Holiday houses in Jessup

New spacious private guest suite

Newly built spacious & exquisitely finished guest suite with private entrance overlooking the woods, located in a serene & exclusive community in Hanover, Howard County. Strategically located less than 10mins from BWI, 15mins from Baltimore & 40mins from DC, it's a haven for business travelers and tourists. It's also within a short driving distance from The Mall in Columbia & Anne Arundel Mall, as well as many exquisite restaurants. The suite boasts a kitchen, dining area, room & full bathroom.

Rancher by Wash/Balt/Annap w/pool table, Kit, Deck

My Columbia House sits between Baltimore, Washington DC, and Annapolis, plus Historic Ellicott City, (county seat), is 8 miles close. The kid friendly neighborhood is central to Columbia village centers offering shops, restaurants, entertainment, lakes, hiking trails + more. Guests will enjoy FiOS Quantum data-multiple Laptop friendly work areas, 2 TVs and data jacks thru-out the home. See owners' favorites' list for local treats like Savage Mill, Ellicott City, or Merriweather Post Pavilion

2 BR/1.5 Bath Basement, Private Entrance & Parking

Entire basement only not the entire house. A basement apartment recently renovated with 2 bedrooms, luxurious full bathroom, powder room, full kitchen, dining room, living room, laundry in the unit, private entrance, private parking (max 2 cars). Host lives upstairs with 1 dog (labradoodle). Everything in the basement is not shared with the host. Pets allowed with $75/trip fee, no fee for service dogs (Note: emotional support animals are pets) 0.5 mile from I-95, 20 minutes from BWI airport.

Private and remodeled one-bedroom apartment.

Your family will be close to everything when you stay at this centrally-located place. This location is 8mins from BWI Airport and Arundel Mills Mall. 5mins to Live Casino 10mins to Fort Meade for Military folks. (Hooah!) 10mins to top Restaurants 20mins to Baltimore Downtown/Inner Harbor 30mins to Annapolis 35mins to Washington DC And a lot of great places for your immediate needs and grocery shopping like Walmart, Costco, Safeway, Aldi etc.. are within walking distance. Enjoy!!!!

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.

Spacious Upscale Townhome Near Hanover and BWI

Spacious property 5 minutes from Arundel Mills Mall and Fort Meade, 20 minutes from Merriweather Post Pavilion and 25 minutes from Baltimore — the ideal base for group and family travel. Full kitchen, community pool and amenities, in-unit washer/dryer, and room for up to 8 across 3 levels. Self-contained studio suite spanning first level included. Walkable to shops, grocery stores, and eateries. Also ideal for professionals on extended assignment near Fort Meade (9 min) and BWI (12 min)

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!

Tranquil Comfort Near Everything

Family-Friendly Lennar Townhome Near BWI, Fort Meade & Arundel Mills Enjoy comfort and convenience in this Lennar townhome in the Groves at Shannon. The home features 3 spacious bedrooms, an open-concept kitchen and living area, a private balcony, and two-car garage parking. A playground is just steps away. Perfect for families or professionals seeking a mid-term stay with quick access to Fort Meade, Baltimore/Washington International Thurgood Marshall Airport, and Arundel Mills.

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.

Cozy Private Apartment in Columbia | King Bed

Relax in this cozy, private apartment in the heart of Columbia, Maryland! Enjoy a spacious king bedroom, private entrance, free parking, a fully equipped kitchen, washer/dryer, and a private patio with a fire pit. Perfect for couples, business travelers, travel nurses, or small families, with space for up to 3 guests. Conveniently located near Merriweather Post Pavilion, The Mall in Columbia, Maryland Live! Casino, BWI Airport, Baltimore, Washington, DC, and I-95.

Weems Creek Cottage, Annapolis Waterfront

(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early. The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch. We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.

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.