Entire home

Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking

Holiday home with kitchen, 8-minute walk to U.S. Naval Academy

Photo gallery for Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking

Celebrate at the custom bar and dining area that greets you!
Welcome to your stay at the Anchor at Annapolis Inn!
The full laundry room is attached to the Naval Academy-themed kitchen
One of two Queen bedrooms on the second floor.
The street view of Anchor at Annapolis Inn

Reviews

9.8 out of 10
Exceptional
4 bedrooms2 bathroomsSleeps 122196 sq ft

Popular amenities

  • Washer
  • Dryer
  • Kitchen
  • Outdoor space
  • Free WiFi

Explore the area

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

Rooms & beds

4 bedrooms (sleeps 12)

2nd Floor Guestroom

2 Single Beds

Master Bedroom 1

1 Queen Bed

Master Bedroom 2

1 Queen Bed

Top Floor Bedroom

+1
5 Single Beds

2 bathrooms

Main Floor

Toilet · Shower only

Second Floor

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Dining area

About this property

Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking

Experience the Difference: Professionally Managed by iTrip Annapolis
Welcome to Modern Elegance in Historic Annapolis
Step into this fully-renovated 1900s home, where modern sophistication meets timeless charm. Lovingly restored, this home offers parking for two cars (or one SUV)—a rare luxury in the heart of downtown Annapolis. Owned by four Naval Academy graduates—three U.S. Marines and one Navy nuclear surface warfare officer—this property stands as a tribute to the enduring bond they forged as members of the Academy's 14th Company and their decade of service to our nation. You’ll feel their legacy of camaraderie and commitment the moment you arrive.

Nestled on one of Annapolis's most picturesque streets, the home is just a block from the Naval Academy's main entrance. The inviting front porch is the perfect perch to soak in the vibrant energy of historic downtown Annapolis, creating a seamless connection between the home and the community’s storied past.

The interior boasts an elegant Great Room with a custom entertainment bar, open dining area, and Naval Academy-inspired decor that sets the tone for your stay. The gourmet kitchen is a chef’s dream, with seating at the breakfast bar for casual gatherings. With spacious accommodations for up to 11 guests, including a stunning top-floor suite, the home caters to families and groups seeking both comfort and style.

Whether visiting for a Naval Academy event, the boat show, or simply to explore Greater Annapolis, this home puts you steps away from local attractions, restaurants, and shops. From relaxing mornings on the front porch to evenings exploring the waterfront, your stay promises to be unforgettable.

Sleeping Arrangements: 4 BR / 2 BA / Sleeps 11
Main Bedroom 1 (2nd Floor): Queen Bed
Main Bedroom 2 (2nd Floor): Queen Bed
Guest Bedroom (2nd Floor): Two Twin Beds
3rd Floor Suite: Open sleeping/living space with 5 Twin Beds

Highlights
Front Porch: New furniture for lounging and enjoying the lively neighborhood views
Custom Bar: Seats 4-5 for entertaining
Gourmet Kitchen: Fully equipped with seating for 4 at the breakfast counter
Dining Area: Accommodates 6-8 guests
Modern Amenities: WiFi, smart TVs, luxury linens, and a boutique-level starter kit
Convenience: Keyless entry, laundry facilities
Parking: Space for 2 cars or 1 SUV
Important Notes
Guests must be 25+ years of age or accompanied by an adult.
No smoking, pets, parties, or events are allowed.
The steep staircase may not suit guests with mobility issues; please inquire if needed.

Distance to Nearby Attractions
U.S. Naval Academy: 1 block
Washington, D.C.: 30 miles
Baltimore: 25 miles

Amenities & Services
Start your stay worry-free with our complimentary starter pack, including coffee, toiletries, and household essentials. All beds come pre-made with freshly laundered linens, ready to welcome you home.

This home promises the perfect blend of history, luxury, and convenience, making it an ideal retreat for your Annapolis adventure.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space

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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

No pets allowed
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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
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

About the area

Annapolis

Located in Annapolis, this holiday home is in the city centre. Hammond-Harwood House and John Smith House are local landmarks, and travellers looking to shop may want to visit Annapolis City Dock and Bay Bridge Market Place Shopping Center. French Soldiers Monument and Annapolis Maritime Museum are also worth visiting. Kayaking and waterskiing offer great chances to get out on the surrounding water, or you can seek out an adventure with horse riding and ecotours nearby.
Map
Annapolis, MD

What's nearby

  • U.S. Naval Academy - 1 min walk - 0.1 km
  • William Paca House - 2 min walk - 0.2 km
  • Annapolis City Dock - 3 min walk - 0.3 km
  • Maryland State House - 5 min walk - 0.4 km
  • Navy-Marine Corps Memorial Stadium - 3 min drive - 2.1 km

Getting around

  • Odenton Station - 22 min drive
  • Fort Meade, MD (FME-Tipton) - 26 min drive

Restaurants

  • ‪The Choptank - ‬6 min walk
  • ‪O'Brien's Oyster Bar & Seafood Tavern - ‬6 min walk
  • ‪Starbucks - ‬6 min walk
  • ‪Annapolis Market House - ‬4 min walk
  • ‪McGarvey's Saloon & Oyster Bar - ‬4 min walk

Frequently asked questions

Is Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking pet-friendly?

No, pets are not allowed at this property.

How much is parking at Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking?

On-site parking is available at the property.

What time is check-in at Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking?

Check-in begins at 4:00 PM.

What time is check-out at Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking?

Checkout is at 11:00 AM.

Where is Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking located?

Located in Historic District, this holiday home is within a 10-minute walk of John Smith House and U.S. Naval Academy. William Paca House and Tose Family Tennis Center are just steps away.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 44 out of 49 reviews
Rating 8 - Good. 4 out of 49 reviews
Rating 6 - Okay. 0 out of 49 reviews
Rating 4 - Poor. 0 out of 49 reviews
Rating 2 - Terrible. 1 out of 49 reviews

9.8/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Cindy H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Third time to stay here. We are always pleased.
Stayed 4 nights in Oct 2025

10/10 Excellent

Joseph W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay, everything was easy, great communication. Really no outdoor hangout space though, which was one of the features we wanted and pics and description led us to think there was one. Also no grill, the app had a grill section but there was no grill. Other than that it was fantastic.
Stayed 2 nights in Sep 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

mike j.

Annapolis trip- Arlington Cemetery Interment

We stayed here in Annapolis to be near family for my Father's burial monday in Arlington National Cemetery. 50 plus family members here from around the country. Very emotional and meaningful trip. Our stay at Anchor at Annapolis Inn was outstanding. Accomodations were great and location across from Naval Academy and 2 blocks from downtown was outstanding. We would stay here again in a heartbeat. Great Experience.

10/10 Excellent

Verified traveller

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

Swim meet at the academy

Great location to the academy and shopping
Stayed 2 nights in Apr 2025

10/10 Excellent

Brian S.

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

Great stay for USNA

Perfect location in DTA. Nice to have parking in back of property. We were able to walk to everything. We were in town for our son’s Naval Academy Induction Day. Gate 1 of USNA is an easy 5 minute walk. Property is great if you have a group. Wide open sitting area in Bar/TV room. Property manager was very attentive and quick to respond. Would highly recommend, and we will likely look to stay here on future visits.
Stayed 3 nights in Jun 2025

10/10 Excellent

Brian D.

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

Wedding close by

Location was great for our needs House met all our needs and was very clean and very welcoming
Stayed 5 nights in Mar 2025

10/10 Excellent

Jimmy C.

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

Miltary Bowl Trip

Fantastic property, amenities and most if all location, location, location!
Stayed 2 nights in Dec 2024

10/10 Excellent

Joshua C.

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

Great stay

Great location and easy check-in/out process.
Stayed 2 nights in Nov 2022

10/10 Excellent

George C.

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

Great stay!

This was the perfect place for my group to stay while visiting for the Army Navy weekend. We had 6 adults and 2 teens and the location within walking distance of both downtown and the Yard were ideal for everyone to sightsee. The house was clean and well maintained, and the first floor (living room/bar/kitchen) made a great place for the group to gather and cook meals. I’d definitely recommend this him and stay here again.
Stayed 3 nights in Dec 2024

10/10 Excellent

Nick S.

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

Great stay on the bay

Wonderful property in a great location. Very cool bar and fun spot to hang out.
Stayed 2 nights in Jun 2023

10/10 Excellent

Kate G.

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

Great location

Location was perfect - steps from down town and an easy walk to Eastport.
Stayed 3 nights in Aug 2022

8/10 Good

Casey M.

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

Great location

Great location, plenty of space, fun house
Stayed 2 nights in Dec 2022

10/10 Excellent

Kenny H., Clearwater, Florida

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

Great location

Enjoy the house in the location. It’s laid out very nice. I would certainly stay there again.
Stayed 3 nights in Jun 2021

8/10 Good

Bradley B.

Liked: Cleanliness, check-in, communication

Great House great property management.

Great Property Management
Stayed 3 nights in Aug 2022

10/10 Excellent

Michele C.

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

Great stay

Great location with plenty of space. Everything is in walking distance. Nicely decorated and well maintained property. Definitely recommend!
Stayed 3 nights in Nov 2022

8/10 Good

Karen W., Henrico, VA

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

Sisters+Spouses Getaway

The proximity to the naval academy, restaurants and shops on Main Street was great. Everything within walking distance.
Stayed 3 nights in Feb 2022

10/10 Excellent

Thomas A S.

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

Bachelor party

The place was immaculate. Given the opportunity would book again.
Stayed 2 nights in Apr 2023

10/10 Excellent

Shawn M.

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

USNA reunion hotspot

Cool spot located centrally to all of the action. Thanks for having us! Beat Army!
Stayed 3 nights in Sep 2023

10/10 Excellent

jane w., st augustine

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

Fun Thanksgiving

As advertised! Great location and space for 6 adults and 2 children.
Stayed 3 nights in Nov 2022

10/10 Excellent

Kim M.

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

Gorgeous, cool historic home two blocks from USNA!

The property managers were very helpful, and the home was perfect for our family to relax, and sit on the porch, or around the cool bar in the family room. Such a beautiful historic home, and well-appointed for all the conveniences. We will stay here again!
Stayed 4 nights in Sep 2021

10/10 Excellent

Celeste H.

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

Holiday visit

This property is beautifully decorated, warm and welcoming. It had every amenity we needed. The location was perfect for a holiday visit. We could pop over to the main city dock area for fabulous restaurants and shops and could also stay the house for a fun evening with friends. Parking was a bonus!
Stayed 2 nights in Dec 2022
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Michael S.

Commissioning Week

Stayed here for a week and strongly recommend without reservation. Location is great to get on the yard and to be in DTA. Place was very clean, well represented per the listing and communication was appropriate. Sleeps 11 very comfortably, everything worked and my family was very happy!

10/10 Excellent

Sam C.

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

Excellent VRBO

They were outstanding and responsive. The house was in immaculate condition and large enough for a big party. Would highly recommend - thank you to the iTrip team!
Stayed 2 nights in Sep 2022

10/10 Excellent

Laurie A.

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

Wedding

Great property close to everything Communication with property manager was great.
Stayed 4 nights in May 2022

10/10 Excellent

Stephanie L.

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

Nap Town Gem!!!

Always a treat to stay at this wonderful home, steps from gate 1. You cannot beat the location, with parking!!! The front porch is a dream!! The bar is so fun for entertaining!!! Walk to everything in DTA; the Yard, restaurants, ego alley!!! Such a fun home!!!
Stayed 3 nights in Apr 2024

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests