Annapolis Rentals
- From $400 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 $400 per night (USD)VRBO
- From $444 per night (USD)
VRBO
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 $444 per night (USD)VRBO
- From $147 per night (USD)
VRBO
Cozy 2br home w\/ parking in downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $147 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Annapolis steps to Harbor and Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Parking included. The heart of Annapolis 1 street from the harbor, fun restaurants & backs to the Naval Academy. This 1s ...
From $275 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 $160 per night (USD)
Expedia
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
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 $160 per night (USD)Expedia
- 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
- Click For Pricing
VRBO
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 $149 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 $149 per night (USD)Expedia
- From $285 per night (USD)
VRBO
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Charming house - a 10-15 min walk to Navy Marine Corps Stadium (<.75mile), a 5 min drive from the US Naval Academy (<1mi ...
From $285 per night (USD)VRBO
- Click For Pricing
Expedia
Pet-friendly Loft in popular Eastport on 2nd Floor
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
**Flexible Commissioning Week Cancellation Policy** The Port is situated in the heart of Eastport’s charm, mere steps f ...
Click For PricingExpedia
- 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 $185 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 $185 per night (USD)Expedia
- From $846 per night (USD)
VRBO
Duke's Den Downtown home with 2 PARKING spots!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
*Flexible Commissioning Week Cancellation Policy* Large Historic Downtown Annapolis gorgeous home with 2 parking spaces ...
From $846 per night (USD)VRBO
- 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 $292 per night (USD)
VRBO
Escape to this Cape Cod home close to everything!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to this charming Cape Cod on half an acre right outside downtown Annapolis. Just 4 minutes to the Stadium and a ...
From $292 per night (USD)VRBO
- From $691 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 $691 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
- From $399 per night (USD)
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 ...
From $399 per night (USD)VRBO
- 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
- Click For Pricing
VRBO
Take your Leave of Absence around gardens with driveway parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
**Flexible Commissioning Week Cancellation Policy** Welcome to this gorgeous luxury home tucked into a quiet cul de sac ...
Click For PricingVRBO
- From $971 per night (USD)
VRBO
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 $971 per night (USD)VRBO
- 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
- From $146 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 $146 per night (USD)VRBO
- From $453 per night (USD)
VRBO
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 $453 per night (USD)VRBO
- From $329 per night (USD)
Expedia
Perfect historic home + Peloton, walk to downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lovely historic home within walking distance from downtown (1 mile from Church Circle) & Navy stadium (5 blocks), hardwo ...
From $329 per night (USD)Expedia
- Click For Pricing
Expedia
Family Tribute Marine's Gate across from Gate 1
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
*Still available for Commissioning Week - 5-night minimum! This Annapolis home, located directly across the street fro ...
Click For PricingExpedia
- From $490 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 $490 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
- From $351 per night (USD)
Expedia
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 $351 per night (USD)Expedia
- From $408 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 $408 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)
VRBO
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)VRBO
- From $500 per night (USD)
Expedia
Sophisticated Charmer with Parking & Views of the USNA Chapel Dome
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Hello and Welcome to Annapolis! You are going to love this home. IMPORTANT: if you are inquiring about USNA Commission ...
From $500 per night (USD)Expedia
- 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
- Click For Pricing
Expedia
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 ...
Click For PricingExpedia
- From $492 per night (USD)
VRBO
Steps to Main Street w View of the Capital private back patio & free off-site parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This beautifully-decorated 4-bedroom home in the heart of Historic Annapolis is located directly behind Main Street. Th ...
From $492 per night (USD)VRBO
- From $750 per night (USD)
VRBO
Annapolis -Eastport - -3 Bedroom- 3 bath with parking
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Delightful Arts and Crafts/ Coastal style home. Main Level is open space concept with 9 ft ceilings and plenty of nat ...
From $750 per night (USD)VRBO
- From $495 per night (USD)
VRBO
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 $495 per night (USD)VRBO
- Click For Pricing
Expedia
Historic Fisher House steps to Main St with parking and private back patio!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Named after the owner’s great-grandfather, who was instrumental in building both Annapolis and Academy fire departments, ...
Click For PricingExpedia
- 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 $650 per night (USD)
VRBO
Steps away from the Chesapeake Bay in the unique Bay Ridge community!
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $650 per night (USD)VRBO
- From $481 per night (USD)
VRBO
2 parking spots and walkable to Main Street at Seashell in the City
- 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 $481 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 $171 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 $171 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 $200 per night (USD)
VRBO
Cozy 1st Floor King George one bedroom apartment right across from USNA
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $200 per night (USD)VRBO
- From $1040 per night (USD)
VRBO
Stunning colonial p on a private 1.6 acre lot situated on Broadneck Peninsula.
- 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 $1040 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 $251 per night (USD)
Expedia
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This 2nd floor unit has all new furniture, bedding and housewares. This is directly across from Gate 2 at the Naval Acad ...
From $251 per night (USD)Expedia
- From $175 per night (USD)
VRBO
Charming Downtown 3rd Floor 1 Bedroom Apt
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Perfect location for all that downtown Annapolis offers, right across from USNA gate 2. Super convenient, park your car ...
From $175 per night (USD)VRBO
- From $1607 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 $1607 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 $358 per night (USD)
Expedia
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This home is spacious and clean and will make your vacation plans a breeze from this central location. Many families, g ...
From $358 per night (USD)Expedia
- Click For Pricing
Expedia
Private Pet-friendly Coastal Suite with water views just minutes to Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
**Be sure to ask about renting the entire home for Commissioning Week and special Annapolis events. Enjoy the serene wa ...
Click For PricingExpedia
- From $500 per night (USD)
VRBO
Downtown Annapolis Townhome ! Beautiful!!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful Remodeled Townhome ! We have thought of everything you will need for an amazing stay. Fully loaded kitchen , ...
From $500 per night (USD)VRBO
- From $318 per night (USD)
VRBO
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 $318 per night (USD)VRBO
- From $225 per night (USD)
VRBO
The Yellow Cottage on Harness Creek
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $225 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 $285 per night (USD)
VRBO
Eastport Condo in Building with Rooftop Water Views of Spa Creek!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
STR21-145036 - PLEASE NOTE: IF YOU REQUEST TO BOOK THIS PROPERTY, YOU WILL BE CONTACTED BY ANNAPOLIS ACCOMMODATIONS, T ...
From $285 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 $360 per night (USD)
VRBO
Eastport Cottage .5 mi from Downtown Annapolis
- 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, to ...
From $360 per night (USD)VRBO
- From $420 per night (USD)
Expedia
Walk to waterfront & USNA with Parking at Historic Wisteria
- Bedrooms:
- 4
- Bathrooms:
- 4
- 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 $420 per night (USD)Expedia
- 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 $295 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 $295 per night (USD)VRBO
- From $519 per night (USD)
VRBO
Bennett House (entire):Haven in Historic Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to the historic neighborhood of Murray Hill! The Bennett House is a charming, light- filled detached home with 3 ...
From $519 per night (USD)VRBO
- From $110 per night (USD)
Expedia
Cozy place close to the city dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Annapolis; where history and nature coincide! You will feel right at home in this confortable 1 bedroom 1 bat ...
From $110 per night (USD)Expedia
- From $402 per night (USD)
VRBO
\"Around the corner\" from everything, private backyard and parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
*Flexible Commissioning Week Cancellation Policy* Welcome to this charming remodeled Eastport Victorian home "Around th ...
From $402 per night (USD)VRBO
- From $175 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 $175 per night (USD)VRBO
- Click For Pricing
VRBO
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 $577 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 $577 per night (USD)VRBO
- From $372 per night (USD)
VRBO
Steps from the water, Easy parking and private backyard patio
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
This professionally-decorated and furnished 2 bedroom, 1.5 bath is located across the Annapolis Waterfront drawbridge in ...
From $372 per night (USD)VRBO
- Click For Pricing
Expedia
\"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 $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
- Click For Pricing
VRBO
Annapolis Family Vacation Rental: Close to downtown and the Naval Academy
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Located: 4.1mi (10 min) from Naval Academy: Annapolis Cove Neighborhood Open floor plan: Kitchen open to living room/sc ...
Click For PricingVRBO
- From $389 per night (USD)
VRBO
Historic Carriage House in the Heart of Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Originally built in 1857, this fully-restored home has a rich history that's been documented from it's original purpose ...
From $389 per night (USD)VRBO
- From $1175 per night (USD)
Expedia
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)Expedia
- From $385 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 $385 per night (USD)VRBO
- From $200 per night (USD)
Expedia
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)Expedia
- 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 $83 per night (USD)
VRBO
Convenient Eastport condo with beautiful water views and community pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
REN - 144875 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $83 per night (USD)VRBO
- From $116 per night (USD)
VRBO
This Eastport condo has a large deck with amazing views of Spa Creek and downtown Annapolis.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
REN - 144911 -THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $116 per night (USD)VRBO
- From $370 per night (USD)
Expedia
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)Expedia
- From $1050 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 $1050 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 $1071 per night (USD)
Expedia
4 BR Colonial home just outside of Annapolis - Beautiful 4 Seasons room overlooking fenced backyard with beautiful pool!
- 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 $1071 per night (USD)Expedia
- Click For Pricing
VRBO
Waterfront home in Eastport with Water taxi service available from property.
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
Click For PricingVRBO
- 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
- Click For Pricing
VRBO
Quaint Cottage is the perfect getaway retreat in Eastport.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by Annapol ...
Click For PricingVRBO
- From $621 per night (USD)
Expedia
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 $621 per night (USD)Expedia