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

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.

9.9 79 reviews

Annapolis, MD

29/08 – 04/09

£183/nighttotal: £1098 (6 )

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.

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.

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.

9.9 211 reviews

Annapolis, MD

01/07 – 08/07

£122/nighttotal: £854 (7 )

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.

Annapolis, MD

03/12 – 06/12

£617/nighttotal: £1851 (3 )

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

2 10

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.

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.

10 4 reviews

Annapolis, MD

04/07 – 05/07

£344/nightfor 1 night

Contemporary Downtown Unit | Near Prime Dining

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 a king-sized bed, 312 square feet of space, and accommodating up to two guests, this pet-friendly lodging includes Wi-Fi, air conditioning, and parking (valet parking available at the Governor Calvert House for £32.30 per day).

10 1 review

Annapolis, MD

04/07 – 05/07

£330/nightfor 1 night

Maryland Inn King | Historic Inns | Pets Allowed

1 2

B&B , Annapolis

This B&B is situated in the heart of Annapolis, just a short walk from the State House and the Naval Academy, offering easy access to the city's historic waterfront, Main Street shops, and local restaurants. The B&B features a range of rooms across three historic buildings, each with its unique character and architecture, offering a glimpse into Annapolis' rich past, and welcoming dogs with a fee.

Annapolis, MD

25/06 – 28/06

£552/nighttotal: £1656 (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.

Annapolis, MD

01/07 – 08/07

£541/nighttotal: £3787 (7 )

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.

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.

Best Annapolis, MD bed and breakfasts with air conditioning

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.

10 1 review

Annapolis, MD

12/07 – 13/07

£146/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.

9.6 11 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.

9.0 2 reviews

Annapolis, MD

25/06 – 28/06

£226/nighttotal: £678 (3 )

Robert Johnson 1 Queen Bed At Historic Inns

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.
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.

Best Annapolis, MD bed and breakfasts with breakfast included

8.2 280 reviews

Annapolis, MD

29/06 – 01/07

£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.

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

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.

9.9 218 reviews

Annapolis, MD

12/07 – 13/07

£203/nightfor 1 night

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.

10 20 reviews

Annapolis, MD

04/07 – 05/07

£277/nightfor 1 night

Waterfront Private Guest Suite In Annapolis

1 2

B&B , Annapolis

This Annapolis guesthouse is located in West Annapolis, approximately 2.4 kilometres from City Dock and the United States Naval Academy.
The spacious 400+ sq ft waterfront suite boasts a separate living area and bedroom, sleeping up to two guests, and includes a 55” HDTV, mini-fridge, microwave, Keurig coffee maker, and private parking; a private boat slip is available at an extra cost.

10 50 reviews

Annapolis, MD

24/07 – 29/07

£211/nighttotal: £1055 (5 )

Air Show And Tall Ships (Balt) - Stay In Annapolis

1 3

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.

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

01/07 – 08/07

£122/nighttotal: £854 (7 )

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.

Annapolis, MD

01/07 – 08/07

£541/nighttotal: £3787 (7 )

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

2 2

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

01/07 – 08/07

£541/nighttotal: £3787 (7 )

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

2 2

B&B , Annapolis

8.2 280 reviews

Annapolis, MD

29/06 – 01/07

£297/nighttotal: £594 (2 )

Inn On Main Annapolis

2 4

B&B , Annapolis

Annapolis, MD

03/12 – 06/12

£617/nighttotal: £1851 (3 )

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

2 10

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 – 28/06

£552/nighttotal: £1656 (3 )

Adventure Annapolis

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.

10 50 reviews

Annapolis, MD

24/07 – 29/07

£211/nighttotal: £1055 (5 )

Air Show And Tall Ships (Balt) - Stay In Annapolis

1 3

B&B , Annapolis

Bed and Breakfast in Annapolis, MD

30 Bed and Breakfasts and Inn in Annapolis, MD

Inviting Charmer In The Heart Of Historic Annapoli

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

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

Charming Home Base For Exploring Annapolis

Coastal Comfort Retreat Near Annapolis, Ev Charger

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

Robert Johnson 2 Doubles | Historic Inns

Contemporary Downtown Unit | Near Prime Dining

Maryland Inn King | Historic Inns | Pets Allowed

Adventure Annapolis

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

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

The Lobster Loft

Ask Staffers For Local Reco’s

Robert Johnson King | Historic Inns | Vintage Vibe

Robert Johnson 1 Queen Bed At Historic Inns

Inn On Main Annapolis

Howard's Cove Retreat

Charming Detached Studio W/ Easy Walk To Downtown.

Waterfront Private Guest Suite In Annapolis

Air Show And Tall Ships (Balt) - Stay In Annapolis

Coastal Comfort Retreat Near Annapolis, Ev Charger

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

Contemporary Downtown Unit | Near Prime Dining

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

Inn On Main Annapolis

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

Adventure Annapolis

Air Show And Tall Ships (Balt) - Stay In Annapolis