Annapolis Rentals
From $714 per night (USD)VRBO
Historic Annapolis Home | 2 Blocks to Main St
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Summary: Historic 1885 row home two blocks from Main Street and steps from the U.S. Naval Academy. Three bedrooms acros ...
From $714 per night (USD)VRBO
From $620 per night (USD)VRBO
Cozy Stay in Downtown Naptown -Located in the heart of Annapolis - 3BR, 2 BA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to 17 Lafayette Ave—your charming retreat in the heart of historic Annapolis! Just steps from downtown, the U.S. ...
From $620 per night (USD)VRBO
From $445 per night (USD)VRBO
Annapolis Town Center Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Escape to our charming 2-bed, 2-bath cottage in Annapolis Town Center! Newly updated, this cozy retreat comfor ...
From $445 per night (USD)VRBO
From $559 per night (USD)Expedia
Historic Row Home in Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
Summary: Steps away from the Naval Academy, St. John's College, State House, City Dock, Yacht Club, St. Mary's Church a ...
From $559 per night (USD)Expedia
From $551 per night (USD)VRBO
Upscale Condo in Annapolis w/Private Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the West Street Hideaway. See the best of Annapolis effortlessly when you book this 2-bed, 2-bath vacation re ...
From $551 per night (USD)VRBO
From $58 per night (USD)VRBO
Efficiency Apartment Close to Annapolis. .
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Furnished efficiency apartment in Annapolis, close to downtown area, and easy access to Highways. Private Entrance, pri ...
From $58 per night (USD)VRBO
From $674 per night (USD)VRBO
Historic Parish House 2-Bedroom Condo Steps to Naval Academy
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Step into a truly exceptional condo nestled in a beautifully preserved historic church, just 2 blocks from the U.S. Nava ...
From $674 per night (USD)VRBO
From $1660 per night (USD)Expedia
18th Century 4bdrm Luxury Historic Home in Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to Lynder's Luxury Lodging-Annapolis. Discover this 4-bedroom Colonial gem in the heart of Downtown Annapolis ( ...
From $1660 per night (USD)Expedia
From $323 per night (USD)VRBO
The Red Door Cottage in Eastport - Pet-Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This stylish, pet-friendly boho retreat is just 1 mile from downtown Annapolis and Eastport’s restaurants—your perfect h ...
From $323 per night (USD)VRBO
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Historic Inn | Steps from Naval Academy & State House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Located in the heart of Annapolis, this historic inn offers easy walking access to landmarks like the United States Nava ...
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Historic Inn Stay | 1 Unit | Heart of Annapolis at State Circle
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites ...
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From $636 per night (USD)VRBO
Coastal Chesapeake cottage in Eastport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our newest listing - The Coastal Cottage on Chesapeake located in the Maritime community of Eastport . This b ...
From $636 per night (USD)VRBO
From $1386 per night (USD)VRBO
Historic Annapolis Charmer <1Mile to NMC Stadium
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 20
IMMACULATE SPACE AND RARE FIND IN DOWNTOWN ANNAPOLIS SLEEPING UP TO 12! Beautifully maintained 1930's home in the middl ...
From $1386 per night (USD)VRBO
From $654 per night (USD)Expedia
Downtown Fleet St home with garage parking EV Walk to USNA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
Friends! We are a USNA family (‘92) and love this town! Walk to bottom of Fleet Street and you are at the docks. Walk to ...
From $654 per night (USD)Expedia
From $438 per night (USD)VRBO
Restful and Charming Home in Eastport
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
We offer a 10% military discount upon request! A cozy home away from home in Eastport located within 1.5 Miles of Histor ...
From $438 per night (USD)VRBO
From $957 per night (USD)VRBO
Annapolis gem with beautiful outdoor dining! Near U.S. Naval Academy
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
In Annapolis this charming 3-bedroom home is moments away from USNA Stadium, and the Naval Academy, and picturesque Cit ...
From $957 per night (USD)VRBO
From $422 per night (USD)VRBO
18th Cent. Charm in Historic Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Lower level furnished apartment, in one of Historic Annapolis's 10 oldest Private residences. Lovely wood, brick & ornam ...
From $422 per night (USD)VRBO
From $732 per night (USD)Expedia
Secluded Cozy Cottage in Historic Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Beautifully restored 1930s cottage w/ open floor plan & vaulted ceilings provide a homey vibe Enjoy having Historic Ann ...
From $732 per night (USD)Expedia
From $1035 per night (USD)VRBO
Walk to the Naval Academy and Historic Annapolis. Private parking at the home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our favorite part of this home is its unbeatable location in downtown Annapolis (DTA)- with private parking. You can wa ...
From $1035 per night (USD)VRBO
From $1390 per night (USD)VRBO
Stunning Annapolis Home! Across from the library, walk to Naval Graduation
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
This 4 BR, 4.5 BA house is perfect for entertaining your guests! Come into our spacious open floor plan. You feel li ...
From $1390 per night (USD)VRBO
From $654 per night (USD)VRBO
Historic Annapolis Hideaway Steps to USNA and Main St w Private Patio & Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis Take a stroll along the brick-lined sidewalks of P ...
From $654 per night (USD)VRBO
From $603 per night (USD)Expedia
Historic Annapolis Union House with Private Patio & Free Off-Site Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the Difference: Professionally Managed by iTrip Annapolis Enjoy Annapolis, MD in this charming Federal-style ...
From $603 per night (USD)Expedia
From $587 per night (USD)VRBO
Downtown Gem! Historic Carriage House Steps to Main St, City Dock & USNA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the Difference: Professionally Managed by iTrip Annapolis Originally built in 1857, this fully-restored home ...
From $587 per night (USD)VRBO
From $646 per night (USD)Expedia
USNA Home Steps to Stadium Dog-Friendly w Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Experience the Difference: Professionally Managed by iTrip Annapolis In Navy jargon, the goat locker is a lounge, sleep ...
From $646 per night (USD)Expedia
From $695 per night (USD)VRBO
Escape Villa in Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Perfect getaway, a short stroll to West Street, the Naval Academy, Navy-Marine Corps Memorial Stadium, City Dock, and Do ...
From $695 per night (USD)VRBO
From $547 per night (USD)VRBO
Gem in Downtown Annapolis, close to USNA, St. John's College
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Comfortable stay on quiet street close to Gate 3 USNA and St. John's College. Quick walk to Maryland State House, Maryla ...
From $547 per night (USD)VRBO
From $640 per night (USD)VRBO
Tastefully decorated fully-equipped Eastport Annapolis house with water views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our renovated 3 story house is located on the peninsula of Eastport, Annapolis. We are across the street from a small m ...
From $640 per night (USD)VRBO
From $518 per night (USD)Expedia
Go Navy! Steps to USNA, City Dock & Street Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Experience the Difference: Professionally Managed by iTrip Annapolis Stay in the heart of Historic Annapolis just steps ...
From $518 per night (USD)Expedia