Search Jessup Cottage Rentals from CA $496

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Browse Select Jessup Cottages

Enjoy the ocean view from this outdoor space with a deck and columned roof.

"Nice weekend getaway!"

Set against a serene backdrop, this house features a beautifully lit facade and a decorative reindeer sculpture on the lawn.

"Pat and Ken were very accommodating for our visit over the holidays. Highly recommended!"

Relax in this serene outdoor space with a wicker sofa, glass table, and wooden bench.

"Very quiet street, our stay was relaxing and just what we needed! "

Stroll to the inviting porch and enjoy the peaceful surroundings from the comfort of a swing.

"Nice small property. Great for get aways and amazing service."

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

"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!"

Stroll up to this charming two-story home with a welcoming front porch and garage, set amidst a beautifully manicured lawn.

Situated in a suburban area, this single-story house features a sloped roof and a front garage.

Enjoy cooking in this well-equipped kitchen with a large island, oven, and stainless steel appliances.

Stroll along the pathway to an entrance surrounded by lush greenery and a curved brick wall.

"We had a very lovely stay . This is an excellent location . "

CA $1,015 total

includes taxes & fees

Aug 4 - Aug 5

Relax on the deck surrounded by a lush lawn and a majestic tree, with a table and chairs perfect for outdoor dining.

"Excellent Property"

CA $916 total

includes taxes & fees

Aug 4 - Aug 5

Enjoy a homey atmosphere on the front porch, surrounded by a small garden and a white picket fence.

"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."

Relax or entertain in this serene outdoor space with a grill and stone pathway.

"Overall great experience: the property was clean located in a nice neighborhood. "

Charming single-story home with a front porch and well-manicured lawn.

Enjoy cooking in this well-equipped kitchen with a skylight above the dining area, featuring a refrigerator, microwave, and stove.

"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 "