
Anne Arundel Area Rentals

- From $642 per night (USD)
VRBO
Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This new 4 bed / 3 bath modern luxury home sleeps 10 and is located in a quiet neighborhood near the Westin Hotel. Once ...
From $642 per night (USD)VRBO
- From $291 per night (USD)
VRBO
Annapolis Garden Suite
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our little oasis! We're tucked away on a beautiful residential street yet 7 minutes away from restaurants, co ...
From $291 per night (USD)VRBO
- From $315 per night (USD)
VRBO
Charming 3BDR Bungalow Near Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in a clean, comfortable bungalow near scenic Annapolis! With 3 bedrooms, 2 baths, ample parking, and a fully stock ...
From $315 per night (USD)VRBO
- From $250 per night (USD)
Expedia
The Heron's Nest at Atlantic Marina
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Bay breezes and magnificent views make this quaint cottage the perfect getaway! Only steps away from the beach, this r ...
From $250 per night (USD)Expedia
- From $896 per night (USD)
VRBO
Custom New Home in Eastport. Less than one mile to Naval Academy and City Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by the host ...
From $896 per night (USD)VRBO
- From $434 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 $434 per night (USD)Expedia
- From $721 per night (USD)
VRBO
Steps to USNA and Main St with Private Patio and Parking at Historic Gem
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Take a stroll along the brick-lined sidewalks of Prince George Street in the Historic District and to this fully-renovat ...
From $721 per night (USD)VRBO
- From $241 per night (USD)
VRBO
Annapolis Tree House Apartment- luxury shower, separate space
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This private treehouse apartment, located above a detached garage, is nestled among the treetops on a wooded acre of lan ...
From $241 per night (USD)VRBO
- From $501 per night (USD)
VRBO
Stylish Midcentury Ranch Pet-Friendly Home Just 1.5 Miles from Navy Stadium One-Level Living
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Stylish Midcentury Ranch Just 1.5 Miles from Navy Stadium! This beautifully renovated 4BR/2BA home is perfectly located ...
From $501 per night (USD)VRBO
- From $584 per night (USD)
Expedia
Historic Downtown Union House with Free Off-Site Parking & Private Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy Annapolis, MD in this charming Federal-style home nestled in the heart of the historic district. Spectacularly res ...
From $584 per night (USD)Expedia
- From $334 per night (USD)
VRBO
Waterfront River Cottage for 2, dog-friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This adorable cottage sits on 3 picturesque acres overlooking the Magothy River. The charming, newly-furnished River Co ...
From $334 per night (USD)VRBO
- From $510 per night (USD)
Expedia
💥Your Annapolis Retreat near the beach and downtown💥
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 16
Welcome to our recently renovated retreat in Annapolis. The place is located minutes from downtown, in the neighborhood ...
From $510 per night (USD)Expedia
- From $366 per night (USD)
VRBO
Cozy Annapolis Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in the heart of Annapolis. Walk to downtown, the Naval Academy and Navy Stadium. Meticulously kept home and newly r ...
From $366 per night (USD)VRBO
- From $324 per night (USD)
Expedia
Club Carp North Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Renovated throughout with three bedrooms and two full baths. This kid-friendly home has a large fenced yard with a swing ...
From $324 per night (USD)Expedia
- From $872 per night (USD)
VRBO
Large Home with Pool & 7 bedrooms; sleeps 21
- Bedrooms:
- 2
- Bathrooms:
- 7
- Sleeps:
- 16
Relax at this large 7-bedroom spacious top-quality home that is ideal for large gatherings where all can be together in ...
From $872 per night (USD)VRBO
- From $376 per night (USD)
Expedia
Waterfront Annapolis Home: Fire Pit & Fishing Pier
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Located on Meridith Creek, which flows out to Whitehall and Chesapeake Bays, this charming vacation rental features a la ...
From $376 per night (USD)Expedia
- Click For Pricing
VRBO
Cheerful 1 bedroom w pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cozy one bedroom with pool outdoor eating space and expansive yard for the kids to play in. Private bedroom, bathroom, a ...
Click For PricingVRBO
- Click For Pricing
Expedia
New Townhome/Room!!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Owner and dog live in townhome. Seeking short rentals only. Spacious one bedroom with private bath for professionals see ...
Click For PricingExpedia
- From $778 per night (USD)
VRBO
Captain's Retreat! Newly Renovated - few steps from the beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Beautiful newly renovated 3500 square foot 4 bedroom 2.5 bath home located in Arundel on the Bay! Steps to the Beach and ...
From $778 per night (USD)VRBO
- From $620 per night (USD)
Expedia
Recently Renovated Annapolis Home - Conveniently Located
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This is the perfect getaway home for an enjoyable and relaxing stay in Annapolis. It is conveniently located within walk ...
From $620 per night (USD)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 $176 per night (USD)
Expedia
Deluxe Basement Guest Suite w/ Luxury Amenities Minutes From BWI/Annapolis/DC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to a luxurious retreat in Odenton. Boasting a stylish 2-bed design, stainless steel appliances, a rainfall shower ...
From $176 per night (USD)Expedia
- Click For Pricing
VRBO
Cozy family-home in the woods, 10 min to Naval Academy!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Embed yourself in the quietness of the woods and birds singing. Our backyard has the 5th largest tree of its species in ...
Click For PricingVRBO
- From $303 per night (USD)
Expedia
CHeerful 3-bedroom waterfront home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this relaxing home by the water for your getaway with private pier.It is perfect for vacations, retreats, mee ...
From $303 per night (USD)Expedia
- From $773 per night (USD)
VRBO
Eastport Historic Firehouse with Parking, Dogs OK
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This is a unique home like none other in downtown Annapolis. Originally the Eastport Volunteer Fire Company, founded in ...
From $773 per night (USD)VRBO
- From $622 per night (USD)
Expedia
Parking & Pet Friendly USNA-themed Annapolis home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This Naval Academy-themed 3 Bedroom home was just fully renovated and is ready to host Annapolis visitors! There are mul ...
From $622 per night (USD)Expedia
- From $709 per night (USD)
VRBO
Spacious Waterfront home with stunning views, pool, pier & parking mins to Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to this beautiful waterfront home in the quiet Cool Spring Cove of the Magothy River in Arnold, MD. Not only do ...
From $709 per night (USD)VRBO
- Click For Pricing
Expedia
New TownHome Rentals
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Owner and dog live in townhome. Seeking short rentals only. Spacious one bedroom with private bath for professionals see ...
Click For PricingExpedia
- From $761 per night (USD)
VRBO
The Santi Paradise
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
If you looking for a unique place to stay come to THE SANTI PARADISE. We value you as our guest and are committed to you ...
From $761 per night (USD)VRBO
- From $826 per night (USD)
Expedia
Cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This clean, peaceful, 5 BR, 4 BA house features a waterfront view from 2 spacious decks in a quiet community. Perfect fo ...
From $826 per night (USD)Expedia
- From $350 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 $350 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- From $563 per night (USD)
VRBO
The Liberty House- Pristine Renovation with parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Liberty House ! Tucked away in the Murray Hill section of downtown Annapolis this home is a spacious retreat ...
From $563 per night (USD)VRBO
- From $1833 per night (USD)
Expedia
Riverfront Retreat 7mil from MD Renaissance Fest!
- Bedrooms:
- 7
- Bathrooms:
- 10
- Sleeps:
- 28
Welcome to your serene retreat on the South River! The heart of this expansive estate is a charming cottage with 5 bedro ...
From $1833 per night (USD)Expedia
- Click For Pricing
VRBO
Luxe Waterside Escape with Pool & Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to The Luxe! A newly renovated 5 bedroom 3.5 bath home on the South River, 15 minutes outside of Annapolis & Nav ...
Click For PricingVRBO
- From $867 per night (USD)
Expedia
Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 13
Chesapeake Paradise ("The Paradise") is a stunning, recently remodeled, luxurious, two-story 6+ bedroom 4 bath waterfron ...
From $867 per night (USD)Expedia
- From $576 per night (USD)
VRBO
One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to East Street ! We invite you come spend some time at our gorgeous large home in the heart of the Historic Dist ...
From $576 per night (USD)VRBO
- From $303 per night (USD)
Expedia
Charming Historic Townhouse Steps From USNA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our charming home nestled next to the prestigious Naval Academy in Annapolis. This inviting 1-bedroom, 1-bath ...
From $303 per night (USD)Expedia
- From $255 per night (USD)
VRBO
The Blue Crab Beach House - Free beach passes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to The Blue Crab just a few blocks from the Chesapeake Bay. You will enjoy staying at our newly renovated luxury ...
From $255 per night (USD)VRBO
- From $422 per night (USD)
VRBO
Location Location Location!!!50 Steps from Main Street and all of the action
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
We welcome you to check out our newest listing in the heart of the Historic District with the BEST front porch in downto ...
From $422 per night (USD)VRBO
- 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 PricingVRBO
- From $1159 per night (USD)
VRBO
Waterfront, Dock, Private Pool ~ Your Chesapeake Oasis Awaits You!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Fantastic location, minutes from Annapolis by land or water. Amazing sunrises and sunsets can be seen sitting in an Adi ...
From $1159 per night (USD)VRBO
- From $992 per night (USD)
VRBO
Annapolis Waterfront home with incredible views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Annapolis waterfront property with stunning views of the Chesapeake bay, Gibson and Dobbins Islands, and the wide open M ...
From $992 per night (USD)VRBO
- From $390 per night (USD)
Expedia
Waterfront North Beach Home ~ 2 Mi to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Highlighted by its coastal charm and scenic location, this well-appointed North Beach home is well-suited for small grou ...
From $390 per night (USD)Expedia
- From $499 per night (USD)
VRBO
Chesapeake Cottages- 2 Quaint Waterfront Retreats
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Our tastefully appointed cottages sit on almost an acre of waterfront land. Peaceful and tranquil, yet close to shops an ...
From $499 per night (USD)VRBO
- From $570 per night (USD)
Expedia
All-stop. Rental Midships.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Whether you have come for Commissioning Week or Boat Show, the aptly named Gatehouse is a centrally located townhome ste ...
From $570 per night (USD)Expedia
- From $515 per night (USD)
VRBO
Hot Tub Haven: Cozy Annapolis Backyard Oasis!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A serene escape awaits you at our cozy 4-bedroom, 2.5 bath retreat! We are just minutes away from Historic Downtown Anna ...
From $515 per night (USD)VRBO
- Click For Pricing
Expedia
Waterfront Home On The Chesapeake Bay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy waterfront home. Watch the sunrise on the Chesapeake Bay. 2 bedroom/1 bathroom in the center of town within walking ...
Click For PricingExpedia
- From $841 per night (USD)
VRBO
Newer Waterfront Home on the Chesapeake Bay
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
2021 built waterfront home with sweeping views of the Chesapeake Bay located on a quiet, private road in the community o ...
From $841 per night (USD)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
- Click For Pricing
VRBO
Historic Annapolis Home, Convenient to Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Historic Annapolis home convenient to downtown, restaurants, shopping, commuter routes and public transportation! -0.5 ...
Click For PricingVRBO
- From $419 per night (USD)
Expedia
Coastal Edgewater Home w/ Private Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Your next maritime retreat awaits at this 5-bedroom, 2-bath Edgewater vacation rental! Featuring 2 Smart TVs, a fully eq ...
From $419 per night (USD)Expedia
- From $1318 per night (USD)
VRBO
Parking at Randall House Across from USNA Gate 1
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
The Randall House is an historic gem in the heart of Downtown Annapolis with PARKING for 3 cars! Built in 1880, The R ...
From $1318 per night (USD)VRBO
- From $160 per night (USD)
Expedia
Hanover!!! Full blast of Fun! Relax and Enjoy!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The property features coffee/tea in a common area, a seasonal outdoor pool, and a business center. Free WiFi in public a ...
From $160 per night (USD)Expedia
- From $1116 per night (USD)
VRBO
Sprawling Luxury Home on a Private Cul De Sac with Gaming Sports Bar, Big Yard Mins to Annapolis
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Spacious custom home - Perfect for Naval Academy families and long visits to Annapolis Enjoy your stay in this expansive ...
From $1116 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- From $1819 per night (USD)
VRBO
Stunning Waterfront Home in Round Bay with multiple living spaces
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Available for Boat Shows! Ask us about the option to add on the 5th bedroom. This beautiful home with unobstructed view ...
From $1819 per night (USD)VRBO
- From $1662 per night (USD)
Expedia
Waterfront Escape Near Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 26
A perfect getaway in a quiet neighborhood with access to Whitemarsh Creek, Rhode River & Chesapeake Bay. Beautiful horse ...
From $1662 per night (USD)Expedia
- From $295 per night (USD)
VRBO
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Lovely home in a great neighborhood!! Private entrance. Excellent location. Brand New 2,300 Sq. ft 3 bedroom basement ap ...
From $295 per night (USD)VRBO
- From $376 per night (USD)
Expedia
Adorable home steps from Navy Stadium!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Can’t beat the space and location of this property for your trip to Annapolis! Just a block away from Navy Stadium for a ...
From $376 per night (USD)Expedia
- From $218 per night (USD)
VRBO
Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A beautiful basement apartment in the city of Annapolis, in the quiet Eastport neighborhood, a walk to marinas, historic ...
From $218 per night (USD)VRBO
- Click For Pricing
Expedia
15 minutes Arundel Mills Casino / Mall , Bwi airport
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 3
Has living room bedroom and eat in kitchen . Good for Travel medical professionals, Military , Vacationers that want t ...
Click For PricingExpedia
- From $170 per night (USD)
VRBO
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Welcome to this beautiful three-bedroom, two full bath, and one half bath home located in the tranquil community of Crof ...
From $170 per night (USD)VRBO
- From $51 per night (USD)
Expedia
Great BEDROOM in a townhouse in the heart of Hanover.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Hello, you will be renting a private bedroom in a Very clean and quiet home Spacious living room and dining room Grea ...
From $51 per night (USD)Expedia
- From $294 per night (USD)
VRBO
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Five blocks to Naval Bagels, Agave, Chessie's Wharf, Evelyn's, Bean Rush Cafe, Rutabagas, Grauls Groceries and other sho ...
From $294 per night (USD)VRBO
- From $769 per night (USD)
Expedia
Riverfront home with multiple decks, central AC, washer/dryer - two dogs OK
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Chase Creek Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $769 per night (USD)Expedia
- From $1418 per night (USD)
VRBO
3-story, dog-friendly home near beaches with home theatre, grill & gaming tables
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 15
Bella Chateau Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $1418 per night (USD)VRBO
- Click For Pricing
Expedia
Newly renovated downtown home with patio, gas grill, and gas fireplace
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Blue Angel's Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For PricingExpedia
- From $924 per night (USD)
VRBO
Updated historic home with parking; near Academy, college & harbor - central AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Anchors Aweigh Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $924 per night (USD)VRBO
- From $1064 per night (USD)
Expedia
Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W/D
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The Ship's Bridge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1064 per night (USD)Expedia
- From $1042 per night (USD)
VRBO
Spacious home with an outdoor pool, screened porch, washer/dryer & central AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Thomas Point Tranquility Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $1042 per night (USD)VRBO
- From $136 per night (USD)
Expedia
Quality and Dependable!! 2 Double Beds
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
You’ll find our guest rooms spacious, affordable and comfortable. Whether your tucking into our huge beds and soft beddi ...
From $136 per night (USD)Expedia
- Click For Pricing
VRBO
Beach House (Annapolis) Bay Ridge Community
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Relax on the front porch while enjoying sweeping views of the Chesapeake Bay. Enjoy the beach right in front of house. P ...
Click For PricingVRBO
- From $1024 per night (USD)
Expedia
Private Pier Waterfront Jolly Roger mins to DTA
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Arrive by car or boat to this waterfront home, located in Crownsville, just outside of Annapolis. The private pier is o ...
From $1024 per night (USD)Expedia
- From $609 per night (USD)
VRBO
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Annapolis Beachfront w/Bay Bridge view - Wake up to a beautiful view of the sunrise over the Chesapeake Bay. Go to sleep ...
From $609 per night (USD)VRBO
- From $257 per night (USD)
VRBO
Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This spacious, well-appointed 1 bedroom, 1 European style bath 2nd floor apartment is in the heart of Eastport. You’ll b ...
From $257 per night (USD)VRBO
- From $792 per night (USD)
VRBO
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis\n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
BOOK YOUR ANNAPOLIS VACATION AT BURLEY CREEK HIDEAWAY! Charming home owned by USNA grads. Lovely waterfront two-level ...
From $792 per night (USD)VRBO
- From $329 per night (USD)
VRBO
Annapolis-Eastport Cottage Home - Walk Everywhere - RV Van Parking & Hook-up too
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Walk to all Annapolis has to offer, once parked you’ll never need a car. Walk to City Dock, marinas, restaurants, pubs ...
From $329 per night (USD)VRBO
- From $463 per night (USD)
VRBO
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Charming private space in a quiet neighborhood. Live like locals and enjoy walking or biking around town. Free street p ...
From $463 per night (USD)VRBO
- From $479 per night (USD)
Expedia
Stay mins to downtown in sunny fenced-in backyard in waterfront community Pet-friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Still available for Commissioning Week 2025! Just minutes from Downtown Annapolis, this charming rambler is located in ...
From $479 per night (USD)Expedia
- From $521 per night (USD)
VRBO
Chesapeake Bay Getaway | New Waterfront With Private Pier | Near Annapolis /USNA
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Gorgeous sunrises from your completely remodeled waterfront cottage! Experience fresh Maryland Crabs or fish caught from ...
From $521 per night (USD)VRBO
- From $634 per night (USD)
VRBO
Charm & Style in this Renovated Eastport Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience a cozy retreat in this inviting 3-bedroom, 2-bathroom cottage, just 3 blocks from the historic Spa Creek Brid ...
From $634 per night (USD)VRBO
- From $866 per night (USD)
VRBO
1 Block to USNA at beautifully renovated Historic Chapel Views with back patio and off-site parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
When the owners decided to find their Annapolis home base, they knew they had to be within walking distance to the one’s ...
From $866 per night (USD)VRBO
- From $359 per night (USD)
VRBO
Chesapeake Bay Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
In less than an hour from the D.C. Metro area you're transported to your own private shore on the Chesapeake Bay. This ...
From $359 per night (USD)VRBO
- Click For Pricing
VRBO
House of Cardz- comforts of home by LLOYD SUITES
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
SUMMARY We are pleased to bring you the "House of Cardz". This is our newest listing since launching the popular "Whiske ...
Click For PricingVRBO
- From $245 per night (USD)
VRBO
Truly Waterfront Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cute cottage tucked away amongst the trees on Stoney Creek in Pasadena Md. Enjoy bird watching from the upper deck just ...
From $245 per night (USD)VRBO
- From $334 per night (USD)
VRBO
Private Annapolis Guest Apartment! Walkable to downtown! Location!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Keep it simple at this peaceful and centrally located guesthouse. This charming guest house w/ private access is located ...
From $334 per night (USD)VRBO
- From $773 per night (USD)
Expedia
Charming Annapolis WaterVIEW Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Charming Annapolis home, just 150 feet from the water, with floor to ceiling windows overlooking the expansive waters o ...
From $773 per night (USD)Expedia
- From $382 per night (USD)
VRBO
Your Annapolis Adventure Starts Here!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your charming Annapolis getaway! This beautifully furnished home is the perfect retreat for your stay in this ...
From $382 per night (USD)VRBO
- From $156 per night (USD)
Expedia
Romantic Two Bedroom Condo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the best of both worlds at this fully renovated two-bedroom, one-bath, one-level condo located in the tranqui ...
From $156 per night (USD)Expedia
- From $364 per night (USD)
VRBO
Sunny Glen Burnie Home - On-Site Water Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Whether you fancy city life or lake living, this Glen Burnie home has it all! Equipped with 3 bedrooms, 2 bathrooms, and ...
From $364 per night (USD)VRBO
- From $751 per night (USD)
Expedia
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
1930's Single family home on adorable cul-de-sac downtown Annapolis with off-street parking! Located off West Street in ...
From $751 per night (USD)Expedia
- From $407 per night (USD)
VRBO
Idyllic Pasadena Retreat with Garden + Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Plan your trip to the Baltimore suburbs when you book this whimsical getaway in Pasadena! Situated 20 miles from the hea ...
From $407 per night (USD)VRBO
- Click For Pricing
Expedia
Family Sized Contemporary in Spacious Neighborhood
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
This is a beautiful, family oriented home sitting on over an acre of spacious flat land! Fantastic for NAVAL ACADEMY fam ...
Click For PricingExpedia
- From $299 per night (USD)
VRBO
Downtown furnished apartment - walking distance to restaurants
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Church owned 2nd Floor apartment in historic house - fully furnished - eat-in kitchen, dining room and living room - has ...
From $299 per night (USD)VRBO
- From $513 per night (USD)
Expedia
Go Navy! Steps to USNA, City Dock & Street Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Stay in the heart of Historic Annapolis just steps from the waterfront, shops, restaurants, and the Naval Academy. Owned ...
From $513 per night (USD)Expedia
- From $713 per night (USD)
VRBO
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 $713 per night (USD)VRBO
- From $202 per night (USD)
Expedia
Tranquility Awaits
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Entire Guest House. One bedroom, one bathroom with loft. Three beds, queen, full and twin. Full kitchen, laundry, dedi ...
From $202 per night (USD)Expedia
- From $264 per night (USD)
VRBO
Bay View Studio Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private ...
From $264 per night (USD)VRBO
- From $884 per night (USD)
Expedia
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 15
Home is clean, spacious, and well-maintained, designed for comfort and convenience. Located in a safe residential neighb ...
From $884 per night (USD)Expedia