Search Jessup Cottage Rentals from CA $495

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Jessup Cottages

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Set against a serene backdrop, this house features a beautifully lit facade and a decorative reindeer sculpture on the lawn.

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!
The Heron's Nest at Atlantic Marina
Situated on a grassy area, this cottage offers a peaceful retreat with a porch for relaxation or dining.

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (301)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina
Secluded Cozy Cottage in Historic Downtown
Stroll along the pathway to an entrance surrounded by lush greenery and a curved brick wall.

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 CA $680
CA $1,101 total
includes taxes & fees
Aug 11 - Aug 12
Secluded Cozy Cottage in Historic Downtown
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!
Enjoy cooking in this well-equipped kitchen with a central island, bar stools, and stainless steel appliances.

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!
Enjoy cooking in this well-equipped kitchen with a central island, oven, and microwave.

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!
House (3 Bedrooms) | 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
Enjoy cooking in this well-equipped kitchen with a large island, oven, and stainless steel appliances.

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!
House (4 Bedrooms) | Interior

DC Area Home: 1 Mi to Light Rail!

3.0 star property
DC Area Home: 1 Mi to Light Rail!
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Relax on the dock with Adirondack chairs and enjoy the serene view.

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
The price is CA $495
CA $913 total
includes taxes & fees
Aug 11 - Aug 12
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Ruscincy’s Rest "minutes drive to Orioles stadium"
Property grounds

Ruscincy’s Rest "minutes drive to Orioles stadium"

Ruscincy’s Rest "minutes drive to Orioles stadium"
Silver Springs Home: Walk to Downtown!
House (4 Bedrooms) | Interior

Silver Springs Home: Walk to Downtown!

3.0 star property
Silver Springs Home: Walk to Downtown!
House w/Water Views of Rock Creek 2BA 2BA Cottage
Relax in this serene outdoor space with a wicker sofa, glass table, and wooden bench.

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

10.0 out of 10, Exceptional, (29)
"Very quiet street, our stay was relaxing and just what we needed! "
House w/Water Views of Rock Creek 2BA 2BA Cottage
Perfect location for USNA Commissioning Week
Interior

Perfect location for USNA Commissioning Week

10.0 out of 10, Exceptional, (84)
"Nice small property. Great for get aways and amazing service."
Perfect location for USNA Commissioning Week
2 Mi to National Mall: Modern DC Home
Stroll through a serene garden, surrounded by lush foliage and trees, along a winding stone pathway.

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
6 Mi to Inner Harbor - Family Home w/ Fenced Yard!
Enjoy a homey atmosphere on the front porch, surrounded by a small garden and a white picket fence.

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

3.0 star property
6 Mi to Inner Harbor - Family Home w/ Fenced Yard!
Spacious Home w/ Tranquil Patio ~ 29 Mi to DC!
Relax in this stylish living room with a large flat-screen TV, comfortable sofa, and ample storage.

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

3.0 star property
Spacious Home w/ Tranquil Patio ~ 29 Mi to DC!
Contemporary colonial cottage, close to dwntown Rockville and metro, accessible.
Enjoy cooking in this well-equipped kitchen with a skylight above the dining area, featuring a refrigerator, microwave, and stove.

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.
Sunny Glen Burnie Home - On-site Water Access
Relax on the covered porch with a comfortable wicker chair and enjoy the view.

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
Situated by a serene body of water, this bench offers a tranquil view of the surrounding shoreline.

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

9.8 out of 10, Exceptional, (29)
"Peaceful, quiet venue with hiking trails and a beautiful location! My family and I enjoyed the lovely home and downtown Annapolis where we savored delicious seafood and quality family-time. The hosts were responsive and the home was charming! Thank you for the terrific experience!"
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Jessup Hotel Reviews

Holiday Inn Baltimore BWI Airport by IHG

Holiday Inn Baltimore BWI Airport by IHG

10/10 Excellent
"Good"
Theresa 1-night trip
Posted 14 hours ago
Holiday Inn Baltimore BWI Airport by IHG