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

9.9 78 reviews

Annapolis, MD

06/27 – 06/29

$377/nighttotal: $754 (2 )

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

1 2

B&B , Annapolis

This family-friendly B&B in the heart of Annapolis offers a non-smoking environment and an excellent location just steps away from People's Brewer Hill Cemetery, Helen Avalynne Tawes Garden, and Maryland Hall for Creative Arts. With excellent user, location, and cleanliness ratings, this B&B is a top choice for travelers.
The B&B features a spacious layout with 1000 square feet of floor area, 2 bedrooms, 1 bathroom, and a guest capacity of 7. Guests can enjoy amenities such as a kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning, a terrace/balcony, a garden, a fitness center, parking, and barbecue grills.

Annapolis, MD

06/20 – 06/26

$252/nighttotal: $1512 (6 )

Explore Local Attraction | Close To Historic Sites

1 2

B&B , Annapolis

This Annapolis bed and breakfast offers a prime location in the historic district, steps from the Maryland State House and the United States Naval Academy, with easy walking access to Main Street's shops and restaurants.
The 247-square-foot guest room, featuring a queen-sized bed, accommodates two guests and includes a private bathroom, Wi-Fi, air conditioning, and access to a fitness center and valet parking at the Governor Calvert House.

9.6 11 reviews

Annapolis, MD

06/30 – 07/03

$179/nighttotal: $537 (3 )

Robert Johnson King | Historic Inns | Vintage Vibe

1 2

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.

Annapolis, MD

06/25 – 06/28

$740/nighttotal: $2220 (3 )

Adventure Annapolis

2 2

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.

9.8 530 reviews

Annapolis, MD

06/23 – 06/25

$152/nighttotal: $304 (2 )

Howard's Cove Retreat

1 2

B&B , Arnold

This Arnold bed and breakfast offers a unique stay in a 200-year-old barn conversion on Howard's Cove off the Severn River, three miles from downtown Annapolis and the Annapolis Mall.
The inn provides a small bedroom with twin beds, a private bathroom, refrigerator, and continental breakfast, plus access to a canoe/kayak and swimming dock, and hosts offer Annapolis sightseeing assistance.

9.9 220 reviews

Annapolis, MD

11/12 – 11/14

$244/nighttotal: $488 (2 )

Cozy Naptown Perch

2 2

B&B , Annapolis

This Murray Hill private suite is located one mile from both the US Naval Academy and historic downtown Annapolis, offering easy walking access to restaurants and the waterfront.
The recently renovated two-bedroom suite sleeps four, includes a common room with coffee/tea setup, an outdoor patio with fire pit, free parking, and complimentary snacks.

10 4 reviews

Annapolis, MD

06/27 – 06/29

$309/nighttotal: $618 (2 )

Contemporary Downtown Unit | Near Prime Dining

1 2

B&B , Annapolis

This Annapolis guesthouse is 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.
The 312-square-foot king room, accommodating up to two guests, includes linens, towels, bathroom essentials, and 24/7 key access and luggage storage; valet parking is available nearby at the Governor Calvert House for an extra fee.

10 9 reviews

Annapolis, MD

06/19 – 06/22

$234/nighttotal: $702 (3 )

Sunny 1br Apt | Quiet Spot Near Downtown Annapolis

1 2

B&B , Arnold

Tide and Timber Retreat, a dog-friendly guesthouse in Arnold, Maryland, is conveniently located 5 miles from the Navy-Marine Corps Memorial Stadium and 6 miles from downtown Annapolis.
This private basement apartment sleeps four, features a full kitchen with dishwasher, in-unit laundry, a dedicated parking spot, access to a shared yard with a children's play area and firepit, and offers flexible check-in/check-out times.

9.8 423 reviews

Annapolis, MD

07/12 – 07/13

$223/nightfor 1 night

Independent Access Garage Apartment, Near Downtown

1 2

B&B , Annapolis

This cozy garage apartment is located in a residential neighborhood in Annapolis, just a 10-minute walk from the downtown area and two blocks from the popular Miss Shirley's breakfast spot. Guests consistently rate this accommodation excellent for its cleanliness, location, and overall experience.
The apartment features a private entrance, a queen-size bed, a private bathroom, and a mini-kitchen with a fridge, microwave, and coffee maker. You'll also find free street parking available on weekends and a free EV charging station just a block away.

9.0 2 reviews

Annapolis, MD

06/25 – 06/28

$283/nighttotal: $849 (3 )

Robert Johnson 1 Queen Bed At Historic Inns

1 2

B&B , Annapolis

This lodging is located just steps from the Maryland State House and the U.S. Naval Academy, offering direct walking access to the historic waterfront, Main Street shops, and local dining establishments.
This B&B offers a "Pure Wellness Room" with air conditioning, internet, a fitness center, parking, and accommodates up to two guests in one bedroom and one bathroom spread across historic buildings, with dog-friendly options available for a fee.

9.9 218 reviews

Annapolis, MD

07/12 – 07/13

$278/nightfor 1 night

Charming Detached Studio W/ Easy Walk To Downtown.

1 2

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.

9.2 130 reviews

Annapolis, MD

06/23 – 06/25

$253/nighttotal: $506 (2 )

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

1 2

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.

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.

8.4 16 reviews

Annapolis, MD

07/12 – 07/13

$161/nightfor 1 night

Governor Calvert 2 Double Beds | Historic Inns

1 2

B&B , Annapolis

This Annapolis bed and breakfast offers a prime downtown location, steps from the Maryland State House and the U.S. Naval Academy, with easy walking access to Main Street shops and restaurants.
The 240-square-foot guest room, accommodating up to four guests with two double beds, includes a television, 24/7 key access, and luggage storage; valet parking is available for an extra fee, and pets are welcome (with a fee).

Best Annapolis, MD bed and breakfasts with breakfast included

8.2 282 reviews

Annapolis, MD

11/12 – 11/14

$197/nighttotal: $394 (2 )

Inn On Main Annapolis

1 2

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.

9.2 23 reviews

Annapolis, MD

06/28 – 06/30

$475/nighttotal: $950 (2 )

Inn At Horn Point

1 2

B&B , Annapolis

This Annapolis bed and breakfast is located in Eastport, within walking distance of the Annapolis Maritime Museum, City Dock, and the U.S. Naval Academy. Travelers will enjoy the convenience of this location and its proximity to the city's main attractions. It has earned excellent user ratings, showcasing its quality and appeal.
The inn offers a garden, a terrace, and a fitness center for relaxation and recreation. Guests can enjoy amenities such as room service, free parking, and a concierge service for a comfortable and convenient stay.

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.

Destinations nearby

Best Annapolis, MD bed and breakfasts with a garden

10 19 reviews

Annapolis, MD

06/19 – 06/21

$349/nighttotal: $698 (2 )

Waterfront Private Guest Suite In Annapolis

1 2

B&B , Annapolis

This Annapolis guesthouse in West Annapolis offers a spacious waterfront suite, a short walk from the Navy-Marine Corps Stadium and 1.5 miles from City Dock and the U.S. Naval Academy.
The 400+ square-foot suite features a separate living area and bedroom, a private 1.5 bathrooms, sleeps two, and includes a 55” HDTV, mini-fridge, microwave, Keurig coffee maker, and private boat slip access (fee applies).

9.9 447 reviews

Annapolis, MD

11/12 – 11/14

$142/nighttotal: $284 (2 )

Our Annapolis Penthouse

1 2

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.

10 48 reviews

Annapolis, MD

08/21 – 08/24

$270/nighttotal: $810 (3 )

Uptown Annapolis - Walkable, Peaceful, Pristine

1 2

B&B , Annapolis

This brand-new Annapolis apartment rental, located in the quiet Homewood neighborhood, is within walking distance of the Navy-Marine Corps Memorial Stadium and the Arts District, with easy access to downtown Annapolis via a short shuttle ride from the Westin Annapolis.
The one-bedroom, one-bathroom unit sleeps four with a full-size sleeper sofa, features a fully equipped kitchen including a dishwasher, and offers a private patio overlooking a wooded area; extended stays are welcome.

9.9 209 reviews

Annapolis, MD

07/01 – 07/08

$163/nighttotal: $1141 (7 )

Coastal Comfort Retreat Near Annapolis, Ev Charger

1 2

B&B , Arnold

This one-bedroom, one-bathroom accommodation is located in Arnold, a safe and family-friendly neighborhood just 4 miles from historic downtown Annapolis and the USNA. It has received excellent ratings for its location, cleanliness, and amenities.
The accommodation has a private entrance, keyless entry, and ample parking. It features a coastal color scheme with a relaxing atmosphere, a spacious bedroom with a seating area and mounted TV, and a luxurious ensuite bathroom with a shower featuring dual shower heads and a towel warmer. Guests have access to a shared 23,000-gallon pool, hot tub, lounge chairs, fire pit, patio/grill, and rocking chairs.

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.

9.9 209 reviews

Annapolis, MD

07/01 – 07/08

$163/nighttotal: $1141 (7 )

Coastal Comfort Retreat Near Annapolis, Ev Charger

1 2

B&B , Arnold

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.

Annapolis, MD

07/16 – 07/19

$686/nighttotal: $2058 (3 )

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

2 5

B&B , Annapolis

Annapolis, MD

12/03 – 12/06

$755/nighttotal: $2265 (3 )

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

2 10

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.

Annapolis, MD

06/20 – 06/26

$1407/nighttotal: $8442 (6 )

This Thoughtfully Styled Home Overlooks The Bay And Is Perfect For Your Annapolis Escape

5 2

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.

9.9 209 reviews

Annapolis, MD

07/01 – 07/08

$163/nighttotal: $1141 (7 )

Coastal Comfort Retreat Near Annapolis, Ev Charger

1 2

B&B , Arnold

Best Annapolis, MD bed and breakfasts with air conditioning

Annapolis, MD

06/27 – 06/29

$257/nighttotal: $514 (2 )

Inviting Charmer In The Heart Of Historic Annapoli

1 2

B&B , Annapolis

9.2 26 reviews

Annapolis, MD

06/30 – 07/03

$171/nighttotal: $513 (3 )

Governor Calvert King | Historic Inns

1 2

B&B , Annapolis

10 1 review

Annapolis, MD

06/27 – 06/29

$300/nighttotal: $600 (2 )

Ask Staffers For Local Reco’s

1 2

B&B , Annapolis

Annapolis, MD

08/21 – 08/24

$398/nighttotal: $1194 (3 )

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

2 2

B&B , Annapolis

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

30 Bed and Breakfast and Inn in Annapolis, MD

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

Explore Local Attraction | Close To Historic Sites

Robert Johnson King | Historic Inns | Vintage Vibe

Adventure Annapolis

Howard's Cove Retreat

Cozy Naptown Perch

Contemporary Downtown Unit | Near Prime Dining

Sunny 1br Apt | Quiet Spot Near Downtown Annapolis

Independent Access Garage Apartment, Near Downtown

Robert Johnson 1 Queen Bed At Historic Inns

Charming Detached Studio W/ Easy Walk To Downtown.

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

Governor Calvert 2 Double Beds | Historic Inns

Inn On Main Annapolis

Inn At Horn Point

Waterfront Private Guest Suite In Annapolis

Our Annapolis Penthouse

Uptown Annapolis - Walkable, Peaceful, Pristine

Coastal Comfort Retreat Near Annapolis, Ev Charger

Coastal Comfort Retreat Near Annapolis, Ev Charger

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

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

This Thoughtfully Styled Home Overlooks The Bay And Is Perfect For Your Annapolis Escape

Coastal Comfort Retreat Near Annapolis, Ev Charger

Inviting Charmer In The Heart Of Historic Annapoli

Governor Calvert King | Historic Inns

Ask Staffers For Local Reco’s

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