
Annapolis Rentals

- From $375 per night (USD)
VRBO
Cozy 2br home w/ parking in downtown Annapolis
- Bedrooms:
- 1
- 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 $375 per night (USD)VRBO
- From $324 per night (USD)
Expedia
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $324 per night (USD)Expedia
- From $545 per night (USD)
VRBO
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
- Bedrooms:
- 3
- 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 $545 per night (USD)VRBO
- From $395 per night (USD)
Expedia
Charming garden row home, easy 4 block walk to the heart of Annapolis.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Incredible location in the Historic District of Annapolis. Walking distance to the Naval Academy, St. Johns College, an ...
From $395 per night (USD)Expedia
- Click For Pricing
VRBO
Stay at Lux Red Door Gem with 3 Parking Spots
- Bedrooms:
- 3
- 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 PricingVRBO
- From $651 per night (USD)
Expedia
Steps to Main St at Historic Home with Capital Views, Private Patio & Free Off-Site Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Experience Historic Annapolis in Comfort and Style This charming 4-bedroom home sits in the heart of Historic Annapolis, ...
From $651 per night (USD)Expedia
- From $642 per night (USD)
VRBO
Sophisticated Charmer with Parking & Views of the USNA Chapel Dome
- Bedrooms:
- 2
- 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 $642 per night (USD)VRBO
- From $694 per night (USD)
Expedia
Walkable to Main Street at Seashell in the City with 2 parking spots
- Bedrooms:
- 2
- 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 $694 per night (USD)Expedia
- From $298 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 $298 per night (USD)VRBO
- From $341 per night (USD)
Expedia
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This 2nd floor apt has new furniture, bedding and housewares. Extremely convenient location to downtown where there's l ...
From $341 per night (USD)Expedia
- From $223 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. Located right across from USNA gate 2. Super convenient, park y ...
From $223 per night (USD)VRBO
- From $434 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 $434 per night (USD)Expedia
- From $674 per night (USD)
VRBO
Downtown Annapolis Townhome ! Beautiful!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful Remodeled Townhome ! We have thought of everything you will need for an amazing stay. Fully loaded kitchen , ...
From $674 per night (USD)VRBO
- From $242 per night (USD)
Expedia
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 $242 per night (USD)Expedia
- From $440 per night (USD)
VRBO
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 $440 per night (USD)VRBO
- From $635 per night (USD)
Expedia
Walk to USNA, Main St w Parking 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 $635 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Beautiful Condo by the Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Beautiful one bedroom Eastport condo with spectacular views of the water and downtown Annapolis. Walking distance to gre ...
From $225 per night (USD)VRBO
- From $558 per night (USD)
Expedia
Stay \"Around the corner\" from Annapolis hot spots with new King bed, fenced-in yard and parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Still available for Commissioning Week 2025! Welcome to this beautifully remodeled Victorian home in Eastport, lovingly ...
From $558 per night (USD)Expedia
- From $483 per night (USD)
VRBO
Walkable Eastport Home with Firepit, Porch & Fenced-in Yard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Welcome to your home away from home in the heart of the Maritime Republic of Eastport—a vibrant, walkable neighborhood j ...
From $483 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
- Click For Pricing
VRBO
A Delight on Dean
- Bedrooms:
- 2
- 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 $1015 per night (USD)
Expedia
Parking for days at the unique Deep in the Heart of Annapolis with large private deck
- Bedrooms:
- 3
- 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 $1015 per night (USD)Expedia
- Click For Pricing
VRBO
New Listing! Walk to USNA/Capitol/Downtown
- Bedrooms:
- 2
- 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 $286 per night (USD)
Expedia
New Downtown Annapolis Condo With Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This newly constructed property brings chic, low-maintenance living to the heart of the Arts District in Annapolis. No ...
From $286 per night (USD)Expedia
- From $434 per night (USD)
VRBO
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Custom home with inlaid floor, wood counters, hand made cabinets, and artistic touches. Beautifully landscaped large pri ...
From $434 per night (USD)VRBO
- From $350 per night (USD)
Expedia
Annapolis Condominium in the heart of the historic center
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Don’t miss our unique two floor condominium in Historic Annapolis downtown with 3 bedrooms (one queen, two rooms with tw ...
From $350 per night (USD)Expedia
- Click For Pricing
VRBO
Chic Condo w/ Balcony in the Heart of Annapolis!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
See the best of Annapolis effortlessly when you book this 2-bed, 2-bath vacation rental! Equipped with all the essential ...
Click For PricingVRBO
- From $417 per night (USD)
Expedia
Spectacular Location: State Circle Apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Stay in this iconic building at the intersection of State Circle and Maryland Avenue in the Historic District of Annapol ...
From $417 per night (USD)Expedia
- From $763 per night (USD)
VRBO
Eastport Historic Firehouse with Parking, Dogs OK
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This is a unique home like none other in downtown Annapolis. Originally the Eastport Volunteer Fire Company, founded in ...
From $763 per night (USD)VRBO
- Click For Pricing
Expedia
Historic Annapolis Home Convenient to Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Historic Annapolis home convenient to downtown, restaurants, shopping, commuter routes and public transportation! -0.5 ...
Click For PricingExpedia
- From $413 per night (USD)
VRBO
Annapolis Downtown Entire Townhome 3 bed 6 guests
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Immerse yourself in the best that the downtown Historic District of Annapolis has to offer while stayin ...
From $413 per night (USD)VRBO
- From $1309 per night (USD)
Expedia
Parking at Randall House Across from USNA Gate 1
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
The Randall House is an historic gem in the heart of Downtown Annapolis with PARKING for 3 cars! Built in 1880, The R ...
From $1309 per night (USD)Expedia
- Click For Pricing
VRBO
5 BDRM across from the USNA Stadium
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Across the street from the Naval Academy Stadium. Open floor plan with stainless steel appliances, two islands, 8-10 per ...
Click For PricingVRBO
- From $463 per night (USD)
Expedia
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Just finished with a few updates to kitchen and bedrooms + all new sheets and towels!new pictures coming soon!! Fantasti ...
From $463 per night (USD)Expedia
- From $850 per night (USD)
VRBO
1 Block to USNA at beautifully renovated Historic Chapel Views with back patio and off-site parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
When the owners decided to find their Annapolis home base, they knew they had to be within walking distance to the one’s ...
From $850 per night (USD)VRBO
- From $715 per night (USD)
Expedia
Private Patio at Charming Hanover House Across from USNA Gate 3
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The fully-renovated 1800 historic home is just steps from USNA’s Gate 3. Located in the heart of historic downtown on a ...
From $715 per night (USD)Expedia
- From $264 per night (USD)
VRBO
Bay View Studio Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private ...
From $264 per night (USD)VRBO
- From $703 per night (USD)
Expedia
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
1930's Single family home on adorable cul-de-sac downtown Annapolis with off-street parking! Located off West Street in ...
From $703 per night (USD)Expedia
- From $397 per night (USD)
VRBO
ACROSS FROM STADIUM - walk to downtown Annapolis.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Across the street from the Navy and Marine Corps Stadium and walking distance to historic downtown Annapolis - you will ...
From $397 per night (USD)VRBO
- From $993 per night (USD)
Expedia
Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Modern Elegance in Historic Annapolis Step into this fully-renovated 1900s home, where modern sophistication ...
From $993 per night (USD)Expedia
- From $495 per night (USD)
VRBO
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
421 Irie City Of Annapolis License Number 145052 Commission weeks: 2025, 2026, 2027 are booked. SORRY!! GO Navy!! ...
From $495 per night (USD)VRBO
- From $570 per night (USD)
Expedia
Historic Annapolis Getaway - 45 steps to Downtown and 150 steps to USNA!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your dream stay nestled in the heart of Historic Downtown Annapolis! Located just 45 feet from downtown Anna ...
From $570 per night (USD)Expedia
- From $195 per night (USD)
VRBO
Beautiful Condo - Water View Near City Dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Check out our winter rates for January, February and March! The Newport Condominium has a beautiful water view of Spa ...
From $195 per night (USD)VRBO
- From $412 per night (USD)
Expedia
Charming Charles Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to our vacation rental nestled in the heart of Downtown Annapolis. Immerse yourself in the rich history ...
From $412 per night (USD)Expedia
- From $495 per night (USD)
VRBO
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Your family will be close to everything when you stay at this centrally-located place. Two blocks to Main Street, the Na ...
From $495 per night (USD)VRBO
- From $930 per night (USD)
Expedia
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Located on one of the most coveted streets in downtown Annapolis, walk to Main St. and City Dock. The Thomas Hyde House ...
From $930 per night (USD)Expedia
- Click For Pricing
VRBO
WALK TO DOWNTOWN ANNAPOLIS, EGO ALLEY, NAVAL STADIUM & ACADEMY
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This home was newly renovated in 2021 and is located in the highly desirable Murray Hill Neighborhood. Conveniently loc ...
Click For PricingVRBO
- From $465 per night (USD)
Expedia
Gorgeous & bright retreat with patio, firepit, W/D, & stunning rooftop views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Skyline Sanctuary Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $465 per night (USD)Expedia
- From $1583 per night (USD)
VRBO
Marvelous Home with Backyard Living Room in Murray Hill
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
NBS23-145336 Welcome to our charming vacation rental house nestled in the picturesque Murray Hill neighborhood of Annapo ...
From $1583 per night (USD)VRBO
- From $721 per night (USD)
VRBO
Eastport Oasis 4 BR 2 BA fully renovated home on quiet street with parking and gorgeous outdoor space
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $721 per night (USD)VRBO
- From $545 per night (USD)
VRBO
Cute bungalow blocks to Stadium
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: This stylish two bedroom home is conveniently located in Annapolis' Germantown neighborhood off West Street, ne ...
From $545 per night (USD)VRBO
- From $228 per night (USD)
VRBO
Maryland Inn 2 Double Beds, Historic Inns, Modern Amenities, Event Space, City Center
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $228 per night (USD)VRBO
- From $228 per night (USD)
VRBO
Enjoy Stepping Back in Time at Charming Hotel in Annapolis - Pet-Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $228 per night (USD)VRBO
- From $448 per night (USD)
VRBO
2 Historic Ambiance Stays Perfect for Romantic Getaways - Pets Allowed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $448 per night (USD)VRBO
- From $170 per night (USD)
VRBO
Authentic 18th Century Hotel Near US Naval Academy - Walking Distance
- 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 $170 per night (USD)VRBO
- From $448 per night (USD)
VRBO
Maryland Inn 2 Doubles, Pet-Friendly, 2 Units
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $448 per night (USD)VRBO
- From $448 per night (USD)
VRBO
2 Maryland Inn 2DBeds, Historic Inns of Annapolis, Waterfront Vicinity
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $448 per night (USD)VRBO
- From $190 per night (USD)
VRBO
Elegant Stay Perfect for Romantic Getaway, Just Steps from Waterfront
- 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 $190 per night (USD)VRBO
- From $239 per night (USD)
VRBO
Unique Victorian Stay w/ Modern Amenities + Steps from Waterfront
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $239 per night (USD)VRBO
- From $458 per night (USD)
VRBO
Robert Johnson Townhouse, Historic Inns, Fireplace, Downtown Locale
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $458 per night (USD)VRBO
- From $218 per night (USD)
VRBO
Governor Calvert 2 Double Beds, Historic Inns, Gym Access, Near Naval Academy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $218 per night (USD)VRBO
- From $170 per night (USD)
VRBO
Maryland Inn King, Historic Inns, Fireplace, Elegant Dining, Waterfront Proximity
- 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 $170 per night (USD)VRBO
- From $239 per night (USD)
VRBO
Robert Johnson 2 Double Beds, Historic Inns, Antique Style, Near Chesapeake Bay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $239 per night (USD)VRBO
- From $458 per night (USD)
VRBO
Elegant Stay Perfect for Exploring Annapolis' Shops and Boutiques.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $458 per night (USD)VRBO
- From $190 per night (USD)
VRBO
Robert Johnson King, Historic Inns, Near Top Dining & City Attractions
- 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 $190 per night (USD)VRBO
- From $218 per night (USD)
VRBO
Charming Downtown Hotel w/ Vintage Character + Modern Amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $218 per night (USD)VRBO
- From $152 per night (USD)
VRBO
Elegant Boutique Hotel Near Maryland State House - Short Walk
- 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 $448 per night (USD)
VRBO
2 Historic Ambiance Stays Perfect for Romantic Getaways - Pets Allowed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $448 per night (USD)VRBO
- From $830 per night (USD)
VRBO
Brand New Spacious Luxury Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
This brand-new build luxury home in Eastport close to downtown Annapolis has everything you and your guests (up to 16 to ...
From $830 per night (USD)VRBO
- From $535 per night (USD)
Expedia
Dog friendly! Next to Navy Stadium and DTA Shuttle!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy your stay in our charming home centrally located directly across from Navy-Marine Corps Memorial Stadium on Taylor ...
From $535 per night (USD)Expedia
- From $335 per night (USD)
VRBO
Vintage Retreat: 5 minute walk to downtown, Naval Academy, Stadium and more.\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Immerse yourself in the rich history of Annapolis at our century-old home in Presidents Hill. With 3 bedrooms, 2 baths, ...
From $335 per night (USD)VRBO
- From $399 per night (USD)
Expedia
Downtown Pinkney House w/Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: The Pinkney house is a 2 bedroom, 2.5 bath town home boasts an unparalleled location within close proximity to ...
From $399 per night (USD)Expedia
- From $560 per night (USD)
VRBO
Historic Annapolis Home!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
🌟 Discover the Allure of Historic Annapolis Living! 🌟 Welcome to your captivating 2-bedroom, 1.5-bath home nestled in ...
From $560 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy the close proximity to all Annapolis has to offer at this row house located next to college creek. Nicely decorat ...
From $300 per night (USD)Expedia
- Click For Pricing
VRBO
Gorgeous House in the Heart of Annapolis, Walk to Everything!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located within walking distance of everything Annapolis has to offer, this 3BR/2.5 Bath historic Craftsman home is beaut ...
Click For PricingVRBO
- From $1748 per night (USD)
Expedia
Spacious Converted Carriage House in Historic District near USNA
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Relax in this updated and sophisticated house near the USNA in Annapolis with the largest garden in downtown. This tranq ...
From $1748 per night (USD)Expedia
- From $528 per night (USD)
VRBO
Stay in Historic apartment 2 blocks from Main St with parking - dog-friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Still available for Commissioning Week 2025! Stay right in the heart of Historic Annapolis, just 2 blocks from Main Str ...
From $528 per night (USD)VRBO
- From $339 per night (USD)
Expedia
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
In the heart of Annapolis, where the bay breeze blows, Stands a small cottage, the Captain's Quarters, a peaceful repos ...
From $339 per night (USD)Expedia
- From $459 per night (USD)
VRBO
Historic dog-friendly home 2 blocks to Main St
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay right in the heart of Historic Annapolis, just 2 blocks from Main Street, and feel like you’re in a hotel suite wit ...
From $459 per night (USD)VRBO
- From $451 per night (USD)
Expedia
Walk to Everything - Historic Art’s District
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
HISTORIC ANNAPOLIS/ART’S DISTRICT Built in 1898, “John Stevens House” in sought-after neighborhood of President’s Hill ...
From $451 per night (USD)Expedia
- From $1293 per night (USD)
VRBO
On-Site Parking, Steps to USNA Gate 3 and Private Patio at Historic Gatehouse
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Historic Charm Across from the Naval Academy Nestled in the heart of Downtown Annapolis, this spacious 5-bedroom, 4.5-ba ...
From $1293 per night (USD)VRBO
- From $418 per night (USD)
Expedia
Charming 3-bedroom house in Annapolis ⚓️🛥️⛵️ on the Chesapeake Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Make yourself at home in this delightful 3-bedroom Annapolis retreat. With a king bed, queen bed, and full bed, this hou ...
From $418 per night (USD)Expedia
- From $683 per night (USD)
VRBO
Charming 3-bedroom house in Annapolis two blocks from the Navy Stadium
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Peaceful house on a quiet street two blocks from the Navy Stadium with easy access to downtown Annapolis via the stadium ...
From $683 per night (USD)VRBO
- Click For Pricing
Expedia
Waterviews, steps to restaurants and downtown from First Mate
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Still available for Commissioning Week 2025! Stunning 4 Bedroom / 3.5 Bath Home in Eastport with Water Views and Expans ...
Click For PricingExpedia
- From $550 per night (USD)
VRBO
Mins to DTA - King Beds - Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your perfect Springtime getaway in the heart of Annapolis! This open-concept home is designed with family gat ...
From $550 per night (USD)VRBO
- From $630 per night (USD)
VRBO
Main Street 4BR Gem – Steps to Waterfront, USNA, Shops & Dining
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Above it All - Downtown Historic Annapolis Vacation Rental on Main Street - Downtown Annapolis Retreat | 4BR Apartment ...
From $630 per night (USD)VRBO
- From $788 per night (USD)
VRBO
Townhome steps from Main St. with private backyard patio & parking
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Welcome to City Gate, conveniently located in downtown Annapolis, just steps from all the shops and restaurants in the H ...
From $788 per night (USD)VRBO
- From $555 per night (USD)
Expedia
Steps to Marinas & Shops w Parking in Eastport
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Eastport's Third Time's the Charm – Steps from Marinas, Dining, and Historic Annapolis This beautiful home is located in ...
From $555 per night (USD)Expedia
- Click For Pricing
VRBO
Downtown Nights on the Water - Classic Cruiser Getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in the heart of Annapolis, this 35-foot Formula boat offers an unforgettable overnight stay. With a small kitche ...
Click For PricingVRBO
- From $591 per night (USD)
Expedia
Less than 1 mile to Navy Stadium, Fenced-in Yard and Dog-Friendly Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
A new home but managed by experienced hosts, iTrip Annapolis, dedicated to exceptional hospitality. Discover the perfect ...
From $591 per night (USD)Expedia
- From $618 per night (USD)
VRBO
Stay in the Heart of Annapolis on King George Street Steps to USNA Gate 1 & Main Street
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Your Historic Annapolis Retreat! Discover this newly-renovated and professionally-decorated gem on the presti ...
From $618 per night (USD)VRBO
- From $523 per night (USD)
Expedia
Family/Group Retreat Near USNA stadium & Downtown Annapolis; Private yard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
ALL NEW! Just minutes from USNA Stadium, downtown Annapolis and US Naval Academy, MBA Homes' Nautical Oasis is perfect f ...
From $523 per night (USD)Expedia
- From $372 per night (USD)
VRBO
Unique and central in Eastport
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Take it easy at this unique and tranquil getaway in historic Eastport. This 4-bedroom, 3-bathroom home has plenty of spa ...
From $372 per night (USD)VRBO
- From $160 per night (USD)
Expedia
Charming townhome with AC and WiFi in delightful Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Property is near naval Acedemy and downtown and harbourit is connected by bus route 70 and green bus and free downtown s ...
From $160 per night (USD)Expedia
- From $756 per night (USD)
VRBO
New Home w Luxe King Suite, Porch Vibes & Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
New Beautiful Home in Downtown Annapolis’ Murray Hill Walk to Downtown with Gourmet Kitchen Welcome to your home-away-f ...
From $756 per night (USD)VRBO
- From $442 per night (USD)
VRBO
Charming 3-bedroom house in Annapolis Eastport! Beautiful fully furnished home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful fully furnished 3 bedroom, 2 bath home, available for short term rental in Eastport Annapolis! 4 minutes uber ...
From $442 per night (USD)VRBO
- From $678 per night (USD)
VRBO
Stunning 4 BR Home - Walking Distance to Stadium
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Summary: This charming 4 BR home is conveniently located in Annapolis' Germantown neighborhood; within walking distance ...
From $678 per night (USD)VRBO
- From $419 per night (USD)
Expedia
Beautiful Historic Flat next to City Dock + USNA
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Just steps from Main Street, City Dock, and the USNA (300 ft), you'll be in the perfect location for exploring Annapolis ...
From $419 per night (USD)Expedia
- From $772 per night (USD)
VRBO
Sing Second Stays—Spacious Annapolis Home Near USNA & Navy Stadium
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Sing Second Stays, a comfortable and spacious retreat in the heart of Annapolis. Just 1.4 miles from Navy-Mar ...
From $772 per night (USD)VRBO
- From $794 per night (USD)
Expedia
Stay in the Heart of Historic Annapolis in this unique two-unit home with parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Stay right in the heart of Historic Annapolis, just 2 blocks from Main Street. This 2-unit property offers the opportun ...
From $794 per night (USD)Expedia