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

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.

8.1 260 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.

9.5 4 reviews

Robert Johnson 1 Queen Bed At Historic Inns

B&B, Annapolis

This Annapolis guesthouse is situated in the historic district, a short walk from the Maryland State House and the United States Naval Academy.
The Pure Wellness Room, offering a queen-size bed, en-suite bathroom, and amenities including air conditioning, parking, and Wi-Fi, comfortably accommodates two guests and allows up to two dogs (under 50 lbs) for an extra fee.

10 1 review

Charming Brick Home With Patio, Wifi, Ac, & Wd - Walk To Everything

B&B, Annapolis

This Annapolis guesthouse is a 40-kilometre drive from Baltimore's Inner Harbour and Power Plant, offering a convenient base for exploring local attractions and a 2.4-kilometre distance to Annapolis Harbour.
The 92-square-meter property features two bedrooms, four bathrooms, air conditioning, WiFi, a fully equipped kitchen with a dishwasher and oven, and a private patio, accommodating up to seven guests.

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

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

B&B, Annapolis

This historic downtown Annapolis townhouse is situated just over 1.7 kilometres from Annapolis Harbour, offering convenient access to the city's waterfront.
This bed and breakfast provides accommodation for up to 11 guests across 2 bedrooms and 4 bathrooms, featuring a fully equipped kitchen, on-site spa, free private parking, and a children's playground.

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.

10 55 reviews

Pristine, Private Apt - Walk To Town/stadium

B&B, Annapolis

This Annapolis apartment, located in Homewood's quiet Arts District, is within walking distance of numerous restaurants, the US Naval Academy, and offers easy access to Annapolis city centre via a short shuttle ride from the Westin Hotel.
The self-catering flat features a mid-century modern design, one bedroom, one bathroom, sleeps up to four guests with a sleeper sofa and optional air mattress, and includes a fully equipped kitchen, private patio, and free parking.

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.

10 8 reviews

Howard's Cove Retreat Apartment

B&B, Arnold

Howard's Cove Retreat, a guest house in Arnold, offers waterfront accommodation on Luce Creek with boating access from a private dock, situated just 5 kilometres from downtown Annapolis and convenient for those visiting the Naval Academy. This two-bedroom, two-bathroom property accommodates up to four guests and features a full kitchen, living area, and outdoor space within a unique 100-year-old barn setting.

No reviews

Robert Johnson King Wellness At Historic Inns

B&B, Annapolis

This guest house in central Annapolis offers immediate access on foot to the United States Naval Academy, Maryland State House, and St. John's College, with the Chesapeake Bay a short distance away for day trips.
This accommodation provides 26 square metres of space for two guests, featuring air conditioning, Wi-Fi, a fitness centre, and pet-friendly rooms, with daily cleaning and a shuttle service available.

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.

Best Annapolis, MD bed and breakfasts with air conditioning

9.9 170 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.