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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.

Family Home On Mayo Peninsula | Deck | Sleeps 10 - Annapolis, MD
10 13 reviews

Family Home On Mayo Peninsula | Deck | Sleeps 10

apartment, Mayo
This Mayo, Ireland vacation home, located in Holly Hill Harbor on the Mayo Peninsula, offers waterfront proximity, easy access to local parks, and is ideal for families and groups.
The three-bedroom, two-bathroom house features a spacious open-concept layout, sleeps up to ten guests, includes a fully equipped kitchen with dishwasher, air conditioning, a private garden, parking, and a freshly renovated deck with outdoor dining.

Best family friendly Annapolis, MD lodging

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

Huge 4br Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking - Annapolis, MD
9.0 14 reviews

Huge 4br Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

apartment, Arnold
This 4-bedroom, 2-bathroom Cape St. Claire rental home in Annapolis offers 2,000 sq ft of living space and accommodates up to 12 guests, featuring a basement bar, firepit, hammock, cornhole, and putting green for outdoor recreation.
This pet-friendly house is conveniently located in Arnold, just 2 minutes from Broadneck Park, 7 minutes from Sandy Point State Park, 13 minutes from the US Naval Academy, and 14 minutes from Historic Downtown Annapolis, with fast Wi-Fi and a dedicated desk for remote work.
Walk To Private Beach+ Near Naval Academy+hot Tub! - Annapolis, MD
10 44 reviews

Walk To Private Beach+ Near Naval Academy+hot Tub!

apartment, Highland Beach
This Highland Beach vacation rental is situated on the peaceful banks of Oyster Creek in Annapolis, offering a picturesque waterfront setting with a private dock perfect for kayaking, fishing, or simply relaxing by the water. The 3-bedroom, 3-bathroom home features a beautifully designed living area with large windows offering breathtaking waterfront views, a landscaped garden, a Jacuzzi, and a cozy living area perfect for relaxing after a day of exploring.
Usna Home Steps To Stadium Dog-friendly W Parking - Annapolis, MD
10 77 reviews

Usna Home Steps To Stadium Dog-friendly W Parking

apartment, Annapolis
This Annapolis home is conveniently located in West Annapolis, just a short walk from shops, restaurants, and the Navy-Marine Corps Memorial Stadium. The apartment consistently receives excellent ratings for location, cleanliness, and overall user experience.
This spacious 3-bedroom rental comfortably sleeps 11 guests and offers 2,200 square feet of living space. The home includes a private backyard with a hot tub, fire pit, and outdoor kitchen, as well as a fully equipped kitchen, a swimming pool, a spa, and a tennis court for your enjoyment.
Annapolis Home, Near Downtown - Annapolis, MD
9.6 80 reviews

Annapolis Home, Near Downtown

apartment, Annapolis
This Annapolis home is located in a quiet residential neighborhood, just a 10-minute drive from the bustling downtown area and close to major shopping centers like Whole Foods and Target. The property consistently receives excellent ratings for cleanliness, location, and overall guest experience.
This spacious house has four bedrooms and two bathrooms, comfortably accommodating up to 11 guests. Enjoy modern amenities like air conditioning, a full kitchen with a fridge and microwave, and a private yard, perfect for relaxing or enjoying outdoor activities.

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.

421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking! - Annapolis, MD
10 143 reviews

421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!

apartment, Annapolis
This Annapolis vacation home is located in Eastport, within walking distance of both the Annapolis Maritime Museum and the U.S. Naval Academy, making it a perfect base for exploring the city's rich history and attractions. This property has earned excellent ratings from previous guests for its comfort and amenities.
The 1100-square-foot house has two bedrooms and two bathrooms, comfortably accommodating up to five guests. Enjoy a private pool, fitness center, and concierge services, along with a fully equipped kitchen, garden, and barbecue grills for a relaxing and enjoyable stay.
Usna King Stay! Private Hot Tub & In-ground Pool - Annapolis, MD
No reviews

Usna King Stay! Private Hot Tub & In-ground Pool

apartment, Crownsville
This Crownsville apartment is located in a district offering convenient access to nearby landmarks.
This spacious residence accommodates up to 14 guests and features a kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, a swimming pool, jacuzzi, and garden.
Prime Eastport Location - Waterfront Condo With Parking - Annapolis, MD
10 29 reviews

Prime Eastport Location - Waterfront Condo With Parking

apartment, Annapolis
This three-bedroom, two-bathroom Annapolis condo is located in Eastport, less than a mile from Spa Creek and the U.S. Naval Academy, and within a 15-minute drive of the Kunta Kinte-Alex Haley Memorial.
The 7-guest unit features a fully equipped kitchen, in-unit laundry, free WiFi, a balcony, a swimming pool, secure parking, and elevator access, offering easy access to Annapolis attractions.
Great Location On Spa Creek - Annapolis, MD
9.7 235 reviews

Great Location On Spa Creek

apartment, Annapolis
This Annapolis apartment is conveniently located in Eastport, just a short walk from Spa Creek, the U.S. Naval Academy, and the lively Annapolis City Dock. The apartment has earned excellent ratings for its location, cleanliness, and overall experience.
This one-bedroom rental offers 610 square feet of space and comfortably accommodates up to four guests. The apartment features a fully equipped kitchen, a private patio, a swimming pool, and a spa, providing everything you need for a relaxing and enjoyable stay.

Neighborhoods and points of interest in Annapolis, MD

Best Annapolis, MD accommodation with a kitchen

Cozy 1st Floor King George One Bedroom Apartment Right Across From Usna - Annapolis, MD
9.6 35 reviews

Cozy 1st Floor King George One Bedroom Apartment Right Across From Usna

apartment, Annapolis
This apartment is located in Annapolis' Historic District, just a short walk from the U.S. Naval Academy and other historical landmarks like the John Smith House. It has received excellent user ratings.
This one-bedroom rental comfortably sleeps up to four guests and features a full kitchen, a terrace, a garden, and parking. You'll also have access to modern amenities like free Wi-Fi, a washer and dryer, and a sofa bed.
Luxury 3-level Townhome Minutes To Annapolis - Annapolis, MD
9.9 55 reviews

Luxury 3-level Townhome Minutes To Annapolis

apartment, Arnold
This spacious three-level townhouse in Arnold, Maryland, is 14 minutes from downtown Annapolis, 29 minutes from Baltimore/Washington International Thurgood Marshall Airport (BWI), 41 minutes from Baltimore, and 49 minutes from Washington, D.C.
The 3-bedroom, 3.5-bathroom property comfortably sleeps eight guests and boasts a fully equipped kitchen, Peloton Tread, free weights, two indoor and two outdoor living areas, a garage, and driveway parking.
The Navy House-walk Or Shuttle Downtown! 3 Bd - Annapolis, MD
9.9 200 reviews

The Navy House-walk Or Shuttle Downtown! 3 Bd

apartment, Annapolis
This Annapolis bungalow is located in a family-friendly neighborhood, three blocks from the U.S. Naval Academy and within a mile of downtown Annapolis's restaurants and bars, offering easy access to the city's attractions and the waterfront via a free shuttle.
The three-bedroom, two-and-a-half-bathroom home comfortably sleeps six to seven guests and features a large backyard with a grill, on-site parking for two cars, plus children's toys and games.
3br Entire Home - Parking - Walk Downtown - Annapolis, MD
9.9 22 reviews

3br Entire Home - Parking - Walk Downtown

apartment, Annapolis
This Annapolis house rental is centrally located, within walking distance of the historic district, the Navy-Marine Corps Memorial Stadium, and Spa Creek.
The three-bedroom, one-bathroom home sleeps eight, features a fully equipped kitchen with dishwasher, in-unit laundry, a private backyard overlooking Spa Creek, and private driveway parking—a rare find in downtown Annapolis.

Best Annapolis, MD accommodation with a balcony

Unique Eastport Bungalow W Yard - Annapolis, MD
8.5 2 reviews

Unique Eastport Bungalow W Yard

house, Annapolis
Luxury Rooftop Pool & Dock Steps To Downtown - Annapolis, MD
10 1 review

Luxury Rooftop Pool & Dock Steps To Downtown

house, Annapolis
Charming Historic Annapolis Home With Two Off-street Parking Places! - Annapolis, MD
10 211 reviews

Charming Historic Annapolis Home With Two Off-street Parking Places!

apartment, Annapolis
Walk To Main Street, City Dock And Usna Gate 1 From Historic Catch 22 With Private Patio - Annapolis, MD
9.8 30 reviews

Walk To Main Street, City Dock And Usna Gate 1 From Historic Catch 22 With Private Patio

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.

Waterfront Gem W/ Dock: 2 Mi To Dwtn Annapolis! - Annapolis, MD
No reviews

Waterfront Gem W/ Dock: 2 Mi To Dwtn Annapolis!

house, Annapolis

Top-Rated Pet-Friendly Lodgings in Annapolis, MD

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

Mins To Downtown In Waterfront Community At Pet-friendly Pinecrest Bungalow - Annapolis, MD
No reviews

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

apartment, Annapolis
4br House Mins To Downtown Annapolis With Firepit, Basement Bar, & Sleeps 12 - Annapolis, MD
10 2 reviews

4br House Mins To Downtown Annapolis With Firepit, Basement Bar, & Sleeps 12

house, Arnold
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
Historic Annapolis Home | 2 Blocks To Main St - Annapolis, MD
9.8 39 reviews

Historic Annapolis Home | 2 Blocks To Main St

apartment, Annapolis

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.

Historic Downtown Annapolis W/ Rooftop Deck - Annapolis, MD
9.9 28 reviews

Historic Downtown Annapolis W/ Rooftop Deck

apartment, Annapolis
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