Jessup Vacation Packages

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Your Jessup Vacation

Organizing your next epic escape is a walk in the park with a Jessup vacation package. The neighborhood of Harpers Choice, which is good for golfing, makes a superb base to uncover the treasures of this vibrant city. Make your trip to Jessup even more exciting by going sightseeing. Arundel Mills Mall, Maryland Live Casino and Laurel Park are some of the top attractions you'll want to explore. No matter your travel plans or the size of your budget, organizing a tailored Jessup vacation is a piece of cake with Expedia.

Top Jessup Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Columbia East-Jessup by IHG

Holiday Inn Columbia East-Jessup by IHG

3 out of 5
Price was CA $1,335, price is now CA $941 per person
CA $941
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.6/10 Excellent! (1,002 reviews)
This was the first holiday inn that did not have breakfast. The information said breakfast available. We all assumed that it was the usual breakfast found at most holiday inns. The room also had only superficial cleaning.

Reviewed on Jul 10, 2026

Element by Marriott Arundel Mills BWI Airport

Element by Marriott Arundel Mills BWI Airport

3 out of 5
Arundel Mills
Price was CA $1,511, price is now CA $992 per person
CA $992
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8/10 Very good! (1,003 reviews)
Amazing

Reviewed on Jul 13, 2026

Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Price was CA $1,754, price is now CA $1,187 per person
CA $1,187
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.4/10 Very good! (1,000 reviews)
remodeling going on, so the bar area was out of commission. convenient ent to shopping restaurants and a grocwry store

Reviewed on Jul 12, 2026

Convention Center PH Free indoor parking

Convention Center PH Free indoor parking

4 out of 5
Downtown Baltimore
Price was CA $1,564, price is now CA $1,091 per person
CA $1,091
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
6/10 (1 review)

Super 8 By Wyndham Baltimore Northwest

Super 8 By Wyndham Baltimore Northwest

2 out of 5
Woodlawn
Price was CA $1,381, price is now CA $983 per person
CA $983
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.2/10 Very good! (1,055 reviews)
The room was humid and the floors were wet. No coffee was available for breakfast. This location is very noisy.

Reviewed on Jul 12, 2026

Ready to book your vacation to Jessup?

 

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Jessup Hotel Deals

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 CA $135 per night from Jul 20 to Jul 21
CA $135
CA $152 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (1,018 reviews)
"This was the first holiday inn that did not have breakfast. The information said breakfast available. We all assumed that it was the usual breakfast found at most holiday inns. The room also had only superficial cleaning."

Reviewed on Jul 10, 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 CA $110 per night from Jul 15 to Jul 16
CA $110
CA $130 total
Jul 15 - Jul 16
includes taxes & fees
8.4/10 Very good! (2,966 reviews)
"Nice older style hotel. Rooms were basic but clean. Bar downstairs was nice and open late"

Reviewed on Jul 13, 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 CA $129 per night from Jul 19 to Jul 20
CA $129
CA $196 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (1,900 reviews)
"My hotel room had black wallpaper, and was very gloomy. It had two windows, but the courtyard outside had a roof, and very little light trickled in. The beds were comfortable, though. Valet parking was $47 a night, and there was a $30 resort fee per day. So a lot of hidden charges. I am not sur I ..."

Reviewed on Jul 12, 2026

Historic Inns of Annapolis
See all 3,951 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.
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Stay near popular Jessup attractions

Historic Savage Mill

7.6/10 (43 reviews)
During your visit to Jessup, you can browse for the perfect souvenirs at Historic Savage Mill. Experience the lively festivals or attend a sporting event in this family-friendly area.
See properties

What to do in Jessup

Two Flight Indoor Skydiving Experience

Two Flight Indoor Skydiving Experience

CA $143
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

CA $31
per adult
Baltimore Orioles Baseball Game at Oriole Park
Grand entrance to the Hard Rock Cafe in Baltimore

Dining at Hard Rock Cafe Baltimore

CA $57
per traveller
Dining at Hard Rock Cafe Baltimore
See all activities in Jessup

Frequently asked questions

How much does a Jessup vacation package cost?
Offering great value package deals from CA $941 on Expedia, you'll be surprised at how little a vacation to Jessup costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Jessup?
You can usually find lower rates and better availability in January, February and March. Explore our cheap Jessup vacation packages and you could land some excellent off-season deals.
How many days is enough for Jessup?
Dedicate around 2 days for your Jessup vacation to really immerse yourself in all that makes this place special. Stroll around key areas, including Savage-Guilford and Dorsey. Then tick off top sights such as Laurel Park and National Security Agency Headquarters. With a well-planned itinerary, you'll be kept busy with room for some downtime too. Want to go beyond Jessup? Consider fitting in an excursion or two.
Is it worth booking a vacation package to Jessup?
It's easy to see why a Jessup vacation is on the must-do list of many travellers. Well-known attractions like Historic Savage Mill are just the start of what you can explore here.
How to find the best Jessup package deals?
Start your search for a Jessup package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Jessup package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Jessup adventure underway.
Is it cheaper to book a Jessup vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking stays and flights separately. Better still, you can personalize your Jessup getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Jessup?
If you're planning a spur-of-the-moment Jessup trip, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Jessup?

  1. Pick your dates: What you want to do in Jessup and your preferred season can help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to cover everything from meals and transportation to activities and airfares. Your hotel will probably be the largest expense during your trip to Jessup.
  3. Decide your trip length: Think about how much time you want to spend exploring Jessup. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a tailored Jessup vacation 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.