
Shady Lake, Annapolis
09/01 – 09/09
$267/nighttotal: $2136 (8 )
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
08/18 – 08/27
$168/nighttotal: $1512 (9 )
Cozy Eastport Hideaway | Walk To City Dock & Usna
1 2apartment , Annapolis
This ground-floor Annapolis apartment rental in Eastport offers convenient street parking and is a short walk from both Eastport's attractions and Annapolis's downtown.
The one-bedroom, one-bathroom unit sleeps four with a queen bed, queen pull-out couch, compact kitchenette (mini-fridge, coffee maker), smart TV, free Wi-Fi, and a newly remodeled bathroom with walk-in shower.
The one-bedroom, one-bathroom unit sleeps four with a queen bed, queen pull-out couch, compact kitchenette (mini-fridge, coffee maker), smart TV, free Wi-Fi, and a newly remodeled bathroom with walk-in shower.

Shady Lake, Annapolis
08/30 – 09/08
$778/nighttotal: $7002 (9 )
Historic Annapolis Home | 2 Blocks To Main St
3 1apartment , Annapolis
This smoke-free Annapolis vacation home is located in the Historic District, a 15-minute walk from the U.S. Naval Academy and Maynard-Burgess House, and under 5 minutes from the Maryland Federation of Art and Ellen O. Moyer Nature Park. This 12,640-square-foot property boasts three bedrooms, two bathrooms, sleeps nine guests, and features a fully equipped kitchen, fenced yard with barbecue grills, and free Wi-Fi.

Shady Lake, Annapolis
09/01 – 09/09
$1060/nighttotal: $8480 (8 )
Beachfront Home Minutes To Downtown Annapolis Dogs Ok
3 1cottage , Annapolis
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.
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.

Shady Lake, Annapolis
09/01 – 09/09
$1014/nighttotal: $8112 (8 )
Villa Annapolitana • Parking 1 Min • Usna 4 Min
1 1apartment , Annapolis
This 1700s home is located in Annapolis, just a short 5-minute walk from the US Naval Academy.
The three-bedroom house features a fully equipped kitchen, a dedicated workspace, and a comfortable basement lounge with gym equipment, accommodating up to 7 guests.
The three-bedroom house features a fully equipped kitchen, a dedicated workspace, and a comfortable basement lounge with gym equipment, accommodating up to 7 guests.

Shady Lake, Annapolis
08/30 – 09/08
$858/nighttotal: $7722 (9 )
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.

Shady Lake, Annapolis
09/01 – 09/09
$1014/nighttotal: $8112 (8 )
Now Available For Usna Commissioning Week! 16-22 May. Easy Walk To Stadium. <Br>your Annapolis Waterfront Retreat For A Weekend Getaway.
1 1cottage , Annapolis
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 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).

Shady Lake, Annapolis
08/18 – 08/27
$556/nighttotal: $5004 (9 )
Historic Chapel Views, Steps To Usna Gate 1 With Private Patio And Off-site Parking
3 2apartment , Annapolis
This Annapolis vacation home is located in the Historic District, a short walk from the U.S. Naval Academy, Chase Lloyd House, Hammond-Harwood House, and St. John's College. It has excellent user, location, and cleanliness ratings.
This 3-bedroom house can comfortably accommodate 7 guests and features a spacious 2,410 square feet of living space. Enjoy amenities like a fully equipped kitchen, a private patio, and a fireplace, perfect for relaxing after a day exploring the city.
This 3-bedroom house can comfortably accommodate 7 guests and features a spacious 2,410 square feet of living space. Enjoy amenities like a fully equipped kitchen, a private patio, and a fireplace, perfect for relaxing after a day exploring the city.

Shady Lake, Annapolis
08/18 – 08/27
$217/nighttotal: $1953 (9 )
Walk To Water, State House, Usna
1 2apartment , Annapolis
This yacht is located in Annapolis' Eastport Conservation District, a short walk from downtown, the US Naval Academy, and the waterfront. It has received excellent ratings for location, cleanliness, and user experience.
The boat has one bedroom with a king-sized bed and a pull-out sofa in the living area, accommodating up to three guests. Amenities include a fully equipped kitchen, a washer and dryer, two Roku TVs, and FiOS WiFi, as well as a plant-based breakfast service.
The boat has one bedroom with a king-sized bed and a pull-out sofa in the living area, accommodating up to three guests. Amenities include a fully equipped kitchen, a washer and dryer, two Roku TVs, and FiOS WiFi, as well as a plant-based breakfast service.

Shady Lake, Annapolis
09/01 – 09/09
$810/nighttotal: $6480 (8 )
Cute Bungalow Blocks To Stadium
2 1apartment , Annapolis
This Annapolis vacation home, located in the Admiral Heights neighborhood, is 0.5 miles from People's Brewer Hill Cemetery and 1.6 miles from the U.S. Naval Academy.
This 1190-square-foot rental boasts three bedrooms, two bathrooms, a private garden with barbecue grills, and accommodates up to six guests with amenities including a fully equipped kitchen, balcony, and free internet.
This 1190-square-foot rental boasts three bedrooms, two bathrooms, a private garden with barbecue grills, and accommodates up to six guests with amenities including a fully equipped kitchen, balcony, and free internet.

Shady Lake, Annapolis
08/18 – 08/27
$588/nighttotal: $5292 (9 )
Usna Home Steps To Stadium Dog-friendly W Parking
3 2apartment , Annapolis
This Annapolis home is conveniently located in West Annapolis, just a short walk from shops, restaurants, and the Navy-Marine Corps Memorial Stadium. The apartment consistently receives excellent ratings for location, cleanliness, and overall user experience.
This spacious 3-bedroom rental comfortably sleeps 11 guests and offers 2,200 square feet of living space. The home includes a private backyard with a hot tub, fire pit, and outdoor kitchen, as well as a fully equipped kitchen, a swimming pool, a spa, and a tennis court for your enjoyment.
This spacious 3-bedroom rental comfortably sleeps 11 guests and offers 2,200 square feet of living space. The home includes a private backyard with a hot tub, fire pit, and outdoor kitchen, as well as a fully equipped kitchen, a swimming pool, a spa, and a tennis court for your enjoyment.

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.













