Jessup Holiday Rentals

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Holiday Rentals in Jessup

Neptune by the Water

9.8 out of 10, Exceptional, (9)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
The price is AU$741
includes taxes & fees
13 July - 14 July
Neptune by the Water

Freshly renovated 3-story home 1 block from USNA!

9.8 out of 10, Exceptional, (34)
"It was a great place to stay- location, layout and everything else was perfect. Would stay again for sure! "
The price is AU$1,069
includes taxes & fees
21 July - 22 July
Freshly renovated 3-story home 1 block from USNA!

Fisher House: Steps From USNA + Covered Parking!

10.0 out of 10, Exceptional, (11)
"The location is perfect!"
The price is AU$953
includes taxes & fees
14 July - 15 July
Fisher House: Steps From USNA + Covered Parking!

★ Midcentury Modern Getaway ★ Prime Location ★

10.0 out of 10, Exceptional, (33)
"This is our second time staying in the property and it’s adorable and so convenient to everything. Ryan was very responsive and easy to work with. "
The price is AU$970
includes taxes & fees
13 July - 14 July
★ Midcentury Modern Getaway ★ Prime Location ★

Cozy 2br home w/ parking in downtown Annapolis

10.0 out of 10, Exceptional, (69)
"Comfortable, clean home. Convenient walking distance to historic downtown Annapolis. "
The price is AU$656
includes taxes & fees
29 July - 30 July
Cozy 2br home w/ parking in downtown Annapolis

Dean Street's Lower Deck House!

The price is AU$690
includes taxes & fees
3 Aug - 4 Aug
Dean Street's Lower Deck House!

Waterfront 1-bedroom in Law apartment first floor in Sparrows Point , 55TV, AC

The price is AU$406
includes taxes & fees
14 July - 15 July
Waterfront 1-bedroom in Law apartment first floor in Sparrows Point , 55TV, AC

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

10.0 out of 10, Exceptional, (17)
"Accommodating hosts, charming house and great location! "
The price is AU$950
includes taxes & fees
31 July - 1 Aug
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

Chesapeake Comfort, Annapolis.

10.0 out of 10, Exceptional, (15)
"Perfect weekend getaway with friends and our pups. Easy walk to downtown Annapolis. The host was very responsive. "
The price is AU$736
includes taxes & fees
22 July - 23 July
Chesapeake Comfort, Annapolis.

Mins to DTA - King Beds - Parking

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house & great location! We will definitely be returning! Thank you Jessica!"
The price is AU$844
includes taxes & fees
22 July - 23 July
Mins to DTA - King Beds - Parking

Large 2 bedroom house with private parking in a nice neighborhood

9.6 out of 10, Exceptional, (26)
"We stayed here for about a month while we found and bought a house. It was very comfortable, near shopping, near a dog park, and a great place to relax after work as well as make our meals and do laundry. Owners were quick to respond to questions or issues, friendly and easy to get along with."
The price is AU$570
includes taxes & fees
22 July - 23 July
Large 2 bedroom house with private parking in a nice neighborhood

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

10.0 out of 10, Exceptional, (6)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
The price is AU$888
includes taxes & fees
14 July - 15 July
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Cozy Home in Beautiful Annapolis

10.0 out of 10, Exceptional, (13)
"Great property and very clean!"
The price is AU$436
includes taxes & fees
13 July - 14 July
Cozy Home in Beautiful Annapolis

Lux New Construction:Steps to the Beach - Sleeps 7

10.0 out of 10, Exceptional, (1)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
The price is AU$1,001
includes taxes & fees
13 July - 14 July
Lux New Construction:Steps to the Beach - Sleeps 7

Londontowne Hideaway

The price is AU$743
includes taxes & fees
14 July - 15 July
Londontowne Hideaway

The Hideaway Spot- Waterfront w/ Dock on Long Cove

9.4 out of 10, Exceptional, (6)
"The property is lovely and the home is truly beautiful and comfortable. I highly recommend staying here; beautiful, peaceful--perfect."
The price is AU$755
includes taxes & fees
15 July - 16 July
The Hideaway Spot- Waterfront w/ Dock on Long Cove

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

9.6 out of 10, Exceptional, (4)
"Nice house in a quiet, safe, residential neighborhood. Clean and comfortable. Easy access to all the attractions in Baltimore. "
The price is AU$768
includes taxes & fees
13 July - 14 July
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

The price is AU$175
includes taxes & fees
14 July - 15 July
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Modern New Suite Close to US Capital and BWI Airport

10.0 out of 10, Exceptional, (1)
"Check in was super easy and he was very nice and accommodating. Location was easy enough to find and his instructions were very clear. Thank you! "
The price is AU$497
includes taxes & fees
13 July - 14 July
Modern New Suite Close to US Capital and BWI Airport

Secluded Tiny Pool House -Private Pool -Self Check in

9.6 out of 10, Exceptional, (7)
"Nice stay at the cozy guest house. Easy access to all that Baltimore has to offer. Host was good and easy to communicate."
The price is AU$327
includes taxes & fees
14 July - 15 July
Secluded Tiny Pool House -Private Pool -Self Check in
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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Frequently asked questions

Are there holiday rentals in Jessup?

Yes, there are holiday rentals in Jessup close to TagParty RECON, 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?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This holiday home rental outside of Jessup is located in the city centre, and has a fireplace, a patio 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Jessup?

With 12 Expedia holiday rentals, you're guaranteed to find just the right place for your Jessup stay.

What can I see and do in Jessup?

Explore the area and family-friendly sights such as TagParty RECON, or get out into nature at a spot like Patuxent River. While in the area, you can also visit popular places such as Arundel Mills Mall 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.