Vacation Home Rentals By Owner In Annapolis, MD

Welcome to this meticulously renovated home where no detail has been overlooked. Step into the kitchen and be captivated by the cherry hardwood cabinets, stainless steel appliances, and stunning granite countertops. The gas stove and glass block tile backsplashes add a touch of sophistication, making it a dream kitchen for any gourmet chef. The heated tile floors provide a cozy atmosphere, ensuring your comfort while you prepare culinary delights.brbrThe open living area features beautiful hardwood floors, complemented by new furniture that adds a touch of elegance to the space. For additional sleeping options, there's a pull-out full sleep sofa. Convenience is key, with a half bath and a full washer/dryer available on the main level.brbrUpstairs, you'll find two bedrooms, each with its own full bath. The master bedroom boasts a luxurious king bed, while the guest room offers a comfortable queen bed. Rest and rejuvenate in these well-appointed spaces after a day of exploration or relaxation.brbrThe private yard with its patio and grill is the perfect outdoor retreat. Enjoy the beautiful landscaping as you unwind on the deep-seating couch and club chairs, or gather around the firepit with friends and family. It's an ideal setting for indulging in a glass of wine and creating unforgettable memories.brbrWhile parking is easy on this quiet one-way street, please note that new parking regulations are in effect. All cars must either Pay-to-Park for up to two hours on street. Guests are encouraged to park in the Hillman Parking Garage located less than 3 blocks from the house, but please feel free to ask about other arrangements for on-street parking for your stay. Arrangements must be made in advance to ensure a hassle-free experience.brbrThis well-appointed home has been designed with your comfort and enjoyment in mind, from the exquisite interior details to the inviting outdoor space. Experience the perfect blend of luxury, convenience, and relaxation during your stay in this exceptional vacation rental.

Beautifully Renovated Historic District Home

Annapolis, Maryland, United States

3

Bed

Bath

6

Sleeps

$831.25

Charming cedar shake duplex home in Historic Annapolis adjacent to the Paca Gardens and the Naval Academy. Custom kitchen with granite countertops, stainless steel appliances, and breakfast nook nestled in a windowed bay. Formal living room with a gas fire place and family room with a large screen TV. Three bedrooms plus a large bonus room (sleeps 6-8), and 2 1/2 baths. Enclosed wraparound porch, private rooftop deck, and two off-street private parking places! Walk to Annapolis waterfront and Main Street in 5-7 minutes.

Charming Historic Annapolis Home With Two Off-street Parking Places!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$615.57

Our 1700s home offers a perfect blend of luxury and comfort. With three beautiful bedrooms, three bathrooms, and a sleek lounge area, it’s a perfect place to relax and unwind. The fully stacked kitchen is ready and waiting for you to cook a perfect meal and enjoy a glass of wine. The location is ideal, with the US Naval Academy just a 5-minute walk away. If you are looking for a peaceful escape or a fun vacation, our property has something for everyone.brbr✔ King Bedsbr✔ Smart TVsbr✔ Sport EquipmentbrbrThe spacebrWelcome to our beautiful home! As you step through the door, you'll be greeted by a warm and inviting atmosphere, complete with comfortable furnishings, luxury decor, and all the amenities you need for a relaxing and enjoyable stay. Whether you're here for a romantic getaway, a family vacation, or a business trip, our property has everything you need to feel right at home.brbrFrom the grand bedrooms to the spacious living areas, our property has been carefully designed to provide you with a comfortable and memorable stay. Enjoy a good night's sleep in our plush beds, relax in the modern lounge area, or prepare a delicious meal in our fully equipped kitchen. Also, with so many top attractions and delicious restaurants nearby, you'll never run out of things to see and do in Annapolis. Book your stay at our property today and start creating memories that will last a lifetime!brbr✔ King Sized Bedsbr✔ Modern Decorbr✔ New Appliancesbr✔ Fresh Towels & Linens br✔ 5☆ Resort Comfortsbrbr❖ LIVING ROOM ❖brbrComing into our sleek living room, you'll be greeted by a grand and inviting atmosphere that will make you feel right at home. You'll first notice the expansive sofa opposite a stunning wall-mounted smart TV and a warm fireplace, perfect for snuggling up and watching your favorite movie, sports game, or TV show. There's also a single chair placed next to the fireplace, providing ample seating for everyone.brbrIf you need a quiet space to unwind or catch up on reading, you'll love the two velvet chairs in the corner of the room, accompanied by a charming small table with a chess board on top. The plush velvet chairs offer a comfortable and intimate space to relax and enjoy a cup of tea or engage in a friendly chess game or board game with loved ones.brbr✔ Plush Sofas & Chairsbr✔ Smart HDTVbr✔ Natural Lightbr✔ Chess & Board Gamesbrbr❖️ KITCHEN & DINING ❖ brbrAs you enter our open-plan kitchen and dining area, a warm and inviting atmosphere beckons you to indulge in a sensory experience. Beautiful wooden units are paired with sleek stainless-steel appliances, including a large refrigerator, cooker, oven, microwave, and dishwasher, while multiple coffee makers offer the perfect start to your day.brbrWith ample worktop space, you can unleash your inner chef and create culinary masterpieces before settling down at the modern dining table, complete with four fitting chairs, or take your delicious breakfast onto the breakfast bar, ready and waiting for you with 2 comfortable stools. A carefully selected vintage-inspired bar tool set will let you mix up bar-quality cocktails and take your mixology skills to the next level. And if you're craving some fresh air, the dining area provides direct access to the two large windows opening in the back of the house, perfect for soaking up the sunshine and relishing in the beautiful surroundings.brbr✔ Microwavebr✔ Gas Stovebr✔ Coffee Makerbr✔ Nespressobr✔ French Pressbr✔ Bialettibr✔ Ovenbr✔ Dishwasherbr✔ Wine, Champaign & Cocktail Glassesbr✔ Dinnerware set for 8br✔ Vintage Cocktail Setbr✔ Toasterbr✔ Blenderbr✔ Fridgebr✔ Freezerbr✔ Sink - Hot & Cold Waterbr✔ Silverwarebr✔ Pots & Pansbr✔ Garbage Disposalbr✔ Dining Table with Seating for 4-6 br✔ Breakfast Bar with 2 Bar Stools brbr❖️ SLEEPING ARRANGEMENTS ❖ brbrWelcome to the master bedroom, greeted by a regal king-sized bed covered in luxurious linens and plump pillows. The room boasts a high vaulted ceiling, which creates a relaxing atmosphere, especially when combined with the warm fireplace at the foot of the bed. Two stylish wooden chairs bask in the natural light that floods the room, and ample storage space is available for your belongings.brbrConnected to the master bedroom, bedroom number 2 awaits you with a serene queen-sized bed and wall-mounted HDTV. The room also features a dedicated workspace, perfect for those who need to attend to work during their stay.brbrDescending to bedroom number 3 in the basement, you'll find another king-sized bed. This one is enveloped in plush bedding to ensure a peaceful night's rest. The modern furnishings provide a luxurious feel, while a stylish single chair and small table offer a comfortable spot to curl up with a good book. This bedroom also includes an ensuite bathroom, adding a touch of privacy and extra convenience.brbrWe can provide a Baby Crib, a Pack 'n Play, and other baby gear, as well as a twin inflatable mattress upon request. brbrIf you need additional blankets or pillows, just ask!brbr♛ Bedroom 1: King Bed br♛ Bedroom 2: King Bed With En-Suite Full Bathroombr♛ Bedroom 3: Additional Bedroom With Queen Bed, HDTV, and Dedicated WorkspacebrbrThe bedrooms are equipped with the following amenities. brbr✔ Premium Pillows, Linens, and Sheetsbr✔ Decoration and Comfortsbr✔ Room-darkening shadesbrbr❖️ BATHROOMS ❖brbrMoving onto the bathrooms, located upstairs and accessible from bedrooms number 1 and 3, you'll be greeted by a spacious, fully-tiled walk-in shower that's perfect for unwinding and relaxing after a long day. The vanity area provides ample room for getting ready, while natural light from the window and skylight floods the space, adding to its serene atmosphere.brbrThe second bathroom, situated in the basement as an ensuite, features a stunning walk-in shower and a large mirror for primping and prepping. With its chic gold accents and modern decor, the bathroom perfectly complements the bedroom's luxurious furnishings. It's the ideal spot to indulge in a revitalizing shower and wash away all the stresses of the daybrbrLast but not least, just off the living room area you will find a small stylish half bathroom with a toilet and sink.brbr✔ Showerbr✔ Vanitybr✔ Mirrorsbr✔ Toiletbr✔ Essential Toiletriesbr✔ Cleaning Productsbrbr❖ BASEMENT LIVING ROOM ❖brbrDescend into the basement lounge and you'll be greeted by a delightful seating area with two plush chairs, inviting you to sink in and relax. This intimate space is perfect for a quiet chat or sharing a glass of wine with your loved ones. And for those fitness enthusiasts, you'll find some basic gym equipment available to help you maintain your routine while you're away.brbr✔ Basic Gym Equipmentbr✔ Comfortable Seating for 2brbr❖ LAUNDRY ❖brbrOur laundry area provides easy access to the washer and dryer, ensuring that you won't have to worry about dirty clothes during your stay. Whether you need to wash a few items or do a full load, our laundry facilities are designed to make the process as easy and convenient as possible. With everything you need right at your fingertips, you can focus on enjoying your trip without having to worry about laundry. brbr✔ Washerbr✔ Dryerbrbrbr❖️ ADDITIONAL FEATURES ❖ brbr✔ Wifibr✔ TVbr✔ Hair dryerbr✔ Washing machinebr✔ Dryerbr✔ Ironbr✔ Board gamesbr✔ Ceiling fanbr✔ Heatingbr✔ Smoke alarmbr✔ Carbon monoxide alarmbr✔ Fire extinguisherbr✔ First aid kitbr✔ Dedicated workspacebrbrAnnapolis, Maryland, United StatesbrHistoric downtown Annapolis is a vibrant, thriving 21st-century neighborhood with 18th-century charm. From historic buildings like the State Capitol to colonial homes and the vivid downtown district of shops and restaurants, there is lots to love here. Not to mention views of Chesapeake Bay with myriads of yachts raising their masts out of the water. Our home is located in the heart of Annapolis, just a block from the State Circle and a minute away from the City Dock waterfront, Market House, restaurants, music venues, and art galleries, offering easy access to a range of attractions and amenities. From the iconic US Naval Academy to the vibrant nightlife of Downtown, there is something for everyone just a few steps away. This rare gem in the historic district's heart offers modern convenience and historical glamour.brbrbrGetting aroundbrOur home is located in the heart of Annapolis, Maryland, offering easy walkable access to various attractions and amenities. Take a stroll around the charming streets of Annapolis, filled with historic homes, unique boutiques, and local restaurants. The nearby waterfront is also a must-visit spot, where you can enjoy a leisurely walk along the harbor or hop on a boat tour to explore the Chesapeake Bay.brbrTop 5 attractions nearby:brbr✔ US Naval Academy (5 mins walk)br✔ Maryland State House (1 min walk)br✔ Annapolis Town Dock (3 mins walk)br✔ William Paca House and Garden (4 mins walk)br✔ St. John's College (6 mins walk)brbrbrTop 7 restaurants nearby:brbr✔ Starbucks (1 min walk)br✔ Market House & Rise Up Coffee (2 mins walk)br✔ Teriyaki house (2 mins walk)br✔ DRY 85 (2 mins walk)br✔ Preserve (1 min walk)br✔ Boatyard Bar & Grill (5 mins by car; 8 mins walk & water taxi)br✔ Bread and Butter Kitchen (6 mins by car; 10 mins walk & water taxi)br

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$408.69

Welcome to your Annapolis retreat! This fully renovated Homewood colonial is ideal for Commissioning Week, Navy games, the Boat Show, and more. Enjoy hardwood floors, a sunny master suite with walk-in closet, bunk room, finished basement, and a spacious private deck. Just minutes from downtown, Navy Stadium, and all that Annapolis has to offer—perfect for families or groups looking for comfort and convenience in a prime location.

Walk to the stadium! - Lighthouse on Glenwood

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1088.17

Welcome to the historic Strohm House, just half a block from Main Street and the City Dock, with the U.S. Naval Academy only steps away — with street parking included! Located in the heart of downtown Annapolis, this three-story 1870 Victorian offers the perfect blend of classic charm and tasteful updates. Outside enjoy multiple spots to relax including the front porch, second floor balcony, or brick patio in the fenced in backyard. Matthew Strohm was the first boxing instructor at the USNA.brbrStep inside to discover a thoughtfully curated historically registered home, full of warm colors, enticing artwork, and inviting spaces. The first floor features a cozy living room with elegant decor, a dining room filled with natural light and sophistication, and a cheerful breakfast nook off the recently updated kitchen — the perfect spot for morning coffee or evening conversation.brbrUpstairs, the second floor offers two bedrooms, one with access to a private balcony overlooking the brick patio and tree-lined backyard — where you can sip wine or read a book. A full bath with jacuzzi sits in between the bedrooms.brbrMake your way to the third floor with its private bedroom suite and charming little full bath, where you can glimpse at the Maryland State House dome over the treetops.brbrEnjoy multiple outdoor spaces designed for unwinding and reconnecting. Watch the world go by from the covered front porch, take in the breeze from a second-floor bedroom balcony, or lounge on the brick patio with a view of the deep backyard filled with trees, hydrangeas and haste plants -- offering a rare oasis in the heart of the historic district. A Weber Spirit II gas grill is located on the patio to help make delicious meals along with new memories. brbrLocated in one of the most desirable neighborhoods in Annapolis, you’re just steps from the vibrant waterfront, top-rated restaurants, boutique shops, and centuries of history with this end rowhome. Whether you're visiting for a Naval Academy event, a romantic getaway, or simply to experience the charm of Maryland’s capital, this home offers the perfect launchpad for your stay.brbrBedrooms and bathrooms breakdown:brbr-2nd floor bedroom #1: Full bed and trundle with 2 twin mattresses (one up one down)br-2nd floor bedroom #2: Queen bed (with balcony overlooking backyard)br-Full bath with jacuzzi in between 2nd floor bedrooms.br-3rd floor bedroom: Full bed and small full bathroom with standup shower.br-Half bath on main floor.brbrLiving area and all bedrooms include TVs with streaming services such as Sling TV, HBO Max, Netflix, Hulu and YouTube.brbrPlease note that the house is historic with narrow staircases and three levels. brbrGuest accessbrGuests use the entire property except the locked cellar and two owners closets inside the house.brbr****Parking Information****brIncludes neighborhood street parking for up to 2 vehicles during your stay. Additional vehicles can use the Hillman Garage for paid parking — by the hour or per day — it's right around the corner from the house.brbrHouse readiness: No need to bring any linens -- and the house will be stocked with supplies that should last at least a few days (paper towels, laundry detergent, etc.).

Annapolis History In Style Next to City Dock with Street Parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$310.0

Summary:brThis private single family home is located on a quarter acre and is just minutes to everything Annapolis has to offer, including a short drive or walk to Quiet Waters Park, and other area attractions.brbrOur fully furnished and family-friendly home offers four bedrooms with two separate living areas, and a fully-stocked kitchen for all your cooking needs. With a play structure on site, patio, and convenient location in a quiet neighborhood, there's something for the whole family!brbrThe Space:brThe house has four full bedrooms (with King, Queen, Full, and twin beds plus one full-sized sleeper sofa), three full bathrooms, and two separate living areas. There is also a full-sized office attached to the master bedroom. There dining space both inside and on the outside patio.brbrOutside, there is a large patio, a play structure with swings for children, and a large fully-fenced backyard.brbrThere is parking for up to five cars in the driveway and garage. The house also features a fully-equipped kitchen for cooking, a large television for relaxing in the evening, and enough space for multiple groups to gather comfortably.brbrThe home features a full- sized washer and dryer. Laundry detergent, shampoo, conditioner, and soap are provided.brbrGuest Access:brThe property features a one-car attached garage and a large driveway which can fit multiple cars. There is no on-street parking in the neighborhood. brbrEntry is via a unique pin code which will be provided upon booking. Touchless entry is also available upon request.brbrThe Neighborhood:brThe property is located in a quiet suburban neighborhood with many trails and and parks nearbybrbrGetting Around:brParking is available on-site. Guests should not park on the street in the neighborhood as there is no on-street parking.brbrOther Things to Note:brThe house is located in a quiet, private neighborhood with lots of trees, while still being close to many shops and restaurants. It is within a short drive of all of Annapolis, plus numerous parksbrbrInteraction with Guests:brGuests will have full access to the house and backyard. No one else is present onsite

Quiet Home Close to Downtown Annapolis and Parks

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1210.14

Summary:brbrSpacious 6BR/5BA Annapolis retreat, perfect for large groups & families! Recently renovated with a chef's kitchen, game room, and two patios. Walk to the Navy Stadium and West Annapolis shops. A quick 5-min drive to the downtown harbor. This home comfortably accommodates up to 12+ guests, offering the ideal base for Naval Academy events, boat shows, or a relaxing getaway.brbrbrbrThe Space:brbrWelcome to your spacious Annapolis retreat, recently renovated and perfectly situated for your family and friends to enjoy all the city has to offer. Whether you're here for Naval Academy events, boat shows, or a relaxing getaway, our home is designed for comfort and connection.brbrbrbrThe heart of the home is a large, well-appointed kitchen that flows into a welcoming family room. Gather around the gas fireplace on comfy couches for a movie night on the large TV. The kitchen is ready for your culinary adventures, complete with a Keurig coffee maker. Step directly from the family room onto a large patio with outdoor seating and a gas grill.brbrbrbrThis updated, spacious home offers multiple living and entertainment spaces, including a fully finished basement, two outdoor patios, six bedrooms, and five bathrooms. For those traveling with little ones, a crib and a selection of children's books and toys are available.brbrbrbr**Bedrooms & Sleeping Arrangements**brbrEach bedroom is equipped with a TV, ceiling fan, and cozy bedding for a restful night.brbr* **Second Floor Master Suite:** Features a King bed, an en-suite bathroom, and a private deck—the perfect spot for your morning coffee or an evening cocktail.brbr* **Second Floor Bedrooms (2):** Each furnished with a comfortable Queen bed.brbr* **Third Floor Bedroom 1:** Contains a Queen bed.brbr* **Third Floor Bedroom 2:** Includes two trundle beds, which can be set up as four twin beds.brbr* **First Floor Bedroom:** Offers a trundle bed that can sleep two guests.brbrbrbr**Entertainment & Work**brbr* The lower level is an entertainer's dream, complete with two large flat-screen televisions, ping pong, air hockey, and cornhole boards.brbr* For those needing to stay connected, the home includes high-speed Wi-Fi and a dedicated workspace.brbrbrbrGuest Access:brbrThe house is exclusively yours, without interruption during your stay, so relax, unwind, and make yourself at home.brbrbrbrThe Neighborhood:brbrLocated right off Rowe Boulevard, West Annapolis is the perfect mixture of residences, retail, and businesses. brbrbrbrThe neighborhood is within walking distance of several local Annapolis favorite restaurants and coffee shops such as Evelyn's, Bean Rush Café, Great Harvest Bread Company and Rutabaga Juicery & Eats.brbrbrbrGetting Around:brbrThe home can fit two smaller vehicles or 1 large vehicle in the driveway and street parking is allowed in the neighborhood.brbrbrbrVehicles are recommended to get around the Annapolis area. If you are traveling to the Downtown area, street parking is very limited, but there are parking garages around the area. Additionally, all of the Rideshare companies offer services to get around.brbrbrbrOther Things to Note:brbr* **Enhanced Cleaning:** This property follows enhanced cleaning and disinfection guidelines provided by the CDC, EPA, and WHO. Our home is thoroughly cleaned, and we have disinfected all bathrooms, kitchens, and major touchpoints before your arrival.brbr* **Laundry:** A laundry room with a full-sized washer and dryer is available for your use.brbr* **Extended Stays:** Planning a longer visit Our property is equipped for extended stays, and discounts may be automatically applied when you enter your dates.brbr* **Commissioning Week:** Please note that Commissioning Week rentals are booked as a 7-night block, from Ring Dance Weekend through Memorial Day Weekend.brbrbrbrBe sure to ask about discounted rates for extended stays.brbrbrbrInteraction with Guests:brbrWe respect our guests' privacy and provide a seamless, contactless stay. You will have the entire home to yourselves without interruption. While we will not be present during your stay, we are always available and just a message or phone call away should you need any assistance or local recommendations.

West Annapolis Cottage- 6BR Walk to Navy Stadium

Annapolis, Maryland, United States

6

Bed

5

Bath

14

Sleeps

$2892.75

Welcome to Lynder's Luxury Lodging-Annapolis. brDiscover this 3-bedroom Colonial gem in the heart of Downtown Annapolis (DTA). Rarely available in it's entirety, this tranquil estate is an easy walk to the best of DTA. brThe property boasts 2 queen beds, 1 king bed, a living room with 2 sofas large enough for the average person to sleep on and 4 bathrooms with 2 soaking tubs and 2 custom slate showers. br On the first floor find a cozy living room with 2 sofas large enough for the average person to sleep on. brGuests can unwind in the wonderful surroundings inside or out. brOn the 1st floor enjoy perusing eclectic art from around the world. Take advantage of the high speed internet, game room with regulation pool table, 75 smart tv and a plethora of games for the borrowing. For those interested in testing their culinary skills, the chefs kitchen is ready for your talents, complete with a Jen-Air gas range with griddle, and all (or most) of the nessessary cookware + a formal dining room with seating for 8-12 to enjoy the gourmet meal and full size washer/dryer to wash drips, spills and linen after. brOutside, guests can lounge on the back patio in the array of comfortable seating, use the bbq grill (propane not included) & enjoy beautiful flora scattered among the multiple flower beds. brGuests can truly feel at home. brWe look forward to welcoming you to kickback, relax, and enjoy everything Historic Annapolis and Lynder's Luxury Lodging have to offer.brbr****This property is the owners personal home and usually only available by the suite as a share****

Charming Historic 3-bedroom Estate in Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$749.58

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrIn Navy jargon, the goat locker is a lounge, sleeping area, and galley on board a naval vessel which is reserved for the exclusive use of chief petty officers. By tradition, all other personnel, including officers and even the commanding officer, must request permission to enter the goat locker. brbr brbrThis fully-renovated home's private backyard sits within a stone's throw to the Navy-Marine Corps Memorial Stadium. It's also just 3 blocks to the bustling West Annapolis shops and restaurants and another 2-3 blocks to downtown Annapolis. However, the home itself has all the bells and whistles for a stay in Annapolis: an all-new furnished back patio and yard with a hot tub, fire-pit, BBQ grill, games and complete with a new outdoor kitchen space for prepping, Inside, you'll find a full kitchen with all new appliances, a coffee bar, a dining room table, a sunroom and a family room, each with their own flatscreen TVs. brbr brbrThe home has 2 Queen bedrooms on the 2nd floor, a guestroom with 4 Twin beds on the 3rd floor and room to sleep 3 more in the Queen sofa bed and Futon on the main floor. There's plenty of parking and keyless front entry. Enjoy the many restaurants, historical attractions, and shops just a short drive from downtown Annapolis, or hunker down in the resort area in the back. brbr brbrSLEEPING ARRANGEMENTS 3 BR / 2 BA/ Sleeps 11: brbr2nd Floor Queen Guest room 1: brbr-Queen Bed brbr-Large flatscreen TV brbr-Shared full bath in the hall brbr brbr2nd Floor Queen Guest room 2: brbr-Queen Bed brbr-Large flatscreen TV brbr-Shared full bath in the hall brbr brbr3rd Floor Guest room: brbr-4 Twin beds brbr-Large flatscreen TV brbr-Shared full bath in the 2nd floor hall brbr brbrMain Floor Family Room brbr-Queen sofa bed brbr-Full bath in main floor hall brbr brbrMain Floor Sunroom brbr-Full-size futon brbr-Full bath in main floor hall brbr brbrHIGHLIGHTS: brbr-Large private furnished back deck with hot tub brbr-Large custom outdoor kitchen with BBQ Gas grill (propane tank provided), sink, food prep area and storage brbr-Outdoor fire-pit, dining table for 6 and games (Corn Hole and Horse Shoes) brbr-Fully-stocked kitchen with breakfast bar seating for 3 brbr-Dining room table seats 6 brbr-High Speed Internet and WiFi brbr-4 Big Flatscreen TV's throughout the home brbr-Ping Pong Table in the basement brbr-Office space with desk and monitor brbr-Luxury linens, complimentary toiletries Starter Kit, and boutique-level service brbr-Parking for maultiple cars/SUVs in driveway brbr-Full laundry 2 Washers & a dryer located inside the home brbr-Pets allowed with $150 pet deposit per pet paid before checkin. brbr-Keyless entry brbr brbrProperty Distance to: brbr-Navy Stadium - brbr-Downtown Annapolis – 1.3 miles brbr-U.S. Naval Academy – 1.7 miles brbr-Washington DC – 32 miles brbr-Baltimore - 32 miles brbr brbr*Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid. brbr*All beds are ready made for you with freshly laundered sheets & towels brbr brbrHouse Rules brbrReservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Be respectful of the house and contents. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. brbrCheck-in time: 4:00 pm brbrCheck-out time: 11:00 am

USNA Home Steps to Stadium Dog-Friendly w Parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$866.58

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrEastport Cape Cod – Walk to Downtown Annapolis brbr brbrWelcome to your Annapolis retreat! This all-new Cape Cod in the heart of Eastport offers modern comfort with a touch of coastal charm. With 4 bedrooms and 2.5 baths, there’s plenty of room for families, couples, or friends traveling together. brbr brbrThe bright, open floor plan makes it easy to gather. Cook in the chef’s kitchen with sleek quartz counters and high-end stainless appliances, then share meals at the dining table for six or breakfast bar for four. After a day exploring historic Annapolis, relax in the cozy living area with the flatscreen TV and streaming apps. brbr brbrThe main floor King suite provides ultimate convenience, while upstairs you’ll find another King en-suite plus two Queen bedrooms that share the same spacious bath (double entrance from the King Suite and the hall). brbr brbrStep outside and you’re in the middle of it all. Stroll across the street to Bakers & Co for morning pastries, wander to the waterfront for sunset cocktails, or explore downtown’s shops, restaurants, and cobblestone streets. The Naval Academy is just a mile away, and day trips to Washington, DC or Baltimore are under an hour away. brbr brbrSleeping Arrangements (Sleeps 8): brbrMain Floor King Suite – ensuite bath w/ stand-up shower and heated floor tiles brbr2nd Floor King En-Suite – private bath + hall access brbr2 Queen Bedrooms – shared large hall bath brbr brbrWhat You’ll Love: brbrChef’s kitchen + seating for 10 brbrHigh-speed WiFi + streaming TV brbrLuxury linens + boutique touches brbrWasher/dryer brbrKeyless entry brbrParking pad for 2 cars brbr brbrDistances: brbrDowntown Annapolis – .5 mile brbrU.S. Naval Academy – .9 mile brbrWashington, DC – 33 miles brbrBaltimore – 32 miles brbr brbrHouse Rules: No smoking or parties. Primary renter must be 25+. Security camera at front door + noise monitor (law compliant). brbr brbrCheck-in: 4 PM | Check-out: 11 AM brbrWhether you’re here for a weekend escape, a family gathering, or a Naval Academy visit, this Eastport gem is the perfect home base.

Walk Everywhere From New Eastport Cape Cod with High-End finishes and Gourmet Kitchen

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$453.72

A's by the Cove is ideally located in the heart of downtown Annapolis's Historic and Art Districts. It is a fully updated & detached home with historic charm and an inviting front porch. Well conceived and open floor plan to include a living room (with queen sleeper sofa), a dedicated workspace, 1/2 bath and eat in kitchen on the first floor and 2 bedrooms and a full bath upstairs. Enclosed rear yard provides an opportunity to create a lovely quiet space out our back door. brbrOne parking spot (in a nearby by public lot - less than 60 yard from the house) is included with your rental, you can walk to West street, Main Avenue or the city dock all in less than 10 min. brbrThe property is equipped with a RabbitAir Air Filtering device which allow the interior air to go through a 6-stage filtering twice every hour. it traps allergens & contaminants. It is certified Asthma & Allergy friendly.brbrA perfect location to enjoy Commissioning Week, Boat Shows and other festivals in Historic Annapolis.brbrA's by the Cove has a minimum age requirement. All adult members of your party must be 21 or older unless they are children traveling as part of a family group. Every guest must be registered and verified on your reservation. We have a strict no party or gathering policy.brbrGuest must sign Rental Agreement and provide Government ID.brbrAlthough you have access to the entire house and private backyard, there is one locked owner closet located in the living room. brbrYour arrival (and departure) are fully contactless. You will be provided with detailed check-in instructions the afternoon prior to your arrival including a code and/or mobile app to enter the home.brbrWe are here for you during your stay, but our level of interaction is entirely up to you. We are only a phone call/message away and will respond usually within minutes during extended business hours. During the overnight, we probably wont get back to you until early the next morning. If there is a life threatening emergency, please contact 911 and then call us and leave us a voicemail. We reserve the right to stop by the property at anytime but will give you at least 4 hours notice except in case of emergency.brbrThe property is equipped with video recording camera outside the home. There are 2 cameras located on the front porch and the backyard for the safety of our guests. One on the front porch looking at the front door and one on the back porch looking at the backyard. Those are used for security purpose only. Any recording is automatically deleted after 30 days. brbrThird Party Reservations (Guest not occupying the home) are strictly forbidden and again any channel policy (airbnb, VRBO, booking...). The guest who made the reservation must be an active occupant of the home for the entire duration of the reservation. Unauthorized guests will be removed from the property and the reservation will be immediately canceled. No refund will be provided regardless of the cancellation policy.

Cozy 2br home w/ parking in downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$552.62

Ideally located between the vibrant West Street and the historic Main Street, our downtown Annapolis home offers easy access to restaurants, shops, bars etc.brWe’ve carefully furnished the space to create an inviting maritime environment with 3 bedrooms and 3.5 bathrooms (en-suite) comfortably accommodating up to 7 guests. brThe high ceilings give an open and airy feel, while the inviting front porch offers a cozy east coast touch. The private backyard is perfect for the summer months .brbrWe offer an open floor pan with 3 bedrooms , 3.5 baths and five beds .. USNA family ownedbrbrUSNA family owned. We offer a paid parking space in a nearby city owned Gotts garage ( about 2 blocks away )brPopular Walking distances brWest st shopping and dining - 1 minbrParking garage - 2 minbrChurch circle - 2 minbrMain St shopping and dining - 3 min brAnnapolis City Dock- 7 minbrUSNA Gate 1- 9 min

Darling on Dean Street- Nautical home w parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$792.3

WATER, WATER everywhere! Our home is centrally located to all the water Bay Ridge has to offer.brbrOur home is located just one house away from the Bay Ridge bluff where panoramic views of the Chesapeake Bay provide a backdrop for drinking coffee or cocktail while watching all the boating action taking place on the Bay.brbrYou’ll also be one block in either direction to 2 different sandy beaches on the Bay - Severn River beach and Mayo beach. Spend the day or evening at a beach bonfire and walk home on the community bike trails offset from the road.brbrIn addition to the Bay, you're also a short walk to Lake Ogleton and the Marina. At the marina there is basketball, pickleball, lake access and of course lots of boats!brbrA one mile walk along the Chesapeake Bay/Bay Dr brings you to our hidden treasure: the Chesapeake Bay Foundation (CBF), a nonprofit dedicate to the restoration and protection of this iconic natural resource. We’ve partnered with CBF to create open spaces and trails where you are free to nature walk the beautiful grounds in peace and serenity.brbrWalk or bike the 3.5 mile perimeter of our community and take it all in: friendly neighbors, on-water activities, lemonade stands, or meditative benches with iconic views - Bay Ridge has a little bit of everything.brbrOUR HOME:brbrTwo zone central A/CbrbrHighspeed WIFIbrbrRoutine lawn carebrbr4 bed / 3 bathbrbrSleeps 6brbrBEDROOMS:- 4/3 full baths- 3 downstairs, 1 upstairsbrbrBEDROOM 1: GYM: Keiser stationary bike, full set of dumbbell weights, bands, yoga equip. Brookstone foot massager and TV. Sofa (very comfortable if sleeping needed for 7th person, sheets provided) and chair.brbrBEDROOM 2 and 3: Queen beds, guest towels, extra sheets and blankets-wrapped in dust proof bags.brbrBEDROOM 4: Master Bedroom-upstairs: Surrounded by windows, King Bed with ensuite bathroom, tub/shower, separate commode room. Vanity and mirror area with chair. Guest towels, extra sheets and blankets-wrapped in dust proof bags.brbrBATHS: 2 full baths downstairs- 1 with tub/shower, 1 with walk-in shower-can be handicap adaptablebrbrLIVING ROOM: Very large living /great room. Game bar with assorted board games, backgammon, chess, cards. 52in TV, Gas fireplace (in-op in summer). Large down sofa and loveseat. Plus a chair and a half/ ottoman in a separate reading area to read, watch boats go by or nap.brbrDINING ROOM: Seating for 6 (or 8 if needed) overlooking and open to living room.brbrKITCHEN: All Jenn-Air appliances. 5 burner gas stove, D/W, Convection/microwave and standard oven. Large double door refrigerator. Oster drip coffee maker, tea pot, double toaster, food chopper, food processor, mixer, blender, rice maker, gourmet wok. Assorted large bowls and serving platters. All you need to cook, spices, basic essentials and of course pots and pansbrbrLAUNDRY ROOM: Washer and dryer, beach towels, iron. Detergent and dryer sheets to start.brbrBREAKFAST ROOM: Buffet server, Seating for 4 or (6 if needed) surrounded by sliding glass doors to either sunporch and/or screen porch.brbrSCREEN PORCH: Beautiful views of Chesapeake Bay. Propane heater (operable in summer), seating for 4 (or 6) at table and 2brlarge cushioned chairs and ottoman. A hammock completes the relaxation on screen porch and another one outside porch under the trees to listen to birds, read or nap!brbrSUN PORCH: Weber gas grill, 2 Adirondack chairs/ ottoman in sun and 4 chairs in large completely fenced in shaded backyard.brbrPARKING: 2 driveways: Lawrence Ave has 2 spots, Barry Ave driveway has total 6 car spots. There is no parking on the roads in community. The garage is locked for owners.brbrDISTANCES: 4.5 miles to Downtown Annapolis and US Naval Academybrbr35 miles to Baltimore and Wash DCbrbrPLEASE BE RESPECTFUL OF OUR NEIGHBORS AND COMMUNITY: 25 mph in entire community, No parties, No DOGS/CATS, brPRICING:brMinimum 14 day rental maximum rental 45 days:brFirst 14 days at $695 daybrDay 15 and on at $650/ daybrNO CHILDREN UNDER 12brCleaning fee $350brMD. LICENSE# STR00686

BY THE BAY

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$339.33

This 2-bed, 1.5-bath townhome mixes modern renovations with 1900 classic charm. It's been lovingly decorated to accommodate 6 guests. You'll love the proximity to downtown Annapolis - simply walk one-half block to Main Street circle and Annapolis City Dock. You'll truly be in the middle of everything in this beautiful historic home!brbrWhy guests love staying at 20 Fleet Street:brbr☼ Historic row home right in the heart of downtown Annapolis with tons of natural light and upgraded features, ideal for families, romantic getaways, or a group of friends visiting historic Annapolis, USNA, and other tourist sitesbr☼ Centrally located in downtown Annapolis, on historic Fleet Street, just 1/2 block from the actionbr☼ Two bedrooms: Primary: king bed; Guest: 2 twin bedsbr☼ The full bathroom is on the second level with both bedrooms and has a tub-shower combo; there is a half-bath on the main living areabr☼ Kitchen with all major appliances, a drip coffee maker, kitchen supplies and tools and morebr☼ Comfortable living room for watching movies and playing games, with a sliding glass door out to a private outdoor space br☼ Two outdoor spaces - one at the ground level is fully fenced with outdoor dining and a gas grill; the other is a fenced rooftop with outdoor diningbr☼ Smart TV in the living roombr☼ Fresh linens, towels, toiletries & essentials providedbr☼ Professionally cleaned before each visitbrbrLook no further than this historic rowhome in downtown Annapolis!brbrPlease note that there is no parking on Fleet Street. Guests are encouraged to park in nearby public parking garages.brbrWe’ll follow up with a short online registration once you book. It’s fast, simple, and helps us prepare for your visit. Non-Airbnb guests will be asked to pay a small damage waiver OR refundable deposit.brbrFor extra flexibility, consider adding trip insurance for a nominal fee. It can cover you if you need to cancel at the last minute.brbr20 Fleet Street 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.

Naval Academy Gate 1

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$406.6

Historic home 1.5 blocks from center of town. Easy walk to the shops, food, harbor, Naval Academy and historic attractions. Full kitchen with gas range if you decide not to partake in the plentiful dining options around town. Outside deck with BBQ a great space for entertaining. Verizon Fios Wi-Fi and central AC. Two bedrooms with full baths plus a queen sleeper sofa. Fits up to 6 guests comfortably. Water front park one block away. Perfect for siting and having your morning coffee

Historic Annapolis Home 1.5 blocks from center of town.

Annapolis, Maryland, United States

3

Bed

Bath

6

Sleeps

$518.0

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrFamily-Friendly Coastal Retreat | Walk to Beach | Near Downtown brbrSlow down, reconnect, and make lasting memories by the Chesapeake Bay—where kids can run freely, parents can unwind, and family time comes easy. Located in the waterfront community of Arundel on the Bay, this bright and welcoming home offers access to a community beach, playground, and quiet streets perfect for biking, strolling, and exploring together. brbr brbrEasy, Comfortable Living brbrRenovated kitchen with modern appliances brbrOpen living spaces for gathering after a day in the sun brbr3 bedrooms + sleeper sofa (sleeps 9) brbrDedicated workspace for remote work brbr brbrCommunity Beach Lifestyle brbrStart your mornings with coffee by the water, spend afternoons building sandcastles or paddling along the Bay, and end your day with sunset walks through this peaceful neighborhood. brbrWalk to sandy community beach brbrPlayground and park nearby brbrQuiet, family-friendly streets brbrBeautiful water views and coastal charm brbr brbrOutdoor Space brbrLarge private backyard for kids to play brbrPropane grill for easy family cookouts brbrSpace for relaxing, dining, and evening downtime brbr brbrSleeping Arrangements (Sleeps 9) brbrPrimary Bedroom: King bed, Smart TV brbrQueen Guest Bedroom: Queen bed, Smart TV brbrBunk Room: Twin-over-Full bunk bed brbrFamily Room: Queen-size sleeper sofa brbr brbrAmenities brbrFully equipped kitchen brbrDining table for 6–8 brbrPropane grill brbrHigh-speed WiFi brbrSmart TVs brbrPrivate office workspace brbrWasher & dryer brbrLuxury linens & towels brbrComplimentary starter supplies brbrKeyless entry brbrParking for 2–3 cars brbrNo pets brbr brbrLocation Highlights brbrDowntown Annapolis – 4 miles brbrU.S. Naval Academy – 5 miles brbrWashington, DC – 35 miles brbrBaltimore – 20 miles brbr brbrHouse Rules brbrMinimum age of primary renter: 25 years brbrNo parties, pets, events, or smoking brbrNo unaccompanied minors brbrRespect the home and neighbors brbrCheck-in: 4:00 PM brbrCheck-out: 11:00 AM

Charming Coastal Retreat w Community Beach Dog-Friendly & Mins to Downtown Annapolis

Annapolis, Maryland, United States

3

Bed

Bath

9

Sleeps

$489.77

NOTE: Posted rates do not apply to Holidays, Boat Shows or Commissioning Week. Theybr will be given on request. Rates are based on 8 persons in the home.brbrThis lovely upscale home in Eastport is located in a small private cul-de-sac neighborhood and offers driveway parking for 4 cars. Only 5 blocks to the Spa Creek Bridge. My Kimber Ridge home is decorated with care and has the charm of this historic town. brbrTwo full-size refrigerators and two laundry rooms make this home an excellent choice. A dream kitchen for those who like to cook. Stocked with just about everything you would need - plus some spices for cooking!brbrThe fenced-in backyard is great for families with young children. Our large deck has bench seating and patio furniture to help you enjoy outdoor dining. And don't forget the gas and charcoal grills! A Pack & Play, stroller, and highchair are an added benefit for young families.brbrPark your car in the driveway and walk to the heart of downtown Annapolis in less than 15 minutes - unless you stop on the Spa Creek bridge and enjoy the view of this great sailing community. brbrDon't forget to check out the comments on this site! brbrYou will be asked to send a copy of your Photo ID. Thank you.br brKeywords: Driveway Parking, Gas Grill, Charcoal Grill, Large Deck, Great Location, Gas Stove & Fireplace. Neighborhood curfew.

Upscale home with parking for 4 cars in driveway. Walk to downtown.

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$494.74

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWalk to waterfront restaurants, hop the water taxi into downtown Annapolis, and unwind by your private fire pit—all from this charming Eastport retreat just minutes from the US Naval Academy. This professionally-decorated 2-bedroom, 1.5-bath home offers the perfect blend of comfort, location, and Eastport charm. Perfect for couples or families traveling with their pups! brbr brbrStart your day with coffee on the sunny front porch, then step into the cozy living room with a large flatscreen TV and Queen sleeper sofa. The open layout leads to a stylish dining area and a fully-stocked gourmet kitchen. Step out back to your private fenced patio and deck, complete with firepit, propane grill, and café seating for 4. brbr brbrUnrestricted street parking available. brbr brbrSleeps 7 | 2BR / 1.5BA brbrKing Bedroom (upstairs) brbrQueen + Twin Trundle Bedroom (upstairs) brbrQueen Sleeper Sofa (main floor) brbr1 Full bath upstairs, 1 Powder room downstairs brbr brbrHIGHLIGHTS brbrFenced backyard with private deck, patio, firepit & grill brbrFront porch seating brbrDining table for 4–6 brbrCafé table for 4 on deck brbrHigh-speed WiFi & large Smart TV brbrWasher & dryer inside the home brbrDog-friendly with $150 non-refundable pet fee (per pet) brbrKeyless entry – check yourself in with an electronic code brbrUnrestricted, easy street parking brbrBoutique-level service with starter amenities provided: coffee, toiletries, paper products, dish soap & more brbrAll beds are made with freshly-laundered linens & towels brbr brbrDistance to: brbrDowntown Annapolis: 1 mile brbrUSNA: 1.5 miles brbrDC: 30 miles | Baltimore: 25 miles brbr brbrHouse Rules: brbrNo smoking, parties, or events. One guest must be 25+. Quiet hours: 10pm–8am. brbrCheck-in: 4PM | Check-out: 11AM

Walk to Waterfront & USNA from Eastport Gem with Fire pit, Porch & Fenced-In Yard

Annapolis, Maryland, United States

Bed

1

Bath

7

Sleeps

$1714.59