Vacation rentals in Jessup

Luxury 1BR/1BA Private Suite Close to DC!

Whether you’re looking for a place to stay a couple of days, weeks, or months, this luxurious basement apartment offers a spacious environment with the perfect touch of style, comfort, and sophistication. Enjoy the electric fireplace, office, reading nook, and your own private spa bathroom. This suite has a private entrance and is located in a very peaceful cul de sac with plenty of restaurants and shopping nearby. The home is located just 20 mins outside of DC. Not suitable for small children.

Cheerful & Spacious Shore Life Beauty!

Welcome to our charming yet peaceful abode & island oasis where sailing, marine life, & bay exploration exceed the standard! This exceptional home is conveniently located to a variety of high quality restaurants, parks, outdoor activities, spas, beaches, wedding venues, & other entertainment including live music, hunting, & antiquing while also being 20-minutes from Annapolis & 1-hour from Baltimore City & DC. Let this be your definitive choice for a magical destination you'll forever remember.

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.

Luna the Destination Camper

Just outside the buzz of D.C., Chesapeake Hideaway offers a peaceful, romantic retreat in the heart of Lanham. Surrounded by the natural beauty of Prince George’s County, this cozy RV features a queen+full bed, soft lighting, and panoramic windows for golden sunset views. Enjoy intimate meals in the charming kitchenette, then unwind on your private deck. Whether you're stargazing or exploring nearby Lake Artemisia and Greenbelt Park, this is the perfect spot to relax and make lasting memories.

Modern 3-Level Stay| Hot Tub | Game Room | Parking

Spacious 5BR home near D.C. with hot tub, fire pit, and game room—perfect for families or groups! Enjoy 3 levels of comfort, a full kitchen, fast Wi-Fi, smart TV, and self check-in. Relax in the private backyard, grill out, or unwind in the hot tub. Pet-friendly and sleeps 12 comfortably. Located in a quiet neighborhood just minutes from downtown Silver Spring and Washington, D.C. Free parking, kid-friendly, and ideal for work trips or weekend getaways. Book your stay today!

Sea Dreamer

Tranquil TIDAL, riverfront, split-level home. Rent the spacious lower level with 2 bedrooms, full custom kitchen, large living room (TVs, sleeper sofas, massage chair), dining/office space, and full bath with luxury shower. Includes soaps, towels, hairdryer. Kitchen equipped for cooking, includes full fridge. Patio with grill/fire-pit, lounging and kayaks. Convenient: 25 min to BWI, 45min to Annapolis, 60min to DC. Ideal for relaxing and exploring!

Family-Friendly, Arcade, Sleeps 8, Prime Location

Family-friendly fun meets unbeatable access! This spacious 3-bedroom Hanover retreat puts you 7 min to Ft. Meade, 10 min to BWI and within easy reach of Baltimore, Annapolis & DC. ✓ Private arcade room & board games for all ages ✓Fully equipped kitchen ✓ High-speed Wi-Fi & dedicated workspace. ✓ Kid gear: high-chair, pack-’n-plays & safety gates Whether work or play, our home is set for comfort—just pack your bags and book your stay today!

Park View near BWI, Light Rail and I97.

Beautiful all new, cozy 1950's home completely remodeled. All hardwood floors, new paint, new kitchen, bath, everything! Clean and quiet home/duplex with a front porch to enjoy morning tea/coffee or evening cocktails. Huge empty park across the street to keep things still. Very quiet neighbors. Owners are onsite and live in the back house for any issues or questions. PLEASE NOTE: We require a 2-night minimum stay on weekends.

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

Charming Saloon Stay near DC & Baltimore

Saddle up at the Charming Saloon, a rustic western-inspired retreat with modern comforts. Perfect for couples or solo travelers, with long-term stays welcome. Just 25 min from DC, 20 min from Baltimore, and 15 min from BWI Airport. Easy access to I-295/I-95, near Maryland LIVE! Casino, Horseshoe Casino, and Laurel Park Racetrack. Cozy, unique, and ideal for quick getaways or extended stays. Your western adventure awaits!

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

Private Duplex near I95, BWI, John Hopkins

Entire private duplex home near BWI airport and BWI business district. Big private driveway and street parking available. Fast wifi with space to work. Quick access to I-95, Maryland 295 and 100 One floor home. No steps! Pack & play with sheets and blankets, high chair and toys