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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A modern living space is presented, featuring a neutral color palette and sleek design. A comfortable sectional sofa is positioned beside a coffee table, with a television mounted on the wall. The kitchenette, equipped with essential appliances, is visible in the background.
Flat in Hanover
4.92 out of 5 average rating, 12 reviews

Farmhouse 1BD 1BA, Central Loc!

Enjoy a stylish experience at this centrally-located place. 1BD 1BA APT is attached to the main home. Totally separate unit including its own entrance, living space, full bathroom, kitchenette, laundry, and private deck. Home is situated in a very quiet neighborhood street and is very close to all major highways like 295, 95, 29, and 100. Arundel Mills Mall, Live Casino, and Fort Meade Military Base are all within a couple miles. The apartment is located between Baltimore and Washington DC.

Guest favourite
Townhouse in Severn
5 out of 5 average rating, 8 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.

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
4.74 out of 5 average rating, 109 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
A spacious living area features comfortable seating arrangements, including a sofa and armchairs. A coffee table made of natural wood adds warmth, while a large mirror reflects light. The open layout leads to a well-equipped kitchen, visible in the background, with ample natural light from large windows.
Townhouse in Hanover
5 out of 5 average rating, 28 reviews

Cozy Hanover/BWI 3-Level Corporate + Group Stay

Modern suburban 4BR townhome near BWI (12 min) and Maryland’s largest mall & MD Live Casino (5 min). Conveniently walk to a grocery store, shops, restaurants. Perfect for multigenerational families, groups, or business travel with multiple workspaces and private areas to gather and relax. Equipped kitchen for cooking and entertaining. Guests enjoy access to a community center with a gym, lounges, pool table, outdoor grill, and seasonal pool. Close to Baltimore, DC, Annapolis, and Columbia.

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
Home in Severn
5 out of 5 average rating, 6 reviews

Elegant 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.

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
4.72 out of 5 average rating, 18 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, 102 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
An outdoor seating area features two vibrant red chairs placed on a mulch bed. A small table stands between the chairs, surrounded by greenery and decorative plants. A bright red door provides an inviting entrance, while a vintage wrought iron fence encloses the area for privacy.
Guest house in Catonsville
4.96 out of 5 average rating, 300 reviews

Fox Cottage *Pet Friendly*

Fox Cottage is a modern addition to our 115 year old Victorian home. It’s a One Bedroom Queen size mattress & memory foam topper. There’s a Loft with a Full Size Memory Foam Mattress. The loft is a cozy space accessible by a vintage wooden ladder. It is not appropriate for people who cannot climb a ladder. There’s an outdoor seating area with a Chiminea to light a fire, enjoy a cup of coffee or wine, work or just listen to the birds.

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.

Popular amenities for Jessup holiday rentals

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