Search accommodations in Annapolis, MD

1103 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • makemytrip
  • oyo
  • yatra
  • goibibo
  • travelguru
  • cleartrip
  • vrbo
  • expedia
  • hotelscom
  • tripcom
  • agoda
Annapolis, MD place to stay
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

1103 Lodgings in Annapolis, MD

Best Annapolis, MD lodging with a pool

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

Rooftop Pool And Spa Creek Views - Luxurious Waterfront Retreat - Annapolis, MD
No reviews

Rooftop Pool And Spa Creek Views - Luxurious Waterfront Retreat

apartment, Annapolis
This waterfront condo in a quiet Eastport cul-de-sac offers Spa Creek views and is located 800 metres from downtown Annapolis and 1.3 kilometres from the U.S. Naval Academy.
This family-friendly apartment features two bedrooms and two bathrooms, accommodating up to seven guests, with amenities including air conditioning, a swimming pool, a furnished balcony, and off-street parking for two cars.
Spacious Luxe Usna Home - Pool, Hot Tub, Grill - Annapolis, MD
9.4 30 reviews

Spacious Luxe Usna Home - Pool, Hot Tub, Grill

apartment, Annapolis
This seven-bedroom Annapolis property, situated in the Murray Hill district, is less than 1.6km from the US Naval Academy and the Annapolis Civil Rights Plaque.
This smoke-free holiday home boasts 307 square metres of floor space, offering four bathrooms, a fully equipped kitchen, garden, parking and sleeps up to fourteen guests.
Waterfront 2-bedroom Condo On Spa Creek - Annapolis, MD
10 15 reviews

Waterfront 2-bedroom Condo On Spa Creek

apartment, Annapolis
This Annapolis Eastport apartment is less than 1.6km from Spa Creek and the United States Naval Academy, and within a 1.6km radius of Annapolis Harbour and the Kunta Kinte Plaque & Alex Haley Memorial.
This two-bedroom, one-bathroom property sleeps six, offering a fully equipped kitchen, private patio, free Wi-Fi, access to a swimming pool, spa, fitness centre, and parking; nearby attractions include the Naval Academy and Annapolis Harbour.
Semper Fi Condo - Annapolis, MD
9.9 32 reviews

Semper Fi Condo

apartment, Annapolis
This Annapolis flat offers a prime location just minutes from downtown, the Royal Naval Academy, and waterfront attractions, with Quiet Waters Park and its dog beach approximately 1.3 kilometres away.
This pet-friendly condo for four guests features air conditioning, a full kitchen with fridge, freezer and microwave, two bathrooms, a private balcony, and access to communal swimming pool and gym facilities, with free parking and secure code-entry building access.

Best family friendly Annapolis, MD lodging

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

Stadium-side Annapolis | Chef Kitchen | Sleeps 10 - Annapolis, MD
9.8 11 reviews

Stadium-side Annapolis | Chef Kitchen | Sleeps 10

apartment, Annapolis
This spacious Annapolis townhouse, ideally situated near the U.S. Naval Academy (two miles away) and Navy-Marine Corps Memorial Stadium, offers easy access to Heineman Park and Harts Cove.
The 223 square metre property boasts four bedrooms, four bathrooms, and sleeps up to ten guests, featuring a chef's kitchen with GE Café appliances, a finished basement, and access to a community pool; kayaking and paddle boarding are readily available at Harts Cove.
Relaxing Oasis 5 Min To Navy Stadium, St Johns, Naval Academy & Downtown - Annapolis, MD
10 99 reviews

Relaxing Oasis 5 Min To Navy Stadium, St Johns, Naval Academy & Downtown

apartment, Annapolis
This family-friendly house is located in Annapolis, just under 2 kilometres from the Navy-Marine Corps Memorial Stadium, Helen Avalynne Tawes Garden, and Peters Cove, and a little over 1.5 kilometres from the US Naval Academy. The house has received excellent reviews from previous guests.
The property has three bedrooms and three bathrooms, comfortably accommodating up to seven guests. This house is equipped with a kitchen, including a fridge, microwave oven, and dishwasher, as well as a terrace, a garden, and a spa.
Eastport Oasis - Annapolis, MD
9.9 63 reviews

Eastport Oasis

apartment, Annapolis
This chic Eastport house, minutes from Annapolis city centre, offers easy access to local attractions.
The four-bedroom, two-bathroom property sleeps nine, boasting a fully equipped kitchen, private garden with fire pit and BBQ, and a newly renovated basement play area; parking, including an electric car charger, is available.
Apartment Near Downtown Annapolis With Private Outdoor Space And Parking - Annapolis, MD
No reviews

Apartment Near Downtown Annapolis With Private Outdoor Space And Parking

apartment, Annapolis
This private lower-level flat offers a secluded retreat on a quiet cul-de-sac, conveniently located 2.1 kilometres from the Navy-Marine Corps Memorial Stadium and 2.4 kilometres from the U.S. Naval Academy.
The Fitzgerald Retreat features two bedrooms, one bathroom, a family room, a kitchenette with a fridge and microwave, air conditioning, and in-unit laundry, accommodating up to four guests with high-speed WiFi, Smart TVs, keyless entry, and parking for two vehicles, plus a private outdoor patio with a fire pit and gas grill.

Frequently asked questions about accommodations in Annapolis, MD

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

    You definitely want to visit the United States Naval Academy, a beautiful campus with a rich history. The Maryland State House is another must-see, being the oldest state capitol building in continuous legislative use in the United States. And of course, you can't miss the Annapolis City Dock, a vibrant waterfront area with shops, restaurants, and plenty of boat watching.
  • What are the most convenient modes of transportation within Annapolis, MD?

    Annapolis is a very walkable city, so you can easily get around on foot. There's also a good public bus system, the Annapolis Area Transit (AAT), that can take you to most places. If you're planning to explore further afield, consider renting a car. And don't forget about the water taxis - a fun and scenic way to get around the harbour.
  • What outdoor activities and adventures are popular in and around Annapolis, MD?

    For outdoor enthusiasts, there are plenty of options. You can go kayaking or paddleboarding on the Chesapeake Bay, explore the trails at Quiet Waters Park, or visit the Sandy Point State Park for a day of sun and sand. And if you're feeling adventurous, try sailing on the bay - there are plenty of charter companies offering trips.
  • What types of accommodations are available in Annapolis, MD?

    You'll find a range of accommodation options in Annapolis, from budget-friendly motels and guesthouses to luxurious hotels and waterfront resorts. There are also plenty of vacation rentals available if you're looking for something more spacious or unique.
  • When is the best time to visit Annapolis, MD?

    Spring and autumn are generally the most pleasant times to visit Annapolis, with mild temperatures and less crowds. If you're looking for warm weather and outdoor activities, summer is a good option. And if you enjoy the festive atmosphere, winter offers the charm of the holiday season.
  • What local dishes and culinary experiences are a must-try in Annapolis, MD?

    You have to try some fresh seafood when you're in Annapolis! The Chesapeake Bay is famous for its blue crabs, so make sure to order a crab cake or steamed crabs. And don't forget to try the local oysters, they're delicious! For a sweet treat, head to the famous Carvel ice cream shop, a local favourite.

Popular destinations

Best Annapolis, MD accommodations with a balcony

Private Annapolis Retreat - Annapolis, MD
No reviews

Private Annapolis Retreat

house, Annapolis
This private retreat is located in Annapolis, 6.9 kilometres from Annapolis Harbour and 33.8 kilometres from Baltimore-Washington International Airport, with the Pier Six Concert Pavilion and Fell's Point nearby.
This spacious six-bedroom, five-bathroom dwelling offers accommodation for up to 23 guests, featuring a fully equipped kitchen, multiple living areas, and outdoor amenities including a sun terrace and barbecue facilities.
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
This charming lighthouse is situated in Eastport, Annapolis, a short walk from downtown Annapolis (1.1 km), the US Naval Academy (1.4 km), and Fourth Street shops and restaurants (0.3 km). This property enjoys excellent user ratings and offers a comfortable and convenient stay.
The lighthouse provides 4 bedrooms and 4 bathrooms, accommodating up to 12 guests. Guests can enjoy a range of amenities and activities, including a gourmet kitchen, a recreation room, multiple outdoor spaces, and family-friendly features.
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.
Luxury Rooftop Pool & Dock Steps To Downtown - Annapolis, MD
10 1 review

Luxury Rooftop Pool & Dock Steps To Downtown

house, Annapolis
This luxury condominium in Annapolis is located a 13-minute walk from Annapolis Harbour and 41.8 kilometres from Baltimore's Inner Harbour.
This air-conditioned holiday home offers 49 square metres of living space with two bedrooms, accommodating up to seven guests, and features a rooftop pool with sea views, private dock access, a well-equipped kitchen, and a fireplace.

Best Annapolis, MD accommodations with a kitchen

Walk To Usna | 2 Br Ensuite | Private Courtyard - Annapolis, MD
No reviews

Walk To Usna | 2 Br Ensuite | Private Courtyard

apartment, Annapolis
This historic two-bedroom townhome is situated on Pinkney Street in downtown Annapolis, a mere 300 metres from the U.S. Naval Academy and a short walk to City Dock.
Guests can enjoy a fully equipped kitchen, private en suite bathrooms for each bedroom, an in-home washer and dryer, and a private enclosed courtyard, with accommodation for up to four people.
Annapolis Gem- Tranquil 4 Br Murray Hill Victorian - Annapolis, MD
9.9 14 reviews

Annapolis Gem- Tranquil 4 Br Murray Hill Victorian

apartment, Annapolis
This 1911 terraced house, situated in the quiet Murray Hill district of Annapolis, is a 1.6 kilometre walk from the historic United States Naval Academy and the shops and restaurants of West and Main Streets.
This pet-friendly four-bedroom, two-bathroom property accommodates up to ten guests and features a spacious open-plan kitchen, living, and dining area, alongside a front porch swing and patio for outdoor relaxation.
Charming Eastport Capecod - Annapolis, MD
10 79 reviews

Charming Eastport Capecod

apartment, Annapolis
This four-bedroom home in Eastport is located just 1.6 kilometres from downtown Annapolis, City Dock, and shops, offering easy access to the city's main attractions. The area is popular for its local pubs and restaurants, making it an ideal location for those seeking a vibrant and convenient stay. The property has consistently received excellent ratings for its cleanliness, location, and user experience.
The property boasts a spacious open-plan kitchen and living room, perfect for entertaining up to 10 guests. Guests can enjoy the large private backyard with a patio, fire pit, and grill, perfect for al fresco dining and relaxation.
Downtown Annapolis Luxury House - Annapolis, MD
10 96 reviews

Downtown Annapolis Luxury House

apartment, Annapolis
This four-bedroom, two-bathroom Annapolis dwelling is located 2.3 kilometres from Church Circle, offering easy access to Annapolis's main attractions.
Sleeping up to eight guests, this spacious house boasts a gourmet kitchen with a six-foot island, a screened porch with outdoor seating, and flexible check-in/check-out times.
©2026 cozycozy.com