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Timeless Charm Meets Modern Comfort

Vacation home near Annapolis City Dock in Annapolis

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Photo gallery for Timeless Charm Meets Modern Comfort

A kitchen with a marble island, wooden cabinets, and pendant lighting.
A patio with a round metal table and four chairs, surrounded by a garden with various plants and a wooden deck.
A living room with a blue sofa, a white armchair, a patterned rug, and a dining area with wooden furniture.
A spacious dining area with a wooden table and chairs, a large cabinet, and a chandelier.
A living room with a fireplace, a television, and a dining area with wooden furniture.

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms3 bathrooms1200 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Annapolis, MD
  • Place, Maryland State House
    ‪3 min walk‬
  • Place, Annapolis City Dock
    ‪3 min walk‬
  • Place, U.S. Naval Academy
    ‪3 min walk‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪37 min drive‬

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About the neighborhood

Annapolis

City center stay.Within a 10-minute walk of this Historic District vacation home, you'll find Annapolis City Dock and U.S. Naval Academy. William Paca House and Hammond-Harwood House are also within half a mile (1 km).
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What's nearby

  • William Paca House - 2 min walk - 0.1 miles
  • St. John's College - 2 min walk - 0.1 miles
  • Maryland State House - 3 min walk - 0.2 miles
  • Annapolis City Dock - 3 min walk - 0.2 miles
  • U.S. Naval Academy - 3 min walk - 0.2 miles

Getting around

  • Odenton Station - 22 min drive
  • Fort Meade, MD (FME-Tipton) - 28 min drive

Restaurants

  • ‪The Choptank - ‬6 min walk
  • ‪Starbucks - ‬6 min walk
  • ‪The Red Bean - ‬5 min walk
  • ‪McGarvey's Saloon & Oyster Bar - ‬4 min walk
  • ‪Iron Rooster - ‬5 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Timeless Charm Meets Modern Comfort

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.

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Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Fireplace

Entertainment

  • Games
  • Smart TV

Outdoor areas

  • Barbecue grill
  • Fenced yard
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Hardwood flooring in public areas
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a village
  • In the city center

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Unit size: 1,200 square feet

Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in available

Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

Property is also known as

18539531-68e3-4ccd-b62b-47620d468d60

Frequently asked questions

How close is Timeless Charm Meets Modern Comfort to the airport?

This vacation home is 20.8 mi (28-min drive) away from the Fort Meade, MD (FME-Tipton) airport, the closest popular airport to the property.

Does Timeless Charm Meets Modern Comfort have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Timeless Charm Meets Modern Comfort to the beach?

This vacation home is 4.1 mi (9-min drive) from Carrs Beach and 4.4 mi (18-min drive) from Sparrows Beach. Don't forget your sunscreen!

Does Timeless Charm Meets Modern Comfort offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Timeless Charm Meets Modern Comfort?

No, there is no casino at this vacation home.

What time is check-in at Timeless Charm Meets Modern Comfort?

Check-in begins at 4:00 PM.

Is there free parking at Timeless Charm Meets Modern Comfort?

Free parking is not available at this vacation home.

Does Timeless Charm Meets Modern Comfort have a pool?

This vacation home does not have a pool.

Does Timeless Charm Meets Modern Comfort have a spa?

There are no spa services available at this vacation home.

How close is Timeless Charm Meets Modern Comfort to downtown Annapolis?

This vacation home is 0.2 mi away from Annapolis.

Timeless Charm Meets Modern Comfort Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 8 out of 9 reviews
Rating 8 - Good. 1 out of 9 reviews
Rating 6 - Okay. 0 out of 9 reviews
Rating 4 - Poor. 0 out of 9 reviews
Rating 2 - Terrible. 0 out of 9 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Karen J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location for visiting USNA
Stayed 3 nights in Feb 2026
Verified review

8/10 Good

Sue H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Walkable to DTA and USNA. Love the uniqueness of the property
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Rayne R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family vacation

We enjoyed being in walking distance of everything we needed for the stay, restaurants, shopping, marina, and history.
Stayed 4 nights in Jul 2025
Verified review

10/10 Excellent

Melissa B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our travel group of six had a wonderful weekend stay in Historic Annapolis. The house was perfect and so well equipped for our needs. Rooms were comfortable and easily accessed from the living space downstairs. The location is perfect for a stay in Annapolis. We would surely return!
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Mary Beth H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house. Very roomy and comfortable
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

Liz L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The kitchen was very well stocked, lots to see and do in walkable distance, fun game collection for evenings, comfortable beds, great size for our family of 4. We had questions about parking. Also, my son left his wallet on checkout day and the owner was very helpful in both instances, taking care of us quickly. We will return!
Stayed 3 nights in Mar 2026
From a partner site

10/10 Excellent

Natalie W.

215 Prince George

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!
Verified review

10/10 Excellent

Courtney G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 6 nights in Oct 2025

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