Family-friendly holiday rentals in Randallstown

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

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.

Dog-Friendly Home | Fenced Side Yard + Full AC

Summer stays are easy at Grandma’s House in Owings Mills, a cozy dog-friendly retreat with full AC, fast Wi-Fi, laundry, driveway parking, a fully stocked kitchen, and fenced side yard. This nostalgic home sits on a peaceful 1/2-acre lot with mature trees and frequent deer sightings. Perfect for sports families, medical travel, local events, and multi-generational visits with a primary bedroom on main level + a private upstairs. Wegmans nearby; about 30 mins to Baltimore. Permit: RHR-2026-00248

The Caretaker's Cottage-Historic Roundabout Hills

The Caretaker's Cottage was built in the 1770s by Ruben Merriwether, and sits near the manor house where he and his ancestors lived at Roundabout Hills. An exceptional space with a fabulous full kitchen perfect for those who like to cook, it is truly a one of a kind place to stay. The house, where John and Fiona live, and the cottage are secluded and private, but close to all of the art, culture, restaurants and dining in the nearby towns of Frederick, Columbia, Baltimore, and Washington, DC.

Cozy Historic Guest House

Located in the heart of Old Ellicott City! This studio is warm, cozy and decorated with almost all vintage furnishings to pay tribute to the 1800s home. The space offers a well stocked bedroom, full bathroom and kitchenette. Relax on the patio or walk to the many cafes and shops on Main Street. Parking is included. The home is built into a hill so you will need to walk up a series of steps & stoned in the back from the parking area to enter. Due to this our home may not be ideal for everyone.

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.

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!

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.

Historic Gatehouse Master Suite

Discover the historic charm of Maryland's scenic horse country! Our Master Suite, part of a Tudor-style gatehouse on a country estate, offers luxury and convenience. Minutes from Hunt Valley and Baltimore, indulge in a Carrera marble bathroom, a private deck with sweeping views, a full-size tennis court, a refreshing pool, and more. Immerse yourself in elegance and history.

Fox Cottage *Pet Friendly*

Fox Cottage is a thoughtfully designed eclectic modern retreat nestled beside our beautifully preserved 115-year-old Victorian home. Tucked along a peaceful, wooded path, this private cottage offers the perfect balance of charm, comfort, and convenience — ideal for couples, professionals, concertgoers, and travelers bringing their furry companions.

Basement Apartment-Private Entry

Basement apartment with private entrance. Free parking on site. Located 20 minutes from BWI Airport and 10 minutes from The Mall in Columbia and Merriweather Post Pavilion. Great neighborhood with running trails and parks.

Spacious rancher close to highways

Great rancher on a quiet street. Sunny spacious deck in back of house. Very close to I-695 and I-795 and I-83. Grocery stores and restaurants short walking distance away. Downtown Baltimore only 30-40 minutes away.