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

This Annapolis rental property, a 2-bedroom, 2-bathroom abode, is located an 11-minute walk from Spa Creek and a 5-minute drive from the Annapolis Maritime Museum, with proximity to Jonas Green State Park and the Kunta Kinte Plaque & Alex Haley Memorial.
This well-equipped vacation home accommodates up to 6 guests, offering amenities such as air conditioning, Wi-Fi, a full kitchen with a microwave and dishwasher, an on-site barbecue, and an in-unit washer and dryer, with parking provided.

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.

This non-smoking cottage is situated downtown in Annapolis, a 12-minute walk from Maryland Hall for the Creative Arts and a 13-minute walk from the historic Maryland State House, offering on-site parking and complimentary Wi-Fi.
This rental accommodates up to 6 guests with 2 bedrooms and 1 bathroom, featuring a fully equipped kitchen, air conditioning, and spa amenities, with proximity to sailing and kayaking activities.

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 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).

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.