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Annapolis Rentals

$Cozy 2br home w\/ parking in downtown Annapolis$
From $380 per night (USD)
VRBO
Cozy 2br home w\/ parking in downtown Annapolis
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A's by the Cove is ideally located in the heart of downtown Annapolis's Historic and Art Districts. It is a fully update ...
From $380 per night (USD)
VRBO
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Expedia
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
Bedrooms:
1
Bathrooms:
3
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 ...
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Expedia
From $676 per night (USD)
VRBO
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Charming house - a 10-15 min walk to Navy Marine Corps Stadium (<.75mile), a 5 min drive from the US Naval Academy (<1mi ...
From $676 per night (USD)
VRBO
$Jode's Retreat \Your home away from home$
From $235 per night (USD)
Expedia
Jode's Retreat \"Your home away from home
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Clear the calendar for an easy-going getaway at "Jode's Retreat"; ideal for USNA events (a 2-minute drive to the stadium ...
From $235 per night (USD)
Expedia
From $394 per night (USD)
VRBO
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Incredible location in the Historic District of Annapolis. Walking distance to the Naval Academy, St. Johns College, an ...
From $394 per night (USD)
VRBO
From $1202 per night (USD)
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 ...
From $1202 per night (USD)
Expedia
From $640 per night (USD)
VRBO
Historic home steps to Main St w Capital views, free off-site parking, patio
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Experience Historic Annapolis in Comfort and Style This charming 4-bedroom home sits in the heart of Historic Annapolis, ...
From $640 per night (USD)
VRBO
From $642 per night (USD)
Expedia
Sophisticated Charmer with Parking & Views of the USNA Chapel Dome
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Hello and Welcome to Annapolis! You are going to love this home. IMPORTANT: if you are inquiring about USNA Commission ...
From $642 per night (USD)
Expedia
From $785 per night (USD)
VRBO
Walkable to Main Street at Seashell in the City with 2 parking spots
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to this gorgeous fully-renovated home, restored to a new modern grandeur, which includes coveted parking for 2 c ...
From $785 per night (USD)
VRBO
From $342 per night (USD)
Expedia
Anchor's Away in the Heart of Eastport!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Downtown in the heart of Eastport Annapolis, this first floor studio condo boasts high ceilings with lots of natural lig ...
From $342 per night (USD)
Expedia
From $244 per night (USD)
VRBO
Cozy 1st Floor King George one bedroom apartment right across from USNA
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy this one bedroom first floor apartment that's right across from Gate 2 of the U.S. Naval Academy. It's a short 1 ...
From $244 per night (USD)
VRBO
From $345 per night (USD)
Expedia
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This 2nd floor apt has new furniture, bedding and housewares. Extremely convenient location to downtown where there's l ...
From $345 per night (USD)
Expedia
From $214 per night (USD)
VRBO
Charming Downtown 3rd Floor 1 Bedroom Apt
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Perfect location for all that downtown Annapolis offers. Located right across from USNA gate 2. Super convenient, park y ...
From $214 per night (USD)
VRBO
From $440 per night (USD)
Expedia
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This home is spacious and clean and will make your vacation plans a breeze from this central location. Many families, g ...
From $440 per night (USD)
Expedia
From $727 per night (USD)
VRBO
Downtown Annapolis Townhome ! Beautiful!!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Beautiful Remodeled Townhome ! We have thought of everything you will need for an amazing stay. Fully loaded kitchen , ...
From $727 per night (USD)
VRBO
$Eastport Cottage .5 mi from Downtown Annapolis\n\n$
From $443 per night (USD)
Expedia
Eastport Cottage .5 mi from Downtown Annapolis\n\n
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Charming Eastport Cottage just 3 blocks from restaurants and bars (Ruth's Chris, Boatyard, O'leary's, Carol's Creek, t ...
From $443 per night (USD)
Expedia
From $662 per night (USD)
VRBO
Walk to USNA and Main Street with Parking at Historic Wisteria
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
How many homes in Downtown Annapolis have 4 Bedrooms with 4 Baths (3 of which are en-suite)?! Just 1-2 blocks from the ...
From $662 per night (USD)
VRBO
$Book for CW 2025! \Around the corner\ from Annapolis hot spots with fenced-in yard and parking$
From $617 per night (USD)
Expedia
Book for CW 2025! \"Around the corner\" from Annapolis hot spots with fenced-in yard and parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Still available for Commissioning Week 2025! Welcome to this beautifully remodeled Victorian home in Eastport, lovingly ...
From $617 per night (USD)
Expedia
From $618 per night (USD)
VRBO
Steps to the marinas with Private back deck, yard and Easy parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This professionally-decorated and furnished 2 bedroom, 1.5 bath is located across the Annapolis Waterfront drawbridge in ...
From $618 per night (USD)
VRBO
$\Dreams upon Weems\ Waterfront Cottage on Weems Creek in Annapolis$
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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 ...
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Expedia
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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. ...
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VRBO
From $1059 per night (USD)
Expedia
Deep in the Heart of Annapolis; Parking for days!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Welcome to this gorgeous Texas-themed downtown Annapolis home. Every inch of this home has custom finishes and has been ...
From $1059 per night (USD)
Expedia
$New Listing! Walk to USNA\/Capitol\/Downtown$
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VRBO
New Listing! Walk to USNA\/Capitol\/Downtown
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Want to enjoy being in downtown Annapolis, but on one of the quieter streets? If that sounds good, this is the place fo ...
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VRBO
$Downtown Annapolis Condo w\/ Free Parking + Coffee$
From $336 per night (USD)
Expedia
Downtown Annapolis Condo w\/ Free Parking + Coffee
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 $336 per night (USD)
Expedia
From $422 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 $422 per night (USD)
VRBO
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 $741 per night (USD)
VRBO
Easy walk to DTA from Historic multi-level Firehouse with parking, dog-friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Inquire about discounted extended stays! This is a unique home like none other in downtown Annapolis. Originally the Ea ...
From $741 per night (USD)
VRBO
From $341 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 $341 per night (USD)
Expedia
$Chic Condo w\/ Balcony in the Heart of Annapolis!$
From $504 per night (USD)
VRBO
Chic Condo w\/ Balcony in the Heart of Annapolis!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
See the best of Annapolis effortlessly when you book this 2-bed, 2-bath vacation rental! Equipped with all the essential ...
From $504 per night (USD)
VRBO
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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 ...
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Expedia
From $413 per night (USD)
VRBO
Annapolis Downtown Entire Townhome 3 bed 6 guests
Bedrooms:
2
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 $1348 per night (USD)
Expedia
Center of Downtown Annapolis across from USNA Gate 1 with Parking at Randall House
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 $1348 per night (USD)
Expedia
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VRBO
5 BDRM across from the USNA Stadium
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Across the street from the Naval Academy Stadium. Open floor plan with stainless steel appliances, two islands, 8-10 per ...
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VRBO
From $513 per night (USD)
Expedia
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Just finished with a few updates to kitchen and bedrooms + all new sheets and towels!new pictures coming soon!! Fantasti ...
From $513 per night (USD)
Expedia
From $895 per night (USD)
VRBO
1 Block to USNA with Chapel Views big back patio and off-site parking
Bedrooms:
3
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 $895 per night (USD)
VRBO
From $779 per night (USD)
Expedia
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
1930's Single family home on adorable cul-de-sac downtown Annapolis with off-street parking! Located off West Street in ...
From $779 per night (USD)
Expedia
From $716 per night (USD)
VRBO
Hanover House across from USNA Gate 3 with private back patio
Bedrooms:
3
Bathrooms:
5
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 $716 per night (USD)
VRBO
From $314 per night (USD)
Expedia
Bay View Studio Apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private ...
From $314 per night (USD)
Expedia
From $391 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 $391 per night (USD)
VRBO
From $833 per night (USD)
Expedia
One Block to Gate 1 at Naval-Academy-themed home, custom bar, onsite parking
Bedrooms:
2
Bathrooms:
5
Sleeps:
11
Welcome to Modern Elegance in Historic Annapolis Step into this fully-renovated 1900s home, where modern sophistication ...
From $833 per night (USD)
Expedia
From $608 per night (USD)
VRBO
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
421 Irie City Of Annapolis License Number 145052 Commission weeks: 2025, 2026, 2027 are booked. SORRY!! GO Navy!! ...
From $608 per night (USD)
VRBO
From $713 per night (USD)
Expedia
Historic Annapolis Getaway - 45 steps to Downtown and 150 steps to USNA!
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
45 steps from the Annapolis City Dock and 150 steps to the United States Naval Academy! Walk to all Shops, Restaurants, ...
From $713 per night (USD)
Expedia
From $239 per night (USD)
VRBO
Beautiful Condo - Water View Near City Dock
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Check out our winter rates for January, February and March! The Newport Condominium has a beautiful water view of Spa ...
From $239 per night (USD)
VRBO
From $431 per night (USD)
Expedia
Charming Charles Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Welcome to our vacation rental nestled in the heart of Downtown Annapolis. Immerse yourself in the rich history ...
From $431 per night (USD)
Expedia
From $495 per night (USD)
VRBO
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Bedrooms:
3
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 $1292 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 $1292 per night (USD)
Expedia
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VRBO
WALK TO DOWNTOWN ANNAPOLIS, EGO ALLEY, NAVAL STADIUM & ACADEMY
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This home was newly renovated in 2021 and is located in the highly desirable Murray Hill Neighborhood. Conveniently loc ...
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VRBO
$Gorgeous & bright retreat with patio, firepit, W\/D, & stunning rooftop views$
From $516 per night (USD)
Expedia
Gorgeous & bright retreat with patio, firepit, W\/D, & stunning rooftop views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Skyline Sanctuary Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $516 per night (USD)
Expedia
From $1566 per night (USD)
VRBO
Marvelous Home with Backyard Living Room in Murray Hill
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
NBS23-145336 Welcome to our charming vacation rental house nestled in the picturesque Murray Hill neighborhood of Annapo ...
From $1566 per night (USD)
VRBO
From $1010 per night (USD)
Expedia
Eastport Oasis 4 BR 2 BA fully renovated home on quiet street with parking
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 $1010 per night (USD)
Expedia
From $511 per night (USD)
VRBO
Cute bungalow blocks to Stadium
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: This stylish two bedroom home is conveniently located in Annapolis' Germantown neighborhood off West Street, ne ...
From $511 per night (USD)
VRBO
From $2274 per night (USD)
VRBO
Elegant Eastport Entertaining Dream House
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
NBS23-145363 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $2274 per night (USD)
VRBO
From $528 per night (USD)
VRBO
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 $528 per night (USD)
VRBO
$Vintage Retreat: 5 minute walk to downtown, Naval Academy, Stadium and more.\n$
From $351 per night (USD)
Expedia
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 $351 per night (USD)
Expedia
$Downtown Pinkney House w\/Parking$
From $506 per night (USD)
VRBO
Downtown Pinkney House w\/Parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
4
Summary: The Pinkney house is a 2 bedroom, 2.5 bath town home boasts an unparalleled location within close proximity to ...
From $506 per night (USD)
VRBO
From $540 per night (USD)
Expedia
Historic Annapolis Home!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
🌟 Discover the Allure of Historic Annapolis Living! 🌟 Welcome to your captivating 2-bedroom, 1.5-bath home nestled in ...
From $540 per night (USD)
Expedia
From $209 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 $209 per night (USD)
VRBO
From $189 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 $189 per night (USD)
VRBO
From $471 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 $471 per night (USD)
VRBO
From $212 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 $212 per night (USD)
VRBO
From $413 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 $413 per night (USD)
VRBO
From $424 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 $424 per night (USD)
VRBO
From $221 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 $221 per night (USD)
VRBO
$Unique Victorian Stay w\/ Modern Amenities + Steps from Waterfront$
From $189 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 $189 per night (USD)
VRBO
From $447 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 $447 per night (USD)
VRBO
From $223 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 $223 per night (USD)
VRBO
From $191 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 $191 per night (USD)
VRBO
From $207 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 $207 per night (USD)
VRBO
From $409 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 $409 per night (USD)
VRBO
From $200 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 $200 per night (USD)
VRBO
$Charming Downtown Hotel w\/ Vintage Character + Modern Amenities$
From $197 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 $197 per night (USD)
VRBO
From $229 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 $229 per night (USD)
VRBO
From $370 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 $370 per night (USD)
VRBO
From $1159 per night (USD)
Expedia
Brand New Spacious Luxury Home
Bedrooms:
5
Bathrooms:
6
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 $1159 per night (USD)
Expedia
$Cute and Close to Downtown! Off street parking w\/ short walk to Academy\/Stadium$
From $300 per night (USD)
VRBO
Cute and Close to Downtown! Off street parking w\/ short walk to Academy\/Stadium
Bedrooms:
2
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)
VRBO
Click For Pricing
Expedia
Gorgeous House in the Heart of Annapolis, Walk to Everything!
Bedrooms:
3
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 Pricing
Expedia
From $514 per night (USD)
VRBO
Walk to Everything - Historic Art’s District
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
HISTORIC ANNAPOLIS/ART’S DISTRICT Built circa 1890, “John Stevens House” in the sought-after neighborhood of “Presiden ...
From $514 per night (USD)
VRBO
From $1068 per night (USD)
Expedia
Steps to USNA Gate 3 at historic Gatehouse, on-site parking
Bedrooms:
5
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 $1068 per night (USD)
Expedia
From $1640 per night (USD)
VRBO
Spacious Converted Carriage House in Historic District near USNA
Bedrooms:
4
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 $1640 per night (USD)
VRBO
From $579 per night (USD)
Expedia
Available for CW 2025 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 $579 per night (USD)
Expedia
From $339 per night (USD)
VRBO
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)
VRBO
From $373 per night (USD)
Expedia
Stay in the heart of Historic Annapolis 2 blocks from Main Street - dog friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Still available for Commissioning Week 2025! Inquire about discounted extended stays! Stay right in the heart of Hist ...
From $373 per night (USD)
Expedia
From $399 per night (USD)
VRBO
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 $399 per night (USD)
VRBO
From $1040 per night (USD)
Expedia
Waterviews, steps to restaurants and downtown from First Mate
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Still available for Commissioning Week 2025! Stunning 4 Bedroom / 3.5 Bath Home in Eastport with Water Views and Expans ...
From $1040 per night (USD)
Expedia
From $627 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 $627 per night (USD)
VRBO
From $604 per night (USD)
Expedia
Build a Snowman at the Beat Army Bungalow
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your perfect holiday retreat in the heart of Annapolis! This open-concept home is designed with family gather ...
From $604 per night (USD)
Expedia
From $798 per night (USD)
VRBO
Experience Annapolis like a local - 4 BR Apartment overlooking Main Street in Annapolis -
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Above it All - Downtown Historic Annapolis Vacation Rental on Main Street - PLEASE NOTE: THIS PROPERTY IS MANAGED BY AN ...
From $798 per night (USD)
VRBO
From $703 per night (USD)
Expedia
Townhome just steps to Main St. with private backyard patio & parking
Bedrooms:
4
Bathrooms:
3
Sleeps:
7
Welcome to City Gate, conveniently located in downtown Annapolis, just steps from all the shops and restaurants in the H ...
From $703 per night (USD)
Expedia
From $570 per night (USD)
VRBO
Book for CW 2025 Steps from marinas and restaurants at Eastport Third Time's the Charm
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Still available for Commissioning Week 2025! Eastport's Third Time's the Charm – Steps from Marinas, Dining, and Histor ...
From $570 per night (USD)
VRBO
From $117 per night (USD)
Expedia
Downtown Nights on the Water - Classic Cruiser Getaway
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in the heart of Annapolis, this 35-foot Formula boat offers an unforgettable overnight stay. With a small kitche ...
From $117 per night (USD)
Expedia
From $714 per night (USD)
VRBO
Less than 1 mile to Navy Stadium, fenced-in yard and dog-friendly home
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Still Available for Commissioning Week 2025! A new home but managed by experienced hosts, iTrip Annapolis, dedicated to ...
From $714 per night (USD)
VRBO
From $542 per night (USD)
Expedia
New listing! Stay in the heart of Annapolis on King George Street steps to Gate 1 & Main Street
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Welcome to Your Historic Annapolis Retreat! Discover this newly-renovated and professionally-decorated gem on the presti ...
From $542 per night (USD)
Expedia
$Private 1-Level Home near AAMC\/USNA; Spa shower; Fire pit; Family-friendly!$
From $540 per night (USD)
VRBO
Private 1-Level Home near AAMC\/USNA; Spa shower; Fire pit; Family-friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Just minutes from USNA Stadium, AAMC Hospital, and downtown Annapolis, Nautical Oasis is perfect for couples, families, ...
From $540 per night (USD)
VRBO
From $278 per night (USD)
VRBO
Adorable 1 bedroom apartment in downtown Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Enjoy a stylish experience at this centrally-located apartment. 2 minute walk to Main Street and all of the att ...
From $278 per night (USD)
VRBO
From $380 per night (USD)
VRBO
2 Bedroom Renovated Condo in Downtown Annapolis
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Summary: Newly renovated 2 bedroom apartment in downtown Annapolis. Steps from Main Street and all that Annapolis has to ...
From $380 per night (USD)
VRBO
$Downtown Annapolis Gem: 3BR\/2BA$
From $660 per night (USD)
VRBO
Downtown Annapolis Gem: 3BR\/2BA
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Welcome to our newly renovated 3BR/2BA apartment in downtown Annapolis! With two king beds, one queen bed, and ...
From $660 per night (USD)
VRBO
From $257 per night (USD)
VRBO
1 room with additional amazing sunroom
Bedrooms:
1
Bathrooms:
3
Sleeps:
3
Summary: Enjoy a wonderful experience at this centrally-located apartment. 2 minute walk to Main Street and all of the a ...
From $257 per night (USD)
VRBO
From $236 per night (USD)
VRBO
Lovely 1 bedroom apartment in downtown Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Summary: Keep it simple at this peaceful ground floor apartment steps from Main Street and all that Annapolis has to off ...
From $236 per night (USD)
VRBO
$Magnolia Harbor Retreat - 4 BR\/3BA HISTORIC DOWNTOWN ANNAPOLIS- QUIET STREET$
From $918 per night (USD)
VRBO
Magnolia Harbor Retreat - 4 BR\/3BA HISTORIC DOWNTOWN ANNAPOLIS- QUIET STREET
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
RENT-001081-2024 - THIS PROPERTY IS MANAGED BY ANNAPOLIS ACCOMMODATION. YOUR RESERVATION IS NOT CONFIRMED UNTIL A TEAM ...
From $918 per night (USD)
VRBO
From $995 per night (USD)
VRBO
Stunning Home Nestled on the Peninsula of Eastport
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This 4 bedroom Annapolis home is an absolute gem, especially with off-street parking! The Craftsman style architecture a ...
From $995 per night (USD)
VRBO

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