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

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Jessup cottages

House (3 Bedrooms) | Interior

1. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
$270 nightly
The price is $308
Sep 24 - Sep 25
Total with taxes and fees
Lakefront Home Firepit BWI Marleycreek River
Exterior

2. 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, (93 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
$279 nightly
The price is $311
Oct 5 - Oct 6
Total with taxes and fees
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
Outdoor dining

3. 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.
$579 nightly
The price is $660
Sep 23 - Sep 24
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Marina

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.
$720 nightly
The price is $821
Sep 23 - Sep 24
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown
House (3 Bedrooms) | Interior

5. 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)
$377 nightly
The price is $443
Sep 27 - Sep 28
Total with taxes and fees
6 Mi to Inner Harbor - Family Home w/ Fenced Yard!
House (3 Bedrooms) | Interior

6. Pets Welcome: Quiet Silver Spring Retreat!

Pets Welcome: Quiet Silver Spring Retreat!
3.0 star property
Silver Spring
$407 nightly
The price is $460
Oct 5 - Oct 6
Total with taxes and fees
Pets Welcome: Quiet Silver Spring Retreat!
House (3 Bedrooms) | Interior

7. 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 8 - Oct 9
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Bed was SO comfortable and the pillows were wonderful. I had stayed the previous two nights in a Best Western and the pillows are limp and lumpy (need replacing), so to come to the DoubleTree, it was pure luxury."
Leslie 1-night trip
Posted less than an hour ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Jessup

Jessup Cottages information

Number of reviews
Accommodation
84 Cottages
Lowest Price
$308
Highest Price
$485

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?
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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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