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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Our top choices for Jessup cottages

The Heron's Nest at Atlantic Marina
Exterior

The Heron's Nest at Atlantic Marina

9.8 out of 10, Exceptional, (302)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Exterior

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

10.0 out of 10, Exceptional, (93)
"We stay at Firefly every time we go to visit our son and his family. It works perfectly for us…an oasis for us, and a fun place for the kids to visit, too. Pat and Ken have been the perfect hosts!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Secluded Cozy Cottage in Historic Downtown
Exterior detail

Secluded Cozy Cottage in Historic Downtown

9.4 out of 10, Exceptional, (13)
"We had a very lovely stay . This is an excellent location . "
The price is HK$3,516
HK$5,799 total
includes taxes & fees
24 Aug - 25 Aug
Secluded Cozy Cottage in Historic Downtown
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Property grounds

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
The price is HK$2,812
HK$5,192 total
includes taxes & fees
3 Sept - 4 Sept
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Rock Creek Cottage, Waterfront, Serene Views
Terrace/patio

Rock Creek Cottage, Waterfront, Serene Views

10.0 out of 10, Exceptional, (6)
"My husband and I enjoyed our stay. The property was actually quite beautiful. The view was lovely as the home sits on a creek. The home provided everything we needed. Shopping and restaurants were very close. If you need to be in the Baltimore/Annapolis area as we had, this property is perfect."
Rock Creek Cottage, Waterfront, Serene Views
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Interior

6 Mi to Dtwn: Family-friendly Home in Annapolis!

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Pets Welcome: Quiet Silver Spring Retreat!
Interior

Pets Welcome: Quiet Silver Spring Retreat!

3.0 star property
Pets Welcome: Quiet Silver Spring Retreat!
Outdoor Pool & Hot Tub: Retreat - 6 Mi to Dtwn!
Interior

Outdoor Pool & Hot Tub: Retreat - 6 Mi to Dtwn!

3.0 star property
Outdoor Pool & Hot Tub: Retreat - 6 Mi to Dtwn!
Vacation Rental w/ Yard in Washington, DC, Area
Microwave, oven, stovetop, dishwasher

Vacation Rental w/ Yard in Washington, DC, Area

3.0 star property
Vacation Rental w/ Yard in Washington, DC, Area
DC Area Home: 1 Mi to Light Rail!
Interior

DC Area Home: 1 Mi to Light Rail!

3.0 star property
DC Area Home: 1 Mi to Light Rail!
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Interior

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
The price is HK$1,469
HK$3,695 total
includes taxes & fees
26 Aug - 27 Aug
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
House w/Water Views of Rock Creek 2BA 2BA Cottage
Terrace/patio

House w/Water Views of Rock Creek 2BA 2BA Cottage

10.0 out of 10, Exceptional, (30)
"Perfect location, we were in town for birthdays and a wedding shower. Short drive to our favorite spots, Two Rivers, Primos & Seaside for steamed crabs. House has everything you need. Will return on our future visits to the Dena. "
House w/Water Views of Rock Creek 2BA 2BA Cottage
6 Mi to Inner Harbor - Family Home w/ Fenced Yard!
Interior

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

3.0 star property
6 Mi to Inner Harbor - Family Home w/ Fenced Yard!
Your Annapolis Waterfront retreat - a short walk to Navy Football Home Games
Interior

Your Annapolis Waterfront retreat - a short walk to Navy Football Home Games

10.0 out of 10, Exceptional, (85)
"Nice small property. Great for get aways and amazing service."
Your Annapolis Waterfront retreat - a short walk to Navy Football Home Games
Silver Springs Home: Walk to Downtown!
Interior

Silver Springs Home: Walk to Downtown!

3.0 star property
Silver Springs Home: Walk to Downtown!
Contemporary colonial cottage, close to dwntown Rockville and metro, accessible.
Fridge, microwave, oven, stovetop

Contemporary colonial cottage, close to dwntown Rockville and metro, accessible.

9.8 out of 10, Exceptional, (20)
"My husband and I came up from Charleston, SC to stay with some local friends for my mother’s funeral. The place was well appointed and clean. In a beautiful neighborhood close to everything. Highly recommended "
Contemporary colonial cottage, close to dwntown Rockville and metro, accessible.
2 Mi to National Mall: Modern DC Home
Interior

2 Mi to National Mall: Modern DC Home

3.0 star property
8.6 out of 10, Excellent, (4)
"Overall great experience: the property was clean located in a nice neighborhood. "
2 Mi to National Mall: Modern DC Home
Spacious Home w/ Tranquil Patio ~ 29 Mi to DC!
Fireplace, books

Spacious Home w/ Tranquil Patio ~ 29 Mi to DC!

3.0 star property
Spacious Home w/ Tranquil Patio ~ 29 Mi to DC!
Sunny Glen Burnie Home - On-site Water Access
Terrace/patio

Sunny Glen Burnie Home - On-site Water Access

3.0 star property
Sunny Glen Burnie Home - On-site Water Access
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Property grounds

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

9.8 out of 10, Exceptional, (29)
"Place was a perfect stay for 6 of us. There was even an extra hidden bedroom. We were able to do a little fishing off the dock and see a lot of wildlife. Easy access (10 minutes) to USNA and downtown Annapolis. "
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
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

Hyatt Regency Baltimore Inner Harbor

Hyatt Regency Baltimore Inner Harbor

10/10 Excellent
"This property was fantastic! Easy check-in/out process, friendly staff. "
Lakeya 1-night trip
Posted 11 hours ago
Hyatt Regency Baltimore Inner Harbor

Frequently asked questions

Why book your cottage in Jessup with Expedia?
Expedia has some terrific cottages in Jessup, so start packing for a memorable holiday 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.