Prime Location! Modern Comfort 1 Block to Gate 1 w/ Parking & Walkability
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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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
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.
O'Brien's Oyster Bar & Seafood Tavern - 6 min walk
Buddy's Crabs & Ribs - 6 min walk
Annapolis Market House - 4 min walk
Frequently asked questions
Is Prime Location! Modern Comfort 1 Block to Gate 1 w/ Parking & Walkability pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Prime Location! Modern Comfort 1 Block to Gate 1 w/ Parking & Walkability?
As of 4 Apr 2026, prices found for a 1-night stay for 2 adults at Prime Location! Modern Comfort 1 Block to Gate 1 w/ Parking & Walkability on 29 June 2026 start from AU$1,214, 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 Prime Location! Modern Comfort 1 Block to Gate 1 w/ Parking & Walkability?
On-site parking is available at the property.
What time is check-in at Prime Location! Modern Comfort 1 Block to Gate 1 w/ Parking & Walkability?
Check-in begins at 4:00 PM.
What time is check-out at Prime Location! Modern Comfort 1 Block to Gate 1 w/ Parking & Walkability?
Checkout is at 11:00 AM.
Where is Prime Location! Modern Comfort 1 Block to Gate 1 w/ Parking & Walkability 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.
Perfect location for a Thanksgiving holiday with the whole family!
Krista K.
Stayed 5 nights in Nov 2025
Response from VrboOwner on 12 Dec 2025
Thanks, Krista! We’re thrilled to hear that Anchor at Annapolis Inn was the perfect location for your Thanksgiving holiday with the whole family. We hope to welcome you back for another wonderful visit in the future!
Awesome location to walk everywhere! It’s a great set up for watching games and having family fun!
Paula O.
Stayed 3 nights in Nov 2025
Response from VrboOwner on 22 Nov 2025
Thanks, Paula! We’re thrilled to hear that Anchor at Annapolis Inn provided an awesome location for your stay. It’s fantastic that you enjoyed the setup for watching games and having family fun. We hope to welcome you back for another wonderful visit in the future!
Melissa~iTripAnnapolis
Thanks, Cindy! We’re thrilled to hear that Anchor at Annapolis Inn continues to please you on your third stay. It’s wonderful to know that our property consistently meets your expectations. We look forward to welcoming you back for another great stay next time you’re in town!
Melissa~iTrip Annapolis
Thank you Joshua and we hope to host you again! - Cathy
From a partner site
10/10 Excellent
mike j.
18 Aug 2025
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.
mike j.
Response from VrboOwner on 21 Aug 2025
Thanks, Mike! We’re honored that Anchor at Annapolis Inn could be a part of such an important and meaningful trip for you and your family. It’s wonderful to hear that the accommodations and location met your needs during this emotional time. We’re glad you found the proximity to the Naval Academy and downtown to be outstanding. We would be privileged to host you again anytime you’re in Annapolis.
Melissa~iTrip Annapolis
Hi Lori! Thank you for allowing us to host your stay & we are thrilled to know you enjoyed your time in the home! We welcome you back anytime, Melissa~iTripAnnapolis
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.
Joseph W.
Stayed 2 nights in Sep 2025
Response from VrboOwner on 30 Sept 2025
Thanks, Joseph! We’re thrilled to hear that Anchor at Annapolis Inn was fantastic for your stay. We’re glad you found everything easy and appreciated the great communication. We apologize for any confusion regarding the outdoor hangout space and the grill. Your feedback is valuable, and we will review the property description and amenities to ensure they accurately reflect what is available. We would love to host you again next time you’re in town.
Melissa~iTrip Annapolis
Wonderful property in a great location. Very cool bar and fun spot to hang out.
Nick S.
Stayed 2 nights in Jun 2023
Response from VrboOwner on 29 June 2023
Nick, thank you for your kind review of Anchor at Annapolis Inn. We are happy to hear you enjoyed your stay. Please come back and stay with us again. Safe Travels!
-Tiffany
Thank you for the kind review of Anchor at Annapolis Inn Casey. We are happy to hear that you enjoyed your stay. We would love the opportunity to host you again.
-Tiffany
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.
Brian S.
Stayed 3 nights in Jun 2025
Response from VrboOwner on 4 July 2025
Thanks, Brian! We're thrilled to hear that Anchor at Annapolis Inn was the perfect location for your son's Naval Academy Induction Day. It's great that you found the parking convenient and enjoyed the easy walk to Gate 1 of USNA. We're glad the property suited your group with its wide open sitting area, and that our team was attentive to your needs. We appreciate your recommendation and look forward to welcoming you back on future visits! Melissa~iTrip Annapolis
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.
George C.
Stayed 3 nights in Dec 2024
Response from VrboOwner on 14 Jan 2025
Thank you George & we welcome you back anytime! Melissa~iTripAnnapolis
Enjoy the house in the location. It’s laid out very nice. I would certainly stay there again.
Kenny H.
Stayed 3 nights in Jun 2021
Response from VrboOwner on 26 July 2021
Thanks, Kenny! Please come back and stay with us again! Glad you enjoyed this home.
Verified
8/10 Good
Bradley B.
29 Aug 2022
Liked: Cleanliness, check-in, communication
Great House great property management.
Great Property Management
Bradley B.
Stayed 3 nights in Aug 2022
Response from VrboOwner on 8 Sept 2022
Thank you so much! The Anchor at Annapolis Inn is a great property! And thank you for your compliment of iTrip Vacations Annapolis! Come back and visit us again! Cathy
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!
Kim M.
Stayed 4 nights in Sep 2021
Response from VrboOwner on 22 Oct 2021
Kim thank you for staying with us at Anchor at Annapolis Inn. We look forward to hosting you again very soon!
The place was immaculate. Given the opportunity would book again.
Thomas A S.
Stayed 2 nights in Apr 2023
Response from VrboOwner on 26 Apr 2023
Thank you for the kind review of Anchor at Annapolis Inn Thomas. We are so happy to hear you enjoyed your stay. We would love the opportunity to host you again. Safe Travels!
-Tiffany
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!
Celeste H.
Stayed 2 nights in Dec 2022
Response from VrboOwner on 20 Dec 2022
Thank you for the wonderful review of Anchor at Annapolis Inn Celeste. We are so glad to hear that you enjoyed your stay. We would love the opportunity to host you again.
-Tiffany
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!
Sam C.
Stayed 2 nights in Sep 2022
Response from VrboOwner on 28 Sept 2022
Thank you so very much for your wonderful review and kind words! We hope you will stay with iTrip Vacations Annapolis again! The Anchor at Annapolis in is a fabulous home! Thank you again! - Cathy
About the host
Hosted by iTrip Vacations Annapolis - Sean Degnan
Languages:
English
Premier Host
They consistently provide great experiences for their guests