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

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.

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.

No reviews

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

B&B, Annapolis

This B&B, offering direct Bay views, is situated a 4-minute walk from Bay Ridge Beach and 8 kilometres from Annapolis Harbour.
This 550 square metre guesthouse accommodates up to 27 guests across 5 bedrooms and 3 bathrooms, providing a non-smoking retreat within easy reach of Baltimore-Washington International Airport.

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.

10 54 reviews

Pristine, Private Apt - Walk To Town/stadium

hotel, 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.

9.9 225 reviews

Charming Detached Studio W/ Easy Walk To Downtown.

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.

No reviews

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

B&B, Highland Beach

This Bed & Breakfast is situated in Highland Beach, 8 kilometres from Annapolis Harbour and 38 kilometres from Baltimore/Washington International Airport.
This 279 square metre guesthouse offers 3 bedrooms, 3 bathrooms, accommodating up to 10 guests, and features a private outdoor swimming pool, a screened porch, air conditioning, and a fully equipped kitchen, with an in-unit washer and dryer for added convenience.

No reviews

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

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 16 reviews

Robert Johnson King | Historic Inns | Vintage Vibe

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.

No reviews

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

B&B, Highland Beach

This lakefront guest house in Highland Beach is located 1.77 kilometres from Bay Ridge Beach and 7.4 kilometres from Annapolis Harbour, with Inner Harbour and Power Plant situated 48.3 kilometres away.
Offering 604 square metres of space, this establishment accommodates up to 23 guests across 5 bedrooms and features a private swimming pool, hot tub, garden, and a terrace with lake views, alongside a fully equipped kitchen and air conditioning.

No reviews

Heart Of Annapolis: Steps To State House - 0.1 Mil

B&B, Annapolis

This Annapolis guesthouse is situated in the historic district, within easy walking distance of the Maryland State House and the United States Naval Academy.
The 247 sq ft (23 sq m) room, sleeping up to two guests, features a queen-sized bed, en-suite bathroom, complimentary Wi-Fi, air conditioning, and a Pure Wellness Room with an in-room filter; valet parking is available nearby.

Best Annapolis, MD bed and breakfasts with air conditioning

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 5 reviews

The Harness Creek Retreat

B&B, Annapolis

This private hilltop guesthouse, situated in the Harness Creek area, offers convenient access to Annapolis, being just 4.8 kilometres from the city centre and its attractions including the United States Naval Academy, shopping, and restaurants.
This two-bedroom, 1.5-bathroom property accommodates up to four guests and features a full kitchen with vineyard views, a living room with a 70-inch television and electric fireplace, and a peaceful garden with a gas fire pit, all ideal for a relaxing stay.

9.9 171 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.

8.2 262 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.

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 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.

Popular destinations

Best Annapolis, MD bed and breakfasts with a garden

No reviews

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

B&B, Annapolis

This dog-friendly riverfront guesthouse in Annapolis offers a prime location with a private dock and waterside patio, situated 1.8 kilometres from Annapolis Harbour and 41.8 kilometres from Baltimore's Inner Harbour.
This spacious 3-bedroom, 4-bathroom property accommodates up to 11 guests, featuring a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, multiple outdoor spaces including two balconies and a garden, and is located 30.6 kilometres from Baltimore-Washington International Airport.

9.9 214 reviews

Captains Quarters Oasis Near Annapolis, Sleeps 4

B&B, Arnold

This Arnold guest suite, situated 6.4 km from Annapolis and 8 km from Sandy Point State Park, offers convenient access to historic sites and outdoor recreation.
The self-contained unit features a king-size bed, en-suite bathroom, fully equipped kitchen, and access to a shared swimming pool, hot tub (seasonal), fire pit, patio, and grill; sleeping up to four guests and welcoming pets.

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

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.

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.

9.9 214 reviews

Captains Quarters Oasis Near Annapolis, Sleeps 4

B&B, Arnold

No reviews

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

B&B, Highland Beach

No reviews

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

B&B, Highland Beach

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.

No reviews

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

B&B, Highland Beach

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.

No reviews

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

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.

10 2 reviews

Chesapeake Bay Retreat Near Downtown Annapolis

B&B, Highland Beach

8.0 7 reviews

Private N/s 2 Double Bed & Bath

B&B, Arnold

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.

No reviews

Heart Of Annapolis: Steps To State House - 0.1 Mil

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.

9.0 2 reviews

Allergy-friendly King Room In Historic Property

B&B, Annapolis

Bed and Breakfast in Annapolis, MD

88 Bed and Breakfasts and Inn in Annapolis, MD

Howard's Cove Retreat Apartment

Allergy-friendly King Room In Historic Property

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

Historic Downtown Townhome With Brick Courtyard, Sunroom & Parking

Pristine, Private Apt - Walk To Town/stadium

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

Charming Detached Studio W/ Easy Walk To Downtown.

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

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

Robert Johnson King | Historic Inns | Vintage Vibe

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

Heart Of Annapolis: Steps To State House - 0.1 Mil

Robert Johnson 1 Queen Bed At Historic Inns

The Harness Creek Retreat

Bay View Studio Apartment

Inn On Main Annapolis

Inn On Main Annapolis

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

Captains Quarters Oasis Near Annapolis, Sleeps 4

Cozy Naptown Perch

Charming Living Room In Beautiful Annapolis With Ac Discount Long Stay

Captains Quarters Oasis Near Annapolis, Sleeps 4

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

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

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

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

Chesapeake Bay Retreat Near Downtown Annapolis

Private N/s 2 Double Bed & Bath

Heart Of Annapolis: Steps To State House - 0.1 Mil

Allergy-friendly King Room In Historic Property