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Our top choices for Jessup cottages

House (3 Bedrooms) | Interior
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Cottage in Rosedale

5 Mi to Downtown Baltimore: Quiet Home w/ Porch
3.0 star property
9.0 out of 10, Wonderful, (2)
"It took a whole day for the house to get warm.No utensils.And last but not least the heat was turned off in the middle of the night.Monday morning was very cold,that’s why we left at nine thirty. "
United States
Cathy
$431 nightly
The price is $498
Dec 24 - Dec 25
Total with taxes and fees
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Outdoor dining
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Cottage in Pasadena

Chesapeake Cottages- 2 Quaint Waterfront Retreats
9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
$579 nightly
The price is $660
Dec 24 - Dec 25
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Exterior detail
Secluded Cozy Cottage in Historic Downtown

Cottage in Historic District

Secluded Cozy Cottage in Historic Downtown
9.6 out of 10, Exceptional, (16)
"Lovely, secluded cottage close to downtown Annapolis. Host was very accommodating and communicated lots of great info. Looking forward to coming back when we can stay longer."
United States
Michael C.
$506 nightly
The price is $577
Jan 5 - Jan 6, 2026
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown
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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Top Jessup Hotel Reviews

Hilton Garden Inn Washington DC/U.S. Capitol

Hilton Garden Inn Washington DC/U.S. Capitol

10/10 Excellent
"Nice stay"
Zaylee 3-night trip
Posted 15 hours ago
Hilton Garden Inn Washington DC/U.S. Capitol

Find out more about Jessup

Jessup Cottages information

Number of reviews
18
Accommodation
73 Cottages
Lowest Price
$498
Highest Price
$660

Frequently asked questions

Why book your cottage in Jessup with Expedia?
Expedia has some terrific cottages in Jessup, so start packing for a memorable vacation on nature's doorstep. If you have a set budget, select how much you'd like to spend and the star rating of your property. Or, use our filters to search for cottages with a hot tub or a kitchen. We'll help you find the perfect digs whatever your bank balance or plans.
How can I find cheap cottages in Jessup?
Expedia can help you easily track down cheap cottages in Jessup. To lock in a fantastic stay in a matter of clicks, try out the filter tool to tailor your search results by budget, star rating and amenities.
What is there to do in Jessup near my cottage?
The most practical travel accessory is a well-thought-out travel plan. Historic Savage Mill is a good spot to kick-start your exploration of Jessup.

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