Annapolis Rentals
- Click For Pricing
VRBO
Custom New Home in Eastport. Less than one mile to Naval Academy and City Dock
- Bedrooms:
- 5
- 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 ...
Click For PricingVRBO
- From $300 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 $300 per night (USD)VRBO
- Click For Pricing
VRBO
Less than a block from Main Street - Heart Of Historic District!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Circa 1847 Townhouse - one of the "Rainbow Houses" that was historically part of the Mann's Tavern. Renovated inside and ...
Click For PricingVRBO
- From $326 per night (USD)
VRBO
Walk to Naval Academy + City Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to The Constellation House, located in the heart of Downtown Annapolis! Within walking distance to the U.S. Nava ...
From $326 per night (USD)VRBO
- From $650 per night (USD)
VRBO
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 $650 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Charming cottage - easy walk to downtown with parking
- 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 $275 per night (USD)VRBO
- From $400 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 $400 per night (USD)VRBO
- From $295 per night (USD)
VRBO
Renovated Historic Home located downtown with parking - Walk everywhere !
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
❤️❤️New kitchen , 2 system central AC and Heat , parking spot , Master bath and deck installed in 2021 New patio in Sp ...
From $295 per night (USD)VRBO
- From $349 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 $349 per night (USD)VRBO
- From $298 per night (USD)
VRBO
Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
We welcome you to our brand new listing on Fleet Street . Purchased in 2016 and taken down to the studs this property is ...
From $298 per night (USD)VRBO
- From $620 per night (USD)
VRBO
Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Absolutely gorgeous downtown waterfront home. Loaded with historical significance and character, all while minutes walki ...
From $620 per night (USD)VRBO
- From $716 per night (USD)
Expedia
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 $716 per night (USD)Expedia
- From $183 per night (USD)
VRBO
Downtown Historic District Annapolis Town Home (built in 2008) with Garage Parking!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 12
REN08-139834 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $183 per night (USD)VRBO
- From $106 per night (USD)
VRBO
Charming \"doll house\" in a delightful Eastport neighborhood.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by Annapol ...
From $106 per night (USD)VRBO
- From $550 per night (USD)
VRBO
3BR Rowhome in Historic District - with Garage Parking for 1 - Location=AMAZING!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
STR21-145020 - Please note: THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YO ...
From $550 per night (USD)VRBO
- From $1177 per night (USD)
Expedia
Murray Hill Gem! Enjoy your Annapolis stay in the beautiful 4 BR\/3 BA historic home.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
NBS22-145062 -THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $1177 per night (USD)Expedia
- From $683 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
STR-143320 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $683 per night (USD)VRBO
- From $1100 per night (USD)
Expedia
Beautiful 4BR Waterfront Home in Historic Downtown Annapolis - Close Proximity to Everything!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $1100 per night (USD)Expedia
- From $107 per night (USD)
VRBO
West Annapolis Condo! Ideal location - Close to downtown Annapolis and commuter routes
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
STR-143827 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $107 per night (USD)VRBO
- From $800 per night (USD)
Expedia
Delightful large Historic Downtown Annapolis Victorian 4BR home has been lovingly restored.
- 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 $800 per night (USD)Expedia
- Click For Pricing
VRBO
Gorgeous renovation in HistoricDistrict -New listing !
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our newest listing in Downtown Annapolis. Brand new renovation with a nautical flair this is the perfect spot ...
Click For PricingVRBO
- From $900 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 $900 per night (USD)Expedia
- From $370 per night (USD)
VRBO
2 BR home in historic Downtown Annapolis. Walk to everything!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $370 per night (USD)VRBO
- From $416 per night (USD)
Expedia
Annapolis Historic District row home with 1 small off street parking space and a small rooftop deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
STR-143392 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $416 per night (USD)Expedia
- From $754 per night (USD)
VRBO
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 $754 per night (USD)VRBO
- From $565 per night (USD)
Expedia
Charming 3BR house in the Heart of the Annapolis Historical District - 3rd fl. private suite
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
STR-143804 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $565 per night (USD)Expedia
- From $457 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 $457 per night (USD)VRBO
- From $237 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 $237 per night (USD)VRBO
- From $1175 per night (USD)
VRBO
Spacious 4 BR with first FL. BR in Eastport is close to everything! AND PARKING!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
REN-00085 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $1175 per night (USD)VRBO
- From $382 per night (USD)
Expedia
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 $382 per night (USD)Expedia
- From $200 per night (USD)
VRBO
Spacious 4 BR with first FL. BR in Eastport is close to everything! AND PARKING!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
REN - 00086 -THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $200 per night (USD)VRBO
- From $595 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 $595 per night (USD)VRBO
- From $140 per night (USD)
VRBO
Brand new Renovation in Historic District with 2 parking spots -walk everywhere
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
***Covid 19 updates. In addition to blocking time between guests per CDC guidelines our professional cleaning staff is p ...
From $140 per night (USD)VRBO
- From $2200 per night (USD)
VRBO
Cool 1870's Historic District Home with modern amenities.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
150 year old, five bed and three bath home with 3,000 square feet is centrally situated in the heart of the Historic Di ...
From $2200 per night (USD)VRBO
- From $163 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 $163 per night (USD)VRBO
- From $185 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 $185 per night (USD)VRBO
- From $431 per night (USD)
VRBO
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 $431 per night (USD)VRBO
- From $90 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 $90 per night (USD)VRBO
- From $1040 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 $1040 per night (USD)VRBO
- From $200 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 $200 per night (USD)VRBO
- From $1600 per night (USD)
VRBO
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 $1600 per night (USD)VRBO
- From $360 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 $360 per night (USD)VRBO
- From $192 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 $192 per night (USD)VRBO
- From $475 per night (USD)
VRBO
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 $475 per night (USD)VRBO
- From $1267 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 $1267 per night (USD)VRBO
- From $330 per night (USD)
VRBO
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 $330 per night (USD)VRBO
- From $1075 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 $1075 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to our newest property in The Exclusive Maritime Eastport section of Annapolis . Just a short stroll ( half mile ...
From $450 per night (USD)VRBO
- From $700 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 $700 per night (USD)VRBO
- From $245 per night (USD)
Expedia
Directly Across from Gate One & Steps from the Waterfront
- 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 $245 per night (USD)Expedia
- From $450 per night (USD)
VRBO
Boutique Historic Home just Steps from the State House!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to the George Taylor House! This lovely historic home dates back to 1810 and has been recently renovated to pro ...
From $450 per night (USD)VRBO
- From $185 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 $185 per night (USD)VRBO
- Click For Pricing
VRBO
1010 VB Eastport, Annapolis MD!!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to historic Eastport! Located in the City of Annapolis, 1.6 miles to the United States Navel Academy. My home is ...
Click For PricingVRBO
- From $440 per night (USD)
VRBO
Upscale home with parking for 4 cars in driveway. Walk to downtown.
- Bedrooms:
- 4
- 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 $440 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingVRBO
- From $477 per night (USD)
Expedia
Amazing views, short walks to great dining!
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
Spring: 2024: Welcome El Oso: Naval Bagels by day, transformed into great Mexican takeout in the evenings! 5 min walk! ...
From $477 per night (USD)Expedia
- From $425 per night (USD)
VRBO
Nautical Feel to This Beautiful Eastport Home
- Bedrooms:
- 3
- 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 $425 per night (USD)VRBO
- From $698 per night (USD)
VRBO
79 Five Star Reviews located in the city of Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This beautifully updated 4 bedroom 3.5 bath home was renovated in 2016 and sleeps 8 comfortably. It is set up 100% for g ...
From $698 per night (USD)VRBO
- From $550 per night (USD)
VRBO
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 $550 per night (USD)VRBO
- From $560 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 $560 per night (USD)VRBO
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- From $1600 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 $1600 per night (USD)VRBO
- From $513 per night (USD)
VRBO
Beautifully Renovated Historic District Home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to this meticulously renovated home where no detail has been overlooked. Step into the kitchen and be captivated ...
From $513 per night (USD)VRBO
- From $700 per night (USD)
VRBO
Charming Historic Annapolis Home With Two Off-street Parking Places!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Charming cedar shake duplex home in Historic Annapolis adjacent to the Paca Gardens and the Naval Academy. Custom kitche ...
From $700 per night (USD)VRBO
- From $800 per night (USD)
VRBO
Unique Listing! Entire Downtown Triplex w\/Private Parking. Sleeps 12-18. Pets ok
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 18
*** Commissioning Wk 2024 AVAILABLE*** Unique opportunity to rent an entire triplex Downtown Annapolis! One property wi ...
From $800 per night (USD)VRBO
- Click For Pricing
Expedia
Gracie's Garden in Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Come stay in a Heavenly Bed in the heart of Annapolis. Located 1 mile from downtown this garden apartment is completely ...
Click For PricingExpedia
- From $390 per night (USD)
VRBO
Charming 1926 renovated home in quite neighborhood perfectly situated
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A centrally located home that exceeds all needs and comfort or your family. Both cozy and spacious from well thought out ...
From $390 per night (USD)VRBO
- From $418 per night (USD)
Expedia
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 ...
From $418 per night (USD)Expedia
- Click For Pricing
VRBO
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 PricingVRBO
- Click For Pricing
Expedia
USNA Commissioning Week - 2 Blocks Away
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Host the perfect USNA Commissioning week family get together - just two blocks from the Naval Academy! Modern convenienc ...
Click For PricingExpedia
- From $582 per night (USD)
VRBO
Riverfront home with kayaks, woodstove, firepit, & central AC - walk to downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Dreams Upon Weems Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $582 per night (USD)VRBO
- From $375 per night (USD)
VRBO
Quiet Neighborhood 2.3 miles from Downtown w\/FREE parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Spinnakers Run, nestled just 2.3 miles from Historic Downtown Annapolis and Eastport with plenty of free park ...
From $375 per night (USD)VRBO
- From $145 per night (USD)
VRBO
Freshly renovated 3-story home 1 block from USNA!
- Bedrooms:
- 3
- 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 $145 per night (USD)VRBO
- From $1370 per night (USD)
Expedia
3-story home near river with patio, firepit, Ping-Pong, grill and wood fireplace
- Bedrooms:
- 7
- 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 $1370 per night (USD)Expedia
- From $612 per night (USD)
VRBO
Historic downtown townhome with brick courtyard, sunroom & parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Corner Courtyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $612 per night (USD)VRBO
- From $275 per night (USD)
Expedia
Cozy suite Located in Presidents Hill
- 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 $275 per night (USD)Expedia
- From $229 per night (USD)
VRBO
Annapolis Family Haven
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is a fantastic place for your family to stay while exploring all that Annapolis has to offer! Nestled in the quiet ...
From $229 per night (USD)VRBO
- From $575 per night (USD)
Expedia
Charming 2 BR Rancher w\/ parking and EV charger! Main floor living and just steps to the stadium
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
NBS23-145253 -THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $575 per night (USD)Expedia
- From $500 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 $500 per night (USD)VRBO
- Click For Pricing
Expedia
Walk to Main Street from Waterfront Condo with pool and parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
This beautifully-renovated and designed 2-bedroom/2-bath condo feels like a luxury hotel suite with views of Spa Creek a ...
Click For PricingExpedia
- From $473 per night (USD)
VRBO
History & Charm Near the Annapolis City Dock
- Bedrooms:
- 3
- 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 $473 per night (USD)VRBO
- From $198 per night (USD)
Expedia
3 Story Stunner in Murray Hill <1 mile from USNA!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
Summary: This is an *amazing* 3 story / 5 bedroom house with a finished basement! This is the perfect house for a large ...
From $198 per night (USD)Expedia
- From $540 per night (USD)
VRBO
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 $540 per night (USD)VRBO
- From $500 per night (USD)
VRBO
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 $500 per night (USD)VRBO
- From $219 per night (USD)
VRBO
Cozy Maryland Retreat Near Sandy Pointe State Park
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Discover the best of Annapolis with ease from this updated 3-bedroom, 1-bathroom home! The vacation rental has all the e ...
From $219 per night (USD)VRBO
- Click For Pricing
Expedia
3 Bedroom Fully Fenced Nautical Themed Home only 6 Minutes from DT Annapolis\n
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Nautical Nest! You'll enjoy comfort and relaxation in this clean, family friendly entire home with a ful ...
Click For PricingExpedia
- From $432 per night (USD)
VRBO
New! Steps from USNA Gates 1 & 3 with large private patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
*Still available for 2024 Commissioning Week - 5-night minimum! Stay in this restored historic Annapolis home, located ...
From $432 per night (USD)VRBO
- From $240 per night (USD)
Expedia
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 $240 per night (USD)Expedia
- From $180 per night (USD)
VRBO
USNA home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
You won't find a better location than this for your Annapolis getaway! Situated near Arundel Center, our home is conven ...
From $180 per night (USD)VRBO
- From $807 per night (USD)
Expedia
Large House Downtown Annapolis with 2 Hot Tubs and 4 parking places
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
This Navy Themed house is located jn downtown annapolis, walking distance to all the shops and restaurants in annapolis ...
From $807 per night (USD)Expedia
- From $1325 per night (USD)
VRBO
Sailor's Caribbean FantaSea -5 BR Creekside Contemporary with Private Dock and Water Taxi Service
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
STR23-145260 - THIS PROPERTY IS MANAGED BY ANNAPOLIS ACOCMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL A TEAM MEM ...
From $1325 per night (USD)VRBO
- From $283 per night (USD)
Expedia
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 ...
From $283 per night (USD)Expedia
- From $670 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 $670 per night (USD)VRBO
- From $340 per night (USD)
VRBO
Nautical charmer near the City Dock with open layout, W\/D, & AC
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Plebe's Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $340 per night (USD)VRBO
- From $435 per night (USD)
VRBO
Ahoy! The Buccaneer awaits you just outside Annapolis - fenced-in yard and rec room
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to The Buccaneer, a family-friendly home located just 3 miles from Historic Downtown Annapolis and Eastport. Thi ...
From $435 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Downtown Annapolis, steps from Main Street, City Dock, and Naval Academy - Apt 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This apartment is centrally located and on one of the loveliest streets in Historic Downtown Annapolis. You will be ste ...
From $250 per night (USD)VRBO
- From $441 per night (USD)
VRBO
Fox Hollow House- The perfect Annapolis Getaway
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Get ready for an awesome family gathering in our spacious 4 bedroom home with the perfect back yard for entertaining! N ...
From $441 per night (USD)VRBO
- From $145 per night (USD)
VRBO
Downtown Annapolis, steps from Main Street, City Dock, and Naval Academy - Apt 3
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This apartment is centrally located and on one of the loveliest streets in Historic Downtown Annapolis. You will be ste ...
From $145 per night (USD)VRBO
- From $180 per night (USD)
VRBO
Downtown Annapolis, steps from Main Street, City Dock, and Naval Academy - Apt 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This apartment is centrally located and on one of the loveliest streets in Historic Downtown Annapolis. You will be ste ...
From $180 per night (USD)VRBO
- From $1033 per night (USD)
VRBO
Stunning 5-bedroom remodel in the heart of Murray Hill.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to 9th wing (USNA reference for the boat schoolers out there!) We are nearing the end of renovations on this sp ...
From $1033 per night (USD)VRBO