Annapolis Rentals
From $519 per night (USD)VRBO
Great Entertaining Spot for any Occassion!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 10
This newly built 2012 Carriage House has all the bells and whistles for a relaxed fiiends and family stay. Enjoy this u ...
From $519 per night (USD)VRBO
From $530 per night (USD)Expedia
Tastefully decorated fully-equipped Eastport Annapolis house with water views
- Bedrooms:
- 3
- 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 $530 per night (USD)Expedia
From $349 per night (USD)VRBO
Cozy 2br home w\/ parking in downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A's by the Cove is ideally located in the heart of downtown Annapolis's Historic and Art Districts. It is a fully update ...
From $349 per night (USD)VRBO
From $376 per night (USD)Expedia
Annapolis steps to Harbor and Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Parking included. The heart of Annapolis 1 street from the harbor, fun restaurants & backs to the Naval Academy. This 1s ...
From $376 per night (USD)Expedia
From $1100 per night (USD)VRBO
Prestigious Historic Annapolis home, parking for 5 cars, walk to everything!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Spacious historic Annapolis home, located mere steps to the Naval Academy and St. John's College. Two blocks from the St ...
From $1100 per night (USD)VRBO
From $366 per night (USD)Expedia
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Quaint 2 BR 1 BA Guest House nestled in the trees by USNA stadium. Enjoy Annapolis historic charm in this rare 2 BR 1 BA ...
From $366 per night (USD)Expedia
From $664 per night (USD)VRBO
Beautifully Renovated Historic District Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this meticulously renovated home where no detail has been overlooked. Step into the kitchen and be captivated ...
From $664 per night (USD)VRBO
From $831 per night (USD)Expedia
Charming Historic Annapolis Home With Two Off-street Parking Places!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Charming cedar shake duplex home in Historic Annapolis adjacent to the Paca Gardens and the Naval Academy. Custom kitche ...
From $831 per night (USD)Expedia
Click For PricingVRBO
Downtown Annapolis Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Two bedroom and two bathroom in Historic Annapolis, only 1 mile from arts district (west street), 2 miles from downtown ...
Click For PricingVRBO
From $187 per night (USD)Expedia
Calico Cottage Guest House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cute-as-a-bugs ear West Annapolis guest cottage. In settled neighborhood just 1.5 miles from the Navy Stadium and less t ...
From $187 per night (USD)Expedia
From $658 per night (USD)VRBO
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Charming house - a 10-15 min walk to Navy Marine Corps Stadium (<.75mile), a 5 min drive from the US Naval Academy (<1mi ...
From $658 per night (USD)VRBO
From $235 per night (USD)Expedia
Jode's Retreat \"Your home away from home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Clear the calendar for an easy-going getaway at "Jode's Retreat"; ideal for USNA events (a 2-minute drive to the stadium ...
From $235 per night (USD)Expedia
From $580 per night (USD)VRBO
Nautical Feel to This Beautiful Eastport Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
From the minute you walk in the door, you will feel the warmth and charm this home offers. Located on the Eastport si ...
From $580 per night (USD)VRBO
From $688 per night (USD)Expedia
Stay close to USNA Stadium with screened-in porch and parking
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to this charming Cape Cod on half an acre right outside downtown Annapolis. Just minutes to the Stadium, Naval ...
From $688 per night (USD)Expedia
From $774 per night (USD)VRBO
80 Five Star Reviews & located in a quiet neighborhood in the City of Annapolis!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This is one of the most charming houses in Murray Hill! Located on a dead end street, this brick colonial with a slate r ...
From $774 per night (USD)VRBO
From $644 per night (USD)Expedia
Lots free parking, hot tub, tree house, outdoor oasis - NOT party house
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Walk downtown or to grocery, restaurants, etc. We live in a nice modernly decorated duplex adjacent to Navy Stadium. I ...
From $644 per night (USD)Expedia
From $712 per night (USD)VRBO
Beautiful Waterfront Townhome In Historic Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful waterfront townhome with three bedrooms 3 1/2 baths, recently renovated and beautifully decorated. 5-minu ...
From $712 per night (USD)VRBO
From $460 per night (USD)Expedia
Historic District\"Crab Cakes and Football\"
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Crab Cakes and Football. Enjoy Historic Downtown Annapolis with convenient walking distance to both City Dock ...
From $460 per night (USD)Expedia
From $1976 per night (USD)VRBO
Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Built in 1875, this delightful house offers total privacy in the heart of downtown Annapolis. Steps from Main St, and t ...
From $1976 per night (USD)VRBO
From $1570 per night (USD)Expedia
Murray Hill Gem - Your Commissioning Week Home Away from Home
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
NBS22-145072 - PLEASE NOTE: IF YOU BOOK THIS PROPERTY, YOU WILL BE CONTACTED BY ANNAPOLIS ACCOMMODATIONS TO FINALIZE AN ...
From $1570 per night (USD)Expedia
From $603 per night (USD)VRBO
Upscale home with parking for 4 cars in driveway. Walk to downtown.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
NOTE: Posted rates do not apply to Holidays, Boat Shows or Commissioning Week. They will be given on request. Rates a ...
From $603 per night (USD)VRBO
From $151 per night (USD)Expedia
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This 1920's Craftsman style bungalow is 1/2 block from the Naval Academy Stadium and within walking distance of the Hist ...
From $151 per night (USD)Expedia
From $437 per night (USD)VRBO
Amazing views, short walks and quick access to USNA events\/Commissioning Week and stadium.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Begin your mornings with wraparound views from the queen bed or coffee on the screened porch, with the same water views ...
From $437 per night (USD)VRBO
From $226 per night (USD)Expedia
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Known as the “Athens of America,” Annapolis is a city abundant with history and culture. This former capital of the Unit ...
From $226 per night (USD)Expedia
From $383 per night (USD)VRBO
Charming garden row home, easy 4 block walk to the heart of Annapolis.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Incredible location in the Historic District of Annapolis. Walking distance to the Naval Academy, St. Johns College, an ...
From $383 per night (USD)VRBO
From $538 per night (USD)Expedia
Eastport Haven House
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 9
Welcome to our custom Craftsman in the exclusive Maritime Eastport section of Annapolis. Surrounded by the city's best r ...
From $538 per night (USD)Expedia
From $884 per night (USD)VRBO
Charming Annapolis Victorian
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. W ...
From $884 per night (USD)VRBO
From $359 per night (USD)Expedia
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Vacations are meant to be carefree! Let the chimes from the Naval Academy chapel start your day. Stroll along our famed ...
From $359 per night (USD)Expedia
From $642 per night (USD)VRBO
Sophisticated Charmer with Parking & Views of the USNA Chapel Dome
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Hello and Welcome to Annapolis! You are going to love this home. IMPORTANT: if you are inquiring about USNA Commission ...
From $642 per night (USD)VRBO
From $425 per night (USD)Expedia
Historic Downtown Charmer, Water Views and Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Life is beautiful in historic downtown Annapolis, with great restaurants, shops and romantic waterfront at your doorstep ...
From $425 per night (USD)Expedia
From $1202 per night (USD)VRBO
Stay at Lux Red Door Gem with 3 Parking Spots
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
The gorgeous Downtown Annapolis home was meticulously remodeled from top-to-bottom in a luxurious fashion. This fully-r ...
From $1202 per night (USD)VRBO
From $627 per night (USD)Expedia
Historic home steps to Main St w Capital views, free off-site parking, patio
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Experience Historic Annapolis in Comfort and Style This charming 4-bedroom home sits in the heart of Historic Annapolis, ...
From $627 per night (USD)Expedia
From $896 per night (USD)VRBO
Annapolis -Eastport - -3 Bedroom- 3 bath with parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Delightful Arts and Crafts/ Coastal style home. Main Level is open space concept with 9 ft ceilings and plenty of nat ...
From $896 per night (USD)VRBO
From $573 per night (USD)Expedia
Cozy 2 BR home with parking and views of the Annapolis Harbor - Walk to everything!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
STR23-145349 - PLEASE NOTE: IF YOU BOOK THIS PROPERTY, YOU WILL BE CONTACTED BY ANNAPOLIS ACCOMMODATIONS TO FINALIZE AN ...
From $573 per night (USD)Expedia
From $1487 per night (USD)VRBO
Beautiful Eastport Home walking distance to downtown and USNA. Includes parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy the best of Eastport and downtown Annapolis in this cute historic home. Home has three levels with space for 10-1 ...
From $1487 per night (USD)VRBO
From $808 per night (USD)Expedia
Steps away from the Chesapeake Bay in the unique Bay Ridge community!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Chesapeake living with a view of the Bay from the lovely outdoor dining area and screened in balcony off of the huge mas ...
From $808 per night (USD)Expedia
From $786 per night (USD)VRBO
Walkable to Main Street at Seashell in the City with 2 parking spots
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this gorgeous fully-renovated home, restored to a new modern grandeur, which includes coveted parking for 2 c ...
From $786 per night (USD)VRBO
From $734 per night (USD)Expedia
Beautifully updated Annapolis Historic District rowhome w\/ parking and rooftop deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
STR21-14492 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $734 per night (USD)Expedia
From $342 per night (USD)VRBO
Anchor's Away in the Heart of Eastport!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Downtown in the heart of Eastport Annapolis, this first floor studio condo boasts high ceilings with lots of natural lig ...
From $342 per night (USD)VRBO
From $203 per night (USD)Expedia
“Athens of America,” Annapolis Apartment One B
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Annapolis is a city abundant with history and culture. This former capital of the United States has a little something f ...
From $203 per night (USD)Expedia
From $244 per night (USD)VRBO
Cozy 1st Floor King George one bedroom apartment right across from USNA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy this one bedroom first floor apartment that's right across from Gate 2 of the U.S. Naval Academy. It's a short 1 ...
From $244 per night (USD)VRBO
From $1284 per night (USD)Expedia
RARELY AVAILABLE FOR COMMISSIONING WEEK! Stunning colonial on a private 1.6 acre lot!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 9
STR00844 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $1284 per night (USD)Expedia
From $1191 per night (USD)VRBO
Luxurious home with parking in historic downtown Annapolis!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
NBS22-145083 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN ...
From $1191 per night (USD)VRBO
From $345 per night (USD)Expedia
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This 2nd floor apt has new furniture, bedding and housewares. Extremely convenient location to downtown where there's l ...
From $345 per night (USD)Expedia
From $214 per night (USD)VRBO
Charming Downtown 3rd Floor 1 Bedroom Apt
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Perfect location for all that downtown Annapolis offers. Located right across from USNA gate 2. Super convenient, park y ...
From $214 per night (USD)VRBO
From $1776 per night (USD)Expedia
Indoor\/Outdoor waterfront oasis with indoor heated pool awaits you in Eastport!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
STR21-144966 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $1776 per night (USD)Expedia
From $429 per night (USD)VRBO
Perfect spot for a Weekend Getaway!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This luxiourious apartment sits right off Main Street and is so centrally located...you can park your car in the city ga ...
From $429 per night (USD)VRBO
From $440 per night (USD)Expedia
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This home is spacious and clean and will make your vacation plans a breeze from this central location. Many families, g ...
From $440 per night (USD)Expedia
From $727 per night (USD)VRBO
Downtown Annapolis Townhome ! Beautiful!!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful Remodeled Townhome ! We have thought of everything you will need for an amazing stay. Fully loaded kitchen , ...
From $727 per night (USD)VRBO
From $430 per night (USD)Expedia
Historic Downtown House with Off Street Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious living with all the modern amenities. Prime location - 1 block from the water, restaurants, and shops. Park you ...
From $430 per night (USD)Expedia
From $303 per night (USD)VRBO
The Yellow Cottage on Harness Creek
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The minute you step into our charming waterfront cottage you will feel right at home! Situated on Harness Creek, in a q ...
From $303 per night (USD)VRBO
From $554 per night (USD)Expedia
Beautiful Historic Home With Great Location!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The "Philip Clayton House" (Annapolis license STR21-144988) is a fully up-dated, historic home in the Federal style dat ...
From $554 per night (USD)Expedia
From $96 per night (USD)VRBO
Amazing Bright Big Window Loft Heart of Eastport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Beautiful furnished or semi furnished loft apartment in Eastport. Views of the Severn river, naval academy , Sailboat’s, ...
From $96 per night (USD)VRBO
From $349 per night (USD)Expedia
Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RENT-000642-2025- PLEASE NOTE: IF YOU REQUEST TO BOOK THIS PROPERTY, YOU WILL BE CONTACTED BY ANNAPOLIS ACCOMMODATIONS ...
From $349 per night (USD)Expedia
From $251 per night (USD)VRBO
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Completely renovated street level 1 bedroom apartment with all the amenities of home. Perfect for a single traveler or ...
From $251 per night (USD)VRBO
From $443 per night (USD)Expedia
Eastport Cottage .5 mi from Downtown Annapolis\n\n
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Charming Eastport Cottage just 3 blocks from restaurants and bars (Ruth's Chris, Boatyard, O'leary's, Carol's Creek, t ...
From $443 per night (USD)Expedia
From $688 per night (USD)VRBO
Walk to USNA and Main Street with Parking at Historic Wisteria
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
How many homes in Downtown Annapolis have 4 Bedrooms with 4 Baths (3 of which are en-suite)?! Just 1-2 blocks from the ...
From $688 per night (USD)VRBO
From $2508 per night (USD)Expedia
Cool 1870's Historic District Home with modern amenities 2 blocks from Gate 3.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
***as of March 29, 2025 VRBO is continuing to deny chronic failures with all automated bookings requests for our proper ...
From $2508 per night (USD)Expedia
From $201 per night (USD)VRBO
“Athens of America,” Annapolis Apartment Two B
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Known as the “Athens of America,” Annapolis is a city abundant with history and culture. This former capital of the Unit ...
From $201 per night (USD)VRBO
From $203 per night (USD)Expedia
“Athens of America,” Annapolis Apartment Two A
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The place to be for all USNA activities. Annapolis is a city abundant with history and culture. This former capital of t ...
From $203 per night (USD)Expedia
From $328 per night (USD)VRBO
Available for Maryland Legislative Session 2024 ! Perfect location!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the essence of Historic Annapolis with this recently renovated Maryland Avenue apartment. Located in the 'Johnson ...
From $328 per night (USD)VRBO
From $137 per night (USD)Expedia
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Annapolis, where history and nature come together! Make yourself at home in this cozy 1-bedroom, 1-bath cond ...
From $137 per night (USD)Expedia
From $596 per night (USD)VRBO
Book CW 2025 \"Around the corner\" from hot spots with new King bed, fenced-in yard, parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Still available for Commissioning Week 2025! Welcome to this beautifully remodeled Victorian home in Eastport, lovingly ...
From $596 per night (USD)VRBO
From $255 per night (USD)Expedia
Brand New Reno in Historic Dist w 2 Parking spots
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Spotless / sanitized !! Renovated upstairs unit two bedroom with TWO parking spots in the Historic District . Everythi ...
From $255 per night (USD)Expedia
Click For PricingVRBO
A Delight on Dean
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Sitting on a quiet, tree lined street, this home enjoys being located in the sought after neighborhood of Murray Hill. ...
Click For PricingVRBO
From $841 per night (USD)Expedia
Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Absolutely gorgeous downtown waterfront home. Loaded with historical significance and character, all while minutes walki ...
From $841 per night (USD)Expedia
From $605 per night (USD)VRBO
Steps to the marinas with Private back deck, yard and Easy parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This professionally-decorated and furnished 2 bedroom, 1.5 bath is located across the Annapolis Waterfront drawbridge in ...
From $605 per night (USD)VRBO
Click For PricingExpedia
\"Dreams upon Weems\" Waterfront Cottage on Weems Creek in Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Waterfront Home on Weems Creek in Annapolis with private water access for paddleboarding, kayaking, boating. Waterfro ...
Click For PricingExpedia
From $312 per night (USD)VRBO
Charming Annapolis Guest House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This charming guest house with private access is in a great location! Just 2 miles from the Naval Academy, Downtown Anna ...
From $312 per night (USD)VRBO
From $567 per night (USD)Expedia
Steps to Main St at Historic Carriage House in the Heart of Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Originally built in 1857, this fully-restored home has a rich history that's been documented from it's original purpose ...
From $567 per night (USD)Expedia
From $531 per night (USD)VRBO
Delightful little Historic District gem - for the antique lover and history buff.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STR21-144963 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $531 per night (USD)VRBO
From $855 per night (USD)Expedia
One block from USNA Gate 1, or 3 blocks from City Dock, this attractive home is close to the center of the universe!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $855 per night (USD)Expedia
From $1256 per night (USD)VRBO
Contemporary waterfront 4BR home close to downtown Annapolis - stunning water views w\/private dock\/pier\/ private pool and kayaks.
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
STR259 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $1256 per night (USD)VRBO
From $879 per night (USD)Expedia
Elegant yet modern historic home in the heart of downtown Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
STR-143426 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $879 per night (USD)Expedia
From $605 per night (USD)VRBO
DOWNTOWN ANNAPOLIS DREAMHOME AWAITS!!! 3 BR charming home sits in the heart of Annapolis within walking distance to all major points of interest AND a Rooftop Deck!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
STR-144253 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $605 per night (USD)VRBO
From $1350 per night (USD)Expedia
Commissioning Week Escape with Pool and Beautiful 4 Seasons room
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
STR00808 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $1350 per night (USD)Expedia
From $954 per night (USD)VRBO
4 BR\/3BA home in the heart of Historic Downtown Annapolis. 1 1\/2 blocks from the Naval Academy
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
STR-141783 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $954 per night (USD)VRBO
From $766 per night (USD)Expedia
REDUCED RATES FOR COMMISSIONING WEEK 2025- Location=AMAZING! Garage Parking for 1
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
STR21-145020 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $766 per night (USD)Expedia
From $907 per night (USD)VRBO
Beautifully maintained historic 3 BR home and just forty yards from the US Naval Academy Barry Gate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
RENT-005995-2024 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN ...
From $907 per night (USD)VRBO
From $216 per night (USD)Expedia
Spacious 2nd Floor Apartment, with its own entrance and off-street parking.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STR- 270 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $216 per night (USD)Expedia
From $507 per night (USD)VRBO
Fully Furnished 4 Bedroom\/3 Bathroom Single Family Home in Annapolis just a few minutes from downtown
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
STR-270 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $507 per night (USD)VRBO
From $1834 per night (USD)Expedia
REDUCED RATE FOR COMMISSIONING WEEK - 2025- DOWNTOWN WATERFRONT HOME
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
NBS23-145368 - This exclusive waterfront property is a rare gem, available for rent only two weeks each year, making it ...
From $1834 per night (USD)Expedia
From $1557 per night (USD)VRBO
4 BR on a Quiet Downtown Annapolis Street: Perfect Blend of Yesteryear Charm and Modern Comforts
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
NBS22-145097 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $1557 per night (USD)VRBO
From $1133 per night (USD)Expedia
Clean, Spacious Family House
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
5 bedrooms (sleeps 9). First-floor wheelchair accessible bedroom with ADA compliant bathroom. Entertaining kitchen and p ...
From $1133 per night (USD)Expedia
From $345 per night (USD)VRBO
Lovely contemporary in water-privileged community
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Well-furnished contemporary home, great for families, located in a quiet family-friendly neighborhood. This home has 3 ...
From $345 per night (USD)VRBO
From $1064 per night (USD)Expedia
Perfect weekend getaway
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Five Star quality private home in the historic Murray Hill neighborhood of Annapolis, around the corner from the town ce ...
From $1064 per night (USD)Expedia
From $733 per night (USD)VRBO
DISCOUNTED FOR USNA COMMISSIONING WEEK 2024 and 2025! Short term and weekends.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Beautiful, remodeled 3 BR home with stunning great room addition, 20' x 20' screened, covered porch with newly added out ...
From $733 per night (USD)VRBO
From $376 per night (USD)Expedia
Charming cottage with parking. Easy walk to downtown.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover this charming, fully furnished cottage ideally accommodating up to six guests. Nestled on a serene street withi ...
From $376 per night (USD)Expedia
From $499 per night (USD)VRBO
Adorable cottage! Walking distance to USNA & downtown! (VRBO only)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Listing will never be posted on Craig's list - VRBO only **Adorable 1930's cape cod, located in the historic Murray Hill ...
From $499 per night (USD)VRBO
From $463 per night (USD)Expedia
Charming Renovated Historic Home Downtown wparking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Professionally UV sanitized and ozone deep cleaned between guests .Cute and comfortable home in the heart of the HISTORI ...
From $463 per night (USD)Expedia
From $425 per night (USD)VRBO
Welcome Aboard the Kathleen Marie!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Unique accommodations on a comfortably equipped 43 foot Hatteras yacht, just a 5 minute drive to historic downtown Annap ...
From $425 per night (USD)VRBO
From $395 per night (USD)Expedia
Fleet St Retreat in Downtown- Great Location !
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
We welcome you to our brand new renovation on Fleet Street . Purchased in 2016 this house was taken down to the studs so ...
From $395 per night (USD)Expedia
Click For PricingVRBO
Cute, cozy rancher close to down town Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Private location with plenty of parking. Newly renovated bathroom, french doors open to deck; great for indoor-outdoor l ...
Click For PricingVRBO
From $395 per night (USD)Expedia
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
A stunning home, “Circa 1885” is a restored piece of Annapolis history. Sitting at one of the two major gateways that l ...
From $395 per night (USD)Expedia
From $501 per night (USD)VRBO
Historic & sunny home w\/ Fireplace steps from USNA & Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful 3-bedroom, 2.5 bath home built in 1900 is located on Prince George Street, one block from Annapolis City ...
From $501 per night (USD)VRBO
From $537 per night (USD)Expedia
Steps to Naval Academy, City Dock, and State House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Located in the heart of downtown Annapolis! Walk to Naval Academy, St. John's College, State House, City Dock, Yacht Clu ...
From $537 per night (USD)Expedia
From $984 per night (USD)VRBO
Stunning Annapolis Home! Across from the library, walk to Naval Graduation
- Bedrooms:
- 5
- Bathrooms:
- 5
- 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 $984 per night (USD)VRBO
From $999 per night (USD)Expedia
Deep in the Heart of Annapolis; Parking for days!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this gorgeous Texas-themed downtown Annapolis home. Every inch of this home has custom finishes and has been ...
From $999 per night (USD)Expedia
Click For PricingVRBO
New Listing! Walk to USNA\/Capitol\/Downtown
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Want to enjoy being in downtown Annapolis, but on one of the quieter streets? If that sounds good, this is the place fo ...
Click For PricingVRBO
From $380 per night (USD)Expedia
Historic Annapolis Home 1.5 blocks from center of town.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Historic home 1.5 blocks from center of town. Easy walk to the shops, food, harbor, Naval Academy and historic attractio ...
From $380 per night (USD)Expedia