Best Hotels at Annapolis MD Downtown 2024 1
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Best Hotels at Annapolis MD Downtown 2024

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Greetings, Internet Stranger! I’m Stella Jane, author of the travel guide Get Lost, and welcome to the best hotels at Annapolis MD Downtown. Annapolis is truly one of the most charming towns in the United States. There’s plenty to do here with all the historic buildings, delicious seafood, and friendly Marylanders. It’s the perfect place to spend a weekend vacation when the weather is nice.

But if you’re going to spend the weekend in Annapolis, you’ll need a place to stay! That’s where this list of the best hotels at Annapolis MD Downtown comes in. I’ll help you find the perfect hotel at a price that you can afford. We have a wide range of choices, so just come with me, and I’ll help you decide what is best.

Stella’s Top 3 Picks: Best Hotels at Annapolis MD Downtown

#1 TOP PICK

Best Hotels at Annapolis MD Downtown 2024 2

⭐️⭐️⭐️⭐️⭐️
INN ON MAIN
✔️ Great location
✔️ Delicious breakfast

#2 PICK

Best Hotels at Annapolis MD Downtown 2024 3

FLAG HOUSE INN
✔️ Family run inn
✔️ Amazing breakfast

#3 PICK

Best Hotels at Annapolis MD Downtown 2024 4

ALL OTHER ANNAPOLIS HOTELS
✔️ Choose your own favorite
✔️ Find the best deals!

Best Hotels at Annapolis MD Downtown

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1) Inn on Main Annapolis

When I enjoy a pleasant weekend in Annapolis, I recommend staying at the Inn on Main Annapolis. It has a perfect location within walking distance of the main attractions in Annapolis, like the harbor, the William Paca House, and even the Naval Academy.

There’s also free wifi, which is important if you need to work on the road, like I do, or if you need to check your Instagram account often, which I don’t.

And speaking of delicious, the breakfast is excellent as well. In fact, I would go so far as to say they really put the breakfast in the phrase bed and breakfast. Finally, compared to many hotels in Annapolis itself, it’s quite affordable. That’s what makes it one of the best hotels at Annapolis MD Downtown.

If you’re looking for an excellent deal on this hotel, click here.

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2) Flag House Inn

If you’re looking for something posh when you’re enjoying one of the best hotels at Annapolis MD Downtown, I recommend trying the Flag House Inn. It has a perfect location right near the Naval Academy, so if you’re in Annapolis because you’re visiting a cadet or an employee of the Naval Academy, this is an excellent choice.

This is a family-run inn, so you’ll be treated with extra special care and attention while you’re there. If you need suggestions about what to do in Annapolis, they’ll be more than happy to assist you. As with many hotels in Annapolis, the Flag House Inn serves breakfast, and theirs is particularly delicious.

The rooms here are beautiful and comfortable, and you’ll feel right at home during your stay here.

You can check rates and availability at this hotel by clicking right here!

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3) Graduate Annapolis

The Graduate Annapolis is a great choice as one of the best hotels at Annapolis MD Downtown if you’re on a bit of a budget during your time in Annapolis. That’s not because it’s super cheap, but because it’s more affordable than many of the hotels at Annapolis MD Downtown. (Annapolis is not exactly what we would call a cheap city.)

That’s why Graduate Annapolis is such a find. It has a great location, just a short walk from St. John’s College, and other beautiful parts of Annapolis. It has its own American restaurant, so you can always get something to eat here if you are too tired to head out elsewhere.

This is also a great hotel to choose if you are traveling with a furry friend because they are pet friendly! They’ve also got free wifi, a 24 hour front desk, and parking on the property, so there’s basically everything you would need.

You can check rates and availability of this hotel by going right here.

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4) Annapolis Waterfront Hotel

One of the reasons Annapolis is such an excellent tourist destination is because of its gorgeous waterfront. That’s why the Annapolis Waterfront Hotel is a wonderful place to stay and definitely one of the best hotels at Annapolis MD Downtown. Of course it’s within the waterfront, but it’s also within walking distance of the Maryland State House and lots of other important attractions.

Basically everything you might want to see in Annapolis is within walking distance of this hotel. That’s why it’s one of the best hotels at Annapolis MD Downtown. But it has other fine qualities, not just the location. There’s free wifi and a coffee maker in the room, as well as room service, which is obviously not free. There is also parking on the property and a 24 hour desk.

People who stay here love the excellent location, comfortable rooms, and friendly staff. I’m sure you will too!

You can check rates and availability of this hotel by going right here.

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5) Hilton Garden Inn Annapolis Downtown

I’ve stayed at Hilton Garden Inns everywhere from Phoenix, Arizona to Jackson, Mississippi. They’re comfortable and affordable, and they often have a convenient location, like this Hilton Garden Inn Annapolis Downtown.

This Hilton Garden Inn is no exception because it has a fantastic location, within walking distance of the Maryland State House so you can learn all about the history of the omnipresent Maryland flag. It’s within walking distance of many great restaurants, but it also has its own restaurant on the property, in case you need to find somewhere for breakfast or dinner. All of these qualities make it one of the best hotels at Annapolis MD Downtown.

There’s parking on the property, though there is a fee to park. (Just be like me and don’t own a car, and there’s no problem.) You also won’t need to get a car to get around Annapolis because it’s so walkable.

You can check rates and availability of this hotel by going right here.

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6) Historic Inns of Annapolis

I would definitely recommend staying at the Historic Inns of Annapolis if you are looking for a cute and charming place to hang your hat during your time in Annapolis. The reason that I say it’s one of the best hotels at Annapolis MD Downtown is that it’s a historic hotel, but because it’s spread across three different buildings, there is plenty of room. You won’t feel cramped in someone’s attic.

It’s also an extremely convenient hotel. It’s within walking distance of the harbor, the Visitor’s Center, the William Paca House, and other attractions. The hotel itself does not have a restaurant but do not worry! It’s right next to plenty of other restaurants where you can find breakfast, lunch, or dinner.

However, even though it doesn’t have a restaurant, it does have a bar and other amenities like a fitness center and free wifi.

You can check rates and availability of this hotel by going right here.

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7) 134 Prince–Luxury Boutique Hotel

If you’re living it up during your time in Annapolis, you should definitely hang your hat at the 134 Prince–Luxury Boutique Hotel. This hotel has luxury in its name for a reason. Of course, at a glamorous location like this, a decadent breakfast, prepared by a real chef, is included, and they have vegetarian and vegan breakfast available, if you so desire. It’s truly one of the best hotels at Annapolis MD Downtown.

There are lots of other luxury touches at the hotel, like drinks available for the guests free of charge–and yes, I do mean alcoholic drinks. There are also luxurious Hermes toiletries and gorgeous, well-appointed rooms.

If you’re familiar with Annapolis, you’ll recognize the famous Prince Street, so you know that this hotel has a fabulous location. If you really want to indulge during your Annapolis vacation, there’s no better choice!

You can check rates and availability of this hotel by going here.

best hotels at annapolis md downtown

8) Westin Annapolis

My final suggest for the best hotels at Annapolis MD Downtown is the Westin Annapolis. It’s a little further away from downtown Annapolis than the other hotels that I suggest, but if you are a fan of the Westin brand, that won’t make much difference to you.

And it’s still less than a mile from downtown, so you’re within walking distance if you want to take a harbor cruise or talk to the ghost of Francis Scott Key or something. Plus, the hotel has free bike rentals if you prefer to get around that way.

This hotel has a restaurant and a fitness center, but it also has some amenities that most hotels in Annapolis don’t have, like an indoor swimming pool and a spa. It also has free wifi and extremely comfy beds, if you’re into that sort of thing.

Check rates and availability of this hotel by going here.

Stella’s Top 3 Picks: Best Hotels at Annapolis MD Downtown

#1 TOP PICK

Best Hotels at Annapolis MD Downtown 2024 2

⭐️⭐️⭐️⭐️⭐️
INN ON MAIN
✔️ Great location
✔️ Delicious breakfast

#2 PICK

Best Hotels at Annapolis MD Downtown 2024 3

FLAG HOUSE INN
✔️ Family run inn
✔️ Amazing breakfast

#3 PICK

Best Hotels at Annapolis MD Downtown 2024 4

ALL OTHER ANNAPOLIS HOTELS
✔️ Choose your own favorite
✔️ Find the best deals!

Best Hotels At Annapolis MD Downtown

Things to Do

Now that you’ve chosen your hotel, you’ll have to decide on some things to do while you’re in Annapolis.

I’d be happy to introduce you to some of my favorite things to do in Annapolis. I might not be a local, but I’ve been visiting the city since I was ten years old, so I think I’m pretty familiar.

1) St Anne’s Church

Annapolis has a number of historic churches, and one of my favorites is St. Anne’s. The coolest thing about this church is the cemetery which features the graves of many prominent citizens of the capital city of Annapolis. I especially liked the fraudulent doctor–if you take a tour of Annapolis, you will learn more about this.

2) Annapolis Harbor

The Annapolis Harbor is famous for so many reasons. Of course, in the heyday of the fishing scene in Maryland, you could get all of the satisfying oysters and crabs and other shellfish that you wanted here. There is still fishing in the Chesapeake Bay, but you are just as likely to see fancy yachts or go sailing on a lighthouse tour while you are here.

Don’t miss the Kunta Kinte-Alex Haley memorial on Annapolis Harbor. It’s dedicated to Roots author Alex Haley and his ancestor Kunta Kinte. Some people say that Kunta Kinte was not really Alex Haley’s ancestor, but I am going to go by what Alex Haley said unless there is some sort of definitive proof that they weren’t related. In any case, Roots is a great series and you should watch it.

3) St. John’s College

This lovely St. John’s campus is not an Ivy League School, nor is it as well known as the Naval Academy. However, it is the third oldest university in the United States. (If you take a tour that goes here, they will definitely ask you which two are older. The correct answer is William and Mary and Harvard, which is the oldest, naturally.

4) William Paca House

Annapolis has truly an extraordinary number of colonial homes. In fact, some say that it has more colonial homes than any other city in America.

On top of that, Annapolis is the only city in America that has the original houses of all its state’s signers of the Declaration of Independence. There were four, and their names were Paca, Chase, Stone, and Carroll. So take advantage of this fact and check out the William Paca House.

5) Maryland State House

Annapolis is the capital city of Maryland, which is why Maryland State House is in Annapolis. This is where the State Senate and House, as well as the new-ish Governor of Maryland hang out, making all the laws for the state and liberally seasoning them with Old Bay.

As I mentioned earlier, Annapolis is the only city to have all the original homes of its signers of the Declaration of Independence still about and fully functioning. You can see their portraits in the State House, and if you spend enough time in Annapolis, you will have learned their names by the time you leave.

6) Hammond Harwood House

The Hammond Harwood House is just about the most gorgeous colonial home that these sad eyes have ever encountered. Even Thomas Jefferson thought it was so pretty that he used to hang around here and sketch it for fun. You can only visit the house on a guided tour, but the tour is worth it.

7) Soapsuds Alley

Soapsuds Alley is one of the cutest spots in Annapolis. One of the little homes on this street, the Hogshead, if you visit during the high season, you’ll learn all about colonial life and get to touch fun reproductions of random colonial objects.

Just keep in mind that these guides are not around all of the time, so be sure to check the website for opening hours and stop by when you can.

8) Seafood Tour

Annapolis is famous for its seafood. So what better thing is there to do in Annapolis than book a seafood related food tour? You can check my favorite one right here.

9) Waterfront Cruise

If you go to spend time at the best hotels at Annapolis MD Downtown and don’t spend some time cruising on the water, I will have no choice but shake my head at you in a disappointed fashion. I mean, I guess it would be okay if you visit Annapolis during the winter, but I do not think that is a great idea anyway.

During the summer, there are a ton of cruise options, but I chose this one because it leaves in the late afternoon and that is the perfect time of day for going on a harbor pleasure cruise.

Try a one day in Annapolis itinerary. Go for 24 hours in Annapolis Maryland. Check out a one day in Baltimore itinerary. Experience 24 hours in Baltimore.

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