A sunset over a city with a river, surrounded by greenery and buildings.

Jessup Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Jessup holiday rentals

1. Cozy Basement Apartment in Columbia

Cozy Basement Apartment in Columbia
Oakland Mills
9.0 out of 10, 14, (14 reviews)
"Clean space, nice area, relatively close to shops and businesses "
United States
Susie A.
The price is AU$179
includes taxes & fees
19 Sept - 20 Sept
Cozy Basement Apartment in Columbia

2. Lower Level Loft - Adorable Studio Apt. Near BWI

Lower Level Loft - Adorable Studio Apt. Near BWI
South Gate
9.0 out of 10, 20, (20 reviews)
"That place is incredible—very cozy and clean."
United States
Nataly
The price is AU$157
includes taxes & fees
16 Sept - 17 Sept
Lower Level Loft - Adorable Studio Apt. Near BWI

3. Centrally Located Rancher w/ Parking, Near BWI &

Centrally Located Rancher w/ Parking, Near BWI &
Severn
9.0 out of 10, 14, (14 reviews)
"Had a good stay"
United States
Katie L.
Centrally Located Rancher w/ Parking, Near BWI &

4. Private Guest Suite in Columbia • King Bed • Free Parking

Private Guest Suite in Columbia • King Bed • Free Parking
Columbia
10.0 out of 10, 6, (6 reviews)
"The suite was very clean and quiet. We had everything we needed to enjoy our week long stay. The convenience to shopping was also a plus. This is the second time we have stayed at the Suite in Columbia and look forward to a return stay in the future."
United States
Ed F.
The price is AU$422
includes taxes & fees
4 Oct - 5 Oct
Private Guest Suite in Columbia • King Bed • Free Parking

5. Modern Luxury Townhome - 2BR/2BA Near Fort Meade & BWI - Private Driveway

Modern Luxury Townhome - 2BR/2BA Near Fort Meade & BWI - Private Driveway
Severn
The price is AU$376
includes taxes & fees
18 Sept - 19 Sept
Modern Luxury Townhome - 2BR/2BA Near Fort Meade & BWI - Private Driveway

6. Large Home w/ Pool, Gym, 7 Bedrooms, Sleeps 21

Large Home w/ Pool, Gym, 7 Bedrooms, Sleeps 21
Severn
9.6 out of 10, 37, (37 reviews)
"This was a weekend celebrating our son's retirement from the Navy. The weather and accommodations were great. The family loved the big yard, front and back, and the pool. We would gladly rent it again if we could get our whole family together."
United States
Perry S.
The price is AU$1,274
includes taxes & fees
22 Sept - 23 Sept
Large Home w/ Pool, Gym, 7 Bedrooms, Sleeps 21

7. Rollingside Guest Suite

Rollingside Guest Suite
Catonsville
10.0 out of 10, 78, (78 reviews)
"Easy and very nice place and neighborhood. Short stay for business trip but would do certainly do again."
United States
Jack B.
The price is AU$259
includes taxes & fees
16 Sept - 17 Sept
Rollingside Guest Suite

8. Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.8 out of 10, 100, (100 reviews)
"Awesome place, great location"
United States
Mark M.
The price is AU$308
includes taxes & fees
16 Sept - 17 Sept
Hidden Fells Point Gem / Private Courtyard Patio

9. Cozy Fells Point Gem / In The Heart of Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
Fells Point
9.8 out of 10, 213, (213 reviews)
"We enjoyed our stay. It was a cute little place and perfect for 3 of us. The area is pretty quiet for the most part. We would definitely stay here again."
United States
Tammy
The price is AU$311
includes taxes & fees
21 Sept - 22 Sept
Cozy Fells Point Gem / In The Heart of Fells Point

10. Fox Cottage *Pet Friendly*

Fox Cottage *Pet Friendly*
Catonsville
10.0 out of 10, 58, (58 reviews)
"Great place to stay. "
United States
Kim P.
The price is AU$416
includes taxes & fees
12 Oct - 13 Oct
Fox Cottage *Pet Friendly*

11. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, 22, (22 reviews)
"Great stay! Very clean home in a quiet neighborhood. Easy drive to downtown, and there’s a local restaurant right down the street. We really enjoyed our stay!"
United States
Taylor C.
The price is AU$320
includes taxes & fees
20 Sept - 21 Sept
Cute, Cozy 2-bedroom house near Annapolis with water access

12. WHOLE SUITE 77 - DE LUXE KING BED in Master Bedroom + LR with 2 SLEEPING SOFAS

WHOLE SUITE 77 - DE LUXE KING BED in Master Bedroom + LR with 2 SLEEPING SOFAS
Silver Spring
9.0 out of 10, 21, (21 reviews)
"Very convenient and very cozy space highly recommend"
United States
Melisa D.
The price is AU$313
includes taxes & fees
16 Sept - 17 Sept
WHOLE SUITE 77 - DE LUXE KING BED in Master Bedroom + LR with 2 SLEEPING SOFAS

13. Sleek and Cozy Micro Fells Point Residence!

Sleek and Cozy Micro Fells Point Residence!
Fells Point
8.8 out of 10, 47, (47 reviews)
"Good location, clean and quick response from owner."
United States
Michael O.
The price is AU$347
includes taxes & fees
16 Sept - 17 Sept
Sleek and Cozy Micro Fells Point Residence!

14. Cozy Modern Micro Apt in the Heart of Fells Point!

Cozy Modern Micro Apt in the Heart of Fells Point!
Fells Point
9.2 out of 10, 41, (41 reviews)
"We had such a great trip! The place was perfect and exactly how pictured! "
United States
Reagan C.
The price is AU$344
includes taxes & fees
27 Sept - 28 Sept
Cozy Modern Micro Apt in the Heart of Fells Point!

15. Charming Federal Hill! One Bedroom With Vibes

Charming Federal Hill! One Bedroom With Vibes
Sharp Leadenhall
9.8 out of 10, 51, (51 reviews)
"I stay here when I'm in town for business and it is so much better than a hotel room! Everything you need and more! Comfortable bed, walkable and host is great!"
United States
Emily W.
The price is AU$302
includes taxes & fees
16 Sept - 17 Sept
Charming Federal Hill! One Bedroom With Vibes

16. Entire House 1BD King Bed near Downtown

Entire House 1BD King Bed near Downtown
3.0 star property
Hollins Market
7.4 out of 10, 17, (17 reviews)
"Great space for the price. Walking distance to the stadium and the ball park. Quiet neighborhood with friendly occupants. Would’ve given 5 stars if the unit was clean but it was not, the table and floors were sticky, window sill was covered with dead fruit flies, and I even had a fly glue strip get stuck to my hand when I tried to look through the blinds…😩The bathtub also needs replacing."
United States
Denise
The price is AU$167
includes taxes & fees
16 Sept - 17 Sept
Entire House 1BD King Bed near Downtown

17. Rooftop Deck Escape! Free Parking!

Rooftop Deck Escape! Free Parking!
South Baltimore
8.6 out of 10, 69, (69 reviews)
"Great location loved the rooftop deck and had fun playing the shuffle board table."
United States
Heather M.
The price is AU$382
includes taxes & fees
21 Sept - 22 Sept
Rooftop Deck Escape! Free Parking!

18. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
The price is AU$430
includes taxes & fees
16 Sept - 17 Sept
Lakefront Home Firepit BWI Marleycreek River

19. Lavish Luxe 2BD/1BA apartment in Federal Hill

Lavish Luxe 2BD/1BA apartment in Federal Hill
South Baltimore
10.0 out of 10, 5, (5 reviews)
The price is AU$532
includes taxes & fees
17 Sept - 18 Sept
Lavish Luxe 2BD/1BA apartment in Federal Hill

20. Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions.

Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions.
Glen Burnie
10.0 out of 10, 14, (14 reviews)
"Perfect for the overnight stay. "
United States
Nathan D.
The price is AU$449
includes taxes & fees
16 Sept - 17 Sept
Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Jessup Hotel Reviews

Find out more about Jessup

Everything you need to know about Jessup holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Jessup holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Jessup holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Jessup holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jessup. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jessup holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jessup holiday rentals we have selected for you start as low as AU$250 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Jessup rentals

At Expedia, we put the best Jessup holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Jessup rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Jessup holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Jessup. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Jessup?

Yes, there are holiday rentals close to the most popular sights in Jessup, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Jessup. Make sure you have time to check out the sporting events and casinos during your trip.

What are some of the best holiday rentals that Jessup has to offer?

Rooftop Deck Escape! Free Parking!: This holiday home rental outside of Jessup is located in the city centre, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Jessup?

Explore the area and family-friendly sights such as Gardens Ice House, or get out into nature at a spot like Patuxent River. While in the area, you can also visit popular places such as M&T Bank Stadium and Oriole Park at Camden Yards.

What are holiday rentals like in Jessup?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Jessup. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for families.