Places to stay in Annapolis, MD

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Annapolis, MD place to stay
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856 Best places to stay in Annapolis, MD

Historic Annapolis~new Interior~5+ Parking Spaces~ - Annapolis, MD
9.9 47 reviews
Annapolis, MD
07/08 – 09/08
SG$1978/nighttotal: SG$3956 (2 )

Historic Annapolis~new Interior~5+ Parking Spaces~

6 12
apartment, Annapolis
The Thomas Hyde House, a six-bedroom property in Annapolis' city centre, offers exceptional proximity to Main Street and City Dock, providing stunning views of the Maryland State House.
This large house sleeps twelve guests and boasts four bathrooms, a fully equipped kitchen including a fridge, microwave, and dishwasher, air conditioning, on-site parking (a rare find downtown), and excellent guest reviews.
Fabulous 5-bedroom House With Ac In Charming Annapolis - Annapolis, MD
8.6 4 reviews
Annapolis, MD
04/07 – 05/07
SG$966/nightfor 1 night

Fabulous 5-bedroom House With Ac In Charming Annapolis

5 2
apartment, Annapolis
This property is a spacious five-bedroom house located in Annapolis, a mere 5-minute drive from the city centre and the Naval Academy, with a bus stop directly opposite for convenient travel.
This detached house accommodates up to ten guests and offers a microwave oven, dishwasher, and air conditioning, with parking available, whilst being a short drive from the Navy-Marine Corps Memorial Stadium and close to Jonas Green State Park for outdoor pursuits.
Stay Aboard The S/v My Studio On Annapolis Harbor - Annapolis, MD
9.9 411 reviews
Annapolis, MD
31/07 – 02/08
SG$431/nighttotal: SG$862 (2 )

Stay Aboard The S/v My Studio On Annapolis Harbor

2 4
boat, Annapolis
This sailboat is docked in a marina in Annapolis, just a short walk from the historic downtown and the Naval Academy. The marina is well-maintained and offers a peaceful setting, perfect for a relaxing getaway. The boat itself has received excellent ratings for cleanliness, location and user experience.
The vessel features two bedrooms, one bathroom and can accommodate up to four guests. Amenities include a kitchen with a fridge and microwave, air conditioning, a garden, parking, and internet access. Guests can also enjoy private sailing cruises on the Chesapeake Bay (weather permitting) and relax in the cozy cockpit.
Cozy Stay In Downtown Naptown - Annapolis, MD
9.8 22 reviews
Annapolis, MD
28/06 – 30/06
SG$559/nighttotal: SG$1118 (2 )

Cozy Stay In Downtown Naptown

3 4
apartment, Annapolis
This Annapolis apartment is centrally located, within easy walking distance of Annapolis's city centre, the United States Naval Academy, and the waterfront.
The three-bedroom, two-bathroom property sleeps eight guests and boasts a full kitchen, fast Wi-Fi, and private outdoor space; nearby attractions include shops, restaurants, and numerous historical sites.
East Street Retreat - Annapolis, MD
10 58 reviews
Annapolis, MD
11/09 – 19/09
SG$446/nighttotal: SG$3568 (8 )

East Street Retreat

1 4
apartment, Annapolis
This East Street apartment is centrally located in Annapolis' Historic District, within walking distance of the United States Naval Academy and City Dock.
The two-bedroom, 1.5-bathroom property boasts an open-plan layout, a private rooftop deck with city views, in-unit laundry, and a kitchen equipped with a fridge, freezer, microwave, and dishwasher; it comfortably sleeps four guests.
Downtown Row Home | Walk To City Dock - Annapolis, MD
10 10 reviews
Annapolis, MD
29/08 – 04/09
SG$509/nighttotal: SG$3054 (6 )

Downtown Row Home | Walk To City Dock

1 2
apartment, Annapolis
This historic row home, situated on Prince George Street, offers prime access within 100 metres of the Naval Academy's Gate 1, City Dock, and Main Street in Annapolis.
This renovated three-level property accommodates up to six guests, featuring two bedrooms, a loft with a daybed, a modern kitchen, a fenced patio, and a balcony with views of the State House, all within walking distance of Annapolis's restaurants and waterfront attractions.
Townhouse - 1 Mile From Downtown Strip - Annapolis, MD
9.8 242 reviews
Annapolis, MD
28/06 – 30/06
SG$514/nighttotal: SG$1028 (2 )

Townhouse - 1 Mile From Downtown Strip

3 4
house, Annapolis
This three-bedroom townhouse is conveniently located in the heart of Annapolis, just a short distance from the city's main attractions and the bustling downtown area. The property has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
The accommodation offers ample space for up to six guests, with three well-appointed bathrooms. It comes equipped with a fully stocked kitchen, including two ovens, a dishwasher, and a variety of cooking utensils, as well as a comfortable pull-out sofa on the first floor. Guests can enjoy a private garden, a fitness centre, and the added convenience of keypad entry.
Prime Eastport Location - Waterfront Condo With Parking - Annapolis, MD
10 27 reviews
Annapolis, MD
25/06 – 28/06
SG$863/nighttotal: SG$2589 (3 )

Prime Eastport Location - Waterfront Condo With Parking

2 2
apartment, Annapolis
This Annapolis apartment, situated in Eastport, is less than 2km from Spa Creek and the United States Naval Academy, offering easy access to the Kunta Kinte-Alex Haley Memorial and Maynard-Burgess House within a 15-minute drive.
The three-bedroom, two-bathroom property sleeps seven guests and includes a full kitchen, terrace, free Wi-Fi, on-site parking, and swimming pool access; nearby attractions include the Naval Academy and the Chesapeake Bay.
Restful And Charming Home In Eastport\n - Annapolis, MD
Annapolis, MD
25/06 – 28/06
SG$569/nighttotal: SG$1707 (3 )

Restful And Charming Home In Eastport\n

3 2
apartment, Annapolis
This three-bedroom apartment in Eastport, Annapolis, is just a short distance from the historic downtown and the US Naval Academy, making it a great base for exploring the city. The area is quiet and residential, offering a peaceful retreat after a day of sightseeing.
The apartment comfortably accommodates six guests and includes a fully equipped kitchen, a spacious living area, and a private terrace with a fire pit. Guests can enjoy the on-site spa, the garden, and the convenience of a washer and dryer in the basement.
Historic Downtown Annapolis Union House With Private Patio & Free Off-site Parking - Annapolis, MD
10 31 reviews
Annapolis, MD
25/06 – 28/06
SG$1002/nighttotal: SG$3006 (3 )

Historic Downtown Annapolis Union House With Private Patio & Free Off-site Parking

3 2
apartment, Annapolis
This three-bedroom apartment is situated in the historic district of Annapolis, a short walk from the city's main street, the waterfront, and the United States Naval Academy.
The 118 square metre property boasts a gourmet kitchen, spa-like bathrooms, and a private patio with a gas grill, ideal for families or groups of up to six guests.
Walk To Dock Usna Stadium- Renovated 2br Downtown - Annapolis, MD
9.7 72 reviews
Annapolis, MD
31/07 – 02/08
SG$510/nighttotal: SG$1020 (2 )

Walk To Dock Usna Stadium- Renovated 2br Downtown

1 4
house, Annapolis
This centrally located Annapolis townhouse is less than 1.6km from the United States Naval Academy and the Navy-Marine Corps Memorial Stadium, offering easy walking access to Main Street and City Dock.
The two-bedroom, 1.5-bathroom property sleeps five guests and features a fully equipped kitchen, jacuzzi, garden, free high-speed internet, and in-home amenities such as a foosball table and a full-size washer/dryer; optional chef services and massages are also available.
Secluded Cottage_ A+ Amenities In Historic Dwntwn - Annapolis, MD
9.9 221 reviews
Annapolis, MD
12/07 – 13/07
SG$837/nightfor 1 night

Secluded Cottage_ A+ Amenities In Historic Dwntwn

2 2
apartment, Annapolis
This charming cottage is located in Annapolis' historic Cornhill district, just a short walk from the State House and the city centre, offering a peaceful retreat in a vibrant area. It has received excellent ratings for location, cleanliness and overall experience.
The cottage has a spacious open-plan layout, comfortably accommodating up to eight guests. The well-equipped kitchen is perfect for preparing meals, and the private laundry, garden and air conditioning add to the comfort of your stay.

Best Annapolis, MD lodgings with a pool

Among the 856 accommodations in Annapolis, MD, here are the 4 best ones with a pool

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. - Annapolis, MD
Annapolis, MD
29/06 – 01/07
SG$1058/nighttotal: SG$2116 (2 )

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.

1 4
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.
2026 Commissioning Week Promo: Book 6 Nights, Get The 7th Free - Annapolis, MD
10 2 reviews
Annapolis, MD
29/06 – 01/07
SG$787/nighttotal: SG$1574 (2 )

2026 Commissioning Week Promo: Book 6 Nights, Get The 7th Free

2 4
apartment, Annapolis
This Eastport condominium provides waterfront accommodation on Spa Creek, situated 800 meters from downtown Annapolis and a 15-minute walk to the U.S. Naval Academy.
This two-bedroom flat accommodates up to five guests and features a private furnished balcony with sweeping views of Spa Creek and historic Annapolis, alongside access to a seasonal waterfront swimming pool and high-speed Wi-Fi.
Luxury Rooftop Pool & Dock Steps To Downtown - Annapolis, MD
10 1 review
Annapolis, MD
29/06 – 01/07
SG$771/nighttotal: SG$1542 (2 )

Luxury Rooftop Pool & Dock Steps To Downtown

2 4
house, Annapolis
This luxury condominium in Annapolis is located a 13-minute walk from Annapolis Harbour and 41.8 kilometres from Baltimore's Inner Harbour.
This air-conditioned holiday home offers 49 square metres of living space with two bedrooms, accommodating up to seven guests, and features a rooftop pool with sea views, private dock access, a well-equipped kitchen, and a fireplace.
Spa Creek Condo | Pool, Deck & Parking - Annapolis, MD
10 8 reviews
Annapolis, MD
17/09 – 22/09
SG$506/nighttotal: SG$2530 (5 )

Spa Creek Condo | Pool, Deck & Parking

1 1
apartment, Annapolis
This Eastport condo provides waterfront living on Spa Creek, a mere 500-metre walk from Downtown Annapolis and the US Naval Academy.
This one-bedroom flat, accommodating up to four guests, features a fully equipped kitchen, air conditioning, a swimming pool, garden, and parking for two vehicles, with a covered deck offering direct Spa Creek views and seasonal access to a shared dock.

Best family friendly Annapolis, MD lodging

Among the 856 accommodations in Annapolis, MD, here are the 4 best for families

Hot Tub Time Machine - Family Friendly Staycation! - Annapolis, MD
9.9 20 reviews
Annapolis, MD
25/06 – 25/07
SG$1014/nighttotal: SG$30420 (30 )

Hot Tub Time Machine - Family Friendly Staycation!

3 2
house, Annapolis
This family-friendly house in Annapolis is situated just a short distance from grocery stores and discount retailers, making it a convenient base for exploring the city. The property consistently receives excellent ratings for its cleanliness, location, and overall experience.
The house is spread across multiple levels, offering privacy and comfort for up to eight guests. It features a range of amenities, including a swimming pool, a jacuzzi, a garden, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay for families.
Luxe Row Home Steps To Usna Gate 3! - Annapolis, MD
10 11 reviews
Annapolis, MD
29/06 – 01/07
SG$529/nighttotal: SG$1058 (2 )

Luxe Row Home Steps To Usna Gate 3!

3 4
house, Naval Academy
This historic Greek Revival residence offers an exceptional location directly opposite the U.S. Naval Academy, just 100 metres from the Navy Chapel and Gate 3, providing central access to downtown Annapolis.
This pet-friendly townhouse accommodates up to eight guests and features three bedrooms, three bathrooms, air conditioning, a well-equipped kitchen with a dishwasher, and a private garden patio, ideal for families visiting the Naval Academy.
Beachfront Home Minutes To Downtown Annapolis Dogs Ok - Annapolis, MD
9.8 41 reviews
Annapolis, MD
29/08 – 04/09
SG$1404/nighttotal: SG$8424 (6 )

Beachfront Home Minutes To Downtown Annapolis Dogs Ok

3 2
cottage, Annapolis
This charming cottage is located just 4 km from downtown Annapolis and 4.5 km from the US Naval Academy, offering a peaceful escape close to the city's attractions. It has received excellent guest reviews, making it a popular choice for travellers seeking a comfortable and well-equipped stay.
The cottage comfortably sleeps 8 guests and features 3 bedrooms and 2 bathrooms, providing ample space for families or groups. Enjoy the private beach with direct bay access, a gourmet kitchen, a spacious garden, and a range of amenities including paddle boards, life jackets, and a barbecue grill.
Moose’s Happy Place - Annapolis, MD
10 113 reviews
Annapolis, MD
06/11 – 08/11
SG$1218/nighttotal: SG$2436 (2 )

Moose’s Happy Place

1 2
house, Annapolis
This newly built house is located on the Eastport Peninsula, just a short walk from the Severn River, Spa Creek, and downtown Annapolis. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property offers three bedrooms and three bathrooms, accommodating up to eight guests. It is equipped with all the necessary amenities for a comfortable stay, including a fully equipped kitchen, air conditioning, a garden, parking, and internet access.

Frequently asked questions about accommodations in Annapolis, MD

  • What are the top attractions and must-see sites in Annapolis, MD?

    Annapolis is packed with historical sites! You've got the iconic Maryland State House, the oldest state capitol still in use in the US, and the US Naval Academy, where you can wander around and maybe catch a midshipman parade. Then there's the Annapolis Maritime Museum, which is great for learning about the city's maritime history, and of course, the charming shops and restaurants along the harbour.
  • What are the best accommodations in Annapolis, MD?

    Among the accommodations in Annapolis, MD, Step Out To Main Street From A Chic Loft, Graduate By Hilton Annapolis and Modern Apartment Over The Heart Of Main Street are the most popular ones.

  • What are the most convenient modes of transportation within Annapolis, MD?

    Annapolis is a very walkable city, so you can easily explore the downtown area on foot. If you're planning to venture further afield, the Annapolis Circulator bus system is a great option. It runs on a loop, connecting key areas like the harbour, the Naval Academy, and the historic district. Taxis are also readily available, and you can even rent a bike to explore the city at your own pace.
  • What are the best accommodations with a pool in Annapolis, MD?

  • What outdoor activities and adventures are popular in and around Annapolis, MD?

    Annapolis is surrounded by beautiful waterways, making it a great spot for water sports. You can rent a kayak or canoe and explore the harbour, go sailing in the Chesapeake Bay, or even take a scenic cruise. For those who prefer to stay on land, the scenic trails around the city are perfect for hiking, biking, and birdwatching. The Anne Arundel County Recreation and Parks Department offers a variety of outdoor activities, including fishing, boating, and camping.
  • What are the best accommodations with a jacuzzi in Annapolis, MD?

  • What types of accommodations are available in Annapolis, MD?

    You've got plenty of options when it comes to accommodation in Annapolis. There are charming bed and breakfasts tucked away in historic neighbourhoods, modern hotels near the harbour, and even some waterfront resorts. If you're looking for something more budget-friendly, there are also some motels and vacation rentals scattered around the city.
  • What are the best accommodations for families and kids in Annapolis, MD?

  • When is the best time to visit Annapolis, MD?

    The best time to visit Annapolis is during the spring or autumn, when the weather is mild and the crowds are smaller. The summer months can be hot and humid, but they're perfect for enjoying the waterfront activities. If you're a fan of winter festivities, you can visit during the holiday season and experience the city's festive atmosphere.
  • What are the best pet friendly accommodations in Annapolis, MD?

  • What local dishes and culinary experiences are a must-try in Annapolis, MD?

    You absolutely must try the Chesapeake Bay blue crabs, steamed and served with Old Bay seasoning. They're a local delicacy! For a more casual dining experience, head to one of the many seafood restaurants along the harbour. You can find everything from fresh oysters and clams to delicious crab cakes. Don't forget to try the local craft beers and wines, too.
  • What are the best accommodations with parking in Annapolis, MD?

    Graduate By Hilton Annapolis, Springhill Suites By Marriott Annapolis and Historic Inns Of Annapolis are the best accommodations with parking in Annapolis, MD.

  • In which part of Annapolis, MD should you consider renting accommodation?

    If you want to be in the heart of the action, staying in the downtown area near the harbour is a great choice. You'll be within walking distance of all the major attractions, restaurants, and shops. For a more peaceful and secluded experience, you can consider renting a room in a bed and breakfast in one of the historic neighbourhoods. If you're travelling with a family, you might prefer a hotel or resort near the waterfront.

Destinations nearby

Best Annapolis, MD accommodations with a balcony

Stadium-side Annapolis | Chef Kitchen | Sleeps 10 - Annapolis, MD
10 10 reviews
Annapolis, MD
29/08 – 04/09
SG$905/nighttotal: SG$5430 (6 )

Stadium-side Annapolis | Chef Kitchen | Sleeps 10

3 2
apartment, Annapolis
This spacious Annapolis townhouse, ideally situated near the U.S. Naval Academy (two miles away) and Navy-Marine Corps Memorial Stadium, offers easy access to Heineman Park and Harts Cove.
The 223 square metre property boasts four bedrooms, four bathrooms, and sleeps up to ten guests, featuring a chef's kitchen with GE Café appliances, a finished basement, and access to a community pool; kayaking and paddle boarding are readily available at Harts Cove.
2026 Commissioning Week Promo: Book 6 Nights, Get The 7th Free - Annapolis, MD
10 113 reviews
Annapolis, MD
29/08 – 04/09
SG$1040/nighttotal: SG$6240 (6 )

2026 Commissioning Week Promo: Book 6 Nights, Get The 7th Free

2 2
apartment, Annapolis
This holiday home is located in Eastport, Annapolis, within a 1.6km walk of the Annapolis Maritime Museum, U.S. Naval Academy, and Spa Creek, making it ideal for exploring the city's attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
The 223 square metre home can accommodate up to 8 guests in its three bedrooms and has a sofa bed. Guests can enjoy a range of amenities, including a garden, a spa, a terrace, and a barbecue.
Downtown Furnished Apartment - Walking Distance To Restaurants - Annapolis, MD
10 10 reviews
Annapolis, MD
25/06 – 28/06
SG$484/nighttotal: SG$1452 (3 )

Downtown Furnished Apartment - Walking Distance To Restaurants

1 2
apartment, Annapolis
This smoke-free flat is located in Annapolis' Historic District, just under a kilometre from the Maynard-Burgess House and the U.S. Naval Academy, and within 500 metres of the Ellen O. Moyer Nature Park and the Maryland Federation of Art. It has received excellent reviews from previous guests.
This comfortable apartment can accommodate up to four guests and features a fully-equipped kitchen, a terrace, and a garden. You can enjoy stunning city views from the rooftop terrace and explore the nearby art galleries and nature parks.
Cute And Close To Downtown! Off Street Parking W/ Short Walk To Academy/stadium - Annapolis, MD
9.2 17 reviews
Annapolis, MD
11/09 – 19/09
SG$409/nighttotal: SG$3272 (8 )

Cute And Close To Downtown! Off Street Parking W/ Short Walk To Academy/stadium

2 4
apartment, Annapolis
This Annapolis Historic District property is less than 1.6km from Peters Cove and the United States Naval Academy, and within a 10-minute walk of Stanton School & Community Centre and the First Baptist Church.
The two-bedroom, two-bathroom house sleeps six guests and boasts a fully equipped kitchen, private balcony, free Wi-Fi, and parking; charcoal grills are available for outdoor cooking.

Best Annapolis, MD accommodations with a kitchen

Chic Renovation On Fleet Street - Annapolis, MD
9.7 102 reviews
Annapolis, MD
29/06 – 01/07
SG$477/nighttotal: SG$954 (2 )

Chic Renovation On Fleet Street

2 4
apartment, Annapolis
This stylish Annapolis city house, situated in the downtown area, offers easy walking access to the United States Naval Academy and the Maryland State House.
The two-bedroom, one-and-a-half-bathroom dwelling boasts a chic open-plan layout, sleeps four guests, includes a fully equipped kitchen with dishwasher, and provides on-site parking at the nearby Hillman City Garage (charges apply).
Cute Bungalow Blocks To Stadium - Annapolis, MD
9.9 67 reviews
Annapolis, MD
29/06 – 01/07
SG$520/nighttotal: SG$1040 (2 )

Cute Bungalow Blocks To Stadium

2 4
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.
Hillsmere Hideaway - Annapolis, MD
9.9 93 reviews
Annapolis, MD
29/08 – 04/09
SG$201/nighttotal: SG$1206 (6 )

Hillsmere Hideaway

1 2
apartment, Annapolis
This Annapolis basement flat is situated in a quiet neighbourhood near Eastport and the city centre, approximately 5 kilometres from the United States Naval Academy.
The self-contained apartment sleeps four, featuring a queen-size bed, a queen-size sofa bed, a fully equipped kitchen, updated bathroom with washer/dryer, private patio with BBQ (seasonal), and off-street parking.
Elegant & Bright Historic Home 3br/2,5ba, 2 Kings, 1 Queen, 5 Min To Usna - Annapolis, MD
10 3 reviews
Annapolis, MD
03/09 – 07/09
SG$1827/nighttotal: SG$7308 (4 )

Elegant & Bright Historic Home 3br/2,5ba, 2 Kings, 1 Queen, 5 Min To Usna

3 2
apartment, Annapolis
This 3-bedroom flat for 7 guests offers an unbeatable location in Annapolis's historic district, a mere 5-minute walk from the US Naval Academy and within 1 minute of the Maryland State House and Annapolis Town Dock.
This 125 square meter residence features a fully equipped kitchen with stainless-steel appliances, a lounge with a fireplace, two king-sized bedrooms, and three bathrooms, with free WiFi and air conditioning provided.
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