Places to stay in Annapolis, MD

1103 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Annapolis, MD place to stay
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

1103 Best places to stay in Annapolis, MD

Best Annapolis, MD lodgings with a pool

Among the 1103 accommodations in Annapolis, MD, here are the 4 best ones with a pool

Captains Quarters Waterfront & Pool - Annapolis, MD
No reviews

Captains Quarters Waterfront & Pool

house, Annapolis
Captains Quarters Waterfront & Pool offers a waterside dwelling in Annapolis, located a short 13-minute walk to Annapolis Harbour and a considerable distance from Baltimore landmarks.
This two-bedroom property, spanning 60 square metres, accommodates up to seven guests and features a private outdoor swimming pool, a fully equipped kitchen, air conditioning, a fireplace, and free private parking.
Spacious Luxe Usna Home - Pool, Hot Tub, Grill - Annapolis, MD
9.8 89 reviews

Spacious Luxe Usna Home - Pool, Hot Tub, Grill

apartment, Annapolis
This five-bedroom Annapolis house, a short walk from the United States Naval Academy and Main and West Streets' restaurants, offers convenient access to Annapolis's key attractions.
Sleeping fourteen guests, this spacious three-storey property boasts five bathrooms, a fully equipped kitchen including a dishwasher, and a gas grill; nearby parking is available.
Great Location On Spa Creek - Annapolis, MD
9.7 235 reviews

Great Location On Spa Creek

apartment, Annapolis
This one-bedroom apartment is conveniently located in Eastport, Annapolis, within walking distance of Spa Creek and the US Naval Academy. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The 57 square metre apartment comfortably accommodates up to four guests. The apartment offers a range of amenities, including a private pool, access to a water park and outdoor pool, a fully equipped kitchen, a terrace, a garden, a spa, parking, and internet access.
Sailboat Experience In Annapolis - Annapolis, MD
8.8 5 reviews

Sailboat Experience In Annapolis

boat, Annapolis
This Annapolis sailboat, a 10-minute walk from Annapolis Harbour, is situated 49.9 kilometres from Carroll Park and 35.4 kilometres from Baltimore-Washington International Thurgood Marshall Airport.
This 150-square-metre vessel offers one bedroom, one bathroom, sleeps four guests, and boasts a fully equipped kitchen, air conditioning, Wi-Fi, and a seasonal outdoor pool; enjoy nearby sailing and explore Annapolis's historic waterfront.

Best family friendly Annapolis, MD lodging

Among the 1103 accommodations in Annapolis, MD, here are the 4 best for families

Dog-friendly Annapolis Apartment | Parking, Private Backyard & Walkable To Shops And Restaurants - Annapolis, MD
10 9 reviews

Dog-friendly Annapolis Apartment | Parking, Private Backyard & Walkable To Shops And Restaurants

apartment, Annapolis
This Eastport flat in Annapolis is situated less than 1.6km from the United States Naval Academy, offering easy access to this historic landmark.
The self-catering apartment, sleeping up to four adults in a king-size bedroom and a queen-size cot, boasts a private fenced backyard, full kitchen, washer/dryer, high-speed internet, and keyless entry; one to two driveway parking spaces are also available.
Secluded Cozy Cottage In Historic Downtown - Annapolis, MD
9.6 22 reviews

Secluded Cozy Cottage In Historic Downtown

cottage, Annapolis
This charming cottage is located in Annapolis' Historic District, just a short walk from the City Dock and within easy reach of the State House and other key landmarks. The cottage is situated in a quiet neighbourhood, offering a peaceful retreat from the bustling city centre.
The cottage is a spacious two-bedroom property that can comfortably accommodate up to eight guests. It features a modern kitchen, a private patio with a BBQ, and a comfortable living area with an electric fireplace, a 55" Roku TV, and a full daybed.
Annapolis Charm Bright 3br In Downtown - Annapolis, MD
9.8 26 reviews

Annapolis Charm Bright 3br In Downtown

apartment, Annapolis
This Annapolis holiday home is situated near Brewer Hill, a 10-minute walk from People's Brewer Hill Cemetery and Maryland Hall for Creative Arts, and 2.7 kilometres from the United States Naval Academy.
The three-bedroom property sleeps eight guests, offering a fully equipped kitchen, private patio, free Wi-Fi, and parking; nearby attractions include the Ballet Theatre of Maryland.
Cozy 2br Home W/ Parking In Downtown Annapolis - Annapolis, MD
9.8 448 reviews

Cozy 2br Home W/ Parking In Downtown Annapolis

apartment, Annapolis
This charming house is situated in Annapolis' Historic District, just a short walk from Spa Creek and the US Naval Academy, placing you in the heart of the city's rich history and culture. It has consistently received excellent ratings for user experience, location, and cleanliness.
The property offers two bedrooms, a sofa bed, and 84 square meters of space, comfortably accommodating up to six guests. The house boasts a fully equipped kitchen, a private garden, a spa, and free Wi-Fi, ensuring a relaxing and enjoyable stay.

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.

Popular destinations

Best Annapolis, MD accommodations with a balcony

Cozy 3br Annapolis Sleeps 6 Private Deck, Parking - Annapolis, MD
No reviews

Cozy 3br Annapolis Sleeps 6 Private Deck, Parking

house, Annapolis
This Annapolis property is located 2.2 kilometres from Sparrows Beach and 4.8 kilometres from Annapolis Harbour, offering convenient access to local attractions.
This holiday home, spanning 6 square metres, accommodates up to 10 guests and features air conditioning, free WiFi, a fully equipped kitchen with a dishwasher and oven, a private deck, and free private parking.
Spacious Historic Home Downtown Annapolis Main St. Book For Commissioning Week! - Annapolis, MD
9.2 25 reviews

Spacious Historic Home Downtown Annapolis Main St. Book For Commissioning Week!

apartment, Annapolis
This historic dwelling is located in the heart of Annapolis' Historic District, just a short walk from City Dock, the US Naval Academy, and Main Street, offering easy access to the city's attractions and amenities. The apartment has received excellent user ratings, reflecting its high standard of comfort and service.
The spacious home features six bedrooms, five bathrooms, and can accommodate up to 16 guests, spanning a generous 353 square metres. Amenities include a fully equipped kitchen, a spa, air conditioning, and a private patio, offering a comfortable and enjoyable stay for families and groups.
Hidden Wine Cellar Eastport Retreat - Annapolis, MD
No reviews

Hidden Wine Cellar Eastport Retreat

house, Annapolis
Hidden Wine Cellar Eastport Retreat is a detached house situated in Annapolis's Eastport district, 2.25 kilometres from Annapolis Harbour and 41.84 kilometres from Addison Road-Seat Pleasant.
This 186 square metre dwelling accommodates up to 10 guests across 2 bedrooms, featuring air conditioning, a fully equipped kitchen, a private balcony, and complimentary private parking, with garden access and cycling opportunities nearby.

Best Annapolis, MD accommodations with a kitchen

Charming Rowhome In Downtown Annapolis - Annapolis, MD
9.6 16 reviews

Charming Rowhome In Downtown Annapolis

house, Annapolis
This historic two-bedroom house is situated in the heart of Historic Annapolis, just 200 metres from the Naval Academy, St. John's College, City Dock, and the State House.
This family-friendly holiday let offers accommodation for four guests with a private patio and grill, a full-size washer and dryer, and is equipped with air conditioning and Wi-Fi.
Royal Hue House Style & Comfort - Annapolis, MD
10 26 reviews

Royal Hue House Style & Comfort

apartment, Annapolis
This three-bedroom Annapolis property is situated in the downtown area, a 2.4km walk from the United States Naval Academy and within walking distance of City Dock, the William Paca House, and the Maryland State House.
The self-catering house offers a stylish three-bedroom, one-and-a-half-bathroom layout sleeping six guests, complete with a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher, plus air conditioning and parking (at a cost of £8 per day, 0.8km away).
Coastal Modern Retreat | Large Group Getaway On 2 - Annapolis, MD
10 3 reviews

Coastal Modern Retreat | Large Group Getaway On 2

apartment, Arnold
This six-bedroom, four-bathroom house in Arnold, Maryland, is situated on a 1.8-acre plot a short drive from Arnold's beaches and local restaurants.
The property boasts two kitchens, two living areas, a deck with a BBQ, and sleeps up to 15 guests, offering a king suite, bunk room, built-in children's bed, and a sofa bed (linen not provided for sofa bed).
Charming 3-bedroom House By The Bay - Annapolis, MD
8.9 13 reviews

Charming 3-bedroom House By The Bay

apartment, Mayo
This three-bedroom London Towne apartment in Mayo is situated near beaches and a shopping centre, offering easy access to local amenities.
Sleeping eight guests, the self-catering property boasts a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and two bathrooms.
©2026 cozycozy.com