Timeless Charm Meets Modern Comfort

Top rated by guests
3-bedroom, 2.5 bathroom charming historic home in downtown Annapolis with room for 6
Updated kitchen with all major appliances
Updated kitchen with all major appliances
Updated kitchen with all major appliances
Updated kitchen with all major appliances
review stars
10Outstanding
(8 Ratings)
"Great location for visiting USNA"
Karen J.
Don't miss out! Price and availability may change
10 / 10
Outstanding(8 Ratings)

House in Annapolis, MD

6 guests · 3 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

This charming 3-bedroom, 2.5 bath historic duplex in downtown Annapolis offers a perfect blend of timeless character and modern amenities. Featuring hardwood floors, classic architectural details, and an updated kitchen and bathrooms, the home is within walking distance of Annapolis' vibrant waterfront, shops, and restaurants. Enjoy the convenience of city living while embracing the rich history and charm of this well-preserved gem. Ideal for those seeking comfort and style in a prime location.

Why guests love staying at 215 Prince George Street:

☼ Historic home right in the heart of downtown Annapolis with tons of charm upgraded features, ideal for families, romantic getaways, or a group of friends visiting historic Annapolis, USNA, and other tourist sites
☼ Centrally located in downtown Annapolis, on historic Prince George Street
☼ Three bedrooms: Primary: king bed; Guest 1: 1 queen bed; Guest 2: 2 twin beds
☼ Two and a half bathrooms: Primary suite has a private bathroom with a walk-in shower; hall bathroom has a tub-shower combo; half bath on the main living level
☼ Kitchen with all major appliances, a drip coffee maker, kitchen supplies and tools and more
☼ Comfortable living room for watching movies and playing games
☼ Private outdoor space - fully fenced with outdoor dining and a gas grill
☼ Smart TV in the living room
☼ Fresh linens, towels, toiletries & essentials provided
☼ Professionally cleaned before each visit

​Look no further than this historic home in downtown Annapolis!

Please note that there is no assigned parking for this property. Guests are encouraged to park in nearby public parking garages overnight. There is short-term hourly parking on Prince George Street.

Please note that parts of this home date back to 1775! So there are some charming quirks that you won't find in new builds, like a low ceiling clearance on the stairs, a step up into the primary suite, a step down and then up in the bedroom hallway, and smaller sinks in some of the bathrooms. It's truly a unique experience!

We’ll follow up with a short online registration once you book. It’s fast, simple, and helps us prepare for your visit. Non-Airbnb guests will be asked to pay a small damage waiver OR refundable deposit.

For extra flexibility, consider adding trip insurance for a nominal fee. It can cover you if you need to cancel at the last minute.

215 Prince George Street is managed by a small, female-owned business. We're committed to making sure all of our guests feel welcome and have the best trip ever. Book your trip with confidence that not only will this property be amazing, but the service and attention you get will be, too.

Amenities at Timeless Charm Meets Modern Comfort

Non-smoking
No pets allowed
Family friendly

Map of Annapolis, MD


Ratings and reviews

10 / 10
Outstanding(8 Ratings)
10 / 10Outstanding·Feb 2026
Great location for visiting USNA
10 / 10Outstanding·Oct 2025
We thoroughly enjoyed our stay at this property. It is a modernized rental that has everything to make your Annapolis stay perfect! The communication with the management company was prompt when I submitted a question. I’ve already rebooked for my next stay!
10 / 10Outstanding·Aug 2025
Great house. Very roomy and comfortable
10 / 10Outstanding·Jul 2025
We enjoyed being in walking distance of everything we needed for the stay, restaurants, shopping, marina, and history.

$$$$
vrbo logo

FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Timeless Charm Meets Modern Comfort. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Timeless Charm Meets Modern Comfort pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Timeless Charm Meets Modern Comfort?

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.