Places to stay in Annapolis, MD

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Annapolis, MD place to stay
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856 Best places to stay in Annapolis, MD

Best Annapolis, MD lodgings with a pool

Among the 856 accommodations in Annapolis, MD, here are the 4 best ones with a pool

Spacious Luxe Usna Home - Pool, Hot Tub, Grill - Annapolis, MD
9.8 27 reviews
Annapolis, MD
28/06 – 30/06
1840 €/nighttotal: 3680 € (2 )

Spacious Luxe Usna Home - Pool, Hot Tub, Grill

5 2
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.
The Retreat @ Back Creek - Annapolis, MD
9.9 38 reviews
Annapolis, MD
06/08 – 10/08
1503 €/nighttotal: 6012 € (4 )

The Retreat @ Back Creek

1 10
apartment , Annapolis
This five-bedroom apartment is located in Eastport, a short walk from Annapolis' historic downtown and bustling City Dock. It has received excellent ratings for location, cleanliness and user experience.
The apartment has three bathrooms and can accommodate up to sixteen guests. It offers a range of amenities, including a heated indoor pool, a spacious great room, a private patio, and a large recreation room with a bar and ping pong table.
Waterfront Eastport Condo W Pool & Parking - Annapolis, MD
9.6 9 reviews
Annapolis, MD
25/06 – 28/06
555 €/nighttotal: 1665 € (3 )

Waterfront Eastport Condo W Pool & Parking

1 2
apartment , Annapolis
This Annapolis apartment, situated in Eastport, is less than 1km from Annapolis city centre and 1.3km from the United States Naval Academy.
Sleeping up to seven guests, this two-bedroom, two-bathroom flat boasts a king-size suite, twin guest room with daybeds, queen sofa bed, rooftop pool (seasonal), and stunning Spa Creek and downtown views.
Waterfront Oasis Of Annapolis Star - Annapolis, MD
10 81 reviews
Annapolis, MD
21/08 – 24/08
344 €/nighttotal: 1032 € (3 )

Waterfront Oasis Of Annapolis Star

2 2
apartment , Arnold
This flat is situated in Annapolis, just a short distance from the Maryland World War II Memorial, Jonas Green State Park, and the Naval Health Clinic. It has received excellent reviews from previous guests.
The apartment is well-equipped and includes a kitchen with a fridge, microwave, and dishwasher. It also offers a range of amenities, such as a private pool, a fireplace, a terrace, and free Wi-Fi.

Best family friendly Annapolis, MD lodging

Among the 856 accommodations in Annapolis, MD, here are the 4 best for families

Gorgeous 6-bedroom Charming Annapolis Retreat - Annapolis, MD
Annapolis, MD
01/07 – 08/07
2429 €/nighttotal: 17003 € (7 )

Gorgeous 6-bedroom Charming Annapolis Retreat

6 2
apartment , Annapolis
This six-bedroom, five-bathroom flat is situated in the Hillsmere district of Annapolis, offering convenient access to Great Frogs Winery, just a short walk away, and Maryland Quiet Waters Park, a mere 1-minute drive.
This property accommodates up to 12 guests and includes amenities such as Wi-Fi, a dishwasher, microwave, oven, barbecue, fireplace, and in-unit laundry facilities.
Cozy, Waterfront, 5br 4ba House W 2 Decks Near Usna & Downtown - Annapolis, MD
10 26 reviews
Annapolis, MD
23/06 – 25/06
875 €/nighttotal: 1750 € (2 )

Cozy, Waterfront, 5br 4ba House W 2 Decks Near Usna & Downtown

5 2
apartment , Highland Beach
This Highland Beach waterfront property, a five-minute walk from the Chesapeake Bay and historic Highland Beach, is situated a short drive from Annapolis city centre, the United States Naval Academy, and Quiet Waters Park.
The five-bedroom, four-bathroom house sleeps ten guests, boasts a well-equipped kitchen, two spacious decks with stunning waterfront views, a tennis court, ample parking, and offers access to free Wi-Fi and a home office/fitness room.
Uptown Annapolis - Peaceful, Sparkling, 1 Bed/1 Bath Apartment, Sleeps 3-4 - Annapolis, MD
10 12 reviews
Annapolis, MD
24/07 – 27/07
303 €/nighttotal: 909 € (3 )

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

2 2
apartment , Annapolis
This Annapolis waterfront property, near Brewer Hill, is a short walk (under 1 km) from People's Brewer Hill Cemetery and Maryland Hall for Creative Arts, and 2.7 km from the United States Naval Academy.
This 70 square metre house offers two bedrooms, one bathroom, plus a sofa bed, sleeping up to four guests, and boasts a fully equipped kitchen, garden, terrace, spa, parking, and laundry facilities.
New Luxury Townhome Near Downtown Annapolis With Multiple Ensuite Bedrooms And Parking - Annapolis, MD
Annapolis, MD
03/12 – 06/12
1125 €/nighttotal: 3375 € (3 )

New Luxury Townhome Near Downtown Annapolis With Multiple Ensuite Bedrooms And Parking

4 10
apartment , Annapolis
This brand-new, four-level farmhouse-style townhome is located just 3.2 kilometres from the U.S. Naval Academy and 2 kilometres from the Navy-Marine Corps Memorial Stadium, offering a convenient base for exploring Annapolis.
This spacious 210 square metre residence accommodates up to 12 guests with five bedrooms, four en-suite bathrooms, a gourmet kitchen, and a terrace, while being dog-friendly and offering ample parking.

Frequently asked questions about accommodations in Annapolis, MD

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

    Annapolis is packed with history! You have to see the US Naval Academy, it's a sight to behold. The State House is another must-see, it's the oldest state capitol building still in use in the US. And don't forget to stroll around the historic district, with its charming cobblestone streets and beautiful 18th-century architecture.
  • What are the best accommodations in Annapolis, MD?

    Among the accommodations in Annapolis, MD, Step Out To Main Street From A Chic Loft, Graduate By Hilton Annapolis and Modern Apartment Over The Heart Of Main Street are the most popular ones.

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

    There's always something going on in Annapolis! The Annapolis Maritime Museum's 'Waterfront Festival' in June is a big one, with live music and boat races. In October, the 'Annapolis Fall Festival' is a real treat, with arts and crafts, food stalls, and plenty of entertainment. And don't miss the 'Christmas in Annapolis' festivities in December, with lights, decorations, and festive cheer.
  • What are the best accommodations with a pool in Annapolis, MD?

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

    Annapolis is quite walkable, especially in the downtown area. You can also easily get around by using the free Circulator bus service. If you need to travel further afield, the Annapolis Area Regional Transportation (AART) provides bus services to surrounding areas. And of course, you can always hire a taxi or ride-sharing service.
  • What are the best accommodations with a jacuzzi in Annapolis, MD?

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

    Annapolis is a great place for outdoor activities. You can take a boat tour of the Chesapeake Bay, go kayaking or paddleboarding on the Severn River, or explore the scenic trails at Quiet Waters Park. If you're feeling adventurous, you can even go fishing or crabbing from the docks.
  • What are the best accommodations for families and kids in Annapolis, MD?

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

    Annapolis has a wide range of accommodation options, from budget-friendly motels to luxurious hotels. There are also plenty of charming bed and breakfasts and vacation rentals available. You can find something to suit every taste and budget.
  • What are the best pet friendly accommodations in Annapolis, MD?

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

    The best time to visit Annapolis really depends on what you're looking for. Spring and autumn are lovely, with mild temperatures and fewer crowds. Summer is great for outdoor activities, but it can get hot and humid. Winter can be chilly, but it's a beautiful time to see the city decked out for the holidays.
  • What are the best accommodations with parking in Annapolis, MD?

    Graduate By Hilton Annapolis, Springhill Suites By Marriott Annapolis and Historic Inns Of Annapolis 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 fresh seafood in Annapolis! The Chesapeake Bay is famous for its blue crabs, so be sure to try them steamed or in a crab cake. And don't forget to sample the local oysters, they're a real delicacy. For a unique experience, try dining at one of the many waterfront restaurants with stunning views of the harbour.
  • In which part of Annapolis, MD should you consider renting accommodation?

    The historic district is a popular choice for accommodation, as it's close to all the main attractions. If you're looking for a more peaceful stay, you could consider renting a property in Eastport, which is a charming waterfront community. And if you're on a budget, you might want to look for accommodation in the outskirts of Annapolis.

Destinations nearby

Best Annapolis, MD accommodations with a balcony

All Newly-designed Water Views, Expansive Yard, Steps To Restaurants And Downtown Annapolis - Annapolis, MD
10 5 reviews
Annapolis, MD
23/06 – 25/06
1047 €/nighttotal: 2094 € (2 )

All Newly-designed Water Views, Expansive Yard, Steps To Restaurants And Downtown Annapolis

3 2
apartment , Annapolis
This Eastport property is a detached house located 500 metres from Annapolis Harbour and the United States Naval Academy, with the Annapolis Maritime Museum and Spa Creek also within a 1-kilometre radius.
This residence accommodates eight guests across five bedrooms, offering amenities such as a fitness centre, barbecue grills, a fireplace, and complimentary WiFi, with air conditioning and parking provided.
Cozy 3br Annapolis Sleeps 10 Private Deck, Parking - Annapolis, MD
Annapolis, MD
25/06 – 28/06
459 €/nighttotal: 1377 € (3 )

Cozy 3br Annapolis Sleeps 10 Private Deck, Parking

1 2
house , Annapolis
This Annapolis property is located 2.2 kilometres from Sparrows Beach and 4.8 kilometres from Annapolis Harbour, offering convenient access to local attractions.
This holiday home, spanning 6 square metres, accommodates up to 10 guests and features air conditioning, free WiFi, a fully equipped kitchen with a dishwasher and oven, a private deck, and free private parking.
Waterfront Suite With Views Of Annapolis, Prime Eastport Location - Annapolis, MD
10 2 reviews
Annapolis, MD
25/09 – 18/10
580 €/nighttotal: 13340 € (23 )

Waterfront Suite With Views Of Annapolis, Prime Eastport Location

2 2
apartment , Annapolis
This Eastport condominium provides waterfront accommodation on Spa Creek, situated 800 meters from downtown Annapolis and a 15-minute walk to the U.S. Naval Academy.
This two-bedroom flat accommodates up to five guests and features a private furnished balcony with sweeping views of Spa Creek and historic Annapolis, alongside access to a seasonal waterfront swimming pool and high-speed Wi-Fi.
Unique And Central In Eastport - Annapolis, MD
10 5 reviews
Annapolis, MD
16/07 – 19/07
606 €/nighttotal: 1818 € (3 )

Unique And Central In Eastport

4 5
apartment , Annapolis
This Eastport bungalow, a restored 1920s property, is situated approximately 1.6 kilometres from Annapolis's city centre, including City Dock, the United States Naval Academy, and the Maryland State House.
The four-bedroom, three-bathroom dwelling sleeps up to ten guests and offers amenities including a private garden, parking, WiFi, two smart TVs, and is within a three-minute walk of the Water Taxi to Annapolis City Dock.

Best Annapolis, MD accommodations with a kitchen

New Downtown Annapolis Condo With Free Parking - Annapolis, MD
10 203 reviews
Annapolis, MD
01/01 – 01/02
218 €/nighttotal: 6758 € (31 )

New Downtown Annapolis Condo With Free Parking

1 2
apartment , Annapolis
This apartment is situated in Annapolis' Historic District, less than 1.6 km from the Annapolis Civil Rights Plaque and the US Naval Academy, offering a peaceful setting close to key attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment has two bedrooms and two bathrooms, spanning 92 square metres, and can comfortably accommodate up to four guests. It features a range of amenities, including a swimming pool, a jacuzzi, a terrace, a garden, and a spa, as well as parking and a fully equipped kitchen.
Spacious Historic Home Downtown Annapolis Main St. Book For Commissioning Week! - Annapolis, MD
9.0 24 reviews
Annapolis, MD
23/06 – 25/06
1712 €/nighttotal: 3424 € (2 )

Spacious Historic Home Downtown Annapolis Main St. Book For Commissioning Week!

6 2
apartment , Annapolis
This historic dwelling is located in the heart of Annapolis' Historic District, just a short walk from City Dock, the US Naval Academy, and Main Street, offering easy access to the city's attractions and amenities. The apartment has received excellent user ratings, reflecting its high standard of comfort and service.
The spacious home features six bedrooms, five bathrooms, and can accommodate up to 16 guests, spanning a generous 353 square metres. Amenities include a fully equipped kitchen, a spa, air conditioning, and a private patio, offering a comfortable and enjoyable stay for families and groups.
West Annapolis Cottage- 6br  Walk To Navy Stadium - Annapolis, MD
9.9 82 reviews
Annapolis, MD
03/12 – 06/12
964 €/nighttotal: 2892 € (3 )

West Annapolis Cottage- 6br Walk To Navy Stadium

1 10
apartment , Annapolis
This West Annapolis holiday home is situated a short distance (approximately 1.6km) from the US Naval Academy football stadium and the shops and restaurants of West Annapolis, with Annapolis Harbour a 5-minute drive away (approximately 3.2km).
Sleeping up to 14 guests in six bedrooms and five bathrooms, the property boasts a fully equipped kitchen, two patios with a gas grill, a games room with ping pong and air hockey, and dedicated parking for two small vehicles.
Private Single Family Home Close To Both Water And Downtown! - Annapolis, MD
9.7 88 reviews
Annapolis, MD
23/06 – 25/06
503 €/nighttotal: 1006 € (2 )

Private Single Family Home Close To Both Water And Downtown!

4 2
house , Annapolis
This four-bedroom house is located in Annapolis, just 2 kilometres from Carrs Beach and 5 kilometres from Annapolis Harbour, offering a convenient base for exploring the city and the coastline. It has received excellent ratings for location, cleanliness, and overall experience.
The house features a private terrace and outdoor dining area, perfect for enjoying meals al fresco. Guests can also benefit from a fully equipped kitchen with a dishwasher, air conditioning, free private parking, Wi-Fi, a children's playground, a garden, and a washing machine.
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