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

Cottage for up to 4 guests with an excellent rating of 99% based on 311 reviews. You will be in Arnold.
Services and facilities: an iron, a fridge and a dish washer. Take advantage of the air conditioning in this accommodation!

Cottage for 4 people with an excellent rating of 100% based on 63 reviews. You will be based in Annapolis.
Services and facilities include air conditioning, a washing machine and a fridge.

This waterfront cottage in West Annapolis provides easy access to the city's attractions and amenities, including the US Naval Academy and Annapolis City Dock (both 1.5 miles away). With excellent user, location, and cleanliness ratings, this cottage is a great choice for travelers looking for a comfortable and convenient stay in Annapolis.
The cottage has a floor area of 700 square feet and can accommodate up to 4 guests. It features a fully equipped kitchen, a comfortable queen bed, and a queen sofabed. The outdoor amenities include a fire pit, picnic area, kayaks, paddle boards, and a canoe.

Cottage for up to 3 guests with an excellent rating of 99% based on 46 reviews. You will be in Annapolis.
Facilities and services include a cleaning service, a dish washer and an iron. Take advantage of the Free Parking with this accommodation in Annapolis!

Cottage listing at 200 dollars for 6 people with an excellent rating of 100% based on 20 reviews. This accommodation is based in Annapolis.
Services and facilities: a garden, a fridge and a child space. This accommodation is ideal for families.

This waterfront cottage in Annapolis offers stunning water views from the hot tub and screened-in porch. It is situated within the gated community of Epping Forest, just minutes from downtown and the Naval Academy. The cottage has excellent user ratings and can accommodate up to 7 guests in its 3 bedrooms and 2 bathrooms, with a floor area of 1400 square feet.
Guests can enjoy amenities such as a private beach, clubhouse, swimming area, and marina. The cottage also features a hot tub, screened-in porch, and ample outdoor seating and entertaining space.

This Annapolis cottage is conveniently located just 1.5 miles from Main Street and less than a mile from USNA Stadium, making it an ideal base for exploring the city's attractions. It has received excellent user ratings, indicating its popularity among previous guests.
The cottage offers a spacious and comfortable layout with 3 bedrooms, 2 bathrooms, and 2 main living areas, accommodating up to 8 guests. It features a fully renovated kitchen with modern appliances and ample space. Guests can enjoy amenities such as air conditioning, parking, and high-speed internet. Nearby water activities include kayaking, motor boating, and sailing.

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.

This waterfront cottage is situated on historic Bembe Beach in Eastport, Annapolis, offering panoramic Chesapeake Bay views and convenient access to the U.S. Naval Academy and downtown Annapolis.
The cottage has 3 bedrooms, 3 bathrooms, and 1780 square feet of living space, accommodating up to 8 guests. It features a private beach with direct access to the Chesapeake Bay, a waterfront balcony with stunning views, a screened-in patio gazebo, and a gourmet kitchen.

Cottage from $224 per night for up to 4 people with an excellent rating of 90% based on 2 reviews. This accommodation is based in Annapolis.
Facilities and services: a kitchen, a fridge and a washing machine. Pets are allowed in this accommodation.

This charming cottage in Riva offers guests a waterfront escape with stunning views. The spacious layout features 4 bedrooms and 3 bathrooms, comfortably accommodating up to 5 guests.
The cottage is conveniently located near local restaurants, shopping, and attractions, making it an ideal base for exploring the area. Guests can enjoy amenities such as a fully equipped kitchen, air conditioning, a jacuzzi, a garden, a fitness center, and parking.

Cottage listing from $200 per night for up to 4 guests. You will be located in Annapolis.
Facilities and services include a fridge, free parking and air conditioning.

Cottage for up to 4 guests with an excellent rating of 99% based on 311 reviews. You will be in Arnold.
Services and facilities: an iron, a fridge and a dish washer. Take advantage of the air conditioning in this accommodation!

This waterfront cottage in West Annapolis provides easy access to the city's attractions and amenities, including the US Naval Academy and Annapolis City Dock (both 1.5 miles away). With excellent user, location, and cleanliness ratings, this cottage is a great choice for travelers looking for a comfortable and convenient stay in Annapolis.
The cottage has a floor area of 700 square feet and can accommodate up to 4 guests. It features a fully equipped kitchen, a comfortable queen bed, and a queen sofabed. The outdoor amenities include a fire pit, picnic area, kayaks, paddle boards, and a canoe.

Cottage listing at 200 dollars for 6 people with an excellent rating of 100% based on 20 reviews. This accommodation is based in Annapolis.
Services and facilities: a garden, a fridge and a child space. This accommodation is ideal for families.

This waterfront cottage in Annapolis offers stunning water views from the hot tub and screened-in porch. It is situated within the gated community of Epping Forest, just minutes from downtown and the Naval Academy. The cottage has excellent user ratings and can accommodate up to 7 guests in its 3 bedrooms and 2 bathrooms, with a floor area of 1400 square feet.
Guests can enjoy amenities such as a private beach, clubhouse, swimming area, and marina. The cottage also features a hot tub, screened-in porch, and ample outdoor seating and entertaining space.

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 situated on historic Bembe Beach in Eastport, Annapolis, offering panoramic Chesapeake Bay views and convenient access to the U.S. Naval Academy and downtown Annapolis.
The cottage has 3 bedrooms, 3 bathrooms, and 1780 square feet of living space, accommodating up to 8 guests. It features a private beach with direct access to the Chesapeake Bay, a waterfront balcony with stunning views, a screened-in patio gazebo, and a gourmet kitchen.

This waterfront cottage in Annapolis offers stunning water views from the hot tub and screened-in porch. It is situated within the gated community of Epping Forest, just minutes from downtown and the Naval Academy. The cottage has excellent user ratings and can accommodate up to 7 guests in its 3 bedrooms and 2 bathrooms, with a floor area of 1400 square feet.
Guests can enjoy amenities such as a private beach, clubhouse, swimming area, and marina. The cottage also features a hot tub, screened-in porch, and ample outdoor seating and entertaining space.

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 Riva offers guests a waterfront escape with stunning views. The spacious layout features 4 bedrooms and 3 bathrooms, comfortably accommodating up to 5 guests.
The cottage is conveniently located near local restaurants, shopping, and attractions, making it an ideal base for exploring the area. Guests can enjoy amenities such as a fully equipped kitchen, air conditioning, a jacuzzi, a garden, a fitness center, and parking.