Annapolis Rentals
From $546 per night (USD)VRBO
Modern Styled Home in Historic Annapolis Eastport Neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Built in 2021 and freshly styled in 2025 with a unique modern European touch, our family-friendly retreat offers the per ...
From $546 per night (USD)VRBO
From $616 per night (USD)VRBO
Downtown Annapolis Gem: 3BR/2BA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to our newly renovated 3BR/2BA apartment in downtown Annapolis! With two king beds, one queen bed, and ...
From $616 per night (USD)VRBO
From $943 per night (USD)VRBO
Magnolia Harbor Retreat - 4 BR/3BA HISTORIC DOWNTOWN ANNAPOLIS- QUIET STREET
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
RENT-001081-2024 - HOME OWNER HAS A PET SO THIS SHOULD BE TAKEN INTO CONSIDERATION WHEN BOOKING BY ANY GUEST WITH ALLERG ...
From $943 per night (USD)VRBO
From $1040 per night (USD)VRBO
Stunning Home Nestled on the Peninsula of Eastport
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This 4 bedroom Annapolis home is an absolute gem, especially with off-street parking! The Craftsman style architecture a ...
From $1040 per night (USD)VRBO
From $652 per night (USD)VRBO
Restriction Retreat - Relax & walk to Main St
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the Restriction Retreat, where trouble checks in. Treat yourself and your family to five-star amenities, an u ...
From $652 per night (USD)VRBO
From $593 per night (USD)VRBO
Annapolis Downtown - Historic Home - Brand New Furnishings. Walk to attractions
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We’re a Navy + Army Family with deep ties to the Naval Academy (and West Point…sorry, Navy fans). We love Annapolis and ...
From $593 per night (USD)VRBO
From $513 per night (USD)VRBO
Heart of Historic District!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This three story 1875 home is located in the Heart of Historic Annapolis. Shops, restaurants, historic sites and the Cit ...
From $513 per night (USD)VRBO
From $382 per night (USD)VRBO
Your Annapolis Adventure Starts Here!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your charming Annapolis getaway! This beautifully furnished home is the perfect retreat for your stay in this ...
From $382 per night (USD)VRBO
From $475 per night (USD)VRBO
Stunning Waterfront Cottage with Breathtaking Views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A Gorgeous, Waterfront setting in the Sailing Capital of the World! Charm, Detail, and Hospitality were not spared in t ...
From $475 per night (USD)VRBO
From $465 per night (USD)VRBO
Large Luxury Apartment In Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bed/2 Bath Apartment with additional family room with brand new queen sleeper sofa in Historic Downtown Annapolis step ...
From $465 per night (USD)VRBO
From $738 per night (USD)VRBO
Waterfront Oasis in Eastport-Easy Walk to Downtown
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to our Waterfront Oasis in the desirable Eastport section of Annapolis. With 4 bedrooms and an open studio spac ...
From $738 per night (USD)VRBO
From $460 per night (USD)Expedia
PERFECT LOCATION in the heart of history
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Be our guest at Historic 19 East Street, in the heart of the Annapolis national landmark district. Walk out the front d ...
From $460 per night (USD)Expedia
From $370 per night (USD)VRBO
Walk everywhere . . .just minutes to historic Annapolis, Updated.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A modern historic gem in a 10 unit building in Eastport or as the locals call it the Maritime Republic of Eastport or "M ...
From $370 per night (USD)VRBO
From $956 per night (USD)VRBO
Beautiful Blend of Restoration and Renovation in this Downtown Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this newly updated rental home, a stunning blend of renovation and restoration located in the heart of the Hi ...
From $956 per night (USD)VRBO
From $360 per night (USD)VRBO
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Amongst the allure of downtown living, lies this quant Annapolis home. This two bedroom, one and a half bath has a spaci ...
From $360 per night (USD)VRBO
From $634 per night (USD)VRBO
Charm & Style in this Renovated Eastport Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience a cozy retreat in this inviting 3-bedroom, 2-bathroom cottage, just 3 blocks from the historic Spa Creek Brid ...
From $634 per night (USD)VRBO
From $257 per night (USD)VRBO
Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This spacious, well-appointed 1 bedroom, 1 European style bath 2nd floor apartment is in the heart of Eastport. You’ll b ...
From $257 per night (USD)VRBO
From $327 per night (USD)VRBO
Annapolis-Eastport Cottage Home - Walk Everywhere - RV Van Parking & Hook-up too
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Walk to all Annapolis has to offer, once parked you’ll never need a car. Walk to City Dock, marinas, restaurants, pubs ...
From $327 per night (USD)VRBO
From $197 per night (USD)VRBO
Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A beautiful basement apartment in the city of Annapolis, in the quiet Eastport neighborhood, a walk to marinas, historic ...
From $197 per night (USD)VRBO
From $570 per night (USD)Expedia
All-stop. Rental Midships.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Whether you have come for Commissioning Week or Boat Show, the aptly named Gatehouse is a centrally located townhome ste ...
From $570 per night (USD)Expedia
From $628 per night (USD)VRBO
Parking & Pet Friendly USNA-themed Annapolis home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This Naval Academy-themed 3 Bedroom home was just fully renovated and is ready to host Annapolis visitors! There are mul ...
From $628 per night (USD)VRBO
From $422 per night (USD)VRBO
Location Location Location!!!50 Steps from Main Street and all of the action
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
We welcome you to check out our newest listing in the heart of the Historic District with the BEST front porch in downto ...
From $422 per night (USD)VRBO
From $563 per night (USD)VRBO
The Liberty House- Pristine Renovation with parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Liberty House ! Tucked away in the Murray Hill section of downtown Annapolis this home is a spacious retreat ...
From $563 per night (USD)VRBO
From $574 per night (USD)VRBO
One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to East Street ! We invite you come spend some time at our gorgeous large home in the heart of the Historic Dist ...
From $574 per night (USD)VRBO
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 $383 per night (USD)Expedia
Cozy Annapolis Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in the heart of Annapolis. Walk to downtown, the Naval Academy and Navy Stadium. Meticulously kept home and newly r ...
From $383 per night (USD)Expedia
From $613 per night (USD)VRBO
Recently Renovated Annapolis Home - Conveniently Located
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This is the perfect getaway home for an enjoyable and relaxing stay in Annapolis. It is conveniently located within walk ...
From $613 per night (USD)VRBO
From $638 per night (USD)VRBO
Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This new 4 bed / 3 bath modern luxury home sleeps 10 and is located in a quiet neighborhood near the Westin Hotel. Once ...
From $638 per night (USD)VRBO
From $896 per night (USD)VRBO
Custom New Home in Eastport. Less than one mile to Naval Academy and City Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by the host ...
From $896 per night (USD)VRBO
From $564 per night (USD)Expedia
★ Midcentury Modern Getaway ★ Prime Location ★
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Immerse yourself in the best that the downtown Historic District of Annapolis has to offer while staying in this complet ...
From $564 per night (USD)Expedia
From $762 per night (USD)VRBO
Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Absolutely gorgeous downtown waterfront home. Loaded with historical significance and character, all while minutes walki ...
From $762 per night (USD)VRBO
From $390 per night (USD)VRBO
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $390 per night (USD)VRBO
From $1338 per night (USD)VRBO
RARELY AVAILABLE -Waterfront Home – Walkable to USNA | 2025/2026 Event Weeks Available
- Bedrooms:
- 2
- 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 $1338 per night (USD)VRBO
From $1634 per night (USD)VRBO
4 BR on a Quiet Downtown Annapolis Street: Perfect Blend of Yesteryear Charm and Modern Comforts
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
NBS22-145097 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $1634 per night (USD)VRBO
From $940 per night (USD)VRBO
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 $940 per night (USD)VRBO
From $345 per night (USD)VRBO
Charming cottage with parking. Easy walk to downtown.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover this charming, fully furnished cottage ideally accommodating up to six guests. Nestled on a serene street withi ...
From $345 per night (USD)VRBO
From $499 per night (USD)VRBO
Adorable cottage! Walking distance to USNA & downtown! (VRBO only)
- Bedrooms:
- 1
- 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 $408 per night (USD)VRBO
Charming Renovated Historic Home Downtown wparking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Professionally UV sanitized and ozone deep cleaned between guests .Cute and comfortable home in the heart of the HISTORI ...
From $408 per night (USD)VRBO
From $416 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 $416 per night (USD)VRBO
From $361 per night (USD)VRBO
Fleet St Retreat in Downtown- Great Location !
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $361 per night (USD)VRBO
From $324 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 $324 per night (USD)VRBO
From $228 per night (USD)VRBO
Brand New Reno in Historic Dist w 2 Parking spots
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Spotless / sanitized !! Renovated upstairs unit two bedroom with TWO parking spots in the Historic District . Everythi ...
From $228 per night (USD)VRBO
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 $524 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 $524 per night (USD)VRBO
From $982 per night (USD)VRBO
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 $982 per night (USD)VRBO
From $830 per night (USD)VRBO
Elegant yet modern historic home in the heart of downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
STR-143426 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $830 per night (USD)VRBO
From $613 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 $613 per night (USD)VRBO
From $947 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 $947 per night (USD)VRBO
From $752 per night (USD)VRBO
Location=AMAZING! Garage Parking for 1
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
STR21-145020 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $752 per night (USD)VRBO
From $902 per night (USD)VRBO
Beautifully maintained historic 3 BR home and just forty yards from the US Naval Academy Barry Gate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
RENT-005995-2024 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN ...
From $902 per night (USD)VRBO
From $2044 per night (USD)VRBO
Cool 1870's home anchored in the Historic District with modern amenities.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Our century-and-a-half-old, five bedroom and three bath home with 3,000 square feet centrally situated in the heart of ...
From $2044 per night (USD)VRBO
From $201 per night (USD)VRBO
“Athens of America,” Annapolis Apartment Two B
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $256 per night (USD)VRBO
“Athens of America,” Annapolis Apartment Two A
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $256 per night (USD)VRBO
From $1389 per night (USD)VRBO
Prestigious Historic Annapolis home, parking for 5 cars, walk to everything!
- Bedrooms:
- 3
- 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 $1389 per night (USD)VRBO
From $539 per night (USD)VRBO
Beautiful Historic Home With Great Location!
- Bedrooms:
- 2
- 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 $539 per night (USD)VRBO
From $1522 per night (USD)VRBO
Indoor/Outdoor waterfront oasis with indoor heated pool awaits you in Eastport!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Waterfront Luxury Retreat in Eastport with Year-Round Indoor Pool, Private Dock, & Kayaks Description Your indoor and o ...
From $1522 per night (USD)VRBO
From $447 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 $447 per night (USD)VRBO
From $226 per night (USD)VRBO
“Athens of America,” Annapolis Apartment One B
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Annapolis is a city abundant with history and culture. This former capital of the United States has a little something f ...
From $226 per night (USD)VRBO
From $425 per night (USD)VRBO
Historic Downtown Charmer, Water Views and Parking!
- Bedrooms:
- 1
- 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)VRBO
From $538 per night (USD)VRBO
Eastport Haven House
- Bedrooms:
- 4
- Bathrooms:
- 4
- 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)VRBO
From $854 per night (USD)VRBO
Charming Annapolis Victorian
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. W ...
From $854 per night (USD)VRBO
From $361 per night (USD)Expedia
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
- Bedrooms:
- 1
- 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 $361 per night (USD)Expedia
From $546 per night (USD)VRBO
Upscale home with parking for 4 cars in driveway. Walk to downtown.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
NOTE: Posted rates do not apply to Holidays, Boat Shows or Commissioning Week. They will be given on request. Rates a ...
From $546 per night (USD)VRBO
From $151 per night (USD)VRBO
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)VRBO
From $397 per night (USD)VRBO
Your Annapolis Waterfront retreat - a short walk to Navy Football Home Games
- 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 $397 per night (USD)VRBO
From $226 per night (USD)VRBO
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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)VRBO
From $570 per night (USD)VRBO
Nautical Feel to This Beautiful Eastport Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $570 per night (USD)VRBO
From $736 per night (USD)VRBO
94 Five Star Reviews located in the City of Annapolis in a quiet neighborhood!
- Bedrooms:
- 3
- 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 $736 per night (USD)VRBO
From $644 per night (USD)VRBO
Lots free parking, hot tub, tree house, outdoor oasis - NOT party house
- Bedrooms:
- 2
- 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)VRBO
From $712 per night (USD)VRBO
Beautiful Waterfront Townhome In Historic Annapolis
- Bedrooms:
- 3
- 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 $495 per night (USD)VRBO
Historic District\"Crab Cakes and Football\"
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Crab Cakes and Football. Enjoy Historic Downtown Annapolis with convenient walking distance to both City Dock ...
From $495 per night (USD)VRBO
From $2075 per night (USD)VRBO
Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!
- Bedrooms:
- 3
- 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 $2075 per night (USD)VRBO
From $604 per night (USD)VRBO
Beautifully Renovated Historic District Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this meticulously renovated home where no detail has been overlooked. Step into the kitchen and be captivated ...
From $604 per night (USD)VRBO
From $831 per night (USD)Expedia
Charming Historic Annapolis Home With Two Off-street Parking Places!
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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
Coastal Cabins.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Charming & cozy, 2- level Victorian style home built in the 1920s. Well stocked w/ modern conveniences for your home awa ...
Click For PricingVRBO
Click For PricingExpedia
Private Eastport Guest Suite in Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a clean, comfortable and private suite in the heart of Eastport. Steps away from Davis' Pub and Forward Brewing as ...
Click For PricingExpedia
Click For PricingVRBO
USNA Commissioning Week - 2 Blocks Away
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Host the perfect USNA Commissioning week family get together - just two blocks from the Naval Academy! Modern convenienc ...
Click For PricingVRBO
From $1109 per night (USD)VRBO
Unique Listing! Entire Downtown Triplex w/Private Parking. Sleeps 12-18. Pets ok
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 18
*** Commissioning Wk 2024 AVAILABLE*** Unique opportunity to rent an entire triplex Downtown Annapolis! One property wi ...
From $1109 per night (USD)VRBO
From $554 per night (USD)VRBO
Waterfront Condo with Rooftop Pool, Spa Creek Views & Prime Eastport Location with Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Waterfront Condo with Spa Creek Views, Rooftop Pool & Prime Eastport Location Experience Annapolis from this beautifull ...
From $554 per night (USD)VRBO
From $653 per night (USD)Expedia
History & Charm Are Only Steps from Main Street and City Dock at Catch 22
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
This charming 3-BR, 2.5-BA townhome is just a 1/2-block from the city dock and is a luxurious vacation getaway in the he ...
From $653 per night (USD)Expedia
From $1107 per night (USD)VRBO
USNA Getaway: Heated Pool, Hot Tub, Indoor Grill!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Summary: NB: The pool is fully functional however, the hot tub and pool heater will remain out of service until mid Sept ...
From $1107 per night (USD)VRBO
From $785 per night (USD)Expedia
Dog-friendly house with yard, deck, firepit, washer/dryer & AC - near golf
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Seas The Bay Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $785 per night (USD)Expedia
From $674 per night (USD)VRBO
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully renovated home in the heart of West Annapolis. The main level has been updated to an open floor plan to acco ...
From $674 per night (USD)VRBO
From $598 per night (USD)Expedia
Historic district home, View of the Capital, WALK Downtown, w/ Outdoor Dining!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy Annapolis, MD in this charming Federal-style home nestled in the heart of the historic district. Newly renovated w ...
From $598 per night (USD)Expedia
From $677 per night (USD)VRBO
Freshly renovated 3-story home 1 block from USNA!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Welcome to The Wardroom! Originally built in 1902 and completely renovated in 2014, this 3 story home is the p ...
From $677 per night (USD)VRBO
From $1751 per night (USD)Expedia
3-story home near river with patio, firepit, Ping-Pong, grill and wood fireplace
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Ensign's Ridge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $1751 per night (USD)Expedia
From $394 per night (USD)VRBO
Charming 1926 Four Bedroom Home w Ample Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A centrally located home that exceeds all needs and comfort or your family. Both cozy and spacious from well thought ou ...
From $394 per night (USD)VRBO
From $444 per night (USD)Expedia
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Corner House – Quaint and Cozy 2 Bedroom Suite with Parking The Corner House is a hidden gem located in the quaint P ...
From $444 per night (USD)Expedia
From $714 per night (USD)VRBO
Historic downtown townhome with brick courtyard, sunroom & parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Corner Courtyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $714 per night (USD)VRBO
From $644 per night (USD)Expedia
Steps to USNA with Large Private Patio & Free Off-Site Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in this restored historic Annapolis home, located just steps from both USNA Gates 1 and 3. The proud Navy graduate ...
From $644 per night (USD)Expedia
From $293 per night (USD)VRBO
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Property is 2 bedrooms and 1 bathroom furnished with brand new furniture. Bedrooms have fitted with comfortable queen si ...
From $293 per night (USD)VRBO
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Large House Downtown Annapolis with 2 Hot Tubs and 4 parking places
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
This Navy Themed house is located jn downtown annapolis, walking distance to all the shops and restaurants in annapolis ...
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From $1338 per night (USD)VRBO
Fabulous Waterfront Contemporary with Rooftop Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
RENT-000856-2025 THIS PROPERTY IS MANAGED BY ANNAPOLIS ACOCMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL A TEAM M ...
From $1338 per night (USD)VRBO
Click For PricingExpedia
Water-view condo with rooftop pool & balcony - minutes from downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
USNA Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
Click For PricingExpedia
From $281 per night (USD)VRBO
Newly Updated EV Charger Ready Peaceful Home in Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to our stylish and modern home, where comfort meets convenience! Here's what you can expect during your stay: ✔ ...
From $281 per night (USD)VRBO
From $417 per night (USD)Expedia
vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover this delightful three-bedroom getaway nestled within the ancient Annapolis historical area! Nestled just a 17-m ...
From $417 per night (USD)Expedia
From $717 per night (USD)VRBO
Charming 3-bedroom house with AC and WiFi in enchanting Annapolis/Eastport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay comfortably in Annapolis at this 3-bedroom house. With 1 king bed, 1 queen bed, and 1 full bed, this tremendous pro ...
From $717 per night (USD)VRBO
From $152 per night (USD)VRBO
Governor Calvert King, Historic Inns, Four-Poster Bed, Dining, Steps from State House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $152 per night (USD)VRBO
From $471 per night (USD)VRBO
Walk everywhere in Annapolis from 1st floor dog-friendly apartment with parking and backyard
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Still available for Commissioning Week 2025! This beautifully-restored 1 bedroom apartment is on the lower level of a 2 ...
From $471 per night (USD)VRBO
From $1378 per night (USD)Expedia
Eastport Classic Charm
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to our Eastport home where hardwood floors, large windows that allow ample natural light, and a cozy fi ...
From $1378 per night (USD)Expedia