Naval-Academy-themed home with custom bar steps to Gate 1 and onsite parking at
House in Annapolis, MD
11 guests · 5 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Free cancellationFull refund if you change your mind
Includes essentialsKitchen or Kitchenette, Air conditioner, Internet / Wifi and more
About this house rental
Visit the magic of Annapolis during the Holiday Season
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, and baby essentials available on request
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.
Welcome to this gorgeous 1900's fully-renovated home, restored to a new modern grandeur, which includes coveted parking for 2 cars or one SUV. Owned by 4 Naval Academy graduates - 3 U.S. Marines and one Navy nuclear surface warfare officer - this home is a tribute to the loyal bond they created in the 14th company at the Academy and continue to share after 10+ years they have served our country. You will feel that energy the moment you pull into the home.
Located on one of the prettiest streets in Annapolis, less than one block from the main entrance to Naval Academy, the front porch will welcome you and provide the perfect place to watch the energy of downtown Historic Annapolis. Next is the enclosed front hallway opening to the stunning Great Room complete with entertainment bar and dining area. Soak in the classic Naval Academy-themed decor while enjoying the large open spaces and bedrooms for up to 11 guests. The large gourmet kitchen features additional seating at the breakfast bar - perfect for gathering in the morning before heading out to see the local sights. The second level features 3 large bedrooms and the top level features a stunning extra large bedroom and sitting room for 5.
Just steps from all Annapolis has to offer, this home is wonderful for families and friends coming in for that special Naval Academy or boat show event, or wanting to take in the sights and sounds of Greater Annapolis. Enjoy the many restaurants, historical attractions, and shops right around the corner!
SLEEPING ARRANGEMENTS 4 BR / 2 BA / Sleeps 11:
Main Bedroom 1:
- Second Floor
- Queen Size Bed
Main Bedroom 2:
- Second Floor
- Queen Size Bed
Guest Bedroom:
-Second Floor
-Two twin beds
3rd Floor Room:
- Open Living and sleeping space
- 5 Twin Beds
HIGHLIGHTS:
- Front Porch with sitting area with new furniture
- Custom Full Bar seats 4-5
- Spacious gourmet kitchen
- Eat-in kitchen counter seats 4
- Dining room table seats 6-8
- WiFi
- Big Screen Smart TV's
- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service
- Parking for 2 cars or 1 SUV
- Washer & dryer located inside the home
- Baby Crib (Pack-nPlay) and stroller available upon request
- Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations.
- Keyless entry. Drive straight to your rental home and enter the back door with an electronic lock code.
Property Distance to:
- U.S. Naval Academy – 1 block
- Washington, DC – 30 miles
- Baltimore - 25 miles
* Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going.
* All beds are ready made for you with freshly laundered sheets & towels.
House Rules
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, and baby essentials available on request
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.
Welcome to this gorgeous 1900's fully-renovated home, restored to a new modern grandeur, which includes coveted parking for 2 cars or one SUV. Owned by 4 Naval Academy graduates - 3 U.S. Marines and one Navy nuclear surface warfare officer - this home is a tribute to the loyal bond they created in the 14th company at the Academy and continue to share after 10+ years they have served our country. You will feel that energy the moment you pull into the home.
Located on one of the prettiest streets in Annapolis, less than one block from the main entrance to Naval Academy, the front porch will welcome you and provide the perfect place to watch the energy of downtown Historic Annapolis. Next is the enclosed front hallway opening to the stunning Great Room complete with entertainment bar and dining area. Soak in the classic Naval Academy-themed decor while enjoying the large open spaces and bedrooms for up to 11 guests. The large gourmet kitchen features additional seating at the breakfast bar - perfect for gathering in the morning before heading out to see the local sights. The second level features 3 large bedrooms and the top level features a stunning extra large bedroom and sitting room for 5.
Just steps from all Annapolis has to offer, this home is wonderful for families and friends coming in for that special Naval Academy or boat show event, or wanting to take in the sights and sounds of Greater Annapolis. Enjoy the many restaurants, historical attractions, and shops right around the corner!
SLEEPING ARRANGEMENTS 4 BR / 2 BA / Sleeps 11:
Main Bedroom 1:
- Second Floor
- Queen Size Bed
Main Bedroom 2:
- Second Floor
- Queen Size Bed
Guest Bedroom:
-Second Floor
-Two twin beds
3rd Floor Room:
- Open Living and sleeping space
- 5 Twin Beds
HIGHLIGHTS:
- Front Porch with sitting area with new furniture
- Custom Full Bar seats 4-5
- Spacious gourmet kitchen
- Eat-in kitchen counter seats 4
- Dining room table seats 6-8
- WiFi
- Big Screen Smart TV's
- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service
- Parking for 2 cars or 1 SUV
- Washer & dryer located inside the home
- Baby Crib (Pack-nPlay) and stroller available upon request
- Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations.
- Keyless entry. Drive straight to your rental home and enter the back door with an electronic lock code.
Property Distance to:
- U.S. Naval Academy – 1 block
- Washington, DC – 30 miles
- Baltimore - 25 miles
* Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going.
* All beds are ready made for you with freshly laundered sheets & towels.
House Rules
Amenities
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Map of Annapolis, MD
RRRR
Reviews
10.0
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!
10.0
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!!!
10.0
My brother retired from the USMC at USNA and we needed somewhere close to the academy to stay, that would accommodate our large family.
The home was PERFECT. Lots of character the starter kits were helpful, and the bottle of wine was appreciated. What a classy touch! Parking spaces were AWESOME! You don’t realize how much you’ll need them - but you will!!!
It was extremely clean and well stocked. It was beautiful and the location was amazing! So close to downtown and the Academy.
It added to a very beautiful event and we hope to go back to spend more time and enjoy.
10.0
These houses are in a great location to the academy. It was very easy walking to the yard!
10.0
Cool spot located centrally to all of the action. Thanks for having us! Beat Army!
10.0
3 old punch drunk Navy boxers gathered with their 7 sons to send off Navy’s own Coach McNally. It was the perfect headquarters and an amazing place for old fighters to gather after the festivities ended downtown. Amazing location and well appointed. Can’t wait to do it again.
10.0
Wonderful property in a great location. Very cool bar and fun spot to hang out.
10.0
The place was immaculate. Given the opportunity would book again.
10.0
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!
8.0
Great location, plenty of space, fun house
10.0
As advertised! Great location and space for 6 adults and 2 children.
10.0
Great location with plenty of space. Everything is in walking distance. Nicely decorated and well maintained property. Definitely recommend!
10.0
Great location and easy check-in/out process.
10.0
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!
10.0
The house was clean, spacious, well decorated, and comfortable. A group of five women stayed for a fantastic weekend in Annapolis and we had plenty of room for everyone. The beds were comfortable, the bathrooms and kitchen were spotless, and we enjoyed the amazing location (very close to the Naval Academy and a few blocks to the main street in Annapolis with shops/restaurants/waterfront). The kitchen had everything we needed and we were able to easily prepare food while we were there. The naval theme throughout the house was tasteful and on point. Highly recommend this place!
10.0
My twin sister & her family stayed in the adjacent unit to mine. Her daughter was getting married. My twin & husband are USNA grads which made the location across from Gate 2 even better. The unit was perfect for 5 adults celebrating a joyous wedding.
The unit is perfectly equipped w laundry, a kitchen and an incredibly comfortable bar/common area. We worked and partied all in the same space.
The location is unbeatable. The street is quieter than Main St. but just a quick walk to all of the action. We loved it. Thank you so much.
8.0
Great Property Management
10.0
Location was perfect - steps from down town and an easy walk to Eastport.
10.0
Wedding weekend
This is the perfect house for guests for a wedding weekend! The house is gorgeous with everything you could want or need for a trip to Annapolis for any reason. The hosts were communicative and helpful. We highly recommend this home!
10.0
Excellent Property
I recently stayed here with my family of five, my brother-in-law’s family of four, and my mother-in-law and father-in-law. Plenty of room for everyone. Also great space to just hang out. Property is conveniently located right near the Naval Academy and all the shops and restaurants/bars of downtown Annapolis. Great location, excellent property.
10.0
Wedding
Great property close to everything
Communication with property manager was great.
10.0
Amazing parade weekend
Quick getaway for three families - one of whom went to USNA and another who used to live in Annapolis. Six adults, five kids, 6-10. We came down for the St. Paddy’s parade and the house provided the perfect home base for all of our activities! We enjoyed coffee and bloody Marys on the porch in the morning and played games out there once the kids were in bed. Beautiful views of the chapel, proximity to everything in DTA and Eastport, and gorgeous decor throughout the home. We’ve already booked a return trip in the fall! Thank you for sharing your home with us.
8.0
Sisters+Spouses Getaway
The proximity to the naval academy, restaurants and shops on Main Street was great. Everything within walking distance.
8.0
Christmas in Annapolis
Very well maintained. Had all necessities.. Enjoyed Christmas
With family from Md, Del, Tx, & PA. Even had an 8ft tree.
Location excellent, within walking distance of downtown
Restaurants & stores. Nice front porch. Bedrooms good
10.0
Family reunion to celebrate milestone bday!
Great gathering space to honor mother turning 95 who lives nearby.
10.0
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!
10.0
Friends wedding
A group of us were in town for a friends wedding in downtown Annapolis and our stay did not disappoint! All of the beds were so comfy and we had more than enough room for the 11 of us. The house is in walking distance to everything which allowed us to enjoy all that Annapolis has to offer! The check in and check out process was seamless - I’d recommend this listing to everyone!
10.0
Great place for large groups!
We loved our stay in Annapolis! Sean and Jen were very helpful as we prepared for our trip and everything was just as pictured when we arrived. The house was fantastic for large groups - lots of gathering space, plenty of dishes and fridge space, and super close to everything so people could walk off on their own with no need for a car. However, there are two parking spots included which we appreciated because street parking nearby has limitations. There’s a cute front porch as well, perfect for morning coffee. I’d definitely stay at this home next time I’m in Annapolis with a big group!
10.0
Excellent Location
Easy walking distance to Gate 3, City Dock, Restaurants, etc. Very close to the chapel and the sound of its bells. So inspiring to hear formation and the Star Spangled Banner each morning. Great house for our family of five but would easily accommodate more.
10.0
Great location
Enjoy the house in the location. It’s laid out very nice. I would certainly stay there again.
10.0
Family Gathering for Navy Retirement
This VRBO rental process (my first time) was very easy, the location was perfect for access to town and USNA, and the house was extremely well furnished.
10.0
USNA Family visit
This was a family trip to visit our daughter at USNA. We were able to walk everywhere and enjoy the town. The kitchen was perfect for grandma to make a big spaghetti dinner for our mid and her friends. Was a perfect spot for all!
10.0
14th Co Cobra Mother’s Day
We throughly enjoyed our stay at Anchor Inn! Imagine our delight when I shared with our daughter and her fellow mids that the owners, like them, we in 14th company!! The house was perfect for feeding and watering our crew and the beds were super comfy. Stellar location, great layout for visiting and easy entry and check-out. Jennifer and Sean at iTrips were amazing to work with and helped us to reschedule when covid messed with our plans. We would love to visit again!
10.0
PERFECT for USNA visit!
We were in town to visit our son at USNA. This house is just steps from Gate1 so the locations is perfect. You are literally looking at the academy while sitting on the beautiful front porch. My mid requested that I cook his favorite meal for him and a "few" of his friends. A few turned into ten but the kitchen was awesome and had everything we needed for a big southern meal. They ended up not getting an overnight but if they had, the set up in the attic with the 5 twin beds would have been perfect. Plenty of room for relaxing. Plenty of hangers and closet space for all the uniforms that need to be hung lol. Everything was clean and Sean, the host, was very polite and quick to answer all my questions. We will defintely stay here again.
10.0
Great house for a golf trip!
Awesome property and location. Would stay here again.
10.0
Great Family Stay
11family members from around the country met for a fun weekend in Annapolis. This location was perfect for walking to shops and restaurants and late night ice cream shops. It was a nice get-away location. We’ll be back.
10.0
Great home, wonderful location
This home was perfect for 2 families meeting up for a NYE getaway. Anchor at Annapolis Inn was walking distance to anywhere you want to go in Annapolis. Steps from the Naval Academy and downtown, the location could not be better. Plenty of space for 2 families to spread out and be comfortable, and we enjoyed the naval themed decor. Very clean, easy communication, and had everything we needed. Great for kids - they loved bunking together upstairs. Hope to be back soon!
10.0
Fantastic, beautiful, and exceptionally clean home in downtown Annapolis!
We had a wonderful stay at the anchor Inn in downtown Annapolis and a fantastic experience! The home is so clean, and so convenient, with all of the amenities possible, and two well sized parking spaces in the back that fit both of our SUVs! It is right downtown within a quick walk to wonderful shops, coffee spots and restaurants too. USNA is a very short walk away and makes transiting to and from very convenient! The property management is fantastic and very thoughtful and extremely helpful. Their communication was wonderful and they are always available! We would highly recommend this home, whether for a short stay or a long term stay! Thank you, again for a wonderful home away from home!
FAQs
How much does this house cost compared to others in Annapolis?
The average price for a rental in Annapolis is R 7,789 per night. This rental is R 5,847 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Naval-Academy-themed home with custom bar steps to Gate 1 and onsite parking at. 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 Naval-Academy-themed home with custom bar steps to Gate 1 and onsite parking at pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Naval-Academy-themed home with custom bar steps to Gate 1 and onsite parking at?
We found 8 amenities for this rental. This includes air conditioner, kitchen or kitchenette, internet / wifi, parking, and laundry.
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2 guests · 1 bedroom · 1 bath
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Nestled in Annapolis, this Hotel is perfect for your next vacation. Enjoy Hilton Garden Inn Annapolis Downtown's top-rated amenities, including Air conditioner, Internet / Wifi and Laundry, and more.
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Hilton Garden Inn Annapolis Downtown
Hotel
in Annapolis3-star
1 king bed
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
The best choice in Annapolis for Hotel, for R 2,148 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
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3 Story Stunner in Murray Hill <1 mile from USNA!
House
in Annapolis14 guests · 7 bedrooms · 4 baths
Garden · Pets allowed · Kitchen or Kitchenette
Indulge in a peaceful retreat at 3 Story Stunner in Murray Hill <1 mile from USNA!, our elegant House in Annapolis. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.
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Ensign's Ridge
House
in AnnapolisGarden · Kitchen or Kitchenette · Air conditioner
Are you ready to indulge in a relaxing getaway? Our House in Annapolis has everything you need for a rejuvenating stay. Treat yourself to Ensign's Ridge's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.
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Indoor/Outdoor waterfront oasis with indoor heated pool awaits you in Eastport!
House
in Annapolis16 guests · 5 bedrooms · 4 baths
Pool · Kitchen or Kitchenette · Air conditioner
Experience the best of Annapolis with this House available for R 31,679. This property is equipped with amenities including Air conditioner, Dishwasher and Fireplace, and more.
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