
Holiday rentals in Jessup
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Top-rated holiday rentals in Jessup
Guests agree: these stays are highly rated for location, cleanliness and more.

Large Home w/ Private Pool, Gym, Sauna, 7 Bedrooms
Relax at this spacious 4,125 sqft, top-quality home on 1 acre. This 7-bedroom, 2.5 bathroom home features a private pool, gym, sauna, and a massive family room with 10 ft ceilings, and a 67 " Smart TV. Enjoy the large 1st class chef's kitchen with all the cooking & serving supplies you will ever need. Enjoy the modern amenities, multiple workspaces, a wrap-around porch, a fire pit, & a grill. Ideal for family events, quiet getaways, sports teams, & business meetings. You are able to have your l

Green House in Savage, MD
Relax with your family and friends in a peaceful, comfortable, and clean home featuring 5 bedrooms and 3 full bathrooms. Conveniently located just 30 minutes from Washington, DC, and only 15 minutes from Baltimore and BWI Airport. Perfect for families, business travelers, and small groups looking for a quiet and relaxing stay Please note: No parties, events, or gatherings are allowed at the property. We kindly ask all guests to respect the home, neighbors, and quiet atmosphere during their stay.

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

Remedy Cottage
Welcome to Remedy Cottage, a place that holds deep sentimental significance for our family. It is a split foyer, two levels with steps leading in each direction from the foyer. It was built in 1978, every inch was renovated in 2022, featuring a brand new kitchen appliances. The interior boasts a modern farmhouse and minimalist design. This location is ideal for visitors to the nation's capital, the NSA, Andrews Air Force Base, and a short driving distance to three major airports in the area.

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.

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.

Elegant & Cozy Home Nestled in Maryland
Relax in this spacious, single-level 4BR, 3BA home in Severn, MD—just minutes from Fort Meade, BWI, Arundel Mills & DC. Recently renovated, this modern retreat features 2 primary suites, a fully stocked kitchen, foosball, pool/ping-pong table, fenced backyard, and more! Ideal for families, professionals, or group getaways. No stairs—perfect for seniors. Fast Wi-Fi, smart TVs, washer/dryer, pet-friendly. Quiet, safe neighborhood with easy access to 495, US-50, and train stations.

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.

The GreenHaus Oasis near Baltimore/DC/Annapolis
Our cozy 1 bedroom 1 bath guesthouse is a great base to explore three great cities: DC (30 min), Baltimore (20 min), and Annapolis (25 min). It is located in a residential neighborhood and is steps away from historic Savage Mill. It is home to several cute antique shops, restaurants, and running trails to explore. Laurel Race track (5 min) Ft. Meade (10 min) UMBC ( 15 min) BWI Airport (20 min)

Spacious Upscale Townhome Near Hanover and BWI
Spacious townhome 5 minutes from Arundel Mills, 9 from Fort Meade, 12 from BWI, 20 from Columbia, 25 from Baltimore — the ideal base for extended work, group, and family travel. Full kitchen, in-unit washer/dryer, dedicated office, and room for 8 across 3 levels, including a first-floor guest suite with its own bath and kitchenette. Gym access. Walkable to shops, grocery stores, and eateries.
Popular amenities for Jessup holiday rentals
Other great holiday rentals in Jessup

Country cabin in Ellicott City

Modern 4BR |10 min to BWI & Fort Meade | Sleeps 8

Chic Columbia Retreat | Theater Room, Deck & Grill

Walk to Stadiums | 2 Rooftop Decks | Parking

Private Guest Suite in Columbia

Quaint & Cozy Hideaway

Glen Burnie Hideaway

Charming Sup. Clean 2 Levels Townhouse, up graded!
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- M&T Bank Stadium
- National Mall
- The White House
- Walter E Washington Convention Center
- Nationals Park
- FedExField
- Johns Hopkins University
- Oriole Park at Camden Yards
- Federal Hill Park
- Arlington National Cemetery
- Capital One Arena
- Georgetown Waterfront Park
- Washington Monument
- National Museum of African American History and Culture
- Betterton Beach
- CFG Bank Arena
- National Harbor
- Howard University
- Smithsonian National Zoological Park
- Baltimore Convention Center
- Museum of the Bible
- Smithsonian National Air and Space Museum
- Patterson Park
- Smithsonian American Art Museum





