Compare best cottages in Annapolis, MD from 100+ sites!

This Annapolis waterfront cottage is located on Bembe Beach in Eastport, offering panoramic Chesapeake Bay views and proximity to downtown Annapolis (4 miles) and the U.S. Naval Academy (4.5 miles). It has excellent user ratings.
The cottage has 3 bedrooms, 2 bathrooms, and can accommodate up to 8 guests. It features a gourmet kitchen, high-speed internet, a big flatscreen TV, luxury linens, and complimentary toiletries. Guests can enjoy a private beach, waterfront views, a spacious family suite, outdoor living areas, water activities, and luxury amenities.

This charming cottage, in the Historic District of Annapolis, offers immediate access to the city's iconic landmarks and attractions. The restored 1930s cottage has an open and airy interior with vaulted ceilings and an open floor plan.
The cottage has 2 bedrooms, 1 bathroom, and can accommodate up to 8 guests. It features a fully equipped gourmet kitchen, a comfortable living area with a large couch, chaise lounge chairs, a 55" Roku TV, and an electric fireplace. The cottage also has a private entrance and patio, and is pet-friendly.

The Yellow Cottage is a waterfront home located in the Hillsmere neighborhood of Annapolis, just a short distance from Jonas Green State Park and the Smithsonian Environmental Research Center. This charming rental consistently receives excellent reviews from guests.
The cottage has two bedrooms and one bathroom, spanning 950 square feet and comfortably sleeping up to six guests. The Yellow Cottage offers a full kitchen, air conditioning, a garden, a spa, and parking, plus waterfront access with stunning views of Harness Creek.

This charming historic house is located in the Annapolis Art District, just off West Street, within walking distance of the Naval Academy, Navy Stadium, shops, bars, restaurants, and the City Docks. It has excellent user, location, and cleanliness ratings.
This 1260 square foot house has two bedrooms, two bathrooms, and can accommodate up to six guests. It offers a fully equipped kitchen, a garden with a BBQ grill, parking for two cars, central AC, high-speed internet, three smart TVs, a Jacuzzi, and a screened front porch.

This waterfront cottage is located in West Annapolis, a short walk from the US Naval Academy's Gate 8 and a 1.5-mile walk to Annapolis City Dock, making it easy to explore the city's historic attractions and vibrant waterfront. This charming cottage enjoys excellent user, location and cleanliness ratings.
The 700 square foot cottage comfortably sleeps four guests and features a fully equipped kitchen, a screened-in porch, and a private dock with stunning views of Weems Creek. Guests can enjoy amenities like a fire pit, picnic area, paddle boards, kayaks, and a 17' Boston Whaler (for experienced boaters at an extra cost).

This Eastport vacation rental offers direct access to a private stretch of Bembe Beach, located 4 miles from downtown Annapolis and the U.S. Naval Academy, and is ideal for Commissioning Week with Blue Angels views.
This family-friendly cottage accommodates up to 8 guests with 3 bedrooms and 3 bathrooms, featuring a gourmet kitchen, water-view dining, a screened-in gazebo, a private balcony with water views, and complimentary use of paddleboards and beach toys during summer.