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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Top guest favourite
The historic building features a distinctive red brick façade, complemented by large windows and decorative trim. Lush green trees provide shade in front, while parked vehicles line the street, enhancing the inviting urban atmosphere.
Flat in Butchers Hill
4.98 out of 5 average rating, 479 reviews

Butchershill- Clean, Fireplace, King Bed, Parking!

My name is John S Marsiglia. Always clean, very comfortable new King Mattress, Warm & Cozy Fireplace, Self checkin , Historic 2207 E Baltimore St. Search online. 900 Sq Ft. 12 ft ceilings,Fully equipped kitchen/kitchenette,Coffee,Tea,Cream,Brita filtered water pitcher,50" 4K smart TV, streaming only, Free Netflix, Prime,top speed WiFi, surround sound, comfortable clean furniture, antiques, oriental rugs, workspace w/desk, modern beautiful bathroom, dual shower heads&seats, private full size W&D

Guest favourite
Townhouse in Severn
5 out of 5 average rating, 17 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.

Superhost
A comfortable living area is presented with a pair of neutral sofas facing each other, accented by decorative pillows. A glass coffee table sits centrally, complemented by small side tables. Soft carpet covers the floor, and warm lighting is provided by a nearby floor lamp.
Flat in Hanover
4.75 out of 5 average rating, 113 reviews

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!!!!

Guest favourite
The living and dining area features a white sofa facing a mounted television. Two round chairs and a circular table with teal chairs create a dining space. Light-colored tiles extend across the floor, complemented by a decorative area rug. Three images of tranquil waters are hung on the wall.
Guest suite in Bloomingdale
4.86 out of 5 average rating, 156 reviews

Convenient, private basement apt near downtown DC

Keep it simple at this private English basement apartment. In-unit washer/dryer, full kitchen, spacious living/dining area. Walking distance to Medstar, Children's National, & VA Hospitals; Catholic, Howard & Trinity Universities. city bus stop 1 block away; metro train (red & green lines) 1 mile away. Less than 5 miles to Union Station, Capitol, White House, & National Mall. We live upstairs with an excitable dog & active toddler. Please book expecting modest city & neighbor noise =)

Guest favourite
The entrance features double glass doors framed by a wooden deck. Seasonal potted plants, including vibrant flowers and greenery, are arranged on either side, while a small pumpkin adds a festive touch. A decorative light fixture hangs nearby, enhancing the welcoming appearance.
Cottage in Glen Burnie
4.91 out of 5 average rating, 219 reviews

Home away from home

This is a small house with private parking close to Baltimore and Annapolis. I have one queen size Murphy bed, one single pull out couch. It has an updated kitchen, updated bathroom, walk-in closet, Internet and heating and cooling. I also have a pellet stove. my kitchen is fully stocked with dishes, knives, forks, pots and pans. The bathroom has towels and rugs. I tried to add all the amenities to make it as comfortable as home. Look at pet rules under the other things to note section.

Top guest favourite
A wooden table is set with a bottle of Walnut Crest Cabernet Sauvignon and two etched wine glasses. A red apple rests in a dark, leather-like bowl, with a serene backdrop of green foliage visible through a screened window.
Guest house in Highland
4.98 out of 5 average rating, 302 reviews

Woodland Retreat

Welcome to our private woodland retreat! This stylish and secluded mid-century modern guesthouse is nestled on five acres in horse country in Highland, Maryland. Totally separate from our owners home, our guesthouse combines the serenity, privacy, and safety you crave with all the conveniences of modern life including: a full bath; kitchenette; internet; and a screened porch with access to our beautiful lighted and heated swimming pool (weather permitting) and adjacent walking trails.

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, 178 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.

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, 106 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
Guest suite in Laurel
4.95 out of 5 average rating, 207 reviews

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!

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
4.9 out of 5 average rating, 41 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
A modern kitchen and dining area features sleek cabinetry and stainless steel appliances. A large table with white chairs occupies the central space, illuminated by soft lighting. A unique pendant light hangs from the ceiling, adding a design element to the contemporary environment.
Flat in Glenmont
4.8 out of 5 average rating, 112 reviews

Luxury 1 BR + Den Apartment (lower level)

Just 35 minutes from the White House and 3 minutes from the Metro, this smart micro-luxury apartment offers private parking, a sunny deck, and a peaceful backyard and a bathroom to die for. Walk to Glenmont Station and hop on the Red Line for direct access to D.C.’s iconic landmarks and museums. Luxury, convenience and comfort in one stylish stay.

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.

Popular amenities for Jessup holiday rentals

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  2. United States
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  4. Anne Arundel County
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