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

Anne Arundel Area Rentals

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 $261 per night (USD)
Expedia
Nice clean townhome in the middle of everything mall, airport, DC, Baltimore ect
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
*Kingsize bed in master bedroom (nice sweet) * Beautiful view front and back *joint his and her bathroom *nice kitchen ...
From $261 per night (USD)
Expedia
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VRBO
Luxury Cottage w/ Bay & Boardwalk Views--steps from the water
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Where new Luxury meets Cottage history and charm. Stay in one of the only cottages right on the Boardwalk that features ...
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VRBO
From $210 per night (USD)
Expedia
Want to get away? Staying with us. Very relaxing.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Our tastefully appointed cottages . Peaceful and tranquil, yet close to shops and restaurants, this property is perfect ...
From $210 per night (USD)
Expedia
From $96 per night (USD)
VRBO
Amazing Bright Big Window Loft Heart of Eastport
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Beautiful furnished or semi furnished loft apartment in Eastport. Views of the Severn river, naval academy , Sailboat’s, ...
From $96 per night (USD)
VRBO
From $611 per night (USD)
VRBO
Spacious, contemporary, wooded home in Epping Forest on the Severn River
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Beautiful home in Epping Forest with large granite counters and stainless kitchen with open floor plan for family gather ...
From $611 per night (USD)
VRBO
From $346 per night (USD)
VRBO
Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
RENT-000642-2025- PLEASE NOTE: IF YOU REQUEST TO BOOK THIS PROPERTY, YOU WILL BE CONTACTED BY ANNAPOLIS ACCOMMODATIONS ...
From $346 per night (USD)
VRBO
From $567 per night (USD)
Expedia
Mins to Annapolis from Waterfront Retreat w Stunning Views of the Bay and Bridge with Fenced-In Yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Relaxing Waterfront Retreat Near Annapolis – Pet Friendly & Packed with Perks! Escape to a tranquil waterfront retreat ...
From $567 per night (USD)
Expedia
From $499 per night (USD)
VRBO
Annapolis Charm - Waterfront Private Fishing Dock Pier Near Beach - Navy Academy
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Kick back and relax in this calm, charming newly renovated coastal farmhouse waterfront two-story home with private pier ...
From $499 per night (USD)
VRBO
From $251 per night (USD)
VRBO
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Completely renovated street level 1 bedroom apartment with all the amenities of home. Perfect for a single traveler or ...
From $251 per night (USD)
VRBO
From $1670 per night (USD)
VRBO
Annapolis Waterfront Oasis with Pool, Hot Tub & Piers with L2 EV Charger
Bedrooms:
4
Bathrooms:
7
Sleeps:
14
Newly Renovated with larger bedrooms and 2 more bathrooms! Enjoy Annapolis with family & friends all year at this extrao ...
From $1670 per night (USD)
VRBO
$Eastport Cottage .5 mi from Downtown Annapolis\n\n$
From $440 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 $440 per night (USD)
Expedia
From $253 per night (USD)
VRBO
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The Perfect rock fishing and crabbing cottage in Deale, Maryland right on Rockhold Creek, with docks and spectacular vi ...
From $253 per night (USD)
VRBO
From $643 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 $643 per night (USD)
Expedia
From $582 per night (USD)
VRBO
Waterfront Family-Friendly Community, Fenced-In Yard and Dog-Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Still available for Commissioning Week 2025! Welcome to the Shore Leave! Just a five minute walk to the beach, five mi ...
From $582 per night (USD)
VRBO
From $1938 per night (USD)
VRBO
Cool 1870's home anchored in the Historic District with modern amenities.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Our century-and-a-half-old, five bedroom and three bath home with 3,000 square feet centrally situated in the heart of ...
From $1938 per night (USD)
VRBO
From $201 per night (USD)
VRBO
“Athens of America,” Annapolis Apartment Two B
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Known as the “Athens of America,” Annapolis is a city abundant with history and culture. This former capital of the Unit ...
From $201 per night (USD)
VRBO
From $256 per night (USD)
Expedia
“Athens of America,” Annapolis Apartment Two A
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The place to be for all USNA activities. Annapolis is a city abundant with history and culture. This former capital of t ...
From $256 per night (USD)
Expedia
From $319 per night (USD)
VRBO
Available for Maryland Legislative Session 2024 ! Perfect location!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy the essence of Historic Annapolis with this recently renovated Maryland Avenue apartment. Located in the 'Johnson ...
From $319 per night (USD)
VRBO
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Expedia
Tudor style house near historic downtown Annapolis
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
A large Tudor style house with plenty of living space; several sitting rooms, a large back porch, an open field and surr ...
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Expedia
From $475 per night (USD)
VRBO
NEW 5 Bedroom Home with Pier by Water
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to this brand-new relaxing home with a pier by the water for your getaway. It is perfect for vacations, retreats ...
From $475 per night (USD)
VRBO
From $144 per night (USD)
Expedia
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to Annapolis, where history and nature come together! Make yourself at home in this cozy 1-bedroom, 1-bath cond ...
From $144 per night (USD)
Expedia
$Stay \Around the corner\ from Annapolis hot spots with new King bed, fenced-in yard and parking$
From $566 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 $566 per night (USD)
VRBO
From $226 per night (USD)
VRBO
Brand New Reno in Historic Dist w 2 Parking spots
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Spotless / sanitized !! Renovated upstairs unit two bedroom with TWO parking spots in the Historic District . Everythi ...
From $226 per night (USD)
VRBO
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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. ...
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VRBO
From $753 per night (USD)
VRBO
Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Absolutely gorgeous downtown waterfront home. Loaded with historical significance and character, all while minutes walki ...
From $753 per night (USD)
VRBO
From $1500 per night (USD)
VRBO
Private Pool Paradise Modest Socials Welcomed
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
Beautiful property with spacious home and grounds perfect for a modest get together of friends and family. If you’re int ...
From $1500 per night (USD)
VRBO
From $1117 per night (USD)
Expedia
Private Waterview Estate with 4 Suites, Hot Tub, Gourmet Kitchen and Game Room
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Welcome to Sanare Estates! The ultra-private waterfront estate is like your own luxury resort, located on 20+ Acres with ...
From $1117 per night (USD)
Expedia
From $486 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 $486 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
From $354 per night (USD)
VRBO
Waterfront Oasis of Annapolis Star
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Studio, furnished apartment above detached garage on family's sprawling property. Queen-bed, with pull out full couch. S ...
From $354 per night (USD)
VRBO
From $327 per night (USD)
VRBO
Charming Annapolis Guest House
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This charming guest house with private access is in a great location! Just 2 miles from the Naval Academy, Downtown Anna ...
From $327 per night (USD)
VRBO
From $197 per night (USD)
VRBO
Guest Quarters at the Inn - 101
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Guest Quarters at the Inn is a vacation rental site situated one block from the Chesapeake Bay in the historic and c ...
From $197 per night (USD)
VRBO
From $186 per night (USD)
Expedia
New Loft w/South River view from treehouse deck!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy the quiet Sylvan Shores neighborhood and a view of the South River and bridges in this new modern apartment that h ...
From $186 per night (USD)
Expedia
From $127 per night (USD)
VRBO
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore the best of Maryland and book a stay at this cozy 1-bed, 1-bath vacation rental home in Lothian! Nestled on a fa ...
From $127 per night (USD)
VRBO
From $381 per night (USD)
Expedia
★ Odenton Oasis ★ Patio - Central to Everything
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Welcome to our beautifully furnished, colonial-style townhome just minutes from MARC station with great proximity to DC, ...
From $381 per night (USD)
Expedia
From $356 per night (USD)
VRBO
BWI, Annapolis, DC, Baltimore, USNA family-sized house with a game room and deck
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
The house is in a quiet residential neighborhood. It has easy access to all major routes: I-97, I-695, I-95, I-295, rout ...
From $356 per night (USD)
VRBO
From $432 per night (USD)
Expedia
Close to US Naval Academy, downtown Annapolis, Maryland Live Casino, BWI Airport
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Very cozy bedrooms with two incredible family rooms to enjoy internet tv, game room, built in bar, beautiful screened in ...
From $432 per night (USD)
Expedia
From $187 per night (USD)
VRBO
Guest Quarters at the Inn - 103
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Guest Quarters at the Inn is a vacation rental site situated one block from the Chesapeake Bay in the historic and c ...
From $187 per night (USD)
VRBO
From $197 per night (USD)
Expedia
Guest Quarters at the Inn - 102
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Guest Quarters at the Inn is a vacation rental site situated one block from the Chesapeake Bay in the historic and c ...
From $197 per night (USD)
Expedia
From $589 per night (USD)
VRBO
Beautiful remodeled waterfront home - 20 minutes from Baltimore!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Come stay at our waterfront home! Our home got a “fresh make over” from the inside- out! Fully remodeled 2 story home wi ...
From $589 per night (USD)
VRBO
From $579 per night (USD)
Expedia
Stay in Heart of Downtown Annapolis Steps to Main St at Historic Carriage House
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Originally built in 1857, this fully-restored home has a rich history that's been documented from it's original purpose ...
From $579 per night (USD)
Expedia
From $716 per night (USD)
VRBO
Waterfront Cheerful 6 BR Home with Private Pier
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Welcome to this brand-new relaxing home with a private pier by the water for your getaway. It is perfect for vacations, ...
From $716 per night (USD)
VRBO
From $1371 per night (USD)
VRBO
Beautiful home w/elevator going to every floor. This house is accessible to all.
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $1371 per night (USD)
VRBO
From $524 per night (USD)
VRBO
Delightful little Historic District gem - for the antique lover and history buff.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
STR21-144963 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $524 per night (USD)
VRBO
From $970 per night (USD)
VRBO
One block from USNA Gate 1, or 3 blocks from City Dock, this attractive home is close to the center of the universe!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $970 per night (USD)
VRBO
From $633 per night (USD)
VRBO
Coastal Cottage - 3 BR -Retreat Near Annapolis | Bay Views | Beach Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
STR-000324 -THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $633 per night (USD)
VRBO
From $830 per night (USD)
VRBO
Elegant yet modern historic home in the heart of downtown Annapolis
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
STR-143426 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $830 per night (USD)
VRBO
From $613 per night (USD)
VRBO
DOWNTOWN ANNAPOLIS DREAMHOME AWAITS!!! 3 BR charming home sits in the heart of Annapolis within walking distance to all major points of interest AND a Rooftop Deck!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
STR-144253 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $613 per night (USD)
VRBO
From $1563 per night (USD)
VRBO
Commissioning Week Escape with Pool and Beautiful 4 Seasons room
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
STR00808 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $1563 per night (USD)
VRBO
From $1444 per night (USD)
VRBO
Water view from every window - Located at the point where the deep water of Saltworks Creek meets the Severn River.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
STR50082- THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $1444 per night (USD)
VRBO
From $1269 per night (USD)
VRBO
Complete WATERFRONT LIVING! 5 BR in Quiet Waterfront Community
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
STR-250 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $1269 per night (USD)
VRBO
From $947 per night (USD)
VRBO
4 BR/3BA home in the heart of Historic Downtown Annapolis. 1 1/2 blocks from the Naval Academy
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
STR-141783 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $947 per night (USD)
VRBO
From $752 per night (USD)
VRBO
Location=AMAZING! Garage Parking for 1
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
STR21-145020 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $752 per night (USD)
VRBO
From $896 per night (USD)
VRBO
Beautifully maintained historic 3 BR home and just forty yards from the US Naval Academy Barry Gate
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
RENT-005995-2024 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN ...
From $896 per night (USD)
VRBO
From $264 per night (USD)
VRBO
Spacious 2nd Floor Apartment, with its own entrance and off-street parking.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
STR- 270 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $264 per night (USD)
VRBO
From $494 per night (USD)
VRBO
4 Bedroom/3 Bathroom with parking minutes from downtown Annapolis
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
STR-270 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $494 per night (USD)
VRBO
From $1338 per night (USD)
VRBO
RARELY AVAILABLE -Waterfront Home – Walkable to USNA | 2025/2026 Event Weeks Available
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
NBS23-145368 - This exclusive waterfront property is a rare gem, available for rent only two weeks each year, making it ...
From $1338 per night (USD)
VRBO
From $1634 per night (USD)
VRBO
4 BR on a Quiet Downtown Annapolis Street: Perfect Blend of Yesteryear Charm and Modern Comforts
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
NBS22-145097 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $1634 per night (USD)
VRBO
From $240 per night (USD)
Expedia
Guest quarters at the inn - 205
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Guest Quarters at the Inn is a vacation rental site situated one block from the -Bay in the historic and charming to ...
From $240 per night (USD)
Expedia
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VRBO
Beautiful, clean and Peaceful surrounded by parks
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
There is a room to rent in a three level floor beautiful townhome . The bedrooms are on the third floor with a full bat ...
Click For Pricing
VRBO
From $294 per night (USD)
VRBO
Spacious Townhouse in the Heart of Washington D.C.
Bedrooms:
1
Bathrooms:
1
Sleeps:
7
Summary Enjoy a clean, quiet and spacious place to call your home. Best for visiting the landmarks of Washington DC. Loc ...
From $294 per night (USD)
VRBO
From $231 per night (USD)
VRBO
Guest quarters at the inn - 204
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Guest Quarters at the Inn is a vacation rental site situated one block from the Chesapeake Bay in the historic and c ...
From $231 per night (USD)
VRBO
From $940 per night (USD)
Expedia
Clean, Spacious Family House
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
5 bedrooms (sleeps 9). First-floor wheelchair accessible bedroom with ADA compliant bathroom. Entertaining kitchen and p ...
From $940 per night (USD)
Expedia
From $321 per night (USD)
VRBO
Lovely contemporary in water-privileged community
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Well-furnished contemporary home, great for families, located in a quiet family-friendly neighborhood. This home has 3 ...
From $321 per night (USD)
VRBO
From $733 per night (USD)
VRBO
DISCOUNTED FOR USNA COMMISSIONING WEEK 2024 and 2025! Short term and weekends.
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Beautiful, remodeled 3 BR home with stunning great room addition, 20' x 20' screened, covered porch with newly added out ...
From $733 per night (USD)
VRBO
From $345 per night (USD)
VRBO
Charming cottage with parking. Easy walk to downtown.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover this charming, fully furnished cottage ideally accommodating up to six guests. Nestled on a serene street withi ...
From $345 per night (USD)
VRBO
From $165 per night (USD)
Expedia
Chesapeake Bayside Loft
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Recently updated 1 bedroom, 1 bathroom loft studio unit with fully equipped kitchen, Smart TV in bedroom and free high s ...
From $165 per night (USD)
Expedia
From $499 per night (USD)
VRBO
Adorable cottage! Walking distance to USNA & downtown! (VRBO only)
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Listing will never be posted on Craig's list - VRBO only **Adorable 1930's cape cod, located in the historic Murray Hill ...
From $499 per night (USD)
VRBO
Click For Pricing
Expedia
Vacation house near Downtown Annapolis
Bedrooms:
4
Bathrooms:
7
Sleeps:
12
Enjoy a weekend away in a secluded house in a lovely neighborhood right outside Annapolis. Our house is set back from th ...
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Expedia
From $407 per night (USD)
VRBO
Charming Renovated Historic Home Downtown wparking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Professionally UV sanitized and ozone deep cleaned between guests .Cute and comfortable home in the heart of the HISTORI ...
From $407 per night (USD)
VRBO
From $416 per night (USD)
VRBO
Welcome Aboard the Kathleen Marie!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Unique accommodations on a comfortably equipped 43 foot Hatteras yacht, just a 5 minute drive to historic downtown Annap ...
From $416 per night (USD)
VRBO
From $408 per night (USD)
VRBO
Walk to the Chesapeake Bay! Herrington Harbour is a few blocks away.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Walk to Herrington Harbour South, Rose Haven's 2 acre waterfront park or the market, hair salon, bar and restaurant. Th ...
From $408 per night (USD)
VRBO
Click For Pricing
Expedia
Quiet One Bedroom for the traveling worker
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
This is a quiet house with everything included except a washer and dryer. We share the kitchen and the bathroom. The hou ...
Click For Pricing
Expedia
From $361 per night (USD)
VRBO
Fleet St Retreat in Downtown- Great Location !
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
We welcome you to our brand new renovation on Fleet Street . Purchased in 2016 this house was taken down to the studs so ...
From $361 per night (USD)
VRBO
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Expedia
Cute, cozy rancher close to down town Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Private location with plenty of parking. Newly renovated bathroom, french doors open to deck; great for indoor-outdoor l ...
Click For Pricing
Expedia
From $395 per night (USD)
VRBO
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
A stunning home, “Circa 1885” is a restored piece of Annapolis history. Sitting at one of the two major gateways that l ...
From $395 per night (USD)
VRBO
From $2878 per night (USD)
VRBO
Nantucket on the Chesapeake Heated Pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Enjoy comfort and convenience in this beautifully-appointed home! Nantucket on the Chesapeake has an old-world feel yet ...
From $2878 per night (USD)
VRBO
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VRBO
Private detached 1bedroom guest house.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Just few miles away from Baltimore downtown, Ft Meade, NSA, Annapolis and Washington DC. Less than 5 miles away from BWI ...
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VRBO
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Expedia
Quiet & Relaxing Waterfront Home Near Annapolis
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Quiet and Relaxing Waterfront home 5 minutes from Downtown Annapolis. Ideal for Business stays, Relocation Home, Get Tog ...
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Expedia
From $488 per night (USD)
VRBO
Historic & sunny home w/ Fireplace steps from USNA & Downtown Annapolis
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This beautiful 3-bedroom, 2.5 bath home built in 1900 is located on Prince George Street, one block from Annapolis City ...
From $488 per night (USD)
VRBO
From $193 per night (USD)
VRBO
A Serene Tiny Home Experience
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnish ...
From $193 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Walk to Beach! King Bed & Free Beach Passes
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
<p>Located in North Beach, this welcoming vacation home brings it all within your reach. Thanks to the convenient onsite ...
From $270 per night (USD)
VRBO
From $273 per night (USD)
Expedia
Cozy Cottage 3 beds 2 baths
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Lovely updated 3 bedroom 2 bathroom cottage walking distance to restaurants, shopping and the beach. Nicely decorated ho ...
From $273 per night (USD)
Expedia
From $1066 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 $1066 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 $358 per night (USD)
VRBO
Historic Annapolis Home 1.5 blocks from center of town.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Historic home 1.5 blocks from center of town. Easy walk to the shops, food, harbor, Naval Academy and historic attractio ...
From $358 per night (USD)
VRBO
From $699 per night (USD)
Expedia
★ Midcentury Modern Getaway ★ Prime Location ★
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Immerse yourself in the best that the downtown Historic District of Annapolis has to offer while staying in this complet ...
From $699 per night (USD)
Expedia
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VRBO
Indoor Soft Hot Tub - Family Stay @ The Cape!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Make some memories at this unique and family-friendly place. Family Friendly Staycation fully outfitted to accommodate ...
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VRBO
From $371 per night (USD)
Expedia
Nice 5 BDR / 3 BATH Home near BWI Airport with WIFI, Beach, Parking, Ambiance
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
Business, Govt. or family trip? Riviera Beach welcomes you to this lovely, elegant, well-lit and sanitized 5 BD/3 BATH h ...
From $371 per night (USD)
Expedia
From $286 per night (USD)
VRBO
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)
VRBO
From $349 per night (USD)
Expedia
Quiet Home Close to Downtown Annapolis and Parks
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: This private single family home is located on a quarter acre and is just minutes to everything Annapolis has to ...
From $349 per night (USD)
Expedia
From $994 per night (USD)
VRBO
West Annapolis Cottage
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Summary: Recently renovated, this is the perfect location for your family & friends to enjoy Naval Academy events, boat ...
From $994 per night (USD)
VRBO
From $446 per night (USD)
VRBO
Quiet Relaxing Waterfront Suisse Chalet
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
This spacious, airy and relaxing 3 bedroom house, comes with a beautiful loft and an additional queen pull out sofa be ...
From $446 per night (USD)
VRBO
From $289 per night (USD)
VRBO
Spacious house, great deck & grill, close to boardwalk, shops, and restaurants.
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Modern three-bedroom, two full bath home with half-bath and new furnishings. Quiet neighborhood easily accessible to Sa ...
From $289 per night (USD)
VRBO
From $588 per night (USD)
Expedia
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to La Maison, a light-filled, stylish 4-bedroom, 2.5-bath waterfront retreat on the South River—just minutes fro ...
From $588 per night (USD)
Expedia
From $359 per night (USD)
VRBO
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in the heart of Annapolis' historic district sits this one bedroom, 1.5 bath cozy apartment. A mere stone's thr ...
From $359 per night (USD)
VRBO
From $988 per night (USD)
VRBO
WATERFRONT Historic Home on the Chesapeake Bay
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
WATERFRONT - Beautiful 4 bedroom, 2 1/2 bathrooms newly renovated charming historic home ON the Chesapeake Bay. New mode ...
From $988 per night (USD)
VRBO
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VRBO
Annapolis House
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Traditional 4 bedroom house in neighborhood with loft. Lots of room to move around in with gated back yard. Only 3 mi ...
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VRBO
From $408 per night (USD)
Expedia
Harbor Breezes at Herrington Harbor
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
If you are looking for a comfortable and clean home for your stay while visiting Herrington Harbor, our beaches or other ...
From $408 per night (USD)
Expedia

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