Holiday houses in Jessup

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.

Lakefront Couples Retreat | Fire Pit & Sunset

Escape to a private lakefront couples retreat steps from Merriweather Post where sunset reflections, peaceful water views, and romantic evenings by the fire pit create an unforgettable stay. Couple retreat invites serenity, offers panoramic views, sun-filled sunroom, and a tranquil patio steps from calm lake. Wake to golden sunsets, sip coffee as geese glide by, and unwind at sunset surrounded by peaceful waterfront beauty. Luxury comfort meets nature in this elegant boutique couple escape.

Cozy Private Suite w/Yard —10 min to BWI/F. Meade

Private and comfortable suite perfectly located for travelers, families, and professionals visiting the area. Enjoy a private entrance, dedicated outdoor space, a peaceful neighborhood, and quick access to everything — 10 minutes to BWI Airport, Fort Meade, Arundel Mills Mall, Live! Casino & Hotel, and major highways. Whether you're on a short trip, long work assignment, or weekend getaway, this suite offers clean, quiet, and convenient comfort with all the essentials for a relaxing stay.

The Lily Pad: Townhome b/w Baltimore & Wash., DC

Welcome to “The Lily Pad,” perfectly curated into a comfortable home environment & conveniently located just off I-95, only 15 minutes from BWI Airport. This townhome is centrally-located between Baltimore (Inner Harbor: 17ish minutes) and Washington, DC (Monuments & Museums: 35-40minutes). Bordering Columbia, MD there are tons of activities, shopping and restaurants near by including several within walking distance. This home is perfect for a family, business travelers, couples and more.

Quaint & Cozy Hideaway

Cozy Basement Suite Apartment Near Top Attractions. I would love to welcome you to our comfortable and inviting basement apartment that is 1295 sq ft. This cozy apartment is the perfect location for couples, travel nurses, and professionals on business, looking to explore the best of what Maryland has to offer. Whether you’re in town for a quick trip or a longer stay, our place provides a welcoming and convenient home base. Book your stay today and start planning your adventure!

Stylish Rancher Near BWI,Forte Meade,Live Casino!

Your family will be close to everything when you stay at this centrally-located home. 3 bed 2 bath single level home with a deck, parking, and washer/dryer. The home is loaded with everything needed to enjoy your stay; WiFi, Smart TVs, linens, kitchenware, blow dryer, iron and more! Located in a safe and quiet neighborhood, but still very convenient. Nearby there's Arundel Mills Mall, Live Casino, Forte Meade, Cinemark Movies, and many more restaurants and activities.

Train Tracks Getaway (Whole house)

All aboard for comfort and charm at Train Track Getaway! This cozy Odenton home is perfect for families and friends, with easy MARC train access to D.C. and Baltimore. Enjoy pancakes on the back porch and marshmallows by the firepit—yes, we’ve got the s’mores kit ready! Inside offers comfy beds, a full kitchen, and space to relax or play. Whether you're visiting Fort Meade or just unwinding, this is your laid-back home base for fun, family, and firepit vibes.

Grey escape studio apt near bwi

This safe and centrally-located studio is minutes away from Bwi and 30 minutes to dc 15 to baltimore. It is ideal for guests needing short stay for work or vacation. Major highways shopping and dining 10 minutes away. This is on lower level of a house and parking is free. One car allowed. Strictly no smoking and partying . Please bring your personal toiletries towels etc.

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.

In-Law/Guest Suite ~~ Red Rose Inn

Red Rose Inn Perfect for business travelers, students, or in between housing. Count on reliable internet and a quiet workspace. Minutes to Columbia, Ft. Meade, Merriweather Post Pavilion, Gateway Drive, NSA, Annapolis Junction, Baltimore, JHU APL, University of Maryland, NASA Goddard and DC. Forget your worries in this spacious and serene space.

Private 1BR Saloon w/ Kitchen & Patio near DC/BWI

Rustic saloon vibes, modern comforts, and two great cities on your doorstep—welcome to the Charming Saloon! In just 25 minutes you can be on the National Mall; in 20 minutes you can be cheering on the Orioles in Baltimore. When you return, your very own western-inspired hideout—with a full kitchen, private bath, and laundry—will be waiting.

Glen Burnie Hideaway

This home is located approximately 17 miles from both Annapolis and Ellicott City, 38 miles from Washington DC, and 15 miles from Baltimore. The home's central location makes it easy to access major highways like 695, 295, 95, 10, and 100. The setup of the house makes it ideal for family or friends to rest and relax.