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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.

Modern Elegance Meets Comfort In Maryland - Annapolis, MD
9.5 4 reviews

Modern Elegance Meets Comfort In Maryland

apartment, Annapolis
This 5-bedroom house in a quiet Annapolis neighborhood offers convenient access, located minutes from downtown Annapolis and the United States Naval Academy.
This pet-friendly residence accommodates up to 16 guests with two living areas, each featuring a kitchen, fireplace, and in-unit laundry, plus a fenced backyard with a deck and entertainment options like a foosball and combo pool/ping-pong table.

Best family friendly Annapolis, MD lodging

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

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
This one-bedroom Annapolis apartment rental is located in the desirable Eastport neighborhood, less than a mile from the U.S. Naval Academy and a short drive from Baltimore and Washington, D.C.
The pet-friendly unit features a private backyard, full kitchen, keyless entry, high-speed internet, washer/dryer, and accommodates up to four guests.
Cozy 2br Home W/ Parking In Downtown Annapolis - Annapolis, MD
8.6 7 reviews

Cozy 2br Home W/ Parking In Downtown Annapolis

house, Annapolis
This 2-bedroom house in downtown Annapolis offers a prime location, just 1.4 miles from Annapolis Harbor and 21 miles from Baltimore-Washington International Airport.
This 900 square foot accommodation sleeps 11 guests and features a fully equipped kitchen, free WiFi, air conditioning, and on-site laundry service, with cycling activities available nearby.
Beautiful Basement Apartment In An Upscale Home - Annapolis, MD
9.8 8 reviews

Beautiful Basement Apartment In An Upscale Home

apartment, Arnold
This basement apartment in Arnold offers a private retreat within a safe, upscale waterfront community, located steps from the Baltimore-Annapolis trail and minutes from Annapolis attractions.
This family-friendly unit accommodates up to three guests and features air conditioning, internet, a full kitchen, parking, a swimming pool, garden, and sauna.
Restful And Charming Home In Eastport - Annapolis, MD
No reviews

Restful And Charming Home In Eastport

apartment, Annapolis
This apartment is located in Eastport, Annapolis, just a short drive from the historic downtown and the US Naval Academy, offering easy access to the city's attractions. The neighborhood is charming and quiet, making it a perfect escape from the hustle and bustle of the city.
This comfortable home features three bedrooms, accommodating up to six guests, and includes a fully equipped kitchen, washer and dryer, and a private outdoor area with a dining table and fire pit. Enjoy the convenience of a Jacuzzi, a spa, and a garden, along with the unique experience of backyard chickens.

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.

Liberty Lookout - Annapolis, MD
No reviews

Liberty Lookout

apartment, Annapolis
This Eastport condo provides waterfront Spa Creek views, located 0.5 miles from downtown Annapolis and 0.8 miles from the U.S. Naval Academy.
This 2-bedroom, 2-bathroom luxury suite accommodates up to 7 guests and features a private furnished balcony, a rooftop pool and terrace with sweeping views, high-speed WiFi, and parking for 2 cars.
Spa Creek Condo Pool Deck & Parking - Annapolis, MD
No reviews

Spa Creek Condo Pool Deck & Parking

apartment, Annapolis
This Annapolis condo is located a 13-minute walk from Annapolis Harbor and 26 miles from Baltimore's Inner Harbor.
This 650 square foot apartment offers 1 bedroom, 1 bathroom, and can accommodate up to 7 guests with amenities including air conditioning, free Wi-Fi, a full kitchen, and direct access to an outdoor swimming pool, plus complimentary private parking.
Hidden Gem At Spa Creek - Annapolis, MD
No reviews

Hidden Gem At Spa Creek

apartment, Annapolis
This top-floor condo in Eastport offers a prime location for viewing the Blue Angels and Spa Creek, within a 0.5-mile walk to downtown Annapolis restaurants and pubs.
This one-bedroom, one-bathroom unit sleeps four and features a remodeled kitchen and bathroom, off-street parking, and a rooftop pool available on summer weekends.
Cozy Annapolis Condo - Annapolis, MD
9.9 77 reviews

Cozy Annapolis Condo

apartment, Annapolis
This Annapolis apartment is centrally located, just a short walk from the historic district, waterfront, and popular restaurants. It boasts excellent ratings for location, cleanliness, and overall user experience. This two-bedroom rental comfortably accommodates up to five guests. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a fitness center, and a garden.

Neighborhoods and points of interest in Annapolis, MD

Best Annapolis, MD accommodation with a kitchen

Gaia House - Annapolis, MD
9.1 58 reviews

Gaia House

house, Annapolis
Gaia House is located in Annapolis, a short drive from the Annapolis Harbor and within easy reach of major attractions like Historic Ships in Baltimore and Inner Harbor. This 100-square-foot house features two bedrooms, one bathroom, and a private patio overlooking a quiet street, making it ideal for families and groups of up to seven guests.
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
This three-bedroom Annapolis rental, located in Admiral Heights, is 1.6 miles from the U.S. Naval Academy and 0.5 miles from People's Brewer Hill Cemetery.
This smoke-free apartment features a private fenced yard, patio, barbecue grills, a fireplace, and accommodates up to six guests with amenities including a refrigerator, microwave, and Wi-Fi.
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway! - Annapolis, MD
9.6 104 reviews

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

apartment, Annapolis
This Annapolis apartment is conveniently located just half a mile from Anne Arundel Medical Center and 2.7 miles from the U.S. Naval Academy, making it ideal for both medical professionals and tourists. The apartment consistently receives excellent ratings from guests.
The one-bedroom unit comfortably accommodates up to three guests. Guests can enjoy a fully-equipped kitchen, a private balcony, free WiFi, and parking, all while staying in a smoke-free environment.
Londontowne Rancher | 3br | Near Waterfront - Annapolis, MD
9.2 10 reviews

Londontowne Rancher | 3br | Near Waterfront

apartment, Mayo
This three-bedroom, two-bathroom Mayo apartment, perfect for families or groups of up to eight, offers easy one-level living and is conveniently located near local restaurants and shops, though the precise distance and neighborhood are unspecified.
The rental includes a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, parking for two cars, keypad entry, and a private yard; complimentary early check-in and late check-out are also available.

Best Annapolis, MD accommodation with a balcony

Lighthouse Inn - Annapolis, MD
No reviews

Lighthouse Inn

house, Annapolis
Pet-friendly Beach Getaway, Relax By The Bay! - Annapolis, MD
9.3 7 reviews

Pet-friendly Beach Getaway, Relax By The Bay!

apartment, Arnold
Spacious Luxe Usna Home - Pool, Hot Tub, Grill - Annapolis, MD
9.4 32 reviews

Spacious Luxe Usna Home - Pool, Hot Tub, Grill

apartment, Annapolis
Renovated 3br Near Sandy Point Beach - Annapolis, MD
10 1 review

Renovated 3br Near Sandy Point Beach

house, Arnold

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.

6bdrm Home, Near Navy Stadium & Downtown Annapolis - Annapolis, MD
8.8 8 reviews

6bdrm Home, Near Navy Stadium & Downtown Annapolis

apartment, Crownsville

Top-Rated Pet-Friendly Lodgings in Annapolis, MD

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

Stadium-side Annapolis | Chef Kitchen | Sleeps 10 - Annapolis, MD
9.9 24 reviews

Stadium-side Annapolis | Chef Kitchen | Sleeps 10

apartment, Annapolis
Semper Fi Condo - Annapolis, MD
9.9 32 reviews

Semper Fi Condo

apartment, Annapolis
Steps From City Dock W Private Fenced-in Backyard At Historic Dog-friendly Philip Clayton House - Annapolis, MD
9.8 8 reviews

Steps From City Dock W Private Fenced-in Backyard At Historic Dog-friendly Philip Clayton House

apartment, Annapolis
Dean Street's Lower Deck House! - Annapolis, MD
10 4 reviews

Dean Street's Lower Deck House!

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.

Annapolis Cozy Beachfront/waterfront W/chesapeake Bay Bridge View - Annapolis, MD
10 35 reviews

Annapolis Cozy Beachfront/waterfront W/chesapeake Bay Bridge View

apartment, Highland Beach
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