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

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  • Upfront pricing

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Jessup cottages

A two-story house with a front porch, a satellite dish, and a mailbox.

1. 6 Mi to Inner Harbor - Family Home w/ Fenced Yard!

6 Mi to Inner Harbor - Family Home w/ Fenced Yard!
3.0 star property
Westfield
10.0 out of 10, Exceptional, (1 review)
$340 nightly
The price is $399
Oct 18 - Oct 19
Total with taxes and fees
6 Mi to Inner Harbor - Family Home w/ Fenced Yard!
A wooden deck with wicker furniture, a round table, and a fire pit.

2. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (24 reviews)
"Excellent Property"
United States
Buu T.
$583 nightly
The price is $665
Oct 19 - Oct 20
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A two-story building with a covered outdoor area, a staircase, and trees with autumn leaves.

3. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
$400 nightly
The price is $449
Nov 5 - Nov 6
Total with taxes and fees
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A marina with multiple boats docked, a building with a distinctive yellow roof, and a clear sky.

4. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (22 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
$714 nightly
The price is $814
Nov 8 - Nov 9
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown
A two-story house with a wooden deck, a garage, and a shed in the backyard.

5. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
$270 nightly
The price is $308
Oct 20 - Oct 21
Total with taxes and fees
Lakefront Home Firepit BWI Marleycreek River
A covered patio with a wicker sofa, a glass coffee table, a wooden table, and a bench.

6. Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
$426 nightly
The price is $485
Oct 19 - Oct 20
Total with taxes and fees
Idyllic Pasadena Retreat With Garden + Hot Tub!
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

Renaissance Baltimore Harborplace Hotel

Renaissance Baltimore Harborplace Hotel

10/10 Excellent
"Great stay"
Celeste 1-night trip
Posted 2 hours ago
Renaissance Baltimore Harborplace Hotel

Find out more about Jessup

Jessup Cottages information

Number of reviews
116
Accommodation
83 Cottages
Lowest Price
$308
Highest Price
$814

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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