What are the must-see sights for first-time visitors on a day trip to Annapolis, MD?

You definitely want to check out the United States Naval Academy, the Maryland State House, and the Annapolis City Dock. It's worth taking a stroll around the historic district and admiring the beautiful colonial architecture.

What are the best bed and breakfasts in Annapolis, MD?

Among the B&Bs in Annapolis, MD, Chesapeake Mornings , Howard's Cove Retreat and Cozy Private Room In Annapolis Home are the most popular ones.

In which districts of Annapolis, MD should you consider booking a bed and breakfast?

The historic district is a great choice, especially around Church Circle and the State House. You'll be close to all the action, but still enjoy a quiet and charming atmosphere. The harbour area is also lovely, offering stunning views and easy access to the water.

What are the best bed and breakfasts with a pool in Annapolis, MD?

Cape Cod Charm Close To Usna & Annapolis - Room 2 , Cape Cod Charm Close To Usna & Annapolis - Room 1 and La Posada De Jorge are the best B&Bs with a pool in Annapolis, MD.

What is the typical weather in Annapolis, MD, and how does it affect outdoor plans?

Annapolis has four distinct seasons. Summers are hot and humid, so you'll want to plan for outdoor activities early in the day or in the evening. Winters can be chilly, with occasional snow, so pack accordingly. Spring and autumn are beautiful with mild temperatures, making them perfect for exploring the city.

What are the best bed and breakfasts with a jacuzzi in Annapolis, MD?

The best B&Bs with a jacuzzi in Annapolis, MD are Cape Cod Charm Close To Usna & Annapolis - Room 2 , Cape Cod Charm Close To Usna & Annapolis - Room 1 and Annapolis Room - 3 Miles From Naval Academy .

What dining options are recommended for solo travelers staying at bed and breakfasts in Annapolis, MD?

For solo travellers, I'd suggest checking out The Chart House, a restaurant with stunning harbour views, or trying the fresh seafood at O'Brien's. Both offer a casual atmosphere and are perfect for a solo dining experience.

What are the best bed and breakfasts for families and kids in Annapolis, MD?

The best B&Bs for families and kids in Annapolis, MD are Detached Bedroom - Private Entrance - En-suite Bath , Loft - Private Room In Annapolis and Calico Cottage Guest House .

What are the best cultural activities and events in and around Annapolis, MD?

The Annapolis Symphony Orchestra puts on fantastic performances, and the Maryland State Arts Council hosts many events throughout the year. For something a little different, try the Annapolis Maritime Museum or explore the historic homes and gardens of the William Paca House and Garden.

What are the best pet friendly bed and breakfasts in Annapolis, MD?

The best pet friendly B&Bs in Annapolis, MD are Cozy Private Room In Annapolis Home , Lovely Private Master Bedroom and Inn On Main Annapolis .

Which hiking trails are recommended for exploring in and around Annapolis, MD?

The scenic hiking trails at Quiet Waters Park are a great option for a short hike with beautiful views. For a longer adventure, head to the Jug Bay Wetlands Sanctuary, where you can enjoy a variety of trails through diverse ecosystems.

What are the best bed and breakfasts with parking in Annapolis, MD?

Chesapeake Mornings , Howard's Cove Retreat and Cozy Private Room In Annapolis Home are the best B&Bs with parking in Annapolis, MD.

What amenities are commonly offered in bed and breakfasts in Annapolis, MD?

Most bed and breakfasts in Annapolis offer a continental breakfast, free Wi-Fi, and comfortable, well-appointed rooms. Some may also have additional amenities like a fireplace, a private patio, or a hot tub.

Annapolis, MD Bed and Breakfasts at the Best Price

8.2 262 reviews

Inn On Main Annapolis

B&B, Annapolis

The Inn on Main Annapolis is located just 1.2 miles from Annapolis Harbour, putting you within easy reach of the city's historic district, charming shops and restaurants. The B&B has received very good user ratings, with an excellent location rating and a very good cleanliness rating.
The rooms are all equipped with free Wi-Fi, air conditioning and flat-screen TVs, providing a comfortable stay. Guests can enjoy a delicious American breakfast every morning, relax on the terrace or dine at the Inn's restaurant, which serves American cuisine.

No reviews

Dog-friendly Riverfront Home With Dock, 2 Balconies, Waterside Patio, & Grill

B&B, Annapolis

This dog-friendly riverfront guesthouse in Annapolis offers a prime location with a private dock and waterside patio, situated 1.8 kilometres from Annapolis Harbour and 41.8 kilometres from Baltimore's Inner Harbour.
This spacious 3-bedroom, 4-bathroom property accommodates up to 11 guests, featuring a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, multiple outdoor spaces including two balconies and a garden, and is located 30.6 kilometres from Baltimore-Washington International Airport.

No reviews

Dog-friendly House With Yard, Deck, Firepit, Washer- Dryer & Ac - Near Golf

B&B, Annapolis

This dog-friendly guesthouse in Annapolis is located 2.7 kilometres from Annapolis Harbour and 29 kilometres from Baltimore's Inner Harbour.
The accommodation offers two bedrooms, three bathrooms, and a capacity for nineteen guests, featuring a fully equipped kitchen, air conditioning, a private garden, and a fire pit, with the convenience of an in-unit washer and dryer.

9.9 171 reviews

Bay View Studio Apartment

studio, Annapolis

This waterfront flat is situated in Annapolis, just a 1.6km walk from the Annapolis Sailing School and Annapolis Landing Marina, and within 5km of the Bay Bridge Market Place Shopping Center and Sparrows Beach. The property has received excellent ratings for location, cleanliness, and overall guest experience.
The apartment has one bedroom, one bathroom, and can accommodate up to four guests comfortably. The 93 square meter space features a fully equipped kitchen, a fireplace, free Wi-Fi, a washing machine, and a terrace with stunning views of the Annapolis harbour. Guests can also enjoy the on-site amenities, including a swimming pool, jacuzzi, garden, and barbecue grills.

No reviews

Colonial-era Charm And Allergy-friendly

B&B, Annapolis

This historic guesthouse in Annapolis offers a blend of 18th-century character and modern comforts, located within a historic district just a short walk from significant landmarks and waterfront attractions.
The accommodation features one bedroom and one bathroom for up to two guests, providing high-speed WiFi, air conditioning, and access to a fitness centre, with valet parking available for an additional fee.

9.9 226 reviews

Cozy Naptown Perch

B&B, Annapolis

This Murray Hill self-catering apartment is located 1.6km from the US Naval Academy and Annapolis's historic city centre, offering easy walking access to restaurants and the waterfront.
The recently renovated two-bedroom suite sleeps four, features a comfortable common room, outdoor patio, fire pit, complimentary snacks, free off-street parking, and is within walking distance of local restaurants and in-town events.

No reviews

Spacious Home With An Outdoor Pool, Screened Porch, Washer Dryer & Central Ac

B&B, Highland Beach

This Bed & Breakfast is situated in Highland Beach, 8 kilometres from Annapolis Harbour and 38 kilometres from Baltimore/Washington International Airport.
This 279 square metre guesthouse offers 3 bedrooms, 3 bathrooms, accommodating up to 10 guests, and features a private outdoor swimming pool, a screened porch, air conditioning, and a fully equipped kitchen, with an in-unit washer and dryer for added convenience.

9.2 35 reviews

Governor Calvert King | Historic Inns

B&B, Annapolis

This Annapolis guesthouse is situated in the city centre, a short walk from the Maryland State House and the United States Naval Academy.
The Governor Calvert King room, measuring 275 sq ft (25.5 sq m), offers a king-size bed, en-suite bathroom, and accommodates two guests; valet parking is available for £31.60 per day.

No reviews

Gorgeous & Bright Retreat With Patio, Firepit, Wd, & Stunning Rooftop Views

B&B, Annapolis

This Annapolis bed and breakfast is situated 1.8 kilometres from Annapolis Harbour, providing straightforward access to Baltimore's Inner Harbour and Power Plant attractions, located 32 kilometres away, with Baltimore-Washington International Airport 29 kilometres distant.
This spacious 78 square metre guesthouse offers one bedroom, three bathrooms, and accommodates up to eleven guests, featuring air conditioning, a fully equipped kitchen with a fridge and microwave, an in-unit washer and dryer, a private patio with a firepit, and rooftop views.

No reviews

Adventure Annapolis

B&B, Annapolis

Adventure Annapolis, a B&B, is located in Annapolis, 1.9 kilometres from Annapolis Harbour and 40 kilometres from Baltimore's Inner Harbour, Power Plant, and Convention Centre.
This accommodation offers 177 square metres of living space with two bedrooms, two bathrooms, and a guest capacity of 15, featuring air conditioning, a kitchen with a fridge, microwave oven, and dishwasher, and a garden.

No reviews

Charming Living Room In Beautiful Annapolis With Ac Discount Long Stay

B&B, Annapolis

This B&B is located in Annapolis's Historic District, offering easy access to the Chesapeake Bay and Sandy Point State Park, approximately 11 kilometres away.
Guests can enjoy a one-bedroom, one-bathroom guesthouse for two, featuring air-conditioned rooms with balconies, a kitchenette, and access to a garden and on-site fitness centre, with a check-out time of 11:00.

9.9 460 reviews

Our Annapolis Penthouse

B&B, Annapolis

This Annapolis studio apartment is situated in the Murray Hill neighbourhood, a short walk (less than 1.6 km) from Annapolis' city centre, Upper West Street's restaurants, and the Academy Stadium.
The self-contained unit, sleeping up to three guests, boasts high ceilings, a private entrance, parking, air conditioning, and a garden; pool access may also be available.

Best Annapolis, MD bed and breakfasts with air conditioning

9.0 2 reviews

Allergy-friendly King Room In Historic Property

B&B, Annapolis

This historic lodging is located in Annapolis's historic district, offering easy access to renowned landmarks such as the Maryland State House, which is 500 meters away, and the United States Naval Academy, 900 meters distant.
This one-bedroom guesthouse accommodates two guests and features 18th-century details, antique furnishings, air conditioning, and complimentary high-speed WiFi, with valet parking available for an extra charge.

9.8 144 reviews

Chic, Sophisticated And Elegant

B&B, Severna Park

This spacious apartment is located in Severna Park, just a short walk from the town centre and 7 kilometres from Annapolis. It has received excellent ratings for its location, cleanliness, and overall experience. The apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. It offers a fully equipped kitchen, a private patio, and easy access to the Baltimore Annapolis Bike Trail, making it ideal for exploring the area.

No reviews

Lakefront Home With Private Pool, Hot Tub, Outdoor Space, Central Ac, & Wd

B&B, Highland Beach

This lakefront guest house in Highland Beach is located 1.77 kilometres from Bay Ridge Beach and 7.4 kilometres from Annapolis Harbour, with Inner Harbour and Power Plant situated 48.3 kilometres away.
Offering 604 square metres of space, this establishment accommodates up to 23 guests across 5 bedrooms and features a private swimming pool, hot tub, garden, and a terrace with lake views, alongside a fully equipped kitchen and air conditioning.

9.2 140 reviews

Stay Right On Main Street Annapolis! Private Room With Queen-sized Bed And Bath.

B&B, Annapolis

The Inn on Main, a guesthouse in Annapolis's city centre, offers convenient access to Annapolis's historic district and waterfront, its precise location remaining unspecified in the provided details.
This one-bedroom, one-bathroom lodging, sleeping up to two guests, features newly renovated rooms with smart TVs, plush linens, and free Wi-Fi, situated above a renowned restaurant with on-site assistance available.