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

Annapolis, MD

25/06 – 25/07

£515/nighttotal: £15450 (30 )

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

2 2

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.

10 1 review

Annapolis, MD

04/07 – 05/07

£328/nightfor 1 night

Ask Staffers For Local Reco’s

1 2

B&B , Annapolis

This historic inn is located in Annapolis's historic district, offering easy access to renowned landmarks.
This B&B provides one bedroom and one bathroom for two guests, featuring 18th-century details, period antiques, air conditioning, complimentary WiFi, and valet parking for a fee.

Annapolis, MD

04/07 – 05/07

£323/nightfor 1 night

Robert Johnson 2 Doubles | Historic Inns

1 2

B&B , Annapolis

This Annapolis guesthouse, situated in the historic district, is within walking distance of the Maryland State House and the United States Naval Academy.
Robert Johnson House, one of three historic buildings comprising this establishment, offers a one-bedroom, one-bathroom room sleeping up to four guests, featuring two double beds, a television, and complimentary Wi-Fi; valet parking is available nearby.

Annapolis, MD

17/09 – 22/09

£528/nighttotal: £2640 (5 )

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

2 1

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.

9.8 530 reviews

Annapolis, MD

29/08 – 04/09

£99/nighttotal: £594 (6 )

Howard's Cove Retreat

1 2

B&B , Arnold

This Howard's Cove guesthouse is situated on the Severn River, a 5km drive from Annapolis city centre and close to the Annapolis Mall.
The self-catering unit, a converted 200-year-old barn, offers waterfront views, canoe/kayak access, a continental breakfast, and a small bedroom with twin beds, private bathroom, TV, and refrigerator; sleeping two guests.

9.9 79 reviews

Annapolis, MD

15/08 – 22/08

£140/nighttotal: £980 (7 )

West Annapolis Hidden Gem <.75mile To Navy Stadium <1mile To Downtown Annapolis

2 2

B&B , Annapolis

This family-friendly guesthouse is located in the city centre of Annapolis, within 2km of People's Brewer Hill Cemetery, Helen Avalynne Tawes Garden, and Maryland Hall for Creative Arts, and a short 3.3km drive from the U.S. Naval Academy. It has received excellent ratings for location, cleanliness and user experience.
The guesthouse has 2 bedrooms and 1 bathroom, covering 93 square metres and accommodating up to 7 guests. Amenities include a fully equipped kitchen, air conditioning, a terrace or balcony, a garden, a fitness centre, parking, and internet access.

9.2 133 reviews

Annapolis, MD

06/11 – 08/11

£166/nighttotal: £332 (2 )

Stay Right On Main Street Annapolis! Private Room With Double Bed And Bath.

1 2

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.

Annapolis, MD

17/09 – 22/09

£320/nighttotal: £1600 (5 )

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

1 1

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.

9.7 13 reviews

Annapolis, MD

04/07 – 05/07

£344/nightfor 1 night

Robert Johnson King | Historic Inns | Vintage Vibe

1 2

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.
Offering king-sized beds, a 24/7 reception, and valet parking at the Governor Calvert House (for a fee), this pet-friendly room sleeps two and includes access to hotel amenities.

Annapolis, MD

12/07 – 13/07

£146/nightfor 1 night

Charming Home Base For Exploring Annapolis

1 2

B&B , Annapolis

This guest house is located in Annapolis's historic district, offering easy access to key attractions.
The B&B provides one bedroom and one bathroom for up to two guests, with air conditioning, WiFi, and a fitness centre, preserving 18th-century details alongside modern comforts.

9.9 218 reviews

Annapolis, MD

06/11 – 08/11

£216/nighttotal: £432 (2 )

Charming Detached Studio W/ Easy Walk To Downtown.

1 2

B&B , Annapolis

This charming studio apartment is located in the heart of Downtown Annapolis, just a short walk from the Maryland State House, the United States Naval Academy, and the Annapolis City Dock. It enjoys an excellent user rating and location rating, and is praised for its cleanliness.
The self-contained apartment is situated above a garage and comfortably accommodates two guests. It includes a queen-size bed, a fully equipped kitchen with a mini-fridge and microwave, a bathroom with toiletries, and a writing desk.

Annapolis, MD

04/07 – 05/07

£251/nightfor 1 night

Inviting Charmer In The Heart Of Historic Annapoli

1 2

B&B , Annapolis

This historic guest house is located in Annapolis's historic district, providing convenient access to renowned landmarks such as the United States Naval Academy, which is approximately 500 meters away.
This non-smoking establishment offers one bedroom and one bathroom, accommodating up to two guests, with complimentary WiFi and air conditioning, while valet parking is available for an additional fee.

Best Annapolis, MD bed and breakfasts with air conditioning

8.2 280 reviews

Annapolis, MD

28/06 – 30/06

£297/nighttotal: £594 (2 )

Inn On Main Annapolis

2 4

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.

9.1 30 reviews

Annapolis, MD

15/08 – 22/08

£125/nighttotal: £875 (7 )

Governor Calvert King | Historic Inns

1 2

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.

Annapolis, MD

29/08 – 04/09

£161/nighttotal: £966 (6 )

Just A Half-mile From Chesapeake Bay & Beaches

1 2

B&B , Annapolis

This historic district guest house in Annapolis offers immediate access to key attractions, situated within a 0.5 kilometre radius of the United States Naval Academy.
The guest house provides 1 bedroom and 1 bathroom for up to 2 guests, featuring air conditioning, complimentary WiFi, and valet parking for £39.27 per night, with a mandatory service fee of £26.65 per night per room and a minimum guest age of 21.

9.8 425 reviews

Annapolis, MD

04/07 – 05/07

£192/nightfor 1 night

Independent Access Garage Apartment, Near Downtown

1 2

B&B , Annapolis

This Annapolis apartment, a self-contained flat in a convenient neighbourhood, is a 1.6km walk from Annapolis' city centre and 0.3km from Miss Shirley's Cafe.
The one-bedroom, one-bathroom apartment sleeps two, features a mini-kitchen, free street parking (with free weekend parking directly outside), bike storage, and is close to an EV charging station; complimentary toiletries and tea/coffee are provided.

Best Annapolis, MD bed and breakfasts with breakfast included

8.2 280 reviews

Annapolis, MD

28/06 – 30/06

£297/nighttotal: £594 (2 )

Inn On Main Annapolis

2 4

B&B , Annapolis

Frequently asked questions about bed and breakfast in Annapolis, MD

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.

Destinations nearby

Best Annapolis, MD bed and breakfasts with a garden

Annapolis, MD

25/06 – 28/06

£525/nighttotal: £1575 (3 )

Adventure Annapolis

2 2

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.

9.4 81 reviews

Annapolis, MD

12/07 – 30/08

£133/nighttotal: £6517 (49 )

The Lobster Loft

2 2

B&B , Annapolis

This two-bedroom apartment is situated in a peaceful neighbourhood just a short walk from the bustling Annapolis City Dock and the historic downtown area. The property has received excellent ratings for its cleanliness, location, and overall experience.
The apartment features two separate living areas, making it ideal for families or groups of up to six people. Amenities include a fully equipped kitchen, air conditioning, a garden, parking, and internet access.

Annapolis, MD

29/08 – 04/09

£484/nighttotal: £2904 (6 )

2-story Downtown Home With Enclosed Yard, Deck, Firepit, Gas Grill & Fireplace

3 2

B&B , Annapolis

This 2-storey downtown Annapolis guesthouse is located an 11-minute walk from Annapolis Harbour and 42 kilometres from Baltimore's Inner Harbour.
This property offers 251 square metres of living space with 3 bedrooms, 4 bathrooms, and a capacity for 15 guests, featuring a private enclosed garden with a deck, firepit, gas grill, and a children's playground.

9.9 211 reviews

Annapolis, MD

29/08 – 04/09

£158/nighttotal: £948 (6 )

Coastal Comfort Retreat Near Annapolis, Ev Charger

1 2

B&B , Arnold

This guest suite is situated in Arnold, Maryland, just 6.4 kilometres from historic downtown Annapolis and the USNA, and 8 kilometres from Sandy Point State Park, making it a convenient base for exploring the area. The accommodation has received excellent ratings for cleanliness, location and user experience.
The self-contained suite can accommodate up to four guests and features a comfortable seating area, a king-size bed and a luxurious ensuite bathroom. Guests can enjoy access to a seasonal outdoor oasis with a swimming pool, hot tub, fire pit and a barbecue area, as well as a fitness centre, a private garden and a dedicated parking space.

Our Favourite Bed and Breakfasts with a Pool in Annapolis, MD

Take a dip whenever you fancy, with on-site swimming pools at these B&Bs in Annapolis, MD making every stay more refreshing.

9.9 211 reviews

Annapolis, MD

29/08 – 04/09

£158/nighttotal: £948 (6 )

Coastal Comfort Retreat Near Annapolis, Ev Charger

1 2

B&B , Arnold

Discover Bed and Breakfasts by the Sea in Annapolis, MD

Relax into a gentle maritime atmosphere at shoreside bed and breakfasts located a brief journey from the coast in Annapolis, MD.

8.4 16 reviews

Annapolis, MD

28/06 – 30/06

£161/nighttotal: £322 (2 )

Governor Calvert 2 Double Beds | Historic Inns

1 4

B&B , Annapolis

Discover Luxury Bed and Breakfasts in Annapolis, MD

These upscale B&Bs in Annapolis, MD set the standard for luxury, offering premium facilities and an exceptional level of service throughout.

10 4 reviews

Annapolis, MD

04/07 – 05/07

£344/nightfor 1 night

Contemporary Downtown Unit | Near Prime Dining

1 2

B&B , Annapolis

Guest-Favourite Guesthouses with Parking in Annapolis, MD

On-site parking at your B&B in Annapolis, MD ensures reaching the waterfront is entirely stress-free every single day.

Annapolis, MD

25/06 – 25/07

£515/nighttotal: £15450 (30 )

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

2 2

B&B , Annapolis

Annapolis, MD

17/09 – 22/09

£528/nighttotal: £2640 (5 )

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

2 1

B&B , Annapolis

8.2 280 reviews

Annapolis, MD

28/06 – 30/06

£297/nighttotal: £594 (2 )

Inn On Main Annapolis

2 4

B&B , Annapolis

Explore Bed and Breakfasts with a Hot Tub in Annapolis, MD

A B&B with a hot tub in Annapolis, MD is tailor-made for an indulgent private soak following a day on the coast.

Annapolis, MD

25/06 – 25/07

£515/nighttotal: £15450 (30 )

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

2 2

B&B , Annapolis

Top-Rated Guesthouses with a Spa in Annapolis, MD

Choose a spa-equipped B&B in Annapolis, MD for the ultimate waterside wellness experience integrated seamlessly into your relaxing stay.

Annapolis, MD

04/07 – 05/07

£251/nightfor 1 night

Inviting Charmer In The Heart Of Historic Annapoli

1 2

B&B , Annapolis

Bed and Breakfast in Annapolis, MD

30 Bed and Breakfasts and Inn in Annapolis, MD

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

Ask Staffers For Local Reco’s

Robert Johnson 2 Doubles | Historic Inns

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

Howard's Cove Retreat

West Annapolis Hidden Gem <.75mile To Navy Stadium <1mile To Downtown Annapolis

Stay Right On Main Street Annapolis! Private Room With Double Bed And Bath.

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

Robert Johnson King | Historic Inns | Vintage Vibe

Charming Home Base For Exploring Annapolis

Charming Detached Studio W/ Easy Walk To Downtown.

Inviting Charmer In The Heart Of Historic Annapoli

Inn On Main Annapolis

Governor Calvert King | Historic Inns

Just A Half-mile From Chesapeake Bay & Beaches

Independent Access Garage Apartment, Near Downtown

Inn On Main Annapolis

Adventure Annapolis

The Lobster Loft

2-story Downtown Home With Enclosed Yard, Deck, Firepit, Gas Grill & Fireplace

Coastal Comfort Retreat Near Annapolis, Ev Charger

Coastal Comfort Retreat Near Annapolis, Ev Charger

Governor Calvert 2 Double Beds | Historic Inns

Contemporary Downtown Unit | Near Prime Dining

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

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

Inn On Main Annapolis

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

Inviting Charmer In The Heart Of Historic Annapoli