Top 10 Best Hotels in Annapolis for 2025 – Comfort Meets Charm
Why Stay in Annapolis Maryland?
Annapolis, Maryland, is more than just a state capital. It’s a historic waterfront town on the Chesapeake Bay, packed with colonial charm, fresh seafood spots, and sailing culture. Choosing the best hotels in Annapolis makes your visit even better.
Whether you’re traveling with children or adults, looking for a luxury hotel, or just want a cozy place to stay, you’ll find great options. Below are ten hotels worth checking out, each with its own unique style.
1. Graduate Annapolis – Trendy & Central
Graduate Annapolis blends interior design inspired by local history with modern comfort. Located near the U.S. Naval Academy, this hotel is perfect for both tourists and business travelers. The lobby features nautical décor, and the rooms are playful yet polished.
Families love it because it works for both children and adults. Guests can easily check availability online and book rooms in advance.
Pros | Cons |
|---|---|
| Unique design and fun décor | Parking can be limited |
| Walking distance to attractions | Can get busy during events |
2. Annapolis Waterfront Hotel – By Chesapeake Bay
This luxury hotel offers unbeatable views of the Chesapeake Bay. You can watch sailboats glide past while enjoying dinner on the terrace.
The rooms are modern, and the service makes guests feel at home. Both adults 18+ and families with children 0–17 enjoy the easy access to boat tours. If you’re thinking about staying by the water, this is the place.
Pros | Cons |
|---|---|
| Stunning bay views | Higher price range |
| On-site dining and bar | Limited pool area |
3. Flag House Inn – Cozy Bed & Breakfast
Located steps from downtown, Flag House Inn offers a warm, homelike vibe. With only a handful of rooms, it feels personal and inviting.
Guests love the hearty breakfasts and friendly staff who go out of their way to help. This hotel is great for couples, solo travelers, and small families. The check-in process is smooth, and you’ll find this place full of charm.
Pros | Cons |
|---|---|
| Personal service and homely feel | Small property with few rooms |
| Close to Naval Academy and shops | Not ideal for large groups |
4. The Westin Annapolis – Modern Comfort
If you prefer sleek style and wellness amenities, The Westin Annapolis is an excellent choice. Rooms are spacious with upscale interior design, and the fitness center is well equipped.
Guests can enjoy an indoor pool, spa services, and on-site dining. It’s a reliable hotel for adults traveling for work or leisure, yet it also accommodates children comfortably.
Pros | Cons |
|---|---|
| Indoor pool and fitness center | Not directly on the waterfront |
| Modern design with spacious rooms | Can be pricey during peak season |
5. Historic Inns of Annapolis – Classic Stay
For travelers who love history, this collection of boutique inns captures old-world elegance. Located in restored buildings, the rooms combine antiques with modern touches. Staying here feels like stepping back in time while keeping today’s comfort.
Both children and adults enjoy the atmosphere, and it’s a great place to learn about local heritage. Guests can check availability online before booking.
Pros | Cons |
|---|---|
| Rich history and character | Some rooms smaller than modern hotels |
| Close to historic attractions | Parking limited |
Conclusion – Which Annapolis Hotel Fits You?
When deciding on the best hotels in Annapolis, think about what matters most. Do you want a luxury hotel with Chesapeake Bay views? A family-friendly place where both children and adults feel comfortable? Or a historic inn that reflects the town’s charm?
No matter your choice, these Annapolis Maryland stays deliver comfort, convenience, and character. Always check availability early, especially during sailing events or holidays, to make sure you get the perfect stay.