadwick Manor, over 520 vacation rentals in Catonsville Manor, and over 70 vacation rentals in Westview Park.

  • Do apartment rentals in Woodlawn have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Woodlawn. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Woodlawn have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in Woodlawn. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Woodlawn have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Woodlawn. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Woodlawn have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Woodlawn. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Woodlawn?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with air conditioning, over 30 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Woodlawn

  • Total vacation rentals

    Explore 60 vacation rentals in Woodlawn

  • Nightly prices starting at

    Woodlawn vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

  • Verified guest reviews

    Over 700 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Woodlawn vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Woodlawn rentals

  • 4.7 Average rating

    Woodlawn stays receive an average rating of 4.7 out of 5 from guests

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