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Annapolis, MD accommodations
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1103 Lodgings in Annapolis, MD

Discover Lodgings by the Sea in Annapolis, MD

Unwind at these welcoming seaside accommodations in Annapolis, MD, perfectly situated for exploring local coastal sights and catching fresh sea breezes.

Charming Cottage 2 Parking Spot Easy Walk Downtown - Annapolis, MD
9.9 296 reviews

Charming Cottage 2 Parking Spot Easy Walk Downtown

apartment, 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.

Best family friendly Annapolis, MD lodging

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

Walk To Downtown W Big Yard Dog-friendly & Parking - Annapolis, MD
10 5 reviews

Walk To Downtown W Big Yard Dog-friendly & Parking

apartment, Annapolis
This 5-bedroom, 2-bathroom rental home in Annapolis is located 0.7 miles from the Navy-Marine Corps Memorial Stadium and 1 mile from downtown shops and restaurants, offering exceptional walkability to waterfront events.
This dog-friendly residence comfortably sleeps up to 12 guests and features a fully equipped kitchen, high-speed WiFi, a sunroom, and on-site laundry and parking.
Weems Creek Cottage, Annapolis  Waterfront - Annapolis, MD
10 257 reviews

Weems Creek Cottage, Annapolis Waterfront

apartment, 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).
Historic Suite 2 Blocks From Main St With On-site Parking & Dog-friendly - Annapolis, MD
10 13 reviews

Historic Suite 2 Blocks From Main St With On-site Parking & Dog-friendly

apartment, Annapolis
This two-bedroom Annapolis apartment is centrally located in Historic Annapolis, just two blocks from Main Street and four blocks from the U.S. Naval Academy.
The unit features a spacious open floor plan, comfortably accommodating six guests, with a full kitchen, in-unit laundry, keyless entry, and high-speed Wi-Fi; pets are welcome.
Uptown Annapolis - Peaceful, Sparkling, 1 Bed/1 Bath Apartment, Sleeps 3-4 - Annapolis, MD
10 13 reviews

Uptown Annapolis - Peaceful, Sparkling, 1 Bed/1 Bath Apartment, Sleeps 3-4

apartment, Annapolis
This Annapolis waterfront home, near Brewer Hill, is a 10-minute walk from People's Brewer Hill Cemetery and Maryland Hall for Creative Arts, and 1.7 miles from the U.S. Naval Academy.
This 750-square-foot vacation rental sleeps four, boasting two bedrooms, one bathroom, a fully equipped kitchen, free Wi-Fi, a terrace, a garden, and a spa, plus on-site parking.

Frequently Asked Questions about accommodations in Annapolis, MD

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

    You can't miss the United States Naval Academy, a beautiful campus with historic buildings and a museum. The Annapolis City Dock is a lively spot with shops, restaurants, and boat tours. And don't forget the Maryland State House, the oldest state capitol building still in use in the United States.
  • What are the best accommodations in Annapolis, MD?

  • Which cultural festivals and seasonal events should visitors attend in Annapolis, MD?

    The Annapolis Maritime Museum's Waterway Festival in June is a great time to celebrate the Chesapeake Bay. The Annapolis Arts Festival in September showcases local artists. In October, the annual Annapolis Fall Festival features live music, food, and crafts.
  • What are the best accommodations with a pool in Annapolis, MD?

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

    Annapolis is a very walkable city, especially downtown. If you're exploring further afield, the Annapolis Area Transit buses are a good option. For longer trips, you can rent a car or use ride-sharing services.
  • What are the best accommodations with a jacuzzi in Annapolis, MD?

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

    You can explore the Chesapeake Bay by kayak or sailboat. There are great hiking trails at Quiet Waters Park and the Jug Bay Wetlands Sanctuary. And of course, you can always take a scenic bike ride along the Annapolis-Baltimore Greenway.
  • What are the best accommodations for families and kids in Annapolis, MD?

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

    Annapolis offers a wide range of accommodations, from historic bed and breakfasts to modern hotels. You'll find everything from budget-friendly motels to luxury resorts, as well as vacation rentals and charming guesthouses.
  • What are the best pet friendly accommodations in Annapolis, MD?

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

    Spring and fall are ideal times to visit Annapolis, with mild temperatures and fewer crowds. Summer is popular for water activities, but it can be hot and humid. Winter offers a quieter experience and festive holiday events.
  • What are the best accommodations with parking in Annapolis, MD?

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

    You have to try the famous Maryland crab cakes, of course! Also, don't miss the fresh seafood at the many restaurants along the waterfront. And for a sweet treat, try a local favorite, Smith Island Cake.
  • In which part of Annapolis, MD should you consider renting accommodation?

    Downtown Annapolis is the heart of the city, with easy access to shops, restaurants, and attractions. If you prefer a quieter stay, consider the historic district of Eastport or the waterfront area of Spa Creek.

Popular destinations

Popular Lodgings with a Pool in Annapolis, MD

A private pool at your Annapolis, MD lodging is the perfect way to complement your vacation with a refreshing swim.

Amazing Views From Spa Creek 2bd Condo With Pool - Annapolis, MD
9.5 85 reviews

Amazing Views From Spa Creek 2bd Condo With Pool

apartment, Annapolis
This yacht is located in Eastport, Annapolis, a short walk from the downtown area and the Naval Academy. It has excellent user, location, and cleanliness ratings. The yacht offers two bedrooms, one bathroom, and can accommodate up to six guests. Amenities include a kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, a garden, a fitness center, parking, and internet access.
Luxury Rooftop Pool & Dock Steps To Downtown - Annapolis, MD
10 1 review

Luxury Rooftop Pool & Dock Steps To Downtown

house, Annapolis
This luxury condo in Annapolis is a 13-minute walk from Annapolis Harbor and 26 miles from Inner Harbor attractions in Baltimore.
This 530 square foot house offers 2 bedrooms, accommodates up to 7 guests, and features a rooftop pool, private dock, air conditioning, and a well-equipped kitchen with a dishwasher, oven, and microwave.
Spa Creek Waterfront | Pool & Parking - Annapolis, MD
10 19 reviews

Spa Creek Waterfront | Pool & Parking

apartment, Annapolis
This Eastport condo provides waterfront living on Spa Creek, a short walk to Downtown Annapolis and the US Naval Academy.
This two-bedroom condo accommodates up to four guests and features a private deck, access to a seasonal community pool, a fully equipped kitchen, and free parking for two cars.
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
10 2 reviews

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 1-bedroom condo in Eastport offers direct marina access on Spa Creek, located 0.3 miles from Historic Downtown Annapolis, 1 mile from the U.S. Naval Academy, and 1.9 miles from Navy Stadium.
This fully remodeled residence accommodates up to 4 guests and features a king bedroom, a queen sleeper sofa, a spa-like bathroom, a well-equipped kitchen with an air fryer and coffee station, dedicated workspace with fast Wi-Fi, and includes two parking spaces, with seasonal access to a rooftop pool and terrace.

Neighborhoods and points of interest in Annapolis, MD

Best Annapolis, MD accommodation with a kitchen

Victory House
4br At Stadiumminutes To Usna & Dta - Annapolis, MD
10 20 reviews

Victory House 4br At Stadiumminutes To Usna & Dta

apartment, Annapolis
This Annapolis rental home in Admiral Heights is situated directly across from Navy-Marine Corps Memorial Stadium, a 5-minute drive to U.S. Naval Academy Gate 8, and an 8-minute drive to downtown Annapolis.
This spacious 4-bedroom, 3-bathroom residence accommodates up to 10 guests and features a fully equipped kitchen, an open-concept living and dining area, and an outdoor firepit, with grocery stores and shopping just a 3-minute drive or 10-minute walk away.
Studio Apt. Historic Annapolis - Annapolis, MD
9.8 26 reviews

Studio Apt. Historic Annapolis

studio, Annapolis
This Annapolis studio apartment is located in the Colonial Historic District, within walking distance of City Dock, Ego Alley, and the U.S. Naval Academy.
The unit features a king-sized bed, a kitchenette with a mini-fridge and microwave, a private bathroom, and a Smart TV; it comfortably sleeps two guests and offers exclusive use of a two-bedroom apartment within a four-unit building.
Bayridge House By Quiet Waters, Thomas Point Parks - Annapolis, MD
No reviews

Bayridge House By Quiet Waters, Thomas Point Parks

apartment, Annapolis
Accommodation. You will be in Annapolis.
Services and facilities include an iron, a washing machine and a kitchen.
Eastport Farmhouse, Dog-friendly - Annapolis, MD
9.9 22 reviews

Eastport Farmhouse, Dog-friendly

apartment, Annapolis
This Annapolis farmhouse, located 1.2 miles from downtown Annapolis and its historic district, offers easy access to shops, restaurants, and attractions.
The three-bedroom, two-bathroom property sleeps six, features a fully equipped kitchen with dishwasher and microwave, a dedicated office space, a private two-acre yard with a fire pit and grill, and provides a pack 'n play for infants.

Best Annapolis, MD accommodation with a balcony

Walk To Downtown Annapolis & Spa Creek From Stunning Craftsman With Game Room, Parking And Backyard - Annapolis, MD
10 21 reviews

Walk To Downtown Annapolis & Spa Creek From Stunning Craftsman With Game Room, Parking And Backyard

apartment, Annapolis
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway! - Annapolis, MD
9.6 103 reviews

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

apartment, Annapolis
Spa Creek Waterfront Pool & Parking - Annapolis, MD
10 1 review

Spa Creek Waterfront Pool & Parking

house, Annapolis
Cute Bungalow Blocks To Stadium - Annapolis, MD
9.8 10 reviews

Cute Bungalow Blocks To Stadium

apartment, Annapolis

Search Luxury Lodgings in Annapolis, MD

A coastal luxury lodging in Annapolis, MD sets a wonderful tone for your trip, with 5-star comfort and premium views.

4br Family Retreat Near Annapolis W/ Large Yard - Annapolis, MD
10 1 review

4br Family Retreat Near Annapolis W/ Large Yard

apartment, Annapolis

Top-Rated Pet-Friendly Lodgings in Annapolis, MD

Bringing your dog to Annapolis, MD? Every lodging in this selection features dog-friendly amenities.

Gorgeous Carriage House Close To Usna, Walk To Stadium, Free Parking,  Pets+kids - Annapolis, MD
10 54 reviews

Gorgeous Carriage House Close To Usna, Walk To Stadium, Free Parking, Pets+kids

apartment, Annapolis
Historic Row Home In Downtown Annapolis - Annapolis, MD
9.7 28 reviews

Historic Row Home In Downtown Annapolis

house, Annapolis
Walk To Shops & Dining From Dog-friendly Apartment W Parking & Private Backyard - Annapolis, MD
10 9 reviews

Walk To Shops & Dining From Dog-friendly Apartment W Parking & Private Backyard

apartment, Annapolis
Downtown Annapolis Apartment - Annapolis, MD
9.8 71 reviews

Downtown Annapolis Apartment

apartment, Naval Academy

Discover Lodgings with On-Site Restaurants in Annapolis, MD

An on-site restaurant at your lodging in Annapolis, MD ensures fresh local food and coastal dishes are available every evening.

Charming Cottage Steps From Navy Stadium - Annapolis, MD
No reviews

Charming Cottage Steps From Navy Stadium

apartment, Annapolis
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