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.

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Home in Laurel
5 out of 5 average rating, 4 reviews

Natural light filled, Beautiful Townhouse

Welcome to this beautiful 3 bedroom; 2.5 Bathroom Townhouse nested in the Quiet, Safe and family friend Russet Community. With lots of walking trails. You will love this well kept place. This house is a walking distance from Walmart super center, Target and a lot of restaurants. Located in a central location. 15minutes from BWI airport. 25 minutes from Washington DC. 25 minutes from Baltimore. About a mile off I - 295. 1 parking space in the driveway and plenty of free street parking.

Guest favourite
Townhouse in Severn
5 out of 5 average rating, 10 reviews

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.

Guest favourite
The bedroom features a spacious bed adorned with a light blanket and decorative pillows. Framed artwork hangs on the walls, complementing the neutral color scheme. Natural light filters through the window, which is covered with horizontal blinds.
Guest suite in Hanover
4.96 out of 5 average rating, 50 reviews

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!

Guest favourite
The bedroom features a spacious bed adorned with a patterned blanket and decorative pillows. A circular area rug adds warmth to the space. Surrounding wall art complements the vintage aesthetic, while table lamps provide soft lighting. A rocking chair and another seating option are positioned nearby.
Guest house in Ellicott City
4.88 out of 5 average rating, 69 reviews

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 in the back from the parking area to enter. Due to this our home may not be ideal for everyone.

Guest favourite
A spacious living area is equipped with comfortable seating options, including a gray sofa, an orange armchair, and a patterned accent chair. A wooden coffee table is centered in the room, and a wall-mounted TV is visible, enhancing the entertainment aspect. Fitness equipment is present in the background.
Flat in Severn
4.92 out of 5 average rating, 36 reviews

Private 1BD Basement Apartment w. Gym

Discover comfort and convenience in this modern Severn, MD basement apartment. With a private bedroom, bathroom, and kitchen (no oven), it’s perfect for up to 4 guests. Stay connected with Wi-Fi, unwind with the smart TV, and stay active in the private gym. Located near Arundel Mills Mall, unique restaurants, and BWI Airport, this cozy retreat offers a quiet neighborhood vibe and easy access to Amtrak. Ideal for travelers seeking a peaceful, functional space to relax or recharge

Superhost
A cozy bedroom area is highlighted by a queen-sized bed with light blue linens and a decorative wall art piece. A small dining table is set for two, featuring plates and cups. A desk with a lamp and a television are also present in the room.
Guest suite in Millersville
4.83 out of 5 average rating, 176 reviews

The Lower Level Loft near BWI

Unwind in this tranquil, stylish in-law suite just minutes from BWI. Located on the lower level of a modern townhouse, it features a private entrance, inviting dining area, spacious bathroom, and a cozy bedroom with a brand-new queen bed and HD TV. One well-lit parking spaces add convenience. The kitchenette includes a mini fridge, air fryer, microwave, coffee maker, and essentials for a relaxing, comfortable stay, with easy access to shops, dining, and major highways.

A modern kitchen showcases sleek cabinetry and stainless-steel appliances, with a large granite countertop island featuring seating for several. Soft lighting is provided by pendant fixtures above, and bright natural light enters through spacious windows, complemented by indoor plants adding a touch of greenery.
Home in Severn
4.68 out of 5 average rating, 19 reviews

Haven in Hanover- January Special

Spacious 3BR, 2.5BA home perfect for relaxing or gathering with loved ones. Enjoy hotel comfort with a cozy, lived-in feel. Approx 10 min from BWI airport and Just 5 min to Live! Casino, 3 min to groceries, and easy access to Baltimore’s great food scene or DC fun—about 45 mins to 1 hour depending on traffic. We’ve hosted many family and friend memories here—now it’s your turn. Unwind, explore, and make yourself at home in this peaceful retreat.

Top guest favourite
A well-lit living area features large windows draped in sheer curtains, allowing natural light to fill the space. Comfortable seating is provided by a gray sectional sofa and two light armchairs. A medium-sized coffee table rests on a patterned area rug, complementing the modern decor.
Home in Jessup
4.99 out of 5 average rating, 103 reviews

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!

Guest favourite
A cozy living area is furnished with a sectional couch adorned with yellow accent pillows. A wooden coffee table sits in front of it. Natural light enters through the window, complemented by a plant on the windowsill. An indoor palm adds greenery to the space.
Guest house in Savage
4.93 out of 5 average rating, 40 reviews

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)

Guest favourite
Tiny home in Elkridge
5 out of 5 average rating, 12 reviews

Tiny House Near BWI airport. (1 guest)

Welcome to this charming space that includes everything you need for a comfortable stay, with its private entrance, parking, bathroom, and kitchenette with essentials, fast Wi-Fi, Smart TV, a dining table, a dedicated workspace, and a split air conditioner for your comfort. Self check-in (5 PM) and check-out (1 PM). NO SMOKING – NO PETS – NO PARTIES.

Top guest favourite
A striking wall art piece features a vibrant red rose contrasted against a muted black-and-white background of a wooden surface. The artwork is displayed in a multi-panel arrangement, adding a modern touch to the décor.
Guest suite in Savage
4.94 out of 5 average rating, 85 reviews

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.

Superhost
Townhouse in Elkridge
5 out of 5 average rating, 4 reviews

Upscale, Central & Cozy TH+ Families & Pets> Parks

Spacious 4BR, 3.5BA home perfect for families or remote workers. Enjoy a full kitchen, cozy living room, high-speed WiFi, work desk, and kid-friendly layout. Unwind on the private patio or explore nearby parks. Easy access to BWI, Baltimore, DC, shopping, and dining makes this stylish Elkridge retreat ideal for both relaxation and productivity.

Popular amenities for Jessup holiday rentals

  1. Airbnb
  2. United States
  3. Maryland
  4. Anne Arundel County
  5. Jessup