
Great Frogs Winery, Annapolis
06/24 – 06/28
$539/nighttotal: $2156 (4 )
Cute Bungalow Blocks To Stadium
2 4apartment , Annapolis
This stylish two-bedroom house is located in Annapolis' Germantown neighborhood, just two blocks from Navy-Marine Corps Memorial Stadium and an 8-minute drive from the USNA and Downtown Annapolis. The home has received excellent ratings for location, cleanliness, and overall user experience.
The house is a two-floor home with a capacity of 6 guests. This Annapolis home offers amenities like a fully equipped kitchen, air conditioning, a fenced-in backyard, and a covered, screened-in eating area.
The house is a two-floor home with a capacity of 6 guests. This Annapolis home offers amenities like a fully equipped kitchen, air conditioning, a fenced-in backyard, and a covered, screened-in eating area.

Great Frogs Winery, Annapolis
06/24 – 06/28
$784/nighttotal: $3136 (4 )
Free Parking & Private Patio Historic Union House
3 4apartment , Annapolis
This beautifully restored Federal-style home is situated in Annapolis' historic district, just 2.5 blocks from Main Street, 1.5 blocks from Spa Creek, and 4 blocks from both the U.S. Naval Academy and City Dock.
This three-bedroom, two-bathroom residence sleeps six guests and boasts a gourmet kitchen with Viking and GE Monogram appliances, a fenced patio with a gas grill, a Sonos sound system, smart TV, and dedicated parking (0.7 miles away).
This three-bedroom, two-bathroom residence sleeps six guests and boasts a gourmet kitchen with Viking and GE Monogram appliances, a fenced patio with a gas grill, a Sonos sound system, smart TV, and dedicated parking (0.7 miles away).

Great Frogs Winery, Annapolis
09/06 – 09/11
$429/nighttotal: $2145 (5 )
Townhouse - 1 Mile From Downtown Strip
1 3house , Annapolis
This Annapolis townhouse is conveniently located near various landmarks and attractions, making it a great base for exploring the city. It has received excellent ratings for location, cleanliness, and overall experience.
The three-bedroom, three-bathroom house comfortably accommodates six guests. It features a fully equipped kitchen with two ovens, a cozy living room with a pull-out sofa, and a private garden. Guests can also enjoy a fitness center, air conditioning, and pet-friendly accommodations.
The three-bedroom, three-bathroom house comfortably accommodates six guests. It features a fully equipped kitchen with two ovens, a cozy living room with a pull-out sofa, and a private garden. Guests can also enjoy a fitness center, air conditioning, and pet-friendly accommodations.

Great Frogs Winery, Annapolis
09/06 – 09/11
$426/nighttotal: $2130 (5 )
Tide & Tallow - Walk To Downtown, Main St, Academy
3 3apartment , Annapolis
Tide & Tallow, a meticulously renovated townhouse in Annapolis's Historic District, offers a prime location within walking distance of the U.S. Naval Academy, City Dock, and Main Street's shops and restaurants.
This three-bedroom, 1.5-bathroom Annapolis rental accommodates six guests and features a fully equipped gourmet kitchen, a private backyard, smart home technology, and high-speed Wi-Fi.
This three-bedroom, 1.5-bathroom Annapolis rental accommodates six guests and features a fully equipped gourmet kitchen, a private backyard, smart home technology, and high-speed Wi-Fi.

Great Frogs Winery, Annapolis
09/06 – 09/11
$1373/nighttotal: $6865 (5 )
Parking At Randall House Across From Usna Gate 1
4 3apartment , Annapolis
This Annapolis home is located in the Historic District, just steps away from the Naval Academy, City Dock, and John Smith House, making it easy to explore the city's rich history and culture. The property has received excellent ratings for location, cleanliness, and overall experience.
This 4-bedroom, 4-bathroom house offers 3,470 square feet of space, comfortably accommodating up to 11 guests. The home features a fully equipped kitchen, a balcony, free Wi-Fi, parking, and a spa, providing everything needed for a relaxing and enjoyable stay.
This 4-bedroom, 4-bathroom house offers 3,470 square feet of space, comfortably accommodating up to 11 guests. The home features a fully equipped kitchen, a balcony, free Wi-Fi, parking, and a spa, providing everything needed for a relaxing and enjoyable stay.

Great Frogs Winery, Annapolis
09/06 – 09/11
$383/nighttotal: $1915 (5 )
Charming Cottage With Parking. Easy Walk To Downtown.
1 3apartment , Annapolis
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 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.

Great Frogs Winery, Annapolis
10/15 – 10/26
$257/nighttotal: $2827 (11 )
Bayside Retreat
1 2apartment , Highland Beach
This Chesapeake Bay cottage apartment rental in Highland Beach is situated in a quiet neighborhood, four miles from Annapolis's downtown area and the United States Naval Academy.
The one-bedroom, one-bathroom unit sleeps two guests and features a fully equipped kitchenette, in-unit laundry, keyless entry, two parking spaces, a private fenced backyard with a fire pit, high-speed internet with YouTube TV access, and proximity to a private beach.
The one-bedroom, one-bathroom unit sleeps two guests and features a fully equipped kitchenette, in-unit laundry, keyless entry, two parking spaces, a private fenced backyard with a fire pit, high-speed internet with YouTube TV access, and proximity to a private beach.

Great Frogs Winery, Annapolis
06/24 – 06/28
$534/nighttotal: $2136 (4 )
Downtown Annapolis Home
1 4apartment , Annapolis
This Annapolis apartment is located in the downtown area, within walking distance of restaurants, bars, and the free purple bus that takes you to City Dock. The apartment has excellent user, location, and cleanliness ratings.
The apartment is a three-bedroom, two-bathroom rental that can accommodate up to six guests. This rental includes a modern kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, a fenced-in backyard with a deck, and parking for four cars.
The apartment is a three-bedroom, two-bathroom rental that can accommodate up to six guests. This rental includes a modern kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, a fenced-in backyard with a deck, and parking for four cars.

Great Frogs Winery, Annapolis
06/24 – 06/28
$533/nighttotal: $2132 (4 )
Mins To Downtown In Waterfront Community At Pet-friendly Pinecrest Bungalow
2 4apartment , Annapolis
This Annapolis waterfront Cape Cod-style cottage is located in a peaceful neighborhood, 2.5 miles from Downtown Annapolis and 3 miles from the U.S. Naval Academy, offering easy access to major attractions.
The three-bedroom, two-bathroom home sleeps up to eight guests, features a fully equipped kitchen, outdoor patio with fire pit and grill, high-speed internet, smart TVs, and is pet-friendly (with a non-refundable deposit); nearby amenities include a community park with Chesapeake Bay views, a beach, boat ramp, and kayak rack.
The three-bedroom, two-bathroom home sleeps up to eight guests, features a fully equipped kitchen, outdoor patio with fire pit and grill, high-speed internet, smart TVs, and is pet-friendly (with a non-refundable deposit); nearby amenities include a community park with Chesapeake Bay views, a beach, boat ramp, and kayak rack.

Great Frogs Winery, Annapolis
10/15 – 10/26
$250/nighttotal: $2750 (11 )
Huge Discounts For Stays By The Week And Month! 1st Class Amemities!
2 2apartment , Riva
This apartment is located in a quiet residential neighborhood in Cape St. John, 2.6 miles from Broad Creek Marsh and within 6 miles of major tourist attractions in Riva, including Annapolis Harbour Center and The Kunta Kinte Alex Haley Memorial. It has excellent user, location and cleanliness ratings.
The apartment has two bedrooms, one bathroom, and can accommodate up to four guests. It is fully equipped with a kitchen, air conditioning, and a private balcony. Guests also have access to a garden and barbecue grills for outdoor grilling and entertainment.
The apartment has two bedrooms, one bathroom, and can accommodate up to four guests. It is fully equipped with a kitchen, air conditioning, and a private balcony. Guests also have access to a garden and barbecue grills for outdoor grilling and entertainment.

Great Frogs Winery, Annapolis
06/24 – 06/28
$607/nighttotal: $2428 (4 )
Ahoy! Game Room, Screened Porch, Yard Mins To Dta
1 4apartment , Annapolis
This Annapolis yacht rental, located 2.5 miles from Historic Downtown Annapolis and 3 miles from the U.S. Naval Academy in a quiet neighborhood, offers convenient access to Capital SUP, Ellen Moyer Park, and the Annapolis Maritime Museum.
Sleeping nine guests across three bedrooms and a queen sleeper sofa, this vessel boasts a fully equipped kitchen, spacious patio, basement entertainment room with games, and is pet-friendly.
Sleeping nine guests across three bedrooms and a queen sleeper sofa, this vessel boasts a fully equipped kitchen, spacious patio, basement entertainment room with games, and is pet-friendly.

Great Frogs Winery, Annapolis
06/24 – 06/28
$1042/nighttotal: $4168 (4 )
The Naval Nook 1.3 Mi. From Downtown Annapolis
1 4apartment , Annapolis
This 3-bedroom apartment is located just outside of Downtown Annapolis, a short 4-minute Uber ride from the city's attractions. The apartment has received excellent ratings for location, cleanliness, and user experience, making it a great choice for travelers.
The spacious apartment has 2 bathrooms and can comfortably accommodate up to 6 guests. The apartment is equipped with modern amenities, including high-speed internet, a fully equipped kitchen, a sunroom, and a backyard with outdoor dining.
The spacious apartment has 2 bathrooms and can comfortably accommodate up to 6 guests. The apartment is equipped with modern amenities, including high-speed internet, a fully equipped kitchen, a sunroom, and a backyard with outdoor dining.













