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Historic Charm Meets Walkable Convenience in the Heart of Annapolis with Parking

Photo gallery for Historic Charm Meets Walkable Convenience in the Heart of Annapolis with Parking

A two-story house with a front porch, a flag, and a well-maintained lawn.
A covered patio with a ceiling fan, wicker furniture, and a red table.
A wooden picnic table with benches in a grassy backyard with a white house in the background.
A cozy living room with a fireplace, comfortable seating, and artwork on the walls.
A bedroom with a bed, a desk, and a chair. There are windows and a lamp on the desk.

Reviews

10 out of 10
Exceptional

Highlights

  • Room to spread out
    Enjoy a spacious layout that gives everyone more room to relax.
  • Firepit available
    One of the few properties with a dedicated outdoor firepit.
  • At the centre of it all
    Stay in a top rated central location, steps from the best attractions, dining, and entertainment.
  • Discover nearby landmarks
    Close to Maryland Hall for Creative Arts
5 bedrooms2 bathroomsSleeps 12

Popular amenities

  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill

Explore the area

View in a map
Annapolis, MD
  • Place, Maryland Hall for Creative Arts
    ‪16 min walk‬
  • Place, Navy-Marine Corps Memorial Stadium
    ‪5 min drive‬
  • Place, Maryland State House
    ‪6 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪35 min drive‬

Rooms & beds

5 bedrooms (sleeps 12)

2nd Floor Gray Guestroom

1 King Bed

2nd Floor Pink Family Guestroom

2 Single Beds and 1 King Bed

2nd Floor Tan Guestroom

1 King Bed

Main Floor Anchor

1 King Bed

Main Floor Black & White

1 King Bed

2 bathrooms

2nd Floor Full Bath

Bathtub or shower · Toilet

Main Floor Full

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Number of living rooms

About this property

Historic Charm Meets Walkable Convenience in the Heart of Annapolis with Parking

Experience the Difference: Professionally Managed by iTrip Annapolis

Welcome to The Yard, a rare ½-acre retreat just steps from Navy Stadium and minutes from Historic Downtown Annapolis.



Welcome to your Annapolis getaway! Situated on an expansive and rare 1/2 acre homesite has one of the largest backyards you'll find this close to Downtown Annapolis. Play football, throw a Frisbee, grill dinner, gather around the fire pit, or simply enjoy room to spread out after a day exploring the city. This beautifully preserved home blends historic charm with modern amenities—perfect for families, friend groups, or Navy families visiting town.



Inside, the main level features two spacious king bedrooms, a full bath, a sun-filled living room, and a delightful four-seasons sunroom—ideal for morning coffee, evening wine, or movie nights on the big-screen TV.



Upstairs, you'll find three additional bedrooms, including a generous combo guest room (with an additional sitting room/bedroom). There’s also a shared full bath and a full laundry room. The entire home has recently been updated to include a modern HVAC system with mini splits and remotes in each bedroom and gathering space.



Sleeping Arrangements 5 Bedrooms, 2 Baths (Sleeps 12):

Second Floor

Family Pink King Bedroom: King bed + Twin plus Twin Trundle

Tan & White Guestroom: King bed

Gray Guestroom: King bed

Full bath in the Second Floor Hallway



Main Floor

Black & White Guestroom: King bed

Anchor Guestroom 2: King bed

Shared full bath on the Main Floor hallway



Home Highlights:

Fully equipped kitchen with stainless steel appliances

Multiple hangout spaces with Flatscreen TVs: Living room, and Four-seasons sunroom with flatscreen Smart TV

Outside: expansive private backyard with fire pit, picnic table and grill

High-speed WiFi + 3 large Smart TVs

Driveway parking for multiple vehicles

Washer/dryer for guest use

Luxury linens + complimentary starter toiletries and paper products

Dog-friendly (with $150 non-refundable pet fee per pet)



Location - Walkable to it all!

Navy-Marine Corps Memorial Stadium – 0.7 miles

U.S. Naval Academy – 1.8 miles

Downtown Annapolis shops & restaurants – 1 mile

Washington, D.C. – 32 miles

Baltimore – 31 miles

Skip the parking hassles and walk to parades, festivals, farmers markets, waterfront events, and cozy cafes. You’ll love being in the heart of it all—without ever needing your car.



House Rules:

Primary renter must be 25+

No parties, smoking, or events

Quiet hours must be observed

Check-in: 4:00 PM | Check-out: 11:00 AM

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 4684464vb
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Annapolis

Homewood, a neighbourhood in Annapolis, is home to this holiday home. Chesapeake Bay Bridge and Stanton School & Community Center are local landmarks, and some of the area's attractions include Maryland Hall for Creative Arts and Helen Avalynne Tawes Garden. Looking to enjoy an event or a game while in town? See what's happening at Navy-Marine Corps Memorial Stadium or Alumni Hall.
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Map
Annapolis, MD

What's nearby

  • Maryland Hall for Creative Arts - 16 min walk - 1.4 km
  • Navy-Marine Corps Memorial Stadium - 5 min drive - 3.2 km
  • Maryland State House - 6 min drive - 2.5 km
  • St. John's College - 6 min drive - 2.8 km
  • Spa Creek - 6 min drive - 2.8 km

Getting around

  • Odenton Station - 19 min drive
  • Fort Meade, MD (FME-Tipton) - 31 min drive

Restaurants

  • ‪McDonald's - ‬16 min walk
  • ‪Taco Bell - ‬9 min walk
  • ‪Wendy's - ‬16 min walk
  • ‪Burger King - ‬16 min walk
  • ‪Shika Sushi & Ramen - ‬16 min walk

Frequently asked questions

Is Historic Charm Meets Walkable Convenience in the Heart of Annapolis with Parking pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Historic Charm Meets Walkable Convenience in the Heart of Annapolis with Parking?

As of 7 Jul, 2026, prices found for a 1-night stay for 2 adults at Historic Charm Meets Walkable Convenience in the Heart of Annapolis with Parking on 11 Aug, 2026 start from S$1,129, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Historic Charm Meets Walkable Convenience in the Heart of Annapolis with Parking?

On-site parking is available at the property.

What time is check-in at Historic Charm Meets Walkable Convenience in the Heart of Annapolis with Parking?

Check-in begins at 4:00 PM.

What time is check-out at Historic Charm Meets Walkable Convenience in the Heart of Annapolis with Parking?

Checkout is at 11:00 AM.

Where is Historic Charm Meets Walkable Convenience in the Heart of Annapolis with Parking located?

Located in Homewood, this holiday home is 0.5 mi (0.8 km) from People's Brewer Hill Cemetery and 1.9 mi (3.1 km) from U.S. Naval Academy. Maryland Hall for Creative Arts and Ballet Theater of Maryland are also within 1 mile (2 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

From a partner site

10/10 Excellent

Heidi A.

Character and Charm

If you're looking for character and charm near downtown Annapolis, THIS is the place to stay! We were visiting from out of town with friends and family for our son's wedding and we loved everything about our stay. It was clean, spacious, furnished with all the necessities, plus all the extras. The king sized beds in every bedroom is definitely a plus, and we were even able to bring our little pup. It definitely felt like home! The check-in/out instructions are clear and easy to follow. We had absolutely no issues during our stay. The individual mini-split units in every room made it easy for everyone to adjust their own rooms accordingly as we had his grandparents with us as well. You're located just minutes from downtown Annapolis with loads of shops, restaurants, creameries, and our favorite, the PA Dutch Farmer's Market. We will definitely return to The Yard for future visits.
Verified

10/10 Excellent

Jessie N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is an absolutely lovely home, conveniently situated on West Street in Annapolis - near DTA, the stadium, the Yard, and the mall. Easy and convenient parking. The home is thoughtfully restored, clean, and well prepared for guests. There is beautiful landscaping and artwork (some for sale) throughout. The beds were comfortable, and there were ample linens and towels. Despite an intense summer heat wave, the house stayed cool throughout the day.
Stayed 3 nights in Jul 2026
Response from VrboOwner on 7 Jul, 2026
Thanks, Jessie!! We are so glad you enjoyed everything. We hope to have you back again very soon. Sean
Verified

10/10 Excellent

Kevin M.

Stayed 4 nights in Apr 2026
Response from VrboOwner on 5 Jun, 2026
Thanks, Kevin! Please come back and stay with us again any time. Sean, iTrip Annapolis

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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