
Shady Lake, Annapolis
08/18 – 08/27
$122/nighttotal: $1098 (9 )
Calico Cottage Guest House, King Bed, Free Parking
1 2house , Annapolis
This smoke-free guesthouse is located on a river, just a short drive from the Navy-Marine Corps Memorial Stadium and the U.S. Naval Academy in Annapolis. Guests consistently rate this accommodation excellent for its location, cleanliness, and overall experience.
The guesthouse offers a comfortable and convenient stay with one bedroom, one bathroom, and a total of 400 square feet. Guests will enjoy a private garden, a terrace, and a kitchen equipped with a fridge and microwave, perfect for a relaxing and enjoyable stay.
The guesthouse offers a comfortable and convenient stay with one bedroom, one bathroom, and a total of 400 square feet. Guests will enjoy a private garden, a terrace, and a kitchen equipped with a fridge and microwave, perfect for a relaxing and enjoyable stay.

Shady Lake, Annapolis
09/01 – 09/09
$431/nighttotal: $3448 (8 )
Eastport Pied -A -Terre
1 1apartment , Annapolis
This one-bedroom Annapolis condo is conveniently located near the Eastport Bridge, offering easy access to both Eastport and downtown Annapolis.
This unit features a fully equipped kitchen, in-unit laundry, elevator access, and a rooftop pool with city views; it sleeps three guests and includes free parking.
This unit features a fully equipped kitchen, in-unit laundry, elevator access, and a rooftop pool with city views; it sleeps three guests and includes free parking.

Shady Lake, Annapolis
08/18 – 08/27
$203/nighttotal: $1827 (9 )
Downtown Annapolis King George 3rd Floor Hideaway
2 2apartment , Annapolis
This apartment is located in Downtown Annapolis, just a short walk from the Annapolis Harbor and 30 miles from Baltimore. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment features one bedroom and one bathroom, offering 700 square feet of living space. You'll enjoy a fully equipped kitchen, a private terrace, and a garden with barbecue facilities, perfect for relaxing after a day exploring Annapolis.
The apartment features one bedroom and one bathroom, offering 700 square feet of living space. You'll enjoy a fully equipped kitchen, a private terrace, and a garden with barbecue facilities, perfect for relaxing after a day exploring Annapolis.

Shady Lake, Annapolis
08/18 – 08/27
$178/nighttotal: $1602 (9 )
Style, Comfort, Walk To Stadium
2 2apartment , Annapolis
This Annapolis house rental in the Admiral Heights neighborhood is conveniently located within walking distance of the Navy-Marine Corps Memorial Stadium and minutes from downtown Annapolis, the U.S. Naval Academy, Eastport, and Town Center, offering easy access to Route 50 (for Washington, D.C.) and Route 97 (for Baltimore).
The two-bedroom, one-bathroom home sleeps four guests and features a fully equipped kitchen with stainless steel appliances, a private deck with a grill, and a 60-inch smart TV with streaming services; nearby attractions include the U.S. Naval Academy and the Maryland State House.
The two-bedroom, one-bathroom home sleeps four guests and features a fully equipped kitchen with stainless steel appliances, a private deck with a grill, and a 60-inch smart TV with streaming services; nearby attractions include the U.S. Naval Academy and the Maryland State House.

Shady Lake, Annapolis
08/18 – 08/27
$423/nighttotal: $3807 (9 )
Renovated Row Home In The Heart Of Downtown Annapolis.two Blocks To Everything
3 2apartment , Naval Academy
This Historic District vacation rental is a 5-minute walk from the U.S. Naval Academy and the William Paca House, offering easy access to Annapolis's historic sites.
This three-bedroom, three-bathroom house sleeps eight guests and features a fully equipped kitchen, patio, Smart TV, and in-unit laundry; enjoy nearby attractions like the John Smith House and 48 Fleet Street.
This three-bedroom, three-bathroom house sleeps eight guests and features a fully equipped kitchen, patio, Smart TV, and in-unit laundry; enjoy nearby attractions like the John Smith House and 48 Fleet Street.

Shady Lake, Annapolis
08/18 – 08/27
$467/nighttotal: $4203 (9 )
2026 Commissioning Week Promo: Book 6 Nights, Get The 7th Free
2 2apartment , Annapolis
This Annapolis vacation home is conveniently located in Eastport, just a short walk from the Annapolis Maritime Museum, the U.S. Naval Academy, and Spa Creek. The property has received excellent ratings for location, cleanliness, and overall user experience.
This 2,400 square foot house comfortably sleeps 8 guests in its three bedrooms and features a sofa bed. The home offers a variety of amenities including a fully equipped kitchen, a terrace or balcony, a garden, a spa, parking, and a game room for family entertainment.
This 2,400 square foot house comfortably sleeps 8 guests in its three bedrooms and features a sofa bed. The home offers a variety of amenities including a fully equipped kitchen, a terrace or balcony, a garden, a spa, parking, and a game room for family entertainment.

Shady Lake, Annapolis
08/30 – 09/08
$689/nighttotal: $6201 (9 )
Fisher House - Downtown Annapolis!
3 1house , Annapolis
Fisher House - Downtown Annapolis! is located in the heart of Annapolis, just a short walk from the vibrant Annapolis Harbor and within easy driving distance of popular attractions like Carroll Park and the Sports Legends Museum at Camden Yards. The house consistently receives excellent ratings for its cleanliness, location, and overall experience, making it a top choice for travelers.
This spacious 3-bedroom home comfortably accommodates up to 13 guests, offering plenty of room to relax and enjoy your stay. The house is equipped with a fully stocked kitchen, a comfortable living area, and a private patio, perfect for enjoying the beautiful Annapolis weather.
This spacious 3-bedroom home comfortably accommodates up to 13 guests, offering plenty of room to relax and enjoy your stay. The house is equipped with a fully stocked kitchen, a comfortable living area, and a private patio, perfect for enjoying the beautiful Annapolis weather.

Shady Lake, Annapolis
08/30 – 09/08
$331/nighttotal: $2979 (9 )
Private Art-filled Guesthouse Near Naval Academy
1 1house , Annapolis
This charming guesthouse is located in the West Annapolis residential neighborhood, where you can explore quaint shops and restaurants nearby. It has excellent user, location, and cleanliness ratings.
The secluded guesthouse has a unique blend of antique curios and Americana decor, a modern kitchen, and an updated bathroom. It can accommodate up to 2 guests and offers a Treetop Getaway experience with key code access for convenience. The homeowners are on-site for assistance. You will enjoy amenities such as a swimming pool, parking, air conditioning, and internet.
The secluded guesthouse has a unique blend of antique curios and Americana decor, a modern kitchen, and an updated bathroom. It can accommodate up to 2 guests and offers a Treetop Getaway experience with key code access for convenience. The homeowners are on-site for assistance. You will enjoy amenities such as a swimming pool, parking, air conditioning, and internet.

Shady Lake, Annapolis
08/30 – 09/08
$263/nighttotal: $2367 (9 )
Bay Ridge Unit By Downtown Annapolis And Quiet Waters Park
2 1apartment , Annapolis
This Annapolis Bay Ridge rental is conveniently located near Downtown Annapolis and Quiet Waters Park, 3.4 miles from Annapolis Harbor.
This 1190-square-foot apartment features two bedrooms, one bathroom, and accommodates up to 11 guests, offering free parking, a fully equipped kitchen, in-unit laundry, and a private garden.
This 1190-square-foot apartment features two bedrooms, one bathroom, and accommodates up to 11 guests, offering free parking, a fully equipped kitchen, in-unit laundry, and a private garden.

Shady Lake, Annapolis
09/01 – 09/09
$620/nighttotal: $4960 (8 )
Port Of Call: 5br Modern Nautical Luxury
1 1apartment , Annapolis
This five-bedroom home in Annapolis, located in the private Anchorage community, is one block from the water and a 10-15 minute drive from downtown Annapolis and the US Naval Academy.
This spacious residence offers accommodations for up to eight guests, featuring a fully equipped chef's kitchen, dual living areas, a private fenced backyard with a firepit, and two remodeled bathrooms, including a primary suite bath.
This spacious residence offers accommodations for up to eight guests, featuring a fully equipped chef's kitchen, dual living areas, a private fenced backyard with a firepit, and two remodeled bathrooms, including a primary suite bath.

Shady Lake, Annapolis
10/17 – 10/21
$644/nighttotal: $2576 (4 )
Eastport Cottage .5 Mi From Downtown Annapolis\n\n
2 2apartment , Annapolis
**Annapolis House**
This vacation home is located in Eastport, a charming district within walking distance of Spa Creek and the U.S. Naval Academy. The house has received excellent ratings for its location, cleanliness, and user experience.
The house has two bedrooms and one bathroom, and it features a fully equipped kitchen, a patio for outdoor dining, a private garden with barbecue grills, and free WiFi. The house is non-smoking and pet-friendly, and it offers parking.
This vacation home is located in Eastport, a charming district within walking distance of Spa Creek and the U.S. Naval Academy. The house has received excellent ratings for its location, cleanliness, and user experience.
The house has two bedrooms and one bathroom, and it features a fully equipped kitchen, a patio for outdoor dining, a private garden with barbecue grills, and free WiFi. The house is non-smoking and pet-friendly, and it offers parking.

Shady Lake, Annapolis
09/01 – 09/09
$958/nighttotal: $7664 (8 )
Weems Creek Cottage, Annapolis Waterfront
1 1house , Annapolis
Weems Creek Cottage is a charming waterfront vacation rental located just 2.7 miles from Annapolis Harbor, offering stunning views of the Chesapeake Bay. The cottage is conveniently situated near the city's vibrant waterfront scene, making it easy to explore Annapolis's historic attractions and bustling harbor.
This cozy cottage provides 700 square feet of space, perfect for accommodating up to 7 guests. The cottage features a fully equipped kitchen, a private spa, and free Wi-Fi, ensuring a comfortable and relaxing stay.
This cozy cottage provides 700 square feet of space, perfect for accommodating up to 7 guests. The cottage features a fully equipped kitchen, a private spa, and free Wi-Fi, ensuring a comfortable and relaxing stay.













