
Anne Arundel Area Rentals

- From $399 per night (USD)
VRBO
The Very Best location - 50 Steps from Main Street
- 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 $399 per night (USD)VRBO
- From $1175 per night (USD)
VRBO
Waterfront, Dock, Private Pool ~ Weekly & Monthly Rentals available!
- 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 $1175 per night (USD)VRBO
- From $997 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 $997 per night (USD)VRBO
- From $360 per night (USD)
VRBO
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 $360 per night (USD)VRBO
- From $665 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 $665 per night (USD)VRBO
- From $559 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 $559 per night (USD)Expedia
- From $496 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 $496 per night (USD)VRBO
- 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)
VRBO
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)VRBO
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Expedia
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 PricingExpedia
- From $383 per night (USD)
VRBO
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 $383 per night (USD)VRBO
- From $1267 per night (USD)
Expedia
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 $1267 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 $1799 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 $1799 per night (USD)VRBO
- From $1286 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 $1286 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 $197 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 $197 per night (USD)VRBO
- From $160 per night (USD)
Expedia
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 $160 per night (USD)Expedia
- From $52 per night (USD)
VRBO
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 $52 per night (USD)VRBO
- From $420 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 $420 per night (USD)Expedia
- From $1256 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 $1256 per night (USD)VRBO
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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 $805 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 $805 per night (USD)VRBO
- From $793 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 $793 per night (USD)Expedia
- From $759 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 $759 per night (USD)VRBO
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Expedia
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 PricingExpedia
- From $1024 per night (USD)
VRBO
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)VRBO
- From $573 per night (USD)
Expedia
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 $573 per night (USD)Expedia
- 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 $652 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 $652 per night (USD)VRBO
- From $327 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 $327 per night (USD)VRBO
- From $499 per night (USD)
Expedia
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 $499 per night (USD)Expedia
- From $505 per night (USD)
VRBO
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 $505 per night (USD)VRBO
- From $494 per night (USD)
Expedia
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 $494 per night (USD)Expedia
- From $579 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 $579 per night (USD)VRBO
- From $655 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 $655 per night (USD)Expedia
- From $337 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 $337 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $223 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 $223 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 $585 per night (USD)
VRBO
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 $585 per night (USD)VRBO
- From $408 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 $408 per night (USD)VRBO
- From $150 per night (USD)
VRBO
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 $150 per night (USD)VRBO
- From $338 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 $338 per night (USD)VRBO
- From $751 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 $751 per night (USD)VRBO
- From $405 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 $405 per night (USD)VRBO
- Click For Pricing
VRBO
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 PricingVRBO
- From $299 per night (USD)
Expedia
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)Expedia
- From $473 per night (USD)
VRBO
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 $473 per night (USD)VRBO
- From $683 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 $683 per night (USD)Expedia
- From $167 per night (USD)
VRBO
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 $167 per night (USD)VRBO
- From $314 per night (USD)
Expedia
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 $314 per night (USD)Expedia
- From $866 per night (USD)
VRBO
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 $866 per night (USD)VRBO
- From $1165 per night (USD)
Expedia
Quiet home with large yard, close to Navy Bridge.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Come relax at our spacious home and enjoy our quiet neighborhood! We are located near the greatest attractions in Annapo ...
From $1165 per night (USD)Expedia
- From $898 per night (USD)
VRBO
USNA Stay w/ Private Pool, King Beds, Furbabies & CHILD FRIENDLY GEAR
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
USNA Family Stay w/Pool - Infant/Toddler Friendly! Enjoy the newest addition to my “Family Friendly Staycation” home ho ...
From $898 per night (USD)VRBO
- From $418 per night (USD)
Expedia
Easy Annapolis lodging - still available for Sailboat Show!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This home (divided/upper floor only) is perfect for families, situated on a quiet residential street with a gorgeous bac ...
From $418 per night (USD)Expedia
- From $384 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 $384 per night (USD)VRBO
- From $1011 per night (USD)
Expedia
Serene Sunsets at Historic Waterfront Home
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy stunning western-facing views across the river and a natural tidal pond from this sprawling historic home that sit ...
From $1011 per night (USD)Expedia
- From $442 per night (USD)
VRBO
Gem in Downtown Annapolis, close to USNA, St. John's College
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Comfortable stay on quiet street close to Gate 3 USNA and St. John's College. Quick walk to Maryland State House, Maryla ...
From $442 per night (USD)VRBO
- From $651 per night (USD)
Expedia
2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Harrison Hall Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $651 per night (USD)Expedia
- Click For Pricing
VRBO
Dock of the Bay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
You'll have a great time at this comfortable place to stay. Bring your dog kayak, boat or paddle board! Fish off the pie ...
Click For PricingVRBO
- From $1007 per night (USD)
Expedia
Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Modern Elegance in Historic Annapolis Step into this fully-renovated 1900s home, where modern sophistication ...
From $1007 per night (USD)Expedia
- From $519 per night (USD)
VRBO
Water Views - Close to Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Come enjoy an Annapolis getaway. Perfect for vacations, and enjoying the Chesapeake Bay, and Maryland's capital city onl ...
From $519 per night (USD)VRBO
- From $158 per night (USD)
Expedia
Blocks to the Boardwalk!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Park right in front of this beautiful cottage enclosed with a white picket fence. Everything is in walking distance fr ...
From $158 per night (USD)Expedia
- From $498 per night (USD)
VRBO
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 $498 per night (USD)VRBO
- From $409 per night (USD)
Expedia
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Come enjoy a relaxing stay in our coastal waterfront cottage in Epping Forest! Just steps from a community pier perfec ...
From $409 per night (USD)Expedia
- From $418 per night (USD)
VRBO
5-years young STUNNING home with water view!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
5-years-young STUNNING home with OPEN concept, soaring ceilings, hardwoods, gas fireplace, separate laundry room, backya ...
From $418 per night (USD)VRBO
- Click For Pricing
Expedia
Near BWI Airport! Free Breakfast + Pool + Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This 1-bedroom condo in Baltimore, Maryland is a comfortable and affordable accommodation perfect for families, groups a ...
Click For PricingExpedia
- From $3824 per night (USD)
VRBO
Lakefront home with private dock, deck, hot tub, firepit, Ping-Pong, large yard
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Base Camp on the Lake Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $3824 per night (USD)VRBO
- From $1605 per night (USD)
Expedia
Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
The Admiral's Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $1605 per night (USD)Expedia
- From $1518 per night (USD)
VRBO
Dog-friendly riverfront home with dock, 2 balconies, waterside patio, & grill
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
The Master Shipwright Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $1518 per night (USD)VRBO
- Click For Pricing
Expedia
Bay Poolhouse
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Bay Pool House License number 000268 ...
Click For PricingExpedia
- From $485 per night (USD)
VRBO
Adjacent to Annapolis~ by beach, 25 acre park next door & TV shows filmed here!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
The charming home is a 3 bedroom 2 full bath that's been professionally decorated and has exotic tiger hardwood flooring ...
From $485 per night (USD)VRBO
- From $522 per night (USD)
Expedia
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Beautiful waterfront property with a private beach and dock thirty minutes from Annapolis. Perfect for family reunions o ...
From $522 per night (USD)Expedia
- From $675 per night (USD)
VRBO
Annapolis Entertainment Complex
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This gorgeous four bedroom four bathroom home in Arnold that sleeps 10 is perfect for entertaining while you’re in Annap ...
From $675 per night (USD)VRBO
- From $449 per night (USD)
VRBO
Stunning Waterfront Cottage with Breathtaking Views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A Gorgeous, Waterfront setting in the Sailing Capital of the World! Charm, Detail, and Hospitality were not spared in t ...
From $449 per night (USD)VRBO
- From $518 per night (USD)
VRBO
Large Luxury Apartment In Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bed/2 Bath Apartment with additional family room with brand new queen sleeper sofa in Historic Downtown Annapolis step ...
From $518 per night (USD)VRBO
- From $1901 per night (USD)
Expedia
New Waterfront Home near Annapolis, MD
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 10
Beautiful waterfront home built in 2013 located on 75 acres of picturesque farmland. Exceptional, award-winning architec ...
From $1901 per night (USD)Expedia
- From $884 per night (USD)
VRBO
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Conveniently located just 4.5 miles from historic Annapolis the Coastie Cottage is the perfect homebase for your next vi ...
From $884 per night (USD)VRBO
- From $753 per night (USD)
VRBO
Waterfront Oasis in Eastport-Easy Walk to Downtown
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to our Waterfront Oasis in the desirable Eastport section of Annapolis. With 4 bedrooms and an open studio spac ...
From $753 per night (USD)VRBO
- From $449 per night (USD)
VRBO
PERFECT LOCATION in the heart of history
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Be our guest at Historic 19 East Street, in the heart of the Annapolis national landmark district. Walk out the front d ...
From $449 per night (USD)VRBO
- From $328 per night (USD)
VRBO
Walk everywhere . . .just minutes to historic Annapolis, Updated.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A modern historic gem in a 10 unit building in Eastport or as the locals call it the Maritime Republic of Eastport or "M ...
From $328 per night (USD)VRBO
- From $527 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 $527 per night (USD)VRBO
- From $638 per night (USD)
VRBO
Waterfront - Wonderful View, Spacious, Relaxing, Lovely Front Porch and Deck
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy a beautiful spacious 5 bedroom 3.5 bath home in a quiet setting overlooking the Magothy River. The home includes t ...
From $638 per night (USD)VRBO
- From $513 per night (USD)
VRBO
Heart of Historic District!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This three story 1875 home is located in the Heart of Historic Annapolis. Shops, restaurants, historic sites and the Cit ...
From $513 per night (USD)VRBO
- From $195 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 $195 per night (USD)Expedia
- From $340 per night (USD)
VRBO
\"PIER JOY!\" - 3BR WATERFRONT HOME W/PRIVATE DOCK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gorgeous view, expansive covered back porch with fans & cascading stairs down to paver patio, fire pit and a dock where ...
From $340 per night (USD)VRBO
- From $689 per night (USD)
Expedia
Jackson's Bunker in Eastport with fenced-in backyard and dog friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Located in the Annapolis "Republic of Eastport", this charming pet-friendly home is a short walk to restaurants, shops, ...
From $689 per night (USD)Expedia
- From $855 per night (USD)
VRBO
Charming 239-year-old former tavern 1 block to water & shops
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
239-year-old home, formerly a tavern & inn where Thomas Jefferson bought salt & stockings. Beautifully furnished with an ...
From $855 per night (USD)VRBO
- From $254 per night (USD)
Expedia
Pristine Downtown 1-Bedroom Steps from State House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy your stay in the heart of Annapolis's historic district, steps away from the Maryland State House and a few minute ...
From $254 per night (USD)Expedia
- From $471 per night (USD)
VRBO
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The Chesapeake Bay awaits you at this Annapolis vacation rental! 'Admiral's Post' is situated under 4 miles from the cit ...
From $471 per night (USD)VRBO
- From $191 per night (USD)
Expedia
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
SPA Weekend!! Enjoy a Private Sauna, Hot Tub, Massage Shower in our Quiet Loft Studio Apt. Pamper yourself with your own ...
From $191 per night (USD)Expedia
- From $2071 per night (USD)
VRBO
Spacious 6-Bedroom Waterfront Retreat
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
WATERFRONT — Available commissioning week 2026, booked commissioning 2027. Beautiful Nantucket style home right on the S ...
From $2071 per night (USD)VRBO
- From $735 per night (USD)
Expedia
USNA Home Steps to Stadium Dog-Friendly w Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
In Navy jargon, the goat locker is a lounge, sleeping area, and galley on board a naval vessel which is reserved for the ...
From $735 per night (USD)Expedia
- Click For Pricing
VRBO
USNA Commissioning Week 2023 Downtown Annapolis House that sleeps 13 people
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
This 3 story half duplex is in the perfect location, situated in historical downtown Annapolis with a modern day feel, r ...
Click For PricingVRBO
- From $182 per night (USD)
Expedia
Cozy Home in Beautiful Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Keep it simple at this peaceful and centrally located Annapolis home. It has all the amenities and essentials of a home ...
From $182 per night (USD)Expedia
- From $282 per night (USD)
VRBO
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Little House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $282 per night (USD)VRBO
- From $1531 per night (USD)
VRBO
Annapolis Bayfront Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Beautifully restored turn of the century beach cottage located on an acre of landscaped property with magnificent views ...
From $1531 per night (USD)VRBO