Steps from the Waterfront with Private Backyard at Historic Philip Clayton House
Experience the Difference: Professionally Managed by iTrip Annapolis
Historic Philip Clayton House – Downtown Annapolis Retreat
Step into Annapolis history at the Philip Clayton House, a landmark residence built in 1834. Located just one block from the City Dock, 3 blocks from the U.S. Naval Academy and the lively shops and restaurants of Downtown Annapolis, this home blends historic character with modern comforts for an unforgettable stay.
With nearly 200 years of stories behind its walls, the home has been thoughtfully renovated to balance original charm with modern livability. A bright family room opens to a private patio and fenced backyard—perfect for morning coffee, al fresco dining, or evenings around the fire pit.
There are 4 spacious bedrooms and 2.5 bathrooms, comfortably accommodating up to 10 guests. The gourmet kitchen serves as the heart of the home, featuring a large central island, top-quality appliances, and plenty of space for family meals or entertaining.
Sleeping Arrangements (Sleeps 10):
King Suite (2nd Floor): King bed with ensuite full bath
Garden Bedroom (2nd Floor): Queen bed
Americana Bedroom (2nd Floor): Queen bed
3rd Floor Bedroom: Two King beds
Additional Baths: Full hall bath on 2nd floor + half bath on main level
Highlights:
Private backyard with dining for 6, Adirondack chairs, and fire pit
Propane BBQ grill
Multiple dining areas in the kitchen, dining and family rooms (total seating for 16)
Smart TVs, WiFi, and luxury linens
Keyless entry and in-home laundry
Dog-friendly ($150 per pet fee to be charged prior to checkin)
Parking: Convenient loading zone on street in front of house with parking around the block in the easy to access Hilman garage. Daily rate $23.25.
Guests must be 25+ or accompanied by an adult
No smoking, parties, or events permitted
Steep staircases may not suit those with mobility issues
Nearby Attractions:
U.S. Naval Academy: 3 blocks
City Dock & Downtown Annapolis: Walking distance
Washington, D.C.: 30 miles
Baltimore: 25 miles
Your stay begins worry-free with a starter kit of coffee, toiletries, and household essentials. Freshly laundered linens await on every bed so you can settle in and enjoy the best of Annapolis—history, charm, and convenience all in one.
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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 Maynard-Burgess 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 Helen Avalynne Tawes Garden are also worth visiting.
O'Brien's Oyster Bar & Seafood Tavern - 5 min walk
The Red Bean - 3 min walk
Chick & Ruth's Delly - 4 min walk
Frequently asked questions
Is Steps from the Waterfront with Private Backyard at Historic Philip Clayton House pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Steps from the Waterfront with Private Backyard at Historic Philip Clayton House?
As of 5 Apr, 2026, prices found for a 1-night stay for 2 adults at Steps from the Waterfront with Private Backyard at Historic Philip Clayton House on 30 Apr, 2026 start from S$1,015, 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 Steps from the Waterfront with Private Backyard at Historic Philip Clayton House?
On-site parking is available at the property.
What time is check-in at Steps from the Waterfront with Private Backyard at Historic Philip Clayton House?
Check-in begins at 4:00 PM.
What time is check-out at Steps from the Waterfront with Private Backyard at Historic Philip Clayton House?
Checkout is at 11:00 AM.
Where is Steps from the Waterfront with Private Backyard at Historic Philip Clayton House located?
Located in Historic District, this holiday home is within a 10-minute walk of Matthew Henson Plaque and U.S. Naval Academy. Thurgood Marshall Memorial and Maryland State House are just steps away.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Wonderful house! Great location! Beds were very comfortable. My only suggestion would be to mention in the description that the master bedroom with the king size bed does not have an actual door that shuts completely. Instead there are two shutter like doors which doesn’t make the bedroom sound proof for privacy.
JoJo T.
Stayed 2 nights in Nov 2025
Response from VrboOwner on 30 Nov, 2025
Thanks, JoJo! We’re thrilled to hear that Phillip Clayton House was wonderful and the location was great for your stay. It’s fantastic that you found the beds very comfortable. We appreciate your suggestion regarding the master bedroom’s doors and will consider this for our property description. We hope to welcome you back for another exceptional visit in the future!
Melissa~iTripAnnapolis
From a partner site
10/10 Excellent
Laura
17 Oct, 2025
Incredible stay in the BEST location
We absolutely loved our stay at this beautiful historic home - built in the 1800s but updated with every modern feature you could want. The house is adorable and spacious with high end appliances, gorgeous decor, and plenty of room for our group of four couples to relax and enjoy. The location couldn’t be better - right downtown and walkable to amazing restaurants, shops, the U.S. Naval Academy, and we even walked to a game at the stadium. We got coffee just 2 blocks away in the mornings and walked along the marina. At night we had dinner & drinks in the home’s adorable backyard patio area. It’s the perfect spot for anyone wanting to experience historic Annapolis with all the comfort and space of a vacation home. Thank you - we can’t wait to come back!
Laura
Response from VrboOwner on 21 Oct, 2025
Thanks, Laura! We’re thrilled to hear that Phillip Clayton House impressed you with its blend of historic charm and modern amenities. It’s wonderful to know that the spacious layout, high-end appliances, and gorgeous decor provided a perfect setting for your group of four couples to relax and enjoy. We’re glad you found the location ideal for exploring downtown Annapolis, with its amazing restaurants, shops, and proximity to the U.S. Naval Academy and stadium. It sounds like you made the most of the backyard patio area for dinner and drinks, and enjoyed morning coffee walks along the marina. We hope to host you again next time you’re in town!
Melissa~iTrip Annapolis
From a partner site
10/10 Excellent
Lauren C.
15 Oct, 2025
Historic home in downtown Annapolis
I have rented homes all over the world but this is a rare gem. First the location is second to none. Right in the heart of downtown, we walked to docks, to shopping, to coffee and out for dinner. This lovely home comfortably slept our family with large gathering rooms and a fabulous outdoor entertaining area. Everything we needed was available in the chefs kitchen. I was looking for an immersive historical experience for my visit to Annapolis and this home was icing on the cake. It’s easy to see why it has welcomed families for many years.
PS: Catch the water taxi at City Dock to the Chart House. Grab a bite to eat in Eastport and walk back over the bridge to Green Street. Inexpensive fun for any age!
Lauren C.
Response from VrboOwner on 21 Oct, 2025
Thanks, Lauren! We’re thrilled to hear that Phillip Clayton House impressed you with its unbeatable location in the heart of downtown Annapolis. It’s wonderful to know that the home comfortably accommodated your family and that you enjoyed the large gathering rooms and fabulous outdoor entertaining area. We’re glad the chef’s kitchen had everything you needed for your stay. It’s fantastic to hear that the home added to your immersive historical experience in Annapolis. Thank you for sharing your tip about the water taxi and the fun adventure to Eastport! We hope to host you again next time you’re in town!
Melissa~iTrip Annapolis
About the host
Hosted by iTrip Vacations Annapolis - Sean Degnan
Languages:
English
Premier Host
They consistently provide great experiences for their guests