Search Cottages in Jessup

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 81 Cottages in Jessup with updated reviews, rates, and availability.

Waterfront River Cottage for 2, dog-friendly

9.2 out of 10, Wonderful, (7)
"It's a beautiful location and we enjoyed our visit."
Waterfront River Cottage for 2, dog-friendly

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

9.8 out of 10, Exceptional, (13)
"The cottage was everything and more than promised. We were vacationing and exploring DC - very convenient to the Metro and it was great having a “home” to come back to in the evening instead of a hotel room. Craig was responsive but gave us our space. We would recommend staying if you are looking for something in the area. You won’t be disappointed. As a bonus, the dogs were very friendly and made us laugh."
Contemporary colonial cottage, close to dwntown Rockville and metro, accessible.

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

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

Chic Baltimore Retreat - 6 Mi to Downtown!

3.0 star property
Chic Baltimore Retreat - 6 Mi to Downtown!

Vacation Rental w/ Yard in Washington, DC, Area

3.0 star property
Vacation Rental w/ Yard in Washington, DC, Area

Amazing views, short walks to great dining!

10.0 out of 10, Exceptional, (78)
"Very well-maintained property in a quiet neighborhood. Although we didn't need anything, host was always available."
Amazing views, short walks to great dining!

Secluded Cozy Cottage in Historic Downtown

10.0 out of 10, Exceptional, (7)
"Such a wonderful experience staying in this poperty for a couple of days. Walking distance to everything. Jennifer was a pleasure and very responsive. May make this an annual visit! Loved Annapolis!"
The price is AED 1,469
AED 2,470 total
includes taxes & fees
24 Feb - 25 Feb
Secluded Cozy Cottage in Historic Downtown

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

10.0 out of 10, Exceptional, (26)
"Amazing house! perfect for my family and our stay in Annapolis. Perfect location to everything. We had all of the amenities we needed and everything was easy to use. If I had one thing negative to say, I wish I could have had my dogs with us, I would have gladly paid a cleaning fee to have them there. Luckily I was able to make other arrangements. Thank you for sharing your house with my family!"
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

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

9.8 out of 10, Exceptional, (22)
"My husband and I stayed here for 3 nights while I recovered from a surgery. It was a perfect, peaceful cottage and beautiful neighborhood. "
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break

10.0 out of 10, Exceptional, (85)
"Our eighth stay at this property was just as good as ever. It is our home-away-from-home when visiting family in Annapolis. Highly recommended!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break

Rare find! Chic cottage, salt water heated pool May 15-Oct15.

10.0 out of 10, Exceptional, (50)
"The house was even nicer than in photos or descriptions. The house very spacious, the pool and pool area were perfect for our needs. The hosts were very gracious, communicative, and easy to work with. I would definitely recommend this property."
Rare find! Chic cottage, salt water heated pool May 15-Oct15.

2 Mi to National Mall: Modern DC Home

3.0 star property
8.6 out of 10, Excellent, (4)
"My daughter's family and myself went to DC for my mother's burial at Arlington. It was a quick trip and we're from the area,though no one lives there now, so we needed a place to stay. This was a convenient location close to places to eat, the Metro, and major roadways. It was clean, comfortable, and safe. I'd definitely recommend. The only negative was the lot parking spot was a little tricky but the on street parking is a good alternative. There were a couple spots the paint needs to be...
2 Mi to National Mall: Modern DC Home

Ideally Located DC Home w/ Pool Table & Patio

3.0 star property
Ideally Located DC Home w/ Pool Table & Patio

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

10.0 out of 10, Exceptional, (24)
"The house provided a clean, bright, spacious, well-equipped place for a family Thanksgiving gathering. It made for a very comfortable few days. The host was very responsive when we had questions before our stay."
House w/Water Views of Rock Creek 2BA 2BA Cottage

Waterfront Cottage by Annapolis w/ Pool & Hot Tub

10.0 out of 10, Exceptional, (2)
"Riva Waterfront “The Cottage” was a perfect place to have our girls getaway to celebrate birthdays. We enjoyed kayaking, relaxing in the hot tub and just relaxing inside and outside. Its location was convenient to go to a winery and downtown Annapolis. The owner and her team were quick to respond when I needed assistance with check-in. I would recommend staying at this lovely property. "
Waterfront Cottage by Annapolis w/ Pool & Hot Tub

Silver Spring Rental: 8 Mi to Washington, DC!

3.0 star property
Silver Spring Rental: 8 Mi to Washington, DC!

Rock Creek Cottage, Waterfront, Serene Views

10.0 out of 10, Exceptional, (1)
"Absolutely amazing place for my husband and I to relax with our midshipmen. Very clean, beautifully decorated and the view on the dock each morning was stunning! Close to restaurants (loved 3 B’s Bakery) and host was awesome! "
Rock Creek Cottage, Waterfront, Serene Views

Walk to Everything - Historic Art’s District

2.0 star property
Walk to Everything - Historic Art’s District

Maryland Home: 3 Mi to Downtown Silver Spring

3.0 star property
8.0 out of 10, Very Good, (1)
"The property renovation was superb and rated at five stars."
Maryland Home: 3 Mi to Downtown Silver Spring

Silver Spring Rental Home ~ 11 Mi to National Mall

3.0 star property
Silver Spring Rental Home ~ 11 Mi to National Mall
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.
Don't see what you're looking for?
See all available properties in Jessup
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Jessup

WhyHotel by Placemakr Columbia

4.0 star property
9.0 out of 10, Wonderful, (645)
"Good place to stay. Very spacious. "
The price is AED 452
AED 511 total
includes taxes & fees
2 Mar - 3 Mar
WhyHotel by Placemakr Columbia

Global Luxury Suites at Capitol Hill

4.0 star property
8.0 out of 10, Very Good, (486)
"Modern, spacious suite can be suitable for a variety of stay/rental uses."
The price is AED 469
AED 970 total
includes taxes & fees
27 Feb - 28 Feb
Global Luxury Suites at Capitol Hill

Reside NoMa, a Wyndham Residence

2.5 star property
8.4 out of 10, Very Good, (197)
"I liked the cleanliness. I didn't like the round table in room right under tv. "
The price is AED 411
AED 477 total
includes taxes & fees
27 Feb - 28 Feb
Reside NoMa, a Wyndham Residence
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.

Frequently asked questions

Why book your cottage in Jessup with Expedia?
We think that traveling should be simple, so if you’re after cottages in Jessup at a competitive price, Expedia delivers. Save those pennies and pick an inexpensive option surrounded by nature, or splurge on a luxury cottage to pamper your loved ones.
How can I find cheap cottages in Jessup?
With Expedia’s convenient filter tool, sourcing cheap cottages in Jessup is easy. To view properties that are very pocket friendly, tailor your search results by budget, star rating and amenities.