Search cheap accommodations in Annapolis, MD from 100+ sites!

1103 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Annapolis, MD accommodations
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

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.

Bay Ridge Unit By Downtown Annapolis And Quiet Waters Park - Annapolis, MD
9.5 11 reviews

Bay Ridge Unit By Downtown Annapolis And Quiet Waters Park

apartment, Annapolis
This Annapolis Bay Ridge rental is conveniently located near Downtown Annapolis and Quiet Waters Park, 3.4 miles from Annapolis Harbor.
This 1190-square-foot apartment features two bedrooms, one bathroom, and accommodates up to 11 guests, offering free parking, a fully equipped kitchen, in-unit laundry, and a private garden.

Best family friendly Annapolis, MD lodging

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

Charming Downtwn Home- Private Parking Patio&yard! - Annapolis, MD
10 152 reviews

Charming Downtwn Home- Private Parking Patio&yard!

apartment, Annapolis
This family-friendly vacation home is located in Annapolis's city center, a short walk from the U.S. Naval Academy and the Annapolis Civil Rights Plaque. The house has earned excellent ratings for location, cleanliness, and overall user experience.
This 1500-square-foot home comfortably accommodates up to 10 guests in its 3 bedrooms. Enjoy a fully equipped kitchen, a relaxing garden, a spa, and a terrace, all within a smoke-free environment.
Stay Mins From Annapolis In Luxury Waterfront Home On Deep Water W Private Pier & Gourmet Kitchen - Annapolis, MD
9.0 12 reviews

Stay Mins From Annapolis In Luxury Waterfront Home On Deep Water W Private Pier & Gourmet Kitchen

apartment, Crownsville
This Crownsville waterfront vacation home, seven miles from Annapolis and eight miles from the U.S. Naval Academy, offers direct access to a private pier with kayaks, paddleboards, and canoes.
The four-bedroom, four-bathroom house comfortably sleeps twelve guests and boasts a spacious gourmet kitchen, a large outdoor patio, high-speed internet, and proximity to attractions like Joyces Marina and Arundel Mills Mall.
Charming City Oasis. Walk To Harbor, Eateries.usna - Annapolis, MD
9.7 116 reviews

Charming City Oasis. Walk To Harbor, Eateries.usna

apartment, Annapolis
This charming cottage is located in a peaceful residential neighborhood just a short walk from Annapolis's vibrant harbor, shops, and restaurants. It consistently receives excellent ratings for its location, cleanliness, and overall experience.
The cottage comfortably accommodates up to six guests with multiple sleeping areas, including a master bedroom and a nautical-themed room. Enjoy modern amenities like smart TVs, Wi-Fi, and a Keurig coffee maker, along with outdoor activities like cornhole and a private patio with a fire pit.
Spacious Beachfront Home With Decks, Gas Grill, Wet Bar, Gas Fireplace, And W/d - Annapolis, MD
No reviews

Spacious Beachfront Home With Decks, Gas Grill, Wet Bar, Gas Fireplace, And W/d

apartment, Highland Beach
This waterfront condo in Highland Beach offers unparalleled Chesapeake Bay views and direct beach access, located near Annapolis Golf Club and Annapolis Landing Marina, approximately 2 miles from Jonas Green State Park.
This 3,350 sq ft residence accommodates up to 10-12 guests with 4 bedrooms, 3 bathrooms, a gas fireplace, a wet bar, and alfresco dining options on the patio and deck.

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.

Semper Fi Condo - Annapolis, MD
10 11 reviews

Semper Fi Condo

apartment, Annapolis
This Annapolis condo offers a prime location, situated just minutes from downtown Annapolis, the U.S. Naval Academy, and waterfront attractions, with convenient access to liquor stores, convenience stores, and restaurants within a 1-minute walk. This pet-friendly apartment accommodates up to 4 guests and features a full kitchen, smart TVs, high-speed Wi-Fi, a private balcony, and access to community amenities including a swimming pool and gym.
Luxury Condo | Walk To Usna  Rooftop Pool - Annapolis, MD
10 8 reviews

Luxury Condo | Walk To Usna Rooftop Pool

apartment, Annapolis
This Eastport condo offers a waterfront location with marina access on Spa Creek, situated 0.3 miles from downtown Annapolis and 0.5 miles from the Naval Academy.
This remodeled luxury apartment features 1 bedroom, 1 bathroom, accommodates up to 4 guests, and includes a full kitchen, dedicated workspace with Wi-Fi, air conditioning, and two dedicated parking spaces, with a shared rooftop pool available seasonally.
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.
The General's House-spacious Home W/pool & Hot Tub - Annapolis, MD
10 12 reviews

The General's House-spacious Home W/pool & Hot Tub

apartment, Crownsville
This 4-bedroom, 4-bathroom Crownsville vacation rental is located in a quiet neighborhood, offering convenient access to Eisenhower Golf Course and Annapolis Bowl, and is a short drive from the Maryland Renaissance Festival and Helen Avalynne Tawes Garden.
This spacious home accommodates up to 14 guests and features a private backyard with a swimming pool, a home theater, a recreation room with a billiard table and wet bar, and a gourmet kitchen.

Neighborhoods and points of interest in Annapolis, MD

Best Annapolis, MD accommodation with a kitchen

Townhouse - 1 Mile From Downtown Strip - Annapolis, MD
9.8 245 reviews

Townhouse - 1 Mile From Downtown Strip

house, Annapolis
This Annapolis townhouse is conveniently located near various landmarks and attractions, making it a great base for exploring the city. It has received excellent ratings for location, cleanliness, and overall experience.
The three-bedroom, three-bathroom house comfortably accommodates six guests. It features a fully equipped kitchen with two ovens, a cozy living room with a pull-out sofa, and a private garden. Guests can also enjoy a fitness center, air conditioning, and pet-friendly accommodations.
Great Location On Spa Creek - Annapolis, MD
9.7 236 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.
Walk To Waterfront Eastport Backyard & Fire Pit - Annapolis, MD
9.6 63 reviews

Walk To Waterfront Eastport Backyard & Fire Pit

apartment, Annapolis
This Annapolis vacation home is located in Eastport, a short walk from both the Annapolis Maritime Museum and the U.S. Naval Academy, offering easy access to these popular destinations. The property has received excellent ratings for user experience, location, and cleanliness.
The 2-bedroom house, with a total floor area of 850 square feet, comfortably sleeps up to 7 guests. Amenities include a fully equipped kitchen, a spacious garden, a terrace, a barbecue grill, and free WiFi, making it ideal for families and groups looking for a relaxing and enjoyable stay.
Historic Annapolis Home | 2 Blocks To Main St - Annapolis, MD
10 20 reviews

Historic Annapolis Home | 2 Blocks To Main St

apartment, Annapolis
This smoke-free Annapolis vacation home is located in the Historic District, a 15-minute walk from the U.S. Naval Academy and Maynard-Burgess House, and under 5 minutes from the Maryland Federation of Art and Ellen O. Moyer Nature Park. This 12,640-square-foot property boasts three bedrooms, two bathrooms, sleeps nine guests, and features a fully equipped kitchen, fenced yard with barbecue grills, and free Wi-Fi.

Best Annapolis, MD accommodation with a balcony

Family Home On Mayo Peninsula | Deck | Sleeps 10 - Annapolis, MD
10 4 reviews

Family Home On Mayo Peninsula | Deck | Sleeps 10

apartment, Mayo
Bayridge House By Quiet Waters, Thomas Point Parks - Annapolis, MD
No reviews

Bayridge House By Quiet Waters, Thomas Point Parks

apartment, Annapolis
Stylish + Fresh Bungalow 2 Blocks From N-mc Stadium - Annapolis, MD
No reviews

Stylish + Fresh Bungalow 2 Blocks From N-mc Stadium

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

Spa Creek Waterfront Pool & Parking

house, 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.

Annapolis Cottage - Annapolis, MD
9.8 36 reviews

Annapolis Cottage

apartment, Highland Beach

Top-Rated Pet-Friendly Lodgings in Annapolis, MD

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

Brilliantly Updated Multi-level Walkable To Navy Stadium & Close To Historic Downtown Annapolis - Annapolis, MD
10 3 reviews

Brilliantly Updated Multi-level Walkable To Navy Stadium & Close To Historic Downtown Annapolis

apartment, Annapolis
Renovated Apt In Historic Dist W/2 Parking Spots - Annapolis, MD
9.9 646 reviews

Renovated Apt In Historic Dist W/2 Parking Spots

apartment, Annapolis
Crab Cakes And Football
Historic District - Annapolis, MD
10 164 reviews

Crab Cakes And Football Historic District

apartment, Annapolis
3-story, Dog-friendly Home Near Beaches With Home Theatre, Grill & Gaming Tables - Annapolis, MD
No reviews

3-story, Dog-friendly Home Near Beaches With Home Theatre, Grill & Gaming Tables

apartment, Highland Beach

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.

Bay View Retreat | 5br / 5.5 Bath | Balconies - Annapolis, MD
No reviews

Bay View Retreat | 5br / 5.5 Bath | Balconies

apartment, Annapolis
©2026 cozycozy.com