Annapolis Rentals
From $298 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 $298 per night (USD)VRBO
From $271 per night (USD)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 ...
From $271 per night (USD)Expedia
From $466 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 $466 per night (USD)VRBO
From $231 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 $231 per night (USD)Expedia
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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 ...
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From $313 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 $313 per night (USD)Expedia
Click For PricingVRBO
Stay at Lux Red Door Gem with 3 Parking Spots
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Visit the magic of Annapolis during the Holiday Season The gorgeous Downtown Annapolis home was meticulously remodeled f ...
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From $836 per night (USD)Expedia
Available for CW 2025 Historic home steps to Main St w Capital views, free off-site parking, patio
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Visit the magic of Annapolis during the Holiday Season Experience Historic Annapolis in Comfort and Style This charming ...
From $836 per night (USD)Expedia
From $618 per night (USD)VRBO
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 $618 per night (USD)VRBO
From $521 per night (USD)Expedia
Walkable to Main Street at Seashell in the City with 2 parking spots
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Visit the magic of Annapolis during the Holiday Season Welcome to this gorgeous fully-renovated home, restored to a new ...
From $521 per night (USD)Expedia
From $342 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 $342 per night (USD)VRBO
From $333 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 $333 per night (USD)Expedia
From $201 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 $201 per night (USD)VRBO
From $432 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 $432 per night (USD)Expedia
From $607 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 $607 per night (USD)VRBO
From $241 per night (USD)Expedia
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 $241 per night (USD)Expedia
From $388 per night (USD)VRBO
Eastport Cottage .5 mi from Downtown Annapolis\n\nNIGHTLY PRICE REDUCTION!!!!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
NIGHTLY PRICE REDUCTION AS OF 11.04.2024! Charming Eastport Cottage just 3 blocks from restaurants and bars (Ruth's Ch ...
From $388 per night (USD)VRBO
From $528 per night (USD)Expedia
Walk to USNA and Main Street with Parking at Historic Wisteria
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Visit the magic of Annapolis during the Holiday Season How many homes in Downtown Annapolis have 4 Bedrooms with 4 Baths ...
From $528 per night (USD)Expedia
From $654 per night (USD)VRBO
Bennett House (entire):Haven in Historic Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the historic neighborhood of Murray Hill! The Bennett House is a charming, light- filled detached home with 3 ...
From $654 per night (USD)VRBO
From $509 per night (USD)Expedia
Still available for CW 2025! \"Around the corner\" from everything w fenced-in yard and parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Visit the magic of Annapolis during the Holiday Season Still available for Commissioning Week 2025! Welcome to this cha ...
From $509 per night (USD)Expedia
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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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From $604 per night (USD)Expedia
Steps to the marinas with Private back deck, yard and Easy parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Visit the magic of Annapolis during the Holiday Season This professionally-decorated and furnished 2 bedroom, 1.5 bath i ...
From $604 per night (USD)Expedia
Click For PricingVRBO
\"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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From $1037 per night (USD)Expedia
Deep in the Heart of Annapolis; Parking for days!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Visit the magic of Annapolis during the Holiday Season Welcome to this gorgeous Texas-themed downtown Annapolis home. Ev ...
From $1037 per night (USD)Expedia
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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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From $379 per night (USD)Expedia
Renovated historic apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the historic neighborhood of Murray Hill! The Bennett House is a charming, light- filled detached home with a ...
From $379 per night (USD)Expedia
From $418 per night (USD)VRBO
Renovated historic apartment
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the historic neighborhood of Murray Hill! The Bennett House is a charming, light- filled detached home with a ...
From $418 per night (USD)VRBO
From $311 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 $311 per night (USD)Expedia
From $399 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 $399 per night (USD)VRBO
From $367 per night (USD)Expedia
Charming 4BR 2BA w\/ outdoor patio & fire pit! 5 min walk to Navy Stadium and DT
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Come stay at this fully updated cozy 4-bedroom 2-bathroom home. Conveniently located with a .6 mile walk to the Naval Ac ...
From $367 per night (USD)Expedia
From $375 per night (USD)VRBO
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 $375 per night (USD)VRBO
From $587 per night (USD)Expedia
Easy walk to DTA from Historic multi-level Firehouse with parking, dog-friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Visit the magic of Annapolis during the Holiday Season Inquire about discounted extended stays! This is a unique home l ...
From $587 per night (USD)Expedia
From $341 per night (USD)VRBO
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)VRBO
From $362 per night (USD)Expedia
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 $362 per night (USD)Expedia
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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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From $410 per night (USD)Expedia
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 $410 per night (USD)Expedia
From $925 per night (USD)VRBO
Center of Downtown Annapolis across from USNA Gate 1 with Parking at Randall House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Visit the magic of Annapolis during the Holiday Season The Randall House is an historic gem in the heart of Downtown Ann ...
From $925 per night (USD)VRBO
Click For PricingExpedia
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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From $699 per night (USD)VRBO
The Navy House~ Walk to Downtown! 3 Bed Bungalow across from Navy Stadium
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Our quiet 3 bed 2.5 bath home is the perfect Annapolis getaway! On a dead end road. A quick walk to the best downtown r ...
From $699 per night (USD)VRBO
From $426 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 $426 per night (USD)Expedia
From $911 per night (USD)VRBO
1 Block to USNA with Chapel Views big back patio and off-site parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Visit the magic of Annapolis during the Holiday Season When the owners decided to find their Annapolis home base, they k ...
From $911 per night (USD)VRBO
From $716 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 $716 per night (USD)Expedia
From $522 per night (USD)VRBO
Hanover House across from USNA Gate 3 with private back patio
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Visit the magic of Annapolis during the Holiday Season The fully-renovated 1800 historic home is just steps from USNA’s ...
From $522 per night (USD)VRBO
From $264 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 $264 per night (USD)Expedia
From $377 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 $377 per night (USD)VRBO
From $780 per night (USD)Expedia
Still available for CW 2025 Steps to Gate 1 at Naval-Academy-themed home, custom bar, onsite parking
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 11
Visit the magic of Annapolis during the Holiday Season Still available for Commissioning Week 2025! Welcome to Modern E ...
From $780 per night (USD)Expedia
From $476 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 $476 per night (USD)VRBO
From $676 per night (USD)VRBO
Historic Annapolis Getaway - 45 steps to Downtown and 156 steps to USNA!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
45 steps from the Annapolis City Dock and 156 steps to the United States Naval Academy! Walk to all Shops, Restaurants, ...
From $676 per night (USD)VRBO
From $175 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 $175 per night (USD)VRBO
Click For PricingExpedia
Charming Charles Retreat- The perfect space for fun and relaxation!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our vacation rental nestled in the heart of Downtown Annapolis. Immerse yourself in the rich history and vibr ...
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From $474 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 $474 per night (USD)VRBO
From $986 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 $986 per night (USD)Expedia
Click For PricingVRBO
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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From $445 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 $445 per night (USD)Expedia
From $2622 per night (USD)VRBO
Premium Home in West Annapolis: Perfect for Navy Events, Boat Shows, Walkable!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
You will be close to everything when you stay at this well appointed, centrally-located home. This elegant, stylish, a ...
From $2622 per night (USD)VRBO
From $482 per night (USD)Expedia
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 $482 per night (USD)Expedia
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 $1549 per night (USD)Expedia
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 $1549 per night (USD)Expedia
From $617 per night (USD)VRBO
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 $617 per night (USD)VRBO
From $532 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 $532 per night (USD)Expedia
From $331 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 $331 per night (USD)VRBO
From $312 per night (USD)Expedia
The Annapolis Pinkney House- complete with parking!
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 4
The Pinkney house is a 2 bedroom, 2.5 bath town home boasts an unparalleled location within close proximity to the Naval ...
From $312 per night (USD)Expedia
From $412 per night (USD)VRBO
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 $412 per night (USD)VRBO
From $202 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 $202 per night (USD)VRBO
From $185 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 $185 per night (USD)VRBO
From $468 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 $468 per night (USD)VRBO
From $206 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 $206 per night (USD)VRBO
From $409 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 $409 per night (USD)VRBO
From $422 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 $422 per night (USD)VRBO
From $203 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 $203 per night (USD)VRBO
From $186 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 $186 per night (USD)VRBO
From $432 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 $432 per night (USD)VRBO
From $200 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 $200 per night (USD)VRBO
From $188 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 $188 per night (USD)VRBO
From $203 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 $203 per night (USD)VRBO
From $394 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 $394 per night (USD)VRBO
From $186 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 $186 per night (USD)VRBO
From $182 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 $182 per night (USD)VRBO
From $189 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 $189 per night (USD)VRBO
From $375 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 $375 per night (USD)VRBO
From $719 per night (USD)VRBO
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 $719 per night (USD)VRBO
From $295 per night (USD)Expedia
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 $295 per night (USD)Expedia
Click For PricingVRBO
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 PricingVRBO
From $394 per night (USD)Expedia
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 $394 per night (USD)Expedia
From $832 per night (USD)VRBO
Available for Christmas Steps to USNA Gate 3 at historic Gatehouse, on-site parking
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Visit the magic of Annapolis during the Holiday Season Historic Charm Across from the Naval Academy Nestled in the heart ...
From $832 per night (USD)VRBO
From $1492 per night (USD)Expedia
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 $1492 per night (USD)Expedia
From $499 per night (USD)VRBO
Available for CW 2025 just 2 blocks from Main St with parking - dog-friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Visit the magic of Annapolis during the Holiday Season Still available for Commissioning Week 2025! Stay right in the h ...
From $499 per night (USD)VRBO
From $334 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 $334 per night (USD)Expedia
From $403 per night (USD)VRBO
Stay in the heart of Historic Annapolis 2 blocks from Main Street - dog friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Visit the magic of Annapolis during the Holiday Season Still available for Commissioning Week 2025! Inquire about disco ...
From $403 per night (USD)VRBO
From $390 per night (USD)Expedia
Steps to marinas from 2nd floor apartment with parking, private balcony
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This beautifully-restored 1 bedroom apartment is on the 2nd level of a 2-unit building in the charming Eastport neighbor ...
From $390 per night (USD)Expedia
From $418 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 $418 per night (USD)VRBO
From $627 per night (USD)Expedia
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)Expedia
From $889 per night (USD)VRBO
Available for CW 2025 Waterviews, steps to restaurants and downtown from First Mate
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Visit the magic of Annapolis during the Holiday Season Still available for Commissioning Week 2025! Stunning 4 Bedroom ...
From $889 per night (USD)VRBO
From $559 per night (USD)VRBO
WATERFRONT 2-Bdrm Townhome, SPA Bthrm, Private Patio, WiFi-Eastport, Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Nestled in a waterfront tranquil setting on Spa Creek, guests can unwind in this superb accommodation. Enjoy the luxury ...
From $559 per night (USD)VRBO
From $745 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 $745 per night (USD)VRBO
From $648 per night (USD)Expedia
Available for CW 2025 City Gate: Townhome downtown with private backyard patio and parking
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 7
Visit the magic of Annapolis during the Holiday Season Welcome to City Gate, conveniently located in downtown Annapolis, ...
From $648 per night (USD)Expedia
From $523 per night (USD)VRBO
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 $523 per night (USD)VRBO
From $450 per night (USD)Expedia
Available for CW 2025 Eastport Third Time's the Charm – Steps from marinas and restaurants
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Visit the magic of Annapolis during the Holiday Season Still available for Commissioning Week 2025! Eastport's Third Ti ...
From $450 per night (USD)Expedia
From $255 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 $255 per night (USD)VRBO
From $349 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 $349 per night (USD)VRBO