Family-friendly holiday rentals in Owings Mills

Our Retreat -in a peaceful setting.

Private- apartment in the lower level of our house. House in a rural setting- you may spot white tail deer or other wildlife.Enjoy the peaceful tranquil setting.We are within 5 minutes by car to Rte 70 and shopping centers. Our space isn't childproof. Workout equipment available for use at your own risk. We control the HVAC and will adjust as requested. May not be suitable for those with mobility issues due to the walk to the entrance. Non smoking. We aren't set up for heavy cooking. No stove.

Grandma’s Garden Cottage: Owings Mills, Dogs OK

Welcome to Grandma’s House, a nostalgic storybook home in Owings Mills. Restorative and cozy, we’re ideal for travelers with pups, sports families, and those seeking access to world-class medical care. Enjoy a fenced side yard and nightly deer sightings across our 1/2acre lot. Features a 'Primary on Main' for easy accessibility and a private upstairs guest space. Fully stocked kitchen, fast Wi-Fi, and heritage charm 30 mins from Baltimore. Wegmans & Ravens training nearby. Permit: RHR-2026-00248

Hickory Haven •1B King •Bsmt Apt •Clean •LG

Walk into a generously spacious, open-concept apt. The comfortable furnishings in this home blend authentic styles with modern design. Start your mornings w/ a meticulously clean bathroom. Enjoy movie night in the large living room, or lay on the comfortable king-sized bed. Read through the night by a warm stove fire. Stay in the backyard and enjoy the serenity of Sykesville! Enjoy the high-speed internet and the large space for your work-at-home needs. Stay-a-while and make the place your home.

Plummer Farmhouse

Want to experience historic Sykesville living? Look no further! This 1892 charmer offers 5 bedrooms and 2.5 baths with over an acre of land and amazing outdoors space (TV, over sized deck, and rail road tracks!). In 2016 Sykesville was named The Coolest Small Town in America and now you get to experience all its "coolness". The farmhouse is located only steps away from the Main Street which hosts boutique shops, great restaurants, distillery, farm markets and trout fishing in Patapsco river.

* Stunning Bungalow Perfect for Everyone *

You'll love your stay at this charming and cozy 1 level bungalow!! It offers a brand new high quality renovation convenient to all the Baltimore hot spots. The open layout coupled with stylish finishes and decor will make you feel right at home. It's fully stocked with almost every possible thing you could imagine for your use! Really no need to bring anything but yourself and clothes. The 3 bedrooms with a movable foldaway queen sofabed can sleep 8 comfortably. Plenty of parking available.

Private Serene Suite with Jacuzzi- Non Smoking

Escape to this serene in-law suite, an extension of the main house, in Baltimore’s safest & quietest area. Ideal for couples, it offers a private Jacuzzi, California king bed, large modern TV, and dedicated HVAC for comfort. The spacious sitting area and luxurious shower create a peaceful retreat. Walk to nearby shops and parks for added convenience. A Tesla charger is available upon request, ensuring convenience for electric vehicle owners. Perfect for a relaxing getaway or city visit.

Gunpowder Retreat

Unwind and relax with friends & family at this peaceful mid-century modern home. Nestled along the Gunpowder Falls State Park you can enjoy long summer days lounging in the pool under a canopy of trees or take an adventure along the hiking trails easily accessible from the back yard. Although there is no reason to leave this oasis, shopping and restaurants are only a five-minute drive away. Enjoy the beauty of nature without giving up modern comforts in this 4 bedroom, 3 bath home.

Stunning 7BR Lux House in Baltimore

We've taken our 18 years of travel and love for creating memorable moments and developed the perfect stay for you. A hidden gem, nestled in the heart of Baltimore, this gorgeous newly-remodeled 7 BR, 4 Bath House has been updated with amenities such as a Built-in Bluetooth theater speaker system, a master suite with dual showers and freestanding tub, and plenty of natural lighting in our charming sunroom. Elevate your time away with a massage therapist, or special event!

Cute cottage studio with full kitchen and laundry

Warm and inviting private upstairs studio with off-street parking, full kitchen, laundry, electronic fireplace, rainhead shower and deck with tranquil garden in the Riderwood area of Towson. Studio is situated next to owner's stone cottage, and is tucked away at the back of 2.5 acres with private bridge and creek. Centrally located to shops, galleries, walking and biking trails, Lake Roland, Baltimore, DC and PA. Especially suitable for a restorative or romantic getaway.

Fox Cottage *Pet Friendly*

Fox Cottage is a modern addition to our 115 year old Victorian home. It’s a One Bedroom Queen size mattress & memory foam topper. There’s a Loft with a Full Size Memory Foam Mattress. The loft is a cozy space accessible by a vintage wooden ladder. It is not appropriate for people who cannot climb a ladder. There’s an outdoor seating area with a Chiminea to light a fire, enjoy a cup of coffee or wine, work or just listen to the birds.

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.

The Guesthouse at Downey Family Farm

Cozy yet spacious renovated log cabin on our small farm in Maryland's picturesque countryside. Large bedrooms, two bathrooms, great Wi-Fi, and fully-equipped kitchen and washer/dryer make this a great place to stay with your family. The Guesthouse is conveniently located with easy access to I-795, and is 35 minutes from BWI Airport.