Home Vacation Home Rentals By Owner In Annapolis, MD

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Exceptional(10)

$1029.67

/ Nightly
Private Vacation Home

Brand New Spacious Luxury Home

Annapolis, Maryland, United States

This brand-new build luxury home in Eastport close to downtown Annapolis has everything you and your guests (up to 16 total!) need for an upgraded stay. Each room has been lovingly curated for a comfortable and unique experience. Guests will sleep in oversized rooms. Private parking and yard!brbrThis home is located in Eastport just outside of downtown Annapolis. It is walking distance to shopping and restaurants.brbrWhy guests love staying at Bay Ridge:brbr☼ Private newly-built home ideal for families, romantic getaways, corporate travel, or a group of friends visiting historic Annapolis, USNA, and other tourist sitesbr☼ Centrally located in Eastport - a historic neighborhood of Annapolis - 1.5 miles to downtown Annapolis, 33 min to BWI airport, 41 minutes to Baltimore, 47 min to Washington DCbr☼ Walking distance to shopping and highly-rated restaurantsbr☼ Right across the street from Annapolis Athletic Club (daily and weekly memberships available)br☼ EV charger (bring your own cable)br☼ Five bedrooms and sleeping accommodations in the finished basement: brPrimary: king bed with large balcony, private bathroom, and huge walk-in closetbrBedroom 2: king bed with a dedicated hall bathbrBedroom 3: two full beds with a dedicated hall bath; 4th bedroom/office: two twin beds with easy access to a half bathbrLoft with 4 twin beds (2 trundle beds)brFinished basement: two twin beds (trundle bed) with access to a full bathbr☼ 4.5 bathrooms: primary bathroom has a dual-showerhead stand-up shower; two hall baths with tub-shower combos; basement bathroom has a tub-shower combo; powder room on main levelbr☼ Large chef's kitchen, with upgraded appliances (gas range), a De'Longhi espresso machine, drip coffee maker, upgraded kitchen supplies and tools and morebr☼ Large dining table with space for 8, plus an extra folding table with 4 chairs is availablebr☼ Two hang-out areas for watching movies and playing gamesbr☼ Smart TV's in hang-out areas and primary bedroombr☼ Basement hangout area with a giant TV and karaoke machine has a wet bar with a wine fridge and sinkbr☼ Attic hangout space with a balcony - perfect for reading, doing yoga and meditating, or setting up with your laptop to send some emailsbr☼ Large cooler for guest usebr☼ Free parking in drivewaybr☼ Private fenced-in backyardbr☼ Fresh linens, towels, toiletries & essentials providedbr☼ Professionally cleaned before each visitbrbr​Look no further than this luxurious and spacious gem in quaint, historic Eastport!brbrWe’ll follow up with a short online registration once you book. It’s fast, simple, and helps us prepare for your visit.brbrFor extra flexibility, consider adding trip insurance for a nominal fee. It can cover you if you need to cancel at the last minute.brbrBay Ridge is managed by a small, female-owned business. We're committed to making sure all of our guests feel welcome and have the best trip ever. Book your trip with confidence that not only will this property be amazing, but the service and attention you get will be, too.brbrThis home is within walking distance of shopping and restaurants. There is free private parking for guests. The driveway can accommodate 3 vehicles.
Bed 6

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Bath 4

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Sleep 16

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Exceptional(41)

$321.1

/ Nightly
Private Vacation Home

Charming Historic Townhouse Steps From USNA

Annapolis, Maryland, United States

Welcome to our charming home nestled next to the prestigious Naval Academy in Annapolis. This inviting 1-bedroom, 1-bathroom accommodation is ideally located within walking distance to downtown, allowing you to explore the city's historic charm and vibrant atmosphere at your leisure.brbrSituated across from the renowned St. John's College, our home offers a picturesque setting with its close proximity to lush green spaces and breathtaking views. Step inside, and you'll find a cozy yet spacious interior that comfortably accommodates up to 4 people.brbrThe bedroom features two comfortable queen beds, providing a restful night's sleep for guests. Additionally, there's a convenient pullout couch in the living area, perfect for extra guests or family members. The tastefully decorated space exudes a welcoming ambiance, ensuring your stay is both relaxing and enjoyable.brbrIn addition to its prime location and comfortable accommodations, our home boasts a full kitchen equipped with all the amenities you need for a convenient and enjoyable stay. Whether you're a culinary enthusiast or simply prefer the convenience of preparing your own meals, our kitchen is fully stocked with appliances, cookware, and utensils.brbrFurthermore, we understand that staying connected and having access to clean clothes are important during your travels. That's why our home includes a washer and dryer, allowing you to conveniently refresh your wardrobe as needed.brbrWhether you're here for a weekend getaway, attending events at the Naval Academy, or exploring the charm of downtown Annapolis, our home provides a delightful home away from home. Book your stay with us and experience the perfect blend of comfort, convenience, and proximity to all that Annapolis has to offer.
Bed 1

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Bath 1

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Sleep 4

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Exceptional(2)

$474.07

/ Nightly
Private Vacation Home

Stunning 4 BR Home - Walking Distance to Stadium

Annapolis, Maryland, United States

Summary:brbrThis charming 4 BR home is conveniently located in Annapolis' Germantown neighborhood; within walking distance to the Navy's Navy-Marine Corps stadium! The home features a large, fenced backyard with a beautiful outdoor deck and fire pit. The home has four bedrooms with king or queen beds, 3.5 bathrooms, and includes a deck off the master suite. The basement includes a Queen-size Murphy bed, the main living room includes a sleeper sofa, and the front room includes a day bed that can sleep two. The home also includes two queen air mattresses. All together, this home is perfect for hosting a large family or group of friends with maximum occupancy of 14 guests! There is a large entertaining kitchen with Wolf range, wine fridge, and other top of the line appliances. Welcome to our home!brbrbrbrThe Space:brbrThis is a 3 floor property (1st floor, 2nd floor, basement) and guests have access to the entire home and fenced in backyard. Guests will enjoy 4 bedrooms and 3.5 bathrooms. There are three bedrooms on the second floor. The primary includes a king bed with a Smart TV and ensuite bathroom. The ensuite bathroom includes a large stand alone bathtub - perfect for relaxing during your stay. The 2nd floor's non-primary bedrooms have a queen sized bed in it with a chest of drawers - perfect for guests staying with us for more than a few days. The second floor's non-primary bedrooms share a bathroom off the hallway. There is also a laundry room containing a full sized washer and dryer on the 2nd floor. brbrbrbrThe basement includes a large living room with a separate bedroom. The basement living room contains a queen-sized Murphy bed in the back which pulls down and can comfortably sleep two additional guests. The basement bedroom also has a queen bed and it does have direct access to the yard from a door in this room. There is a three-quarters bathroom in the basement (sink, toilet, and shower) as well as another washer and dryer pair. brbrbrbrThe main floor contains our living room, which includes a sleeper sofa which can pull out to a full-sized bed and comfortably sleep two additional guests. The front room of the house has a day bed, which can open up and sleep two guests, as well as a smaller eating area. Our kitchen is a spacious chef’s kitchen that includes a Wolf range with flattop and wine fridge. The peninsula is a great prep and entertainment space that allows three guests to sit in stools. Next to the kitchen is the eating area, which can host up to 8 people. In total, our home can host 15 people for dining inside. brbrbrbrThe entire property is fenced in, perfect for guests with dogs. Please ensure you clean up after your furry friends. There is a semi-covered outdoor porch to the rear of the home that makes early mornings with a cup of coffee or late evenings with a glass of wine a relaxing way to enjoy the ambiance of Annapolis. Similarly, outside on the deck and lower patio are two separate seating areas - perfect for outdoor meals starting in the spring through the fall! brbrbrbrOur home does have a driveway that can host 3 vehicles parked in tandem but there is also free street parking in front of the house. Spaces are usually readily available but not guaranteed. Please be respectful of neighbors when parking. Please utilize the driveway before street parking and please try to park in spots in front of our house. It is recommended that guests bring no more than 4 cars so that they don't block spaces in front of neighbors' houses.brbrbrbrGuest Access:brbrGuests have access to the entire house and backyard except for locked storage closets.brbrbrbrThe Neighborhood:brbrThis home is conveniently located in Annapolis's Germantown neighborhood off West Street, near downtown Annapolis. brbr brbrPerfect for Navy sporting events and boat shows, this home is approx. a 15 min walk to Navy-Marine Corps Memorial Stadium and an 8 minute drive from USNA and Downtown Annapolis. brbr brbrAnnapolis' Germantown neighborhood is wonderful! There are tons of restaurants, bars, and boutiques on West St. brbr brbrWalk along the old brick sidewalks much as George Washington or Thomas Jefferson did in the days when Annapolis was the capital of the United States. Architecturally, Annapolis boasts some of the finest 17th and 18th century buildings in the country – including the residences of all four Maryland signers of the Declaration of Independence. brbr brbrAnnapolis is the home of the United States Naval Academy, founded in 1845, and of St. John's College, the third oldest institution of higher learning in the United States. brbr brbrStroll along our waterfront and enjoy the charm of our City Dock. Watch the boats as they cruise our famous Ego Alley. Sit on the seawall and watch the sailboat races as they return to the harbor and see why Annapolis is “America’s Sailing Capital.”brbrbrbrGetting Around:brbrWe recommend that guests either rent a car or (even better) use car sharing options such as taxis or Uber / Lyft services.brbrbrbrOther Things to Note:brbrTo help ensure a smooth, secure, and enjoyable stay for all guests, please review the following important information before booking: brbr brbrCheck-In & Identity Verification Policy brbr brbrAll reservations require the primary guest (the booker) to complete a secure online check-in process prior to arrival. This includes: brbr brbr-Uploading a valid, unexpired government-issued photo ID brbr-Uploading a selfie to confirm identity brbr-Reviewing and signing our rental agreement brbr brbrThis process is similar to hotel check-in and is required because we do not typically have staff on site. Check-in instructions will only be provided once this process is complete. brbr brbrIf you would like to review the rental agreement before booking, please feel free to contact us. brbr brbrIn some cases, we may also request a security deposit and/or apply a damage waiver fee in accordance with booking channel policies. brbr brbrGuest Count & Occupancy Policy brbr brbrEach listing includes a maximum number of guests based on unit type and local regulations. Additional guests are welcome for an added nightly fee: brbr brbr-4 & 5+ bedroom units: $50 per guest, per night after 8 or 10 guests, respectively brbr brbrPlease ensure your guest count is entered accurately at booking. We will confirm the number of guests after reservation. If the guest count changes, pricing may be adjusted accordingly. For safety and compliance purposes, exterior security cameras are used to verify occupancy. Unreported additional guests may result in additional charges. brbr brbrPet Policybrbr brbrThis is a pet-friendly property. While our cleaning team is thorough, guests with severe pet allergies should be aware that dogs, cats, or other animals may have stayed in the space previously.brbr brbrPet fees:brbr brbr$30 per night, per petbrbr$150 per week, per petbrbr$300 per month, per petbrbr brbrPet fees are included in the accommodation rate as long as you choose the appropriate quantity of pets when completing a booking. We confirm this with all guests post booking confirmation. brbr brbrLocal Reservation Policy brbr brbrReservations under 7 nights from guests residing in the local area may be subject to cancellation at our discretion. We handle exceptions on a case-by-case basis. brbr brbrEarly Check-In & Late Check-Out Policy brbr brbrEarly arrivals and late departures are not guaranteed and must be approved in advance. If approved, the following fees apply: brbr brbr-Up to 1 hour: $100brbr-1–2 hours: $200 brbr-2–3 hours: $300 brbr-3+ hours: $400 or the cost of an additional night (whichever is greater) brbr brbrPlease do not assume availability without confirmation. brbr brbrSmoking Policy brbr brbrSmoking is not permitted anywhere on the property, including indoor and outdoor areas. If evidence of smoking is found, an additional cleaning fee of $500 will be applied in accordance with the booking channel's cleaning and damage policies. brbr brbrSpecial Request Policy brbr brbrRequests for items such as pack-n-plays, high chairs, or other non-standard amenities should be submitted at least 7 days before check-in to ensure availability. Requests made closer to arrival will be accommodated if possible but cannot be guaranteed. brbr brbrWe understand that this is a detailed list, and we truly appreciate you taking the time to review it. These guidelines help us maintain a safe, well-cared-for property and ensure a great experience for every guest. Our goal is always for you to feel comfortable, welcome, and well taken care of during your stay.brbrbrbrInteraction with Guests:brbrWe always have a team member in the greater Annapolis area available to assist. I personally live 15-20 minutes away and can assist when in town. I have a property manager who helps me and she lives about an hour away. One of us should be available to help in case of an emergency although it could take us several hours to arrive on site if we are otherwise indisposed.
Bed 4

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Bath 3

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Sleep 14

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Private Vacation Home

Bay Ridge House- Charming 2-Bedroom Home – Large Backyard, Family-Friendly, Clos

Annapolis, Maryland, United States

Summary:brbrRelax and unwind in this charming 2-bedroom, 2 bathroom home just 10 minutes from Downtown Annapolis and the U.S. Naval Academy. Perfect for families or small groups, this cozy retreat features a spacious living area, fully equipped kitchen, and a large fenced backyard ideal for entertaining, grilling, or enjoying a peaceful evening outdoors.brbrWith free parking, high-speed Wi-Fi, and smart TVs, this home is designed for comfort and convenience. Whether you’re visiting for a weekend getaway, Academy event, or Chesapeake Bay adventure, this gem is the perfect home base for your stay.brbrbrbrThe Space:brbrWhere you will sleep:brbrThe master bedroom is located on the first floor of the home and comes with a queen size bed and a master bathroom. brbrThe second bedroom comes with a King size bed with adjacent full size bathroom and plenty of room for clothing storage. brbrbrbrOther home features: brbrWalking distance to public parkbrbrLocated minutes from the Severn River and Chesapeake Bay. brbrMinutes from multiple fully equipped marinas brbrThe driveway can accommodate up to 4 vehiclesbrbrbrbrGuest Access:brbrYou will have access to the entire home during your stay!brbrbrbrGetting Around:brbrUsing a vehicle or ride share service is recommended for this areabrbrbrbrOther Things to Note:brbrSTR01144brbrbrbrSmoking Policy brbr brbrSmoking is not permitted anywhere on the property, including indoor and outdoor areas. If evidence of smoking is found, an additional cleaning fee of $500 will be applied in accordance with the booking channel's cleaning and damage policies.brbrbrbrInteraction with Guests:brbrI am available via messaging, text or call to assist you.
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Bath 2

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Sleep 4

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Exceptional(16)

$448.08

/ Nightly
Private Vacation Home

Wright's Cottage- Pet's Welcome & EV Charging

Annapolis, Maryland, United States

Summary:brWe offer a very tiny, mostly original, cottage built in the 1940’s. Located in the community of Bon Haven, large trees and cool breezes give a cozy, country feel, yet you are so close to the bustling areas of Annapolis! There is RV/EV hookup, an outdoor wood-stove, and a propane grill for your use. The yard in the back of the cottage is fully fenced so your furry friend can freely play. Everything is very laid back at Wright’s cottage. Come relax and take the time to enjoy being you!brbrThe Space:brWright’s Cottage offers 1 bedroom and bath. There is a full kitchen and one living room area. The back sun room contains the washer and dryer. brbrThe RV/EV hookup is 240V/32amp brbrOn the other side of your fenced area you will find freely sauntering dogs, cats, rabbits, fox, birds, deer … and occasionally a gerbil, hamster or a hermit crab or two depending on the season.brbrLucky for us, our neighbors all cherish pets as much as we do and you will certainly witness several dogs and cats playing on the property (outside of your fenced area) during your stay. Please keep this in mind if your pet (or you!) does not appreciate such a raucous. brbrNext door to our home is our neighborhood friendly dog, Keith, a big brown oaf and he may greet you with an obnoxious bark and goofy smile. His smile is your typical Chessie smile and he proudly shows you all of his teeth. He isn’t trying to be a jerk, he’s just in his happy place.brbrGuest Access:brYou will have access to the entire home during your stay.brbrOther Things to Note:brWe are delighted to be back on Airbnb with our new and improved cottage! Whether you have visited before, or this is your first time, we sincerely welcome you and your pets.brbrWe are always looking to improve the cottage and your experience. Please don’t hesitate to reach out to us with any questions, concerns, or even suggestions!brbrInteraction with Guests:brWe are available via Airbnb message in the app by text and phone
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Bath 1

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Sleep 2

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