Jessup Holidays

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Top hotels in Jessup

Holiday Inn Columbia East-Jessup by IHG

Holiday Inn Columbia East-Jessup by IHG

3 out of 5
7900 Washington Blvd Jessup MD
Fully refundable
The price is S$128 per night from 2 Aug to 3 Aug
S$128
2 Aug - 3 Aug
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"When I checked in, they didn’t clean the room at all. Desk table all dirty and bacteria, fridge is messed with old food . I have to call Front desk to remove the food:"

Reviewed on 13 Jul, 2026

Holiday Inn Columbia East-Jessup by IHG
Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
20 W Baltimore St Baltimore MD
Fully refundableReserve now, pay when you stay
The price is S$147 per night from 16 Jul to 17 Jul
S$147
16 Jul - 17 Jul
includes taxes & fees
8.4/10 Very good! (2,969 reviews)
"The staff was helpful & kind but the property itself was dirty & outdated."

Reviewed on 14 Jul, 2026

Lord Baltimore Hotel
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is S$185 per night from 2 Aug to 3 Aug
S$185
2 Aug - 3 Aug
includes taxes & fees
9/10 Wonderful! (1,910 reviews)
"I enjoyed my beautiful, functional, appropriately sized (i.e., small) room in the stately Maryland House. Though the street outside was bustling, the interior was quiet and peaceful. The staffers I met were lovely and helpful, and everything was tasteful. (Except the lobby coffee. That was ..."

Reviewed on 15 Jul, 2026

Historic Inns of Annapolis
See all 3,956 properties in Jessup
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Jessup attractions

Historic Savage Mill

7.6/10 (43 reviews)
This 19th-century cotton mill now houses artisan boutiques, galleries, and dining in its historic architecture. Explore the unique shops or follow nearby trails for a perfect blend of history and contemporary creativity.
See properties

What to do in Jessup

Two Flight Indoor Skydiving Experience

Two Flight Indoor Skydiving Experience

S$131
per traveller
94% of travellers recommend
Two Flight Indoor Skydiving Experience
Baltimore Orioles Baseball Game at Oriole Park

Baltimore Orioles Baseball Game at Oriole Park

S$26
per adult
Baltimore Orioles Baseball Game at Oriole Park
Downtown Baltimore History and Culture Self-Guided Audio Tour

Downtown Baltimore History and Culture Self-Guided Audio Tour

S$13
per traveller
Downtown Baltimore History and Culture Self-Guided Audio Tour
See all activities in Jessup

Frequently asked questions

How much does a Jessup holiday package cost?
You'll find cheap prices on Expedia for your Jessup escape. However, factors like the hotel choice, length of stay and season will determine how much your holiday to Jessup costs.
What are the cheapest months to go to Jessup?
January, February and March are great times to look for cheap Jessup holiday packages. Opting to travel in quieter periods means you can usually find lower prices on flights and hotels.
How many days is enough for Jessup?
The ideal duration of your Jessup holiday depends on what you'd like to see. Usually, a few days to a week will give you plenty of time to go to all the leading sights and discover some hidden treasures along the way.
Is it worth booking a holiday package to Jessup?
Jessup is a good holiday destination with attractions like Historic Savage Mill among the many things to keep you entertained. Whether you're travelling with the family or getting away with friends, a Jessup holiday promises fun for everyone.
How to find the best Jessup package deals?
Use Expedia's handy filters to find some terrific Jessup package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Jessup package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your holiday package well in advance.
Is it cheaper to book a Jessup holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging flights and hotels separately. Better still, you can personalise your Jessup getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a holiday package to Jessup?
If you have your Jessup holiday dates locked in, book early to snap up some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Jessup?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Jessup.
  2. Plan your budget wisely: On top of the cost of your stay, you should consider other expenses too. These include food, transportation and flights. Also, put aside a little extra for unexpected expenses that could arise during your trip to Jessup.
  3. Decide how long to go away for: Now that you know more about Jessup, you can figure out the perfect length of your break. Put together a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customised Jessup holiday package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.