Annapolis, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Annapolis, Maryland on RentalSaver.com!

Annapolis Rentals

From $463 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 $463 per night (USD)
VRBO
From $304 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 $304 per night (USD)
Expedia
From $364 per night (USD)
VRBO
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 $364 per night (USD)
VRBO
From $610 per night (USD)
Expedia
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 $610 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
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Expedia
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 Pricing
Expedia
From $581 per night (USD)
VRBO
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 $581 per night (USD)
VRBO
From $636 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 $636 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 $244 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 $244 per night (USD)
Expedia
From $345 per night (USD)
VRBO
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 $345 per night (USD)
VRBO
From $214 per night (USD)
Expedia
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 $214 per night (USD)
Expedia
From $432 per night (USD)
VRBO
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 $432 per night (USD)
VRBO
From $727 per night (USD)
Expedia
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 $727 per night (USD)
Expedia
$Eastport Cottage .5 mi from Downtown Annapolis\n\n$
From $446 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 $446 per night (USD)
VRBO
From $552 per night (USD)
Expedia
Walk to USNA and Main Street 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 $552 per night (USD)
Expedia
$Stay \Around the corner\ from Annapolis hot spots with new King bed, fenced-in yard and parking$
From $547 per night (USD)
VRBO
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 $547 per night (USD)
VRBO
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Expedia
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. ...
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Expedia
From $437 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 $437 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 ...
Click For Pricing
Expedia
From $1118 per night (USD)
VRBO
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 $1118 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $264 per night (USD)
VRBO
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 $264 per night (USD)
VRBO
From $422 per night (USD)
Expedia
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)
Expedia
From $342 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 $342 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $417 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 $417 per night (USD)
VRBO
From $636 per night (USD)
Expedia
Parking at Historic Firehouse Easy Walk to Annapolis & Dog-Friendly
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Inquire about discounted extended stays! This is a unique home like none other in downtown Annapolis. Originally the Ea ...
From $636 per night (USD)
Expedia
Click For Pricing
VRBO
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 Pricing
VRBO
From $413 per night (USD)
Expedia
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)
Expedia
From $1173 per night (USD)
VRBO
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 $1173 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $450 per night (USD)
VRBO
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 $450 per night (USD)
VRBO
From $807 per night (USD)
Expedia
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 $807 per night (USD)
Expedia
From $731 per night (USD)
VRBO
***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 $731 per night (USD)
VRBO
From $578 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 $578 per night (USD)
Expedia
From $319 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 $319 per night (USD)
VRBO
From $394 per night (USD)
Expedia
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 $394 per night (USD)
Expedia
From $789 per night (USD)
VRBO
Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Welcome to Modern Elegance in Historic Annapolis Step into this fully-renovated 1900s home, where modern sophistication ...
From $789 per night (USD)
VRBO
From $571 per night (USD)
Expedia
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 $571 per night (USD)
Expedia
From $583 per night (USD)
VRBO
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 $583 per night (USD)
VRBO
From $239 per night (USD)
Expedia
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 $239 per night (USD)
Expedia
From $419 per night (USD)
VRBO
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 $419 per night (USD)
VRBO
From $495 per night (USD)
Expedia
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)
Expedia
From $1052 per night (USD)
VRBO
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 $1052 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
From $460 per night (USD)
VRBO
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 $460 per night (USD)
VRBO
From $1583 per night (USD)
Expedia
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)
Expedia
From $844 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 $844 per night (USD)
VRBO
From $579 per night (USD)
Expedia
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 $579 per night (USD)
Expedia
From $464 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 $464 per night (USD)
VRBO
$Vintage Retreat: 5 minute walk to downtown, Naval Academy, Stadium and more.\n$
From $331 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 $331 per night (USD)
Expedia
From $404 per night (USD)
VRBO
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 $404 per night (USD)
VRBO
From $591 per night (USD)
Expedia
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 $591 per night (USD)
Expedia
From $205 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 $205 per night (USD)
VRBO
From $188 per night (USD)
Expedia
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 $188 per night (USD)
Expedia
From $469 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 $469 per night (USD)
VRBO
From $221 per night (USD)
Expedia
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 $221 per night (USD)
Expedia
From $410 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 $410 per night (USD)
VRBO
From $422 per night (USD)
Expedia
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)
Expedia
From $228 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 $228 per night (USD)
VRBO
From $201 per night (USD)
Expedia
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 $201 per night (USD)
Expedia
From $494 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 $494 per night (USD)
VRBO
From $245 per night (USD)
Expedia
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 $245 per night (USD)
Expedia
From $202 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 $202 per night (USD)
VRBO
From $221 per night (USD)
Expedia
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 $221 per night (USD)
Expedia
From $451 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 $451 per night (USD)
VRBO
From $211 per night (USD)
Expedia
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 $211 per night (USD)
Expedia
From $224 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 $224 per night (USD)
VRBO
From $230 per night (USD)
Expedia
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 $230 per night (USD)
Expedia
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 $967 per night (USD)
Expedia
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 $967 per night (USD)
Expedia
From $300 per night (USD)
VRBO
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)
VRBO
Click For Pricing
Expedia
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 ...
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Expedia
From $1444 per night (USD)
VRBO
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 $1444 per night (USD)
VRBO
From $531 per night (USD)
Expedia
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 $531 per night (USD)
Expedia
From $320 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 $320 per night (USD)
VRBO
From $455 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 $455 per night (USD)
Expedia
From $461 per night (USD)
VRBO
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 $461 per night (USD)
VRBO
From $943 per night (USD)
Expedia
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 $943 per night (USD)
Expedia
From $388 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 $388 per night (USD)
VRBO
From $683 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 $683 per night (USD)
Expedia
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VRBO
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 Pricing
VRBO
From $874 per night (USD)
Expedia
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 - PLEASE NOTE: THIS PROPERTY IS MANAGED BY AN ...
From $874 per night (USD)
Expedia
From $797 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 $797 per night (USD)
VRBO
From $585 per night (USD)
Expedia
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 $585 per night (USD)
Expedia
From $601 per night (USD)
VRBO
Steps From Marinas and Restaurants & Private Backyard at Eastport Third Time's the Charm
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Still available for Commissioning Week 2025! Eastport's Third Time's the Charm – Steps from Marinas, Dining, and Histor ...
From $601 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
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Expedia
From $719 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 $719 per night (USD)
VRBO
From $496 per night (USD)
Expedia
Stay in the heart of Annapolis on King George Street steps to 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 $496 per night (USD)
Expedia
From $537 per night (USD)
VRBO
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 $537 per night (USD)
VRBO
From $420 per night (USD)
Expedia
Take it easy at this unique and tranquil getaway in historic Eastport
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Take it easy at this unique and tranquil getaway in historic Eastport. This 4-bedroom, 3-bathroom home has plenty of spa ...
From $420 per night (USD)
Expedia
From $107 per night (USD)
VRBO
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 $107 per night (USD)
VRBO
From $635 per night (USD)
Expedia
New Property! Escape to Downtown Annapolis Murray Hill Home with Luxe King Suite and Porch Vibes
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 $635 per night (USD)
Expedia
From $420 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 $420 per night (USD)
VRBO
From $523 per night (USD)
Expedia
Charming 3-bedroom house with WiFi, AC in awesome Annapolis
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to a wonderful 3-bedroom house in Annapolis. This cozy retreat features 2 full beds and 1 bunk bed, perfect for a ...
From $523 per night (USD)
Expedia
From $574 per night (USD)
VRBO
Beautiful 4BR - 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 $574 per night (USD)
VRBO
From $453 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 $453 per night (USD)
Expedia
From $849 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 $849 per night (USD)
VRBO
From $557 per night (USD)
Expedia
Modern Styled Home in Historic Annapolis Eastport Neighborhood
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Built in 2021 and freshly styled in 2025 with a unique modern European touch, our family-friendly retreat offers the per ...
From $557 per night (USD)
Expedia

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