Anne Arundel Area Rentals
From $821 per night (USD)VRBO
Waterfront Home w Pool, Pier & Parking Mins to Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to this beautiful waterfront home in the q ...
From $821 per night (USD)VRBO
From $764 per night (USD)Expedia
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 $764 per night (USD)Expedia
From $980 per night (USD)VRBO
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 $980 per night (USD)VRBO
From $383 per night (USD)Expedia
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 $383 per night (USD)Expedia
From $1350 per night (USD)VRBO
Waterfront Home, Dock, Private Pool & Beach
- 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 $1350 per night (USD)VRBO
From $531 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 $531 per night (USD)Expedia
From $638 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 $638 per night (USD)VRBO
From $702 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 $702 per night (USD)Expedia
From $560 per night (USD)VRBO
Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A serene escape awaits you at our cozy 4-bedroom, 2.5 bath retreat! We are just minutes from Historic Downtown Annapolis ...
From $560 per night (USD)VRBO
From $459 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 $459 per night (USD)Expedia
From $882 per night (USD)VRBO
Parking at Randall House Across from USNA Gate 1
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Experience the Difference: Professionally Managed by iTrip Annapolis The Randall House is an historic gem in the heart ...
From $882 per night (USD)VRBO
From $857 per night (USD)Expedia
Sprawling Luxury Home on a Private Cul De Sac with Gaming Sports Bar, Big Yard Mins to Annapolis
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Experience the Difference: Professionally Managed by iTrip Annapolis Spacious custom home - Perfect for Naval Academy f ...
From $857 per night (USD)Expedia
From $1752 per night (USD)VRBO
Stunning Waterfront Home in Round Bay with multiple living spaces
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Experience the Difference: Professionally Managed by iTrip Annapolis Available for Boat Shows! Ask us about the option ...
From $1752 per night (USD)VRBO
From $381 per night (USD)Expedia
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 $381 per night (USD)Expedia
From $255 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 $255 per night (USD)VRBO
From $244 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 $244 per night (USD)Expedia
From $1016 per night (USD)VRBO
Private Pier Waterfront Jolly Roger mins to DTA
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Experience the Difference: Professionally Managed by iTrip Annapolis Arrive by car or boat to this waterfront home, loc ...
From $1016 per night (USD)VRBO
From $773 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 $773 per night (USD)Expedia
From $352 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 $352 per night (USD)VRBO
From $732 per night (USD)VRBO
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
- 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 $732 per night (USD)VRBO
From $371 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 $371 per night (USD)VRBO
From $491 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 $491 per night (USD)Expedia
From $601 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 $601 per night (USD)VRBO
From $596 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 $596 per night (USD)VRBO
From $647 per night (USD)VRBO
Historic Chapel Views, Steps to USNA Gate 1 w Private Patio & Off-Site Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Experience the Difference: Professionally Managed by iTrip Annapolis When the owners decided to find their Annapolis ho ...
From $647 per night (USD)VRBO
From $395 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 $395 per night (USD)VRBO
From $272 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 $272 per night (USD)VRBO
From $790 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 $790 per night (USD)Expedia
Click For PricingVRBO
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 ...
Click For PricingVRBO
From $229 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 $229 per night (USD)Expedia
From $633 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 $633 per night (USD)VRBO
From $518 per night (USD)Expedia
Go Navy! Steps to USNA, City Dock & Street Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Experience the Difference: Professionally Managed by iTrip Annapolis Stay in the heart of Historic Annapolis just steps ...
From $518 per night (USD)Expedia
From $625 per night (USD)VRBO
Historic Hanover House Across from USNA Gate 3 w Private Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis The fully-renovated 1800 historic home is just ste ...
From $625 per night (USD)VRBO
From $227 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 $227 per night (USD)Expedia
From $388 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 $388 per night (USD)VRBO
From $1016 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 $1016 per night (USD)Expedia
From $1201 per night (USD)VRBO
USNA Stay w Private Pool, Hot Tub, King Beds, Child Safe & Stocked, Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
USNA Family Stay w/Pool - Infant/Toddler Friendly! New in 2026: Blue and Gray Bedding Themes, NEW 8 Person Hot Tub, More ...
From $1201 per night (USD)VRBO
From $532 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 $532 per night (USD)VRBO
From $935 per night (USD)VRBO
Serene Sunsets at Historic Waterfront Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Experience the Difference: Professionally Managed by iTrip Annapolis Enjoy stunning western-facing views across the riv ...
From $935 per night (USD)VRBO
From $547 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 $547 per night (USD)VRBO
From $890 per night (USD)VRBO
Prime Location Modern Comfort 1 Block to Gate 1 w Bar & Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to Modern Elegance in Historic Annapolis ...
From $890 per night (USD)VRBO
From $614 per night (USD)Expedia
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 $614 per night (USD)Expedia
From $716 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 $716 per night (USD)VRBO
From $707 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 $707 per night (USD)Expedia
From $417 per night (USD)VRBO
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Amongst the allure of downtown living, lies this quant Annapolis home. This two bedroom, one and a half bath has a spaci ...
From $417 per night (USD)VRBO
From $584 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 $584 per night (USD)VRBO
From $545 per night (USD)VRBO
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 $545 per night (USD)VRBO
From $951 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 $951 per night (USD)VRBO
From $571 per night (USD)VRBO
Chesapeake Paradise LITE 4+br3ba Peaceful Watrfrnt
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This is a fabulous 4-5 bedroom 3-ba House, affectionately called Porchlandia, with spectacular views on a lush, waterfro ...
From $571 per night (USD)VRBO
From $574 per night (USD)VRBO
Stunning Waterfront Cottage in the Sailing Capital of the World!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Experience an exceptional waterfront setting in the Sailing Capital of the World. This upgraded 2‑bedroom, 1‑bath cottag ...
From $574 per night (USD)VRBO
From $638 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 $638 per night (USD)VRBO
From $2274 per night (USD)Expedia
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 $2274 per night (USD)Expedia
From $950 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 $950 per night (USD)VRBO
From $668 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. We feature a main level open floor plan ...
From $668 per night (USD)VRBO
From $629 per night (USD)VRBO
Historic Annapolis Getaway - 45 steps to Downtown and 150 steps to USNA!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Skridt fra Annapolis By Dock og US Naval Academy- gåtur til alle butikker, restauranter og downtown begivenheder. Denne ...
From $629 per night (USD)VRBO
From $842 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 $842 per night (USD)VRBO
From $302 per night (USD)VRBO
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 $302 per night (USD)VRBO
From $315 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 $315 per night (USD)Expedia
From $268 per night (USD)VRBO
Annapolis Spa Retreat, Sauna, Jacuzzi, King Bed Couples Quiet Loft Apt. Getaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Escape to your own private spa retreat just minutes from Downtown Annapolis. This quiet loft studio is designed for tota ...
From $268 per night (USD)VRBO
From $646 per night (USD)Expedia
USNA Home Steps to Stadium Dog-Friendly w Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Experience the Difference: Professionally Managed by iTrip Annapolis In Navy jargon, the goat locker is a lounge, sleep ...
From $646 per night (USD)Expedia
From $1577 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 $1577 per night (USD)VRBO
From $111 per night (USD)Expedia
Lower Level Loft - Adorable Studio Apt. Near BWI
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Kick back and relax in this calm, stylish space. Newly updated in-law suite with private entrance & outdoor space on bo ...
From $111 per night (USD)Expedia
From $536 per night (USD)VRBO
West River Waterfront Escape with Boat Lift, Kayaks & Bay Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Waterfront West River Retreat with Private Pier, Kayaks & Chesapeake Bay Views Enjoy the best of Maryland waterfront li ...
From $536 per night (USD)VRBO
From $1215 per night (USD)VRBO
42 Acres of Serenity & Nature Just 15 Miles To Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Hole In the Wall Farm I is a large open concept home situated on 42 picturesque acres just 15 minutes from Annapolis. I ...
From $1215 per night (USD)VRBO
From $945 per night (USD)VRBO
Gather, Relax & Explore — Townhome 1 Block from State Capitol Building with Backyard & Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to Naptown Nook, conveniently located in d ...
From $945 per night (USD)VRBO
From $333 per night (USD)Expedia
Large 2 bedroom house with private parking in a nice neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Bring the whole family to this great private duplex with lots of room for fun. You will be close to many attractions. Lo ...
From $333 per night (USD)Expedia
Click For PricingVRBO
MODERN 2022 NEWLY BUILT TOWNHOME
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a stylish experience at this centrally-located and newly-built (2022) Eastport Annapolis townhome. Spacious two li ...
Click For PricingVRBO
From $695 per night (USD)VRBO
Escape Villa in Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Perfect getaway, a short stroll to West Street, the Naval Academy, Navy-Marine Corps Memorial Stadium, City Dock, and Do ...
From $695 per night (USD)VRBO
From $338 per night (USD)VRBO
Searenity Stays, a Cozy Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy 3 Bd, 2 Bth Near Chesapeake Bay, Parks & Playgrounds Currently decorated for Christmas! (Decor to be removed after ...
From $338 per night (USD)VRBO
From $1215 per night (USD)Expedia
Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
The location is ideal - one short block to USNA Gate 3, and just 4 blocks to the downtown waterfront. Home has a privat ...
From $1215 per night (USD)Expedia
From $336 per night (USD)VRBO
Annapolis Charm –Bright 3BR in Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to this spacious and fully furnished home, designed to be your comfortable home away from home. Spanning three l ...
From $336 per night (USD)VRBO
From $758 per night (USD)VRBO
4BR-Gameroom-Firepit-Gym-Walkable-Sleeps 13
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
This is the perfect house for your family friendly visit to Annapolis! *Please no bachelor/bachelorette parties Enjoy ...
From $758 per night (USD)VRBO
From $444 per night (USD)VRBO
Charming 1926 Four Bedroom Home w Ample Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A centrally located home that exceeds all needs and comfort or your family. Both cozy and spacious from well thought ou ...
From $444 per night (USD)VRBO
From $996 per night (USD)Expedia
House near Patapsco River 2700 square feet
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Paradise Beach Retreat Whether you're planning to explore Pasadena, Annapolis, Baltimore, or Washington, DC, this stunn ...
From $996 per night (USD)Expedia
From $467 per night (USD)VRBO
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Bring your boat, your fishing gear, and your appetite for coastal charm! This 3BR/2BA Annapolis cottage offers access to ...
From $467 per night (USD)VRBO
From $535 per night (USD)Expedia
HiddenParadise in Scenic community, mins to attractions & WaterFront. Sleeps 9
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
**Absolutely no parties allowed in the unit. Family unit celebrations ok but must be discussed with host ahead of time. ...
From $535 per night (USD)Expedia
From $651 per night (USD)VRBO
Waterfront home with private pier mins to Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the Difference: Professionally Managed by iTrip Annapolis Enjoy the magnificent waterfront views from this c ...
From $651 per night (USD)VRBO
From $495 per night (USD)VRBO
Brand-new Modern Pasadena Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This cozy new home is located in the heart of Pasadena on a quiet end in Rivera Beach, just a few houses away from publi ...
From $495 per night (USD)VRBO
From $142 per night (USD)VRBO
Spacious Private Basement
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
New to Vrbo!! Private basement w/entrance. Great for PCS season. Just few miles away from Baltimore downtown, Ft Meade, ...
From $142 per night (USD)VRBO
From $695 per night (USD)VRBO
Modern Bay Dream
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy the Chesapeake Bay in this brilliant 3-bedroom, 3-bathroom mid-century modern home nestled in the heart of Deale, ...
From $695 per night (USD)VRBO
From $150 per night (USD)VRBO
Stunning four-bedroom town home located in Millersville
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
This property is a Stunning four-bedroom town home that can accommodate up to 9 guests comfortably. The bedrooms are wel ...
From $150 per night (USD)VRBO
From $662 per night (USD)Expedia
Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis Watch the sunrise on the private beach at Oh Happy ...
From $662 per night (USD)Expedia
From $903 per night (USD)VRBO
A quiet, family retreat home on the Chesapeake Bay, south of Annapolis MD
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
A perfect spot for relaxing, reading, and writing, or as a home-base for visiting the many cultural and natural attracti ...
From $903 per night (USD)VRBO
From $936 per night (USD)VRBO
Pristine Waterfront Home with Expansive Views.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
**Monthly discounts only apply for Off-Season rentals (October-April) If relaxing in luxury on the water is what you a ...
From $936 per night (USD)VRBO
From $1038 per night (USD)VRBO
Unique Listing! Entire Downtown Triplex w/Private Parking! Sleeps 12-18. Pets ok
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 18
Unique opportunity to rent an entire triplex Downtown Annapolis! One property with 3 nearly identical side-by-side uni ...
From $1038 per night (USD)VRBO
From $1136 per night (USD)VRBO
Beautiful Blend of Restoration and Renovation in this Downtown Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this newly updated rental home, a stunning blend of renovation and restoration located in the heart of the Hi ...
From $1136 per night (USD)VRBO
From $882 per night (USD)VRBO
BY THE BAY
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
WATER, WATER everywhere! Our home is centrally located to all the water Bay Ridge has to offer. Our home is located jus ...
From $882 per night (USD)VRBO
From $131 per night (USD)VRBO
Comfort and Convenience! Pet-friendly Unit with Fully equipped Kitchen!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Comfort and convenience. It’s like you never left home. This listing is for a room within a hotel. ✦ Your room is 505 ...
From $131 per night (USD)VRBO
From $651 per night (USD)VRBO
3 bdrm close to city center, great yard & parking! Perfect for cooks and pets!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Approx .7 mile to stadium, 1.4 to Naval Academy. Walk to free shuttle at Park Place and to great coffee every morning fr ...
From $651 per night (USD)VRBO
From $422 per night (USD)Expedia
18th Cent. Charm in Historic Downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Lower level furnished apartment, in one of Historic Annapolis's 10 oldest Private residences. Lovely wood, brick & ornam ...
From $422 per night (USD)Expedia
From $732 per night (USD)VRBO
Secluded Cozy Cottage in Historic Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Beautifully restored 1930s cottage w/ open floor plan & vaulted ceilings provide a homey vibe Enjoy having Historic Ann ...
From $732 per night (USD)VRBO
From $296 per night (USD)Expedia
Lovely bay views with kayaks, bikes, fire pit, crabbing & more
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Charming 3 bedroom, 2 bathroom private cottage is situated in a friendly community along the beautiful Chesapeake Bay. ...
From $296 per night (USD)Expedia
From $387 per night (USD)VRBO
The Hideaway Spot- Waterfront w/ Dock on Long Cove
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Take a moment to unplug in nature with beautiful waterfront views! Perfect space for a family of four, two adult couples ...
From $387 per night (USD)VRBO
From $1684 per night (USD)VRBO
Waterfront Architectural Masterpiece with private dockage available.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Heron Point House is an owner imagined home, designed by one of the region's leading architects and built to perfection. ...
From $1684 per night (USD)VRBO
From $139 per night (USD)VRBO
Nautical Adventure Awaits in Annapolis Suites! Pets Allowed Here! Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Modern family units with private kitchens for the ultimate Annapolis experience This listing is for a room within a hot ...
From $139 per night (USD)VRBO
From $113 per night (USD)VRBO
Your Home Base for Exploring Charm City! Fully-equipped Kitchen, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Comfortable rooms near Baltimore attractions with a free airport shuttle service This listing is for a room within a ho ...
From $113 per night (USD)VRBO
From $1035 per night (USD)VRBO
Walk to the Naval Academy and Historic Annapolis. Private parking at the home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our favorite part of this home is its unbeatable location in downtown Annapolis (DTA)- with private parking. You can wa ...
From $1035 per night (USD)VRBO
From $736 per night (USD)VRBO
Charming Home located minutes from the Naval Academy and Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Private 4BR, 2.5BA luxurious Gem was recently upgraded, and tastefully decorated awaits your arrival. The ranch style ho ...
From $736 per night (USD)VRBO
From $508 per night (USD)VRBO
Prime Eastport Location - Waterfront Condo w Pool & Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Experience the Difference: Professionally Managed by iTrip Annapolis Waterfront Condo with Spa Creek Views, Rooftop Poo ...
From $508 per night (USD)VRBO
From $608 per night (USD)Expedia
Walk to Main St, City Dock, USNA from Historic Catch 22 w Private Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Experience the Difference: Professionally Managed by iTrip Annapolis This charming 3-BR, 2.5-BA townhome is just a 1/2- ...
From $608 per night (USD)Expedia