What are the must-see attractions for a 2 days stay in Annapolis, MD?

For a two-day trip, you should definitely visit the United States Naval Academy, a beautiful campus with historic buildings and a museum. You can also take a stroll around the Annapolis City Dock, with its charming shops and restaurants. And don't miss the Maryland State House, the oldest state capitol building still in use in the United States.

What are the best apartments in Annapolis, MD?

Among the apartments in Annapolis, MD, Step Out To Main Street From A Chic Loft , Modern Apartment Over The Heart Of Main Street and Brand New Renovation In Historic District With 2 Parking Spots -Walk Everywhere are the most popular ones.

Which neighborhoods in Annapolis, MD are best for renting an apartment?

The best neighbourhoods to find an apartment are probably Downtown Annapolis, close to the City Dock and all the action, or the quieter area of Eastport, which is known for its beautiful waterfront views and charming homes.

What are the best apartments with a pool in Annapolis, MD?

Directly Across From Usna Gate One & Steps From The Waterfront And Main Street , Beautiful Condo - Water View Near City Dock and Your Annapolis Adventure Starts Here are the best apartments with a pool in Annapolis, MD.

What are the top cultural and historical sites in Annapolis, MD?

Annapolis is steeped in history, so you'll find plenty of cultural and historical sites. The William Paca House and Garden is a beautiful 18th-century home that gives a glimpse into the life of a wealthy colonial family. And of course, the United States Naval Academy is a must-see for any history buff, with its impressive buildings and museum.

What are the best apartments with a jacuzzi in Annapolis, MD?

The best apartments with a jacuzzi in Annapolis, MD are Charming Annapolis Waterview Home , Charming Annapolis Victorian and Bay View Studio Apartment .

What makes Annapolis, MD unique or famous?

Annapolis is known for being the capital of Maryland and for its beautiful waterfront location on the Chesapeake Bay. It's also a historic city, with many buildings dating back to the 18th century. And of course, it's home to the United States Naval Academy, which brings a unique atmosphere to the city.

What are the best apartments for families and kids in Annapolis, MD?

The best apartments for families and kids in Annapolis, MD are South River Park Apartment , Athens Of America - Annapolis Apartment One B and Cozy 2br Home W\/ Parking In Downtown Annapolis .

Where can you find the best local markets and street food in Annapolis, MD?

For local markets and street food, head to the Annapolis Farmers Market, held every Saturday from April to November. You'll find fresh produce, local crafts, and delicious food from local vendors. The City Dock also has a number of food stalls and restaurants offering local delicacies.

What are the best pet friendly apartments in Annapolis, MD?

The best pet friendly apartments in Annapolis, MD are Brand New Renovation In Historic District With 2 Parking Spots -Walk Everywhere , Renovated Historic Home Located Downtown With Parking - Walk Everywhere and Directly Across From Usna Gate One & Steps From The Waterfront And Main Street .

How is the public transportation system in Annapolis, MD?

Annapolis has a decent public transportation system, with the Annapolis Area Transit (AAT) providing bus services throughout the city and surrounding areas. However, it's more convenient to get around by car, especially if you want to explore the surrounding areas.

What are the best apartments with parking in Annapolis, MD?

Brand New Renovation In Historic District With 2 Parking Spots -Walk Everywhere , Annapolis Condominium In The Heart Of The Historic Center and Charming Row House In Historic District are the best apartments with parking in Annapolis, MD.

Which seasonal events or festivals should apartment renters look forward to in Annapolis, MD?

Annapolis is a lively city with a calendar packed with events. In the spring, you have the Annapolis Spring Sailboat Show, and in the summer, there's the Annapolis Maritime Festival, a celebration of the city's maritime heritage. In the fall, you can enjoy the Annapolis Wine Festival, and during the winter, there's the Annapolis Christmas Parade.

What amenities are typically included in apartments in Annapolis, MD?

Apartments in Annapolis typically include basic amenities like central heating and air conditioning, a refrigerator, stove, and oven. Some apartments might also offer laundry facilities, parking, and a balcony or patio.

What leisure activities are available for relaxation in Annapolis, MD?

Annapolis offers a variety of leisure activities. You can relax on the beaches of the Chesapeake Bay, take a boat tour, or visit one of the many parks and gardens in the city. For a more active experience, you can go hiking or biking on the scenic trails around the city.

Annapolis, MD Holiday Apartments and Self Catering

9.7 30 reviews

Spacious 5 Br House - 5 Min Walk To N-mc Stadium!

apartment, Annapolis

This Germantown property, two blocks from the Navy-Marine Corps Memorial Stadium and a 13-kilometre drive from the United States Naval Academy, offers convenient access to Annapolis's key attractions.
Sleeping up to 15 guests in five bedrooms (three main bedrooms and two basement rooms with bunk beds), this three-bathroom house features a jacuzzi, full-sized washer/dryer, basement kitchenette, foosball table, fenced yard, and covered porch; pet-friendly (fee applies).

10 4 reviews

Dean Street's Lower Deck House!

apartment, Annapolis

This Annapolis holiday flat is situated in the Historic District, less than 0.8 kilometres from the Banneker-Douglass Museum and ARTFX Gallery.
The one-bedroom, one-bathroom apartment features a fully equipped kitchen with dishwasher and microwave, in-unit laundry, air conditioning, free Wi-Fi, and is within walking distance of Annapolis City Dock and other attractions.

10 41 reviews

The Sail Loft

apartment, Annapolis

This three-bedroom Annapolis apartment, less than 0.16 km from Spa Creek and a 10-minute walk from Annapolis's city centre, offers easy access to all major attractions.
Sleeping eight guests comfortably, the property boasts a huge balcony overlooking Spa Creek, a fully equipped kitchen including a dishwasher, two bathrooms, and access to a shared garden; ideal for families exploring this historic Maryland city.

10 21 reviews

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown And Stadium. Parking!

apartment, Annapolis

This Annapolis holiday home is centrally located, within 1.6km of the US Naval Academy and the Annapolis Civil Rights Plaque, and within a 10-minute drive of Asbury United Methodist Church and People's Brewer Hill Cemetery.
The two-bedroom, one-bathroom property sleeps four guests and boasts a fully equipped kitchen, jacuzzi, private patio, and free Wi-Fi, offering a relaxing retreat with easy access to Annapolis's key attractions.

9.8 17 reviews

Ahoy! Game Room, Screened Porch, Yard Mins To Dta

apartment, Annapolis

This family-friendly Annapolis apartment, situated 4km from Historic Annapolis and Eastport, offers easy access to the US Naval Academy (4.8km), the Annapolis Maritime Museum, and Ellen Moyer Park (walking distance).
Sleeping up to nine guests in three bedrooms, the property boasts a fully equipped kitchen, basement entertainment room with arcade and foosball, a four-season patio, and access to nearby water activities including paddleboarding and kayaking.

10 146 reviews

Perfect Eastport Location, Walk Everywhere

apartment, Annapolis

This two-bedroom flat is located in Eastport, a short walk from downtown Annapolis and its attractions, offering a peaceful atmosphere just a short distance from the city's bustling waterfront. The property has excellent user, location and cleanliness ratings.
The flat has one bathroom and includes a kitchen with a fridge, microwave oven and dishwasher. Guests can enjoy a garden, air conditioning, internet access, parking and are welcome to bring their families.

9.9 29 reviews

Eastport Escape

apartment, Annapolis

This spacious Annapolis duplex in Eastport is within easy walking distance of Annapolis's city centre and the United States Naval Academy.
The three-bedroom, two-bathroom property sleeps seven guests, boasts a private garden, off-street parking, and a fully equipped kitchen including a dishwasher; a master suite soaker tub adds a touch of luxury.

9.8 44 reviews

Naptowns Nauti Flat

apartment, Annapolis

This Annapolis city centre flat is situated two blocks (approximately 0.16 km) from the Annapolis waterfront and within easy walking distance of historic landmarks such as the United States Naval Academy.
The one-bedroom apartment sleeps four guests and includes a fully equipped kitchen with fridge, freezer, and microwave, plus air conditioning, parking, and a garden; nearby attractions include boutique shops and restaurants.

10 22 reviews

Game Days & Family Stays At Dog-friendly Home Near Navy Stadium W Private Fenced-in Yard

apartment, Annapolis

This four-bedroom Annapolis holiday home, situated in the Admiral Heights neighbourhood, is 1.1km from the Navy-Marine Corps Memorial Stadium and 3.2km from both the city centre and the United States Naval Academy.
Sleeping nine guests comfortably, this self-catering property boasts a private garden with fire pit, a fully equipped kitchen with stainless steel appliances, two bathrooms, and parking, all within easy reach of Annapolis's key attractions.

9.4 30 reviews

Spacious Luxe Usna Home - Pool, Hot Tub, Grill

apartment, Annapolis

This seven-bedroom Annapolis property, situated in the Murray Hill district, is less than 1.6km from the US Naval Academy and the Annapolis Civil Rights Plaque.
This smoke-free holiday home boasts 307 square metres of floor space, offering four bathrooms, a fully equipped kitchen, garden, parking and sleeps up to fourteen guests.

10 6 reviews

Pool Loft Suite | Bay Access & Beach Passes

apartment, Arnold

This Cape St. Claire/Broadneck apartment, ten minutes from Annapolis city centre and the United States Naval Academy, offers easy access to shopping and Sandy Point State Park (approx. 24km).
The 65 square metre self-contained flat includes one bedroom, two bathrooms, sleeps four, and boasts a private pool, garden, parking for two cars, and keyless entry; beach passes for the community waterfront area are also provided.

10 20 reviews

Family Oasis|spa Shower|near Usna Stadium & Dta

apartment, Annapolis

Nautical Oasis, a single-storey house in Annapolis, is situated less than 2.4km from the US Naval Academy Stadium, Anne Arundel Medical Center, and Annapolis city centre.
This three-bedroom, two-bathroom property sleeps seven, boasting a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, a private garden with fire pit, and a luxurious spa shower; guests can enjoy the entire house privately.

Best family friendly Annapolis, MD Holiday Apartments and Self Catering Accommodations

Among the 720 accommodations in Annapolis, MD, here are the 4 best family friendly holiday apartments

9.9 77 reviews

Cute Bungalow Blocks To Stadium

apartment, Annapolis

This stylish two-bedroom house is located in Annapolis' Germantown neighbourhood, just 2.4 kilometres from the Navy-Marine Corps Memorial Stadium and an 8-minute drive from the USNA and downtown Annapolis. This property enjoys excellent ratings for location, cleanliness, and user experience.
The house has two bedrooms and one bathroom, accommodating up to six guests. It offers a fully equipped kitchen, a private garden, and a covered outdoor eating area, perfect for enjoying meals al fresco.

9.9 85 reviews

Historic Chapel Views, Steps To Usna Gate 1 W Private Patio & Off-site Parking

apartment, Annapolis

This three-bedroom house is situated in Annapolis' Historic District, within a 1.6 km walk of the US Naval Academy and a 0.8 km walk from the Hammond-Harwood House.
The property offers a spacious 224 square metre living space, perfect for families or groups of up to seven, with a fully equipped kitchen, a patio, and a barbecue grill.

10 1 review

Two Historic Rowhomes In Downtown Annapolis

apartment, Annapolis

This accommodation offers two connected historic row homes in downtown Annapolis, a short 100 metres from the Maryland Federation of Art and the French Soldiers Monument.
This family-friendly property, ideal for up to 12 guests, features four bedrooms, three bathrooms, two kitchens, and a patio, with in-unit laundry and air conditioning provided.

9.9 31 reviews

Historic Row Home | Hot Tub - 1 Block From Gate 1!

apartment, Annapolis

This three-storey house, perfect for families and pets, is situated in central Annapolis, a short walk from the US Naval Academy, St. John's College, and City Dock.
Offering three bedrooms, two bathrooms, sleeping up to nine guests, the property boasts a chef's kitchen, multiple outdoor spaces including a BBQ grill, and is equipped with air conditioning and internet access.

Best Holiday Apartments and Self Catering Accommodations in Annapolis, MD with a pool

Among the 720 accommodations in Annapolis, MD, here are the 4 best apartments with a pool

10 1 review

Luxury Annapolis Condo, Fully Remodeled, Rooftop Pool & Marina, Free Parking, 0.3 Mi To Downtown. Perfect For Navy Games, Academy Visits, Or A Waterfront Getaway.

apartment, Annapolis

This Eastport condominium provides waterfront access near Annapolis marinas and sailing events, situated within walking distance of downtown Annapolis and its dining options, as well as cultural attractions such as the Annapolis Maritime Museum and The Colonial Players.
This one-bedroom condominium accommodates up to four guests, featuring a fully stocked kitchen, a king bedroom with memory foam beds, a luxurious rainfall shower, and two dedicated parking spaces, complemented by a rooftop pool with harbour views.

10 14 reviews

Waterfront 2-bedroom Condo On Spa Creek

apartment, Annapolis

This Annapolis Eastport apartment is less than 1.6km from Spa Creek and the United States Naval Academy, and within a 1.6km radius of Annapolis Harbour and the Kunta Kinte Plaque & Alex Haley Memorial.
This two-bedroom, one-bathroom property sleeps six, offering a fully equipped kitchen, private patio, free Wi-Fi, access to a swimming pool, spa, fitness centre, and parking; nearby attractions include the Naval Academy and Annapolis Harbour.

10 5 reviews

Waterfront Retreat With Pool, Pier And Kayaks

apartment, Riva

This waterside residence in Riva, located on the South River, offers excellent access to historic Annapolis, just a few kilometres away.
This spacious four-bedroom flat accommodates up to nine guests and features a private pool, kayaks, a game room, and a fire pit table, ideal for family holidays with amenities such as a Pack 'n Play and high chair.

10 16 reviews

Pool Loft Suite | Bay Access & Beach Passes

apartment, Arnold

This self-contained apartment in the Cape St. Claire/Broadneck area of Arnold offers easy access to local beaches and is approximately 20 kilometres from Annapolis.
The one-bedroom, one-bathroom property sleeps four, features a fully equipped kitchen with dishwasher, private parking, a shared pool, and a handicap-accessible chair lift.

Frequently asked questions about apartment rentals in Annapolis, MD

What are the must-see attractions for a 2 days stay in Annapolis, MD?
For a two-day trip, you should definitely visit the United States Naval Academy, a beautiful campus with historic buildings and a museum. You can also take a stroll around the Annapolis City Dock, with its charming shops and restaurants. And don't miss the Maryland State House, the oldest state capitol building still in use in the United States.
What are the best apartments in Annapolis, MD?
Among the apartments in Annapolis, MD, Step Out To Main Street From A Chic Loft, Modern Apartment Over The Heart Of Main Street and Brand New Renovation In Historic District With 2 Parking Spots -Walk Everywhere are the most popular ones.
Which neighborhoods in Annapolis, MD are best for renting an apartment?
The best neighbourhoods to find an apartment are probably Downtown Annapolis, close to the City Dock and all the action, or the quieter area of Eastport, which is known for its beautiful waterfront views and charming homes.
What are the best apartments with a pool in Annapolis, MD?
Directly Across From Usna Gate One & Steps From The Waterfront And Main Street, Beautiful Condo - Water View Near City Dock and Your Annapolis Adventure Starts Here are the best apartments with a pool in Annapolis, MD.
What are the top cultural and historical sites in Annapolis, MD?
Annapolis is steeped in history, so you'll find plenty of cultural and historical sites. The William Paca House and Garden is a beautiful 18th-century home that gives a glimpse into the life of a wealthy colonial family. And of course, the United States Naval Academy is a must-see for any history buff, with its impressive buildings and museum.
What are the best apartments with a jacuzzi in Annapolis, MD?
The best apartments with a jacuzzi in Annapolis, MD are Charming Annapolis Waterview Home, Charming Annapolis Victorian and Bay View Studio Apartment.
What makes Annapolis, MD unique or famous?
Annapolis is known for being the capital of Maryland and for its beautiful waterfront location on the Chesapeake Bay. It's also a historic city, with many buildings dating back to the 18th century. And of course, it's home to the United States Naval Academy, which brings a unique atmosphere to the city.
What are the best apartments for families and kids in Annapolis, MD?
The best apartments for families and kids in Annapolis, MD are South River Park Apartment, Athens Of America - Annapolis Apartment One B and Cozy 2br Home W\/ Parking In Downtown Annapolis.
Where can you find the best local markets and street food in Annapolis, MD?
For local markets and street food, head to the Annapolis Farmers Market, held every Saturday from April to November. You'll find fresh produce, local crafts, and delicious food from local vendors. The City Dock also has a number of food stalls and restaurants offering local delicacies.
What are the best pet friendly apartments in Annapolis, MD?
The best pet friendly apartments in Annapolis, MD are Brand New Renovation In Historic District With 2 Parking Spots -Walk Everywhere, Renovated Historic Home Located Downtown With Parking - Walk Everywhere and Directly Across From Usna Gate One & Steps From The Waterfront And Main Street.
How is the public transportation system in Annapolis, MD?
Annapolis has a decent public transportation system, with the Annapolis Area Transit (AAT) providing bus services throughout the city and surrounding areas. However, it's more convenient to get around by car, especially if you want to explore the surrounding areas.
What are the best apartments with parking in Annapolis, MD?
Brand New Renovation In Historic District With 2 Parking Spots -Walk Everywhere, Annapolis Condominium In The Heart Of The Historic Center and Charming Row House In Historic District are the best apartments with parking in Annapolis, MD.
Which seasonal events or festivals should apartment renters look forward to in Annapolis, MD?
Annapolis is a lively city with a calendar packed with events. In the spring, you have the Annapolis Spring Sailboat Show, and in the summer, there's the Annapolis Maritime Festival, a celebration of the city's maritime heritage. In the fall, you can enjoy the Annapolis Wine Festival, and during the winter, there's the Annapolis Christmas Parade.
What amenities are typically included in apartments in Annapolis, MD?
Apartments in Annapolis typically include basic amenities like central heating and air conditioning, a refrigerator, stove, and oven. Some apartments might also offer laundry facilities, parking, and a balcony or patio.
What leisure activities are available for relaxation in Annapolis, MD?
Annapolis offers a variety of leisure activities. You can relax on the beaches of the Chesapeake Bay, take a boat tour, or visit one of the many parks and gardens in the city. For a more active experience, you can go hiking or biking on the scenic trails around the city.

Popular destinations

Best Annapolis, MD holiday apartments with air conditioning

9.9 32 reviews

Upscale Condo In Annapolis W/private Parking

apartment, Annapolis

This Annapolis flat, located on West Street, offers excellent access to the Annapolis City Marina, the Maryland State House, and the Annapolis City Dock, placing you within easy reach of key historical sites and waterfront attractions.
This well-appointed condo accommodates up to six guests across two bedrooms and two bathrooms, featuring a private furnished balcony and modern amenities, with a dishwasher and air conditioning ensuring a comfortable stay.

10 21 reviews

Historic Annapolis Home | 2 Blocks To Main St

apartment, Annapolis

This Annapolis holiday home is situated in the Historic District, within a 0.9km walk of the US Naval Academy and Maynard-Burgess House, and under 0.5km from the Maryland Federation of Art and Ellen O Moyer Nature Park.
The 1174 square metre property boasts four bedrooms, two bathrooms, sleeps nine guests, and includes a fully equipped kitchen, private garden, terrace, free Wi-Fi, and barbecue facilities.

9.7 4 reviews

The Pool Loft At Poplar Hill

apartment, Arnold

The Pool Loft at Poplar Hill, a one-bedroom apartment in Annapolis, Maryland, is situated 14.8 km from Annapolis Harbour and 41.8 km from Baltimore's Inner Harbour and Camden Yards.
This 65 square metre flat sleeps seven guests and offers amenities including a fully equipped kitchen with dishwasher, a swimming pool, garden, parking, and free Wi-Fi.

10 1 review

South River Waterfront | Pier, Hot Tub & Elevator

apartment, Riva

This three-storey waterfront property in Edgewater, Annapolis, Maryland, offers convenient access to South River Golf Links and Annapolis, with Washington D.C. also easily reachable by public transport or ride-sharing services.
This luxurious 279 square metre residence boasts three bedrooms, five bathrooms, a jacuzzi, private pier, and multiple terraces offering captivating river views, accommodating up to eight guests and including a gourmet kitchen, elevator, and integrated sound system.

Best pet-friendly Annapolis, MD holiday apartments

Among the 720 accommodations in Annapolis, MD, here are the 4 best pet friendly holiday apartments

No reviews

Mins To Downtown In Waterfront Community At Pet-friendly Pinecrest Bungalow

apartment, Annapolis

This Annapolis waterfront property is situated within a 2.4km walk of the Bay Bridge Market Place Shopping Centre and Maryland Quiet Waters Park, and under 1.6km from Historic Mount Moriah AME Church and the Historical Society of Talbot County.
This four-bedroom, two-bathroom holiday home sleeps eight guests and boasts a spa, fitness centre, garden, terrace, and parking, plus an arcade/game room and barbecue facilities.

10 256 reviews

Directly Across From Usna Gate One & Steps From The Waterfront And Main Street!

apartment, Annapolis

This apartment is located in downtown Annapolis, just a short walk from the US Naval Academy Main Gate and the Annapolis Harbour, making it ideal for exploring the city's historic charm. The property has received excellent user ratings, making it a popular choice for travellers.
The three-bedroom apartment, spanning 111 square metres, comfortably accommodates eight guests. The apartment offers a range of amenities including a fully equipped kitchen, a private courtyard, parking, and access to a spa, ensuring a relaxing and enjoyable stay.

10 131 reviews

Cute Downtwn Townhouse Onsite Parking & Patio!

apartment, Annapolis

This Annapolis townhome, situated in the President's Hill neighbourhood, is a short walk from West Street and approximately 1.6km from the United States Naval Academy and stadium.
The newly renovated two-bedroom property, sleeping up to six guests with a queen sleeper sofa, offers on-site laundry, a private patio, shared gas grill, and firepit, plus off-street parking for two cars.

10 12 reviews

The General's House-spacious Home W/pool & Hot Tub

apartment, Crownsville

This four-bedroom, four-bathroom holiday home in Crownsville offers a resort-style backyard with a private pool and hot tub, a dedicated home theatre, and a recreation room with games and a billiard table, providing ample space and entertainment for up to 14 guests. Located approximately 10-16 kilometres from the Maryland Renaissance Festival and Helen Avalynne Tawes Garden, this spacious property is also conveniently situated within a 10-15 minute drive of Eisenhower Golf Course and Annapolis Bowl, ensuring easy access to local attractions and amenities.

Best apartment offers in Annapolis, MD

720 Holiday apartments Annapolis, MD