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

You have to see the United States Naval Academy, which is always impressive. The State House is another must-see, and you can get a great view of the city from the top of the dome. If you have time, a walk around the historic district will give you a glimpse of Annapolis's colonial past.

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 the most popular area for bed and breakfasts, as it's close to the main attractions. You can also find some charming options in the Eastport neighborhood, which is known for its waterfront views and quaint shops.

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

For solo travelers, I recommend trying out The Chart House on the harbor for a nice dinner. It's known for its seafood and beautiful views. For a more casual bite, try the Annapolis Market House, which has a variety of restaurants and shops.

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

Annapolis is home to the Maryland State Arts Council and hosts many cultural events throughout the year. Check out the Annapolis Symphony Orchestra or visit the Annapolis Maritime Museum. The city also has a vibrant arts scene, with galleries and studios scattered throughout the historic district.

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 , Front Room - Private Room In Annapolis and Calico Cottage Guest House .

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

If you're looking for a scenic hike, try the Quiet Waters Park trails. It's a beautiful park with over 340 acres of woods and waterfront. For a shorter hike, check out the trails at the Annapolis City Dock.

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 .

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 parking. Some also have amenities like swimming pools, hot tubs, and fireplaces.

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.

Annapolis, MD B&B, Guest Houses and Inns

No reviews

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

B&B, Annapolis

This Annapolis bed and breakfast is situated 1.1 miles from Annapolis Harbor and 25 miles from Baltimore's Inner Harbor and Power Plant, offering rooftop views and an outdoor patio with a firepit. The 840 square foot accommodation features one bedroom, three bathrooms, and can host up to 11 guests, with amenities including air conditioning, a fully equipped kitchen with a dishwasher and oven, and an in-unit washer and dryer.

9.9 225 reviews

Charming Detached Studio W/ Easy Walk To Downtown.

B&B, Annapolis

This centrally located studio in Downtown Annapolis offers a private retreat just steps away from restaurants, shops, and attractions. With excellent user and location ratings, this studio provides a comfortable and convenient base for exploring the city.
The studio features a queen bed, full bathroom, kitchenette, writing table, and wireless internet. Guests can enjoy essential amenities such as toiletries, tea, and coffee, as well as a separate entrance for added privacy.

No reviews

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

B&B, Highland Beach

This B&B in Highland Beach is located in Annapolis, 5 miles from Annapolis Harbor, 24 miles from Baltimore-Washington International Airport, and approximately 30 miles from the Inner Harbor and Power Plant.
This 3,000 square foot lodging offers 3 bedrooms, 3 bathrooms, and accommodates up to 10 guests with amenities including a private outdoor pool, screened porch, full kitchen, central air conditioning, and an in-unit washer and dryer.

10 5 reviews

The Harness Creek Retreat

B&B, Annapolis

This private hilltop B&B in Annapolis' Harness Creek area is situated just 3 miles from downtown attractions including the United States Naval Academy, the waterfront, and various shops and restaurants.
This 2-bedroom, 1.5-bathroom guesthouse accommodates up to four guests and features a kitchen with vineyard views, a living room with a large TV and electric fireplace, a separate living area, a private backyard with a gas fire pit, and parking for up to 10 cars.

9.9 171 reviews

Bay View Studio Apartment

B&B, Annapolis

This waterfront apartment is located in Annapolis, just a 10-minute walk from the Annapolis Sailing School and Annapolis Landing Marina, offering easy access to the city's historic downtown and its many attractions. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
This spacious one-bedroom apartment comfortably accommodates up to four guests with a floor area of 1000 square feet. Enjoy a range of amenities, including a swimming pool, jacuzzi, terrace, garden, and parking, as well as modern conveniences like a fully equipped kitchen, free Wi-Fi, and a washing machine.

9.0 2 reviews

Maryland Inn 2 Doubles | Historic Inns

B&B, Annapolis

This Annapolis bed and breakfast is located in the historic district, within walking distance of the Maryland State House, the United States Naval Academy, and the waterfront.
The inn features three historic buildings with a total of one bedroom and one bathroom, accommodating up to four guests, and offers amenities like a fitness center, parking, and pet-friendly accommodations.

No reviews

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

B&B, Annapolis

This dog-friendly, riverfront bed and breakfast in Annapolis is located 1.1 miles from Annapolis Harbor and 26 miles from Baltimore's Inner Harbor, offering direct water access from its private dock.
This 4170 square foot guesthouse accommodates up to 11 guests in 3 bedrooms and 4 bathrooms, featuring a fully equipped kitchen with a dishwasher and oven, air conditioning, a terrace, a balcony, and a garden with a grill.

No reviews

Waterfront Home With Scenic Porches, Yard, Grill, Jetted Tub, Central Ac, & Wd

B&B, Highland Beach

This waterfront bed and breakfast in Highland Beach is an 11-minute walk from Bay Ridge Beach, 4.4 miles from Annapolis Harbor, and 24 miles from Baltimore - Washington International Airport.
This B&B offers 3 bedrooms, 4 bathrooms, and can accommodate up to 19 guests, featuring air conditioning, a full kitchen with a dishwasher and microwave, laundry facilities, and an outdoor grilling area.

9.9 460 reviews

Our Annapolis Penthouse

B&B, Annapolis

This studio apartment in Annapolis' Murray Hill neighborhood is conveniently located within walking distance of the city center, Upper West Street restaurants, and Academy Stadium. The studio enjoys excellent ratings for user experience, location, and cleanliness.
The studio features a separate entrance through the garage, offering privacy and a spacious, sunny layout with cathedral ceilings. It can comfortably accommodate up to three guests and includes amenities like air conditioning, a garden, parking, and potential pool access.

9.8 16 reviews

Robert Johnson King | Historic Inns | Vintage Vibe

B&B, Annapolis

This Annapolis bed and breakfast is located in the historic district, steps from the Maryland State House and the U.S. Naval Academy, with easy walking access to Main Street's shops and restaurants.
Each 312-square-foot guest room offers a king-sized bed, private bathroom, and amenities including Wi-Fi, air conditioning, and accommodates up to two guests; valet parking is available at the nearby Governor Calvert House for an additional fee.

8.2 262 reviews

Inn On Main Annapolis

B&B, Annapolis

The Inn on Main Annapolis is located just a short walk from the bustling Annapolis Harbor, with easy access to the city's vibrant waterfront attractions, restaurants, and shops. Guests consistently rate the inn highly for its cleanliness, location, and overall experience. The inn offers a variety of comfortable rooms, each with a private bathroom, ensuring privacy and convenience. Amenities include a restaurant, bar, terrace, and garden, allowing guests to enjoy a relaxing stay with a range of options for dining, relaxation, and exploration.

No reviews

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

B&B, Annapolis

This historic downtown townhome offers a B&B experience in Annapolis, situated 1.1 miles from Annapolis Harbor and 25 miles from Baltimore's Inner Harbor.
This lodging accommodates up to 11 guests in 2 bedrooms and features a full kitchen with a fridge, microwave, and dishwasher, air conditioning, a spa, concierge service, and private parking.

Browse Waterfront Bed and Breakfasts in Annapolis, MD

Soak up the refreshing maritime atmosphere at these seaside bed and breakfasts in Annapolis, MD, located short distances from popular shoreside attractions.

No reviews

Serene Waterfront Home With Kayaks, Paddle Board, Grill, Firepit, Wd, And Ac

B&B, Herald Harbor

This waterfront homestay in Crownsville, Maryland, is located 11 miles from Annapolis Harbor and 14 miles from Baltimore Washington International Airport.
This spacious 1390 square foot B&B features two bedrooms, two bathrooms, a full kitchen, air conditioning, a balcony, and offers kayaks, a paddleboard, a barbecue grill, and a firepit for guest enjoyment.

Best Annapolis, MD bed and breakfasts with breakfast included

8.2 262 reviews

Inn On Main Annapolis

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 have to see the United States Naval Academy, which is always impressive. The State House is another must-see, and you can get a great view of the city from the top of the dome. If you have time, a walk around the historic district will give you a glimpse of Annapolis's colonial past.
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 the most popular area for bed and breakfasts, as it's close to the main attractions. You can also find some charming options in the Eastport neighborhood, which is known for its waterfront views and quaint shops.
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 dining options are recommended for solo travelers staying at bed and breakfasts in Annapolis, MD?
For solo travelers, I recommend trying out The Chart House on the harbor for a nice dinner. It's known for its seafood and beautiful views. For a more casual bite, try the Annapolis Market House, which has a variety of restaurants and shops.
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 are the best cultural activities and events in and around Annapolis, MD?
Annapolis is home to the Maryland State Arts Council and hosts many cultural events throughout the year. Check out the Annapolis Symphony Orchestra or visit the Annapolis Maritime Museum. The city also has a vibrant arts scene, with galleries and studios scattered throughout the historic district.
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, Front Room - Private Room In Annapolis and Calico Cottage Guest House.
Which hiking trails are recommended for exploring in and around Annapolis, MD?
If you're looking for a scenic hike, try the Quiet Waters Park trails. It's a beautiful park with over 340 acres of woods and waterfront. For a shorter hike, check out the trails at the Annapolis City Dock.
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.
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 parking. Some also have amenities like swimming pools, hot tubs, and fireplaces.
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.

Popular destinations

Best Annapolis, MD bed and breakfasts with a garden

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 downtown Annapolis guesthouse, is located above a renowned restaurant, placing it steps from Annapolis's major attractions like the United States Naval Academy. This pet-friendly lodging boasts a private room with a 33+ inch smart TV, Hulu Live TV, free Wi-Fi, and a private bathroom with a marble vanity, accommodating up to two guests.

No reviews

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

B&B, Highland Beach

This lakefront Bed and Breakfast in Highland Beach is located 1.1 miles from Bay Ridge Beach and 4.6 miles from Annapolis Harbor, offering picturesque views and a tranquil atmosphere.
This 6,500-square-foot B&B features 5 bedrooms, accommodating up to 23 guests, with amenities including air conditioning, a swimming pool, a jacuzzi, a private terrace, a garden, and a full kitchen.

No reviews

Adventure Annapolis

B&B, Annapolis

Adventure Annapolis, a bed and breakfast, is located in Annapolis, 1.2 miles from Annapolis Harbor and 25 miles from Baltimore attractions like the Power Plant and Baltimore Convention Center.
This 1910 square foot B&B offers 2 bedrooms, 2 bathrooms, and accommodates up to 15 guests with air conditioning, a full kitchen featuring a fridge, microwave, and dishwasher, and a private patio.

9.8 144 reviews

Chic, Sophisticated And Elegant

B&B, Severna Park

This Severna Park apartment is located just a short walk from the town center and a short drive from Annapolis, the Naval Academy, Baltimore, and Washington D.C., making it ideal for exploring the region. With excellent user, location, and cleanliness ratings, this property offers a comfortable and convenient stay.
The apartment features two bedrooms and one bathroom, comfortably accommodating up to four guests. Enjoy modern amenities like Wi-Fi, a TV with Chromecast, a private patio, and a fully equipped kitchen with a fridge, microwave, and dishwasher.

Neighborhoods and points of interest in Annapolis, MD

Compare Bed and Breakfasts with a Pool in Annapolis, MD

On-site pool access at your B&B in Annapolis, MD provides a refreshing swim to complement your day by the water.

9.9 214 reviews

Captains Quarters Oasis Near Annapolis, Sleeps 4

B&B, Arnold

This Arnold, Maryland guest suite is located four miles from Annapolis and five miles from Sandy Point State Park, offering easy access to historic sites and outdoor recreation.
The fully furnished, pet-friendly suite features a king-size bed, en-suite bathroom, keyless entry, and access to a shared pool, hot tub (seasonal), firepit, patio, and grill; it comfortably accommodates four guests.

No reviews

Splendid Home With Private Pool, Fire Pit, Several Decks & Balconies

B&B, Riva

This B&B in Annapolis is located 8.8 miles from Annapolis Harbor and within a 26-27 mile radius of Baltimore attractions like the Sports Legends Museum at Camden Yards and Pier Six Concert Pavilion.
This 5120 square foot Bed and Breakfast accommodates up to 23 guests with 4 bedrooms and 3 bathrooms, featuring a private swimming pool, fire pit, garden, children's playground, and a well-equipped kitchen with a dishwasher, oven, and microwave.

No reviews

King Master Suite With Den Room

B&B, Crownsville

This Crownsville, Maryland B&B, registration number 145024, offers a convenient, centrally located stay with easy access to local attractions, though specific distances require further inquiry.
The one-bedroom, one-bathroom guesthouse comfortably sleeps four guests and includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, a swimming pool, jacuzzi, and garden.

Traveler-Approved Bed and Breakfasts with Parking in Annapolis, MD

Parking is effortless, as every B&B near the water in Annapolis, MD includes free on-site spaces for your coastal vacation.

10 2 reviews

Chesapeake Bay Retreat Near Downtown Annapolis

B&B, Highland Beach

No reviews

Annapolis By St John College Cat Food $50

B&B, Annapolis

8.0 7 reviews

Private N/s 2 Double Bed & Bath

B&B, Arnold

No reviews

Annapolis Home 5 Miles From Downtown Annapolis

B&B, Annapolis

Guest-Favorite B&bs with Jacuzzi in Annapolis, MD

Coming home to a private hot tub after the beach changes everything. These B&Bs in Annapolis, MD are designed for total relaxation.

10 1 review

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

B&B, Annapolis

Browse B&bs with a Terrace in Annapolis, MD

Every B&B in Annapolis, MD on this list includes a balcony, perfect for taking in the scenery.

9.8 434 reviews

Independent Access Garage Apartment, Near Downtown

B&B, Annapolis

Best Annapolis, MD bed and breakfasts with air conditioning

No reviews

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

B&B, Annapolis

No reviews

Riverfront Home With Multiple Decks, Central Ac, Washerdryer - Two Dogs Ok

B&B, Arnold

9.9 226 reviews

Cozy Naptown Perch

B&B, Annapolis

No reviews

Charming Living Room In Beautiful Annapolis With Ac Discount Long Stay

B&B, Annapolis

Search best guest house in Annapolis, MD from 100+ sites!

88 Bed and Breakfast and Inn in Annapolis, MD

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

Charming Detached Studio W/ Easy Walk To Downtown.

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

The Harness Creek Retreat

Bay View Studio Apartment

Maryland Inn 2 Doubles | Historic Inns

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

Waterfront Home With Scenic Porches, Yard, Grill, Jetted Tub, Central Ac, & Wd

Our Annapolis Penthouse

Robert Johnson King | Historic Inns | Vintage Vibe

Inn On Main Annapolis

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

Serene Waterfront Home With Kayaks, Paddle Board, Grill, Firepit, Wd, And Ac

Inn On Main Annapolis

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

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

Adventure Annapolis

Chic, Sophisticated And Elegant

Captains Quarters Oasis Near Annapolis, Sleeps 4

Splendid Home With Private Pool, Fire Pit, Several Decks & Balconies

King Master Suite With Den Room

Chesapeake Bay Retreat Near Downtown Annapolis

Annapolis By St John College Cat Food $50

Private N/s 2 Double Bed & Bath

Annapolis Home 5 Miles From Downtown Annapolis

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

Independent Access Garage Apartment, Near Downtown

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

Riverfront Home With Multiple Decks, Central Ac, Washerdryer - Two Dogs Ok

Cozy Naptown Perch

Charming Living Room In Beautiful Annapolis With Ac Discount Long Stay