Vacation Rentals By Owner In Annapolis, MD

Welcome to this newly updated rental home, a stunning blend of renovation and restoration located in the heart of the Historic District. As you step through the front door, you'll be greeted by a beautifully appointed interior that seamlessly blends modern amenities with historic charm.brbrLocated just steps away from Main Street, this home is situated on a quiet street that offers the perfect balance of convenience and tranquility. You can easily explore all the attractions and amenities that the town has to offer while enjoying the peace and quiet of your own private sanctuary.brbrEvery detail of the home has been carefully curated to create an unforgettable vacation experience. From the stylish decor to the luxurious bedding and linens, you'll feel pampered and comfortable throughout your stay.brbrEnjoy the privacy of the backyard - a beautiful oasis that provides a perfect place to relax and unwind. Or, relax on the front porch with a book or a glass of wine in the comfortable deep cushion wicker chairs and watch Annapolis saunter by. brbrFour bedrooms - king, two queens and two twins offer you a variety of sleeping options for you and your guests. And three and a half baths, and full washer/dryer give you all the comforts and amenities you expect.brbrIf you're looking for a vacation rental home that offers the perfect blend of modern convenience and historic charm, look no further than this beautifully appointed home in the heart of the Historic District.brbrAnd, if you are planning to bring one or two cars with you on your visit, we have your parking covered. Resident 24/7 street parking is allowed for up to two cars. If you have more than two cars with you, we have helpful information for where you can park additional cars.

Beautiful Blend of Restoration and Renovation in this Downtown Home

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1657.18

Summary:brThis newly renovated 4-bedroom, 3.5 bathroom home is perfectly situated in the heart of historic downtown Annapolis, making it the ideal retreat for those looking to experience the charm and excitement of the city. Modern elegance featuring high-end finishes, designer furnishings, and thoughtful touches throughout. The home also offers the convenience of on-site parking for 2 vehicles and is within walking distance to the USNA, Annapolis’ best restaurants, shops, and waterfront attractions.brbrThe Space:brUpon entering, you’re greeted by an open-concept living space with abundant natural light, sleek hardwood floors, and a cozy yet sophisticated ambiance. The gourmet kitchen boasts top-of-the-line stainless steel appliances, quartz countertops, and a spacious island that’s perfect for entertaining. The dining area is surrounded by ample natural light and seating. There is also an additional office space and sitting room.brbrWhere you will sleep: brbrThe master suite is a serene oasis with a king-sized bed, a spa-like ensuite bathroom with a walk-in shower, and ample closet space. brbrOn the second floor, there are two additional bedrooms are equally inviting, each with plush bedding, tasteful decor, and easy access to a stylish shared bathroom. brbrOn the third floor you will find a bedroom that comes with three beds, ample closet space and a full size bathroom.

Downtown Annapolis Duke's House

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$607.19

Welcome to our beautifully renovated historic home in the heart of Annapolis! The Fisher House, built in 1885, honors the owner’s great-grandfather, a key figure in the city's fire departments. Nestled just two blocks from Main Street, you’ll have easy access to Annapolis' historic sites, cozy winter shops, delightful dining, and all things Naval Academy!brWe are pet-friendly! Small dogs, 30lbs or less, are welcome to join your stay!brbrStepping out from the charming Fisher House, you find yourself two blocks from the heart of historic Annapolis, ready to explore the city's rich heritage and picturesque surroundings. Just a stone's throw away from this central location, you can begin your journey by strolling down Main Street, where a myriad of boutique shops, cozy cafes, and art galleries await.brbrHeading east from Fisher House, you'll soon reach the majestic Chesapeake Bay, offering breathtaking views and a refreshing breeze. If you're in the mood for a leisurely walk, the scenic Annapolis City Dock is the perfect destination. Here, you can admire elegant sailboats and dine at waterfront restaurants, savoring delicious seafood dishes while soaking in the maritime atmosphere.brbrTo delve deeper into Annapolis' history, venture north from Fisher House to visit the Maryland State House, the oldest state capitol still in continuous legislative use. Marvel at its grand architecture and explore the nearby Maryland State House Square, where you can learn about the city's colonial past through informative plaques and exhibits.brbrIf you're looking to further immerse yourself in Annapolis' maritime culture, consider taking a boat tour from the Annapolis Harbor. Discover the city's maritime traditions, lighthouses, and scenic beauty as you glide along the waterways, providing a unique perspective of the city.brbrFor those interested in the arts, the Arts District of Annapolis, located to the west of Fisher House, boasts numerous galleries and theaters. You can spend hours appreciating local artworks and catching live performances, enriching your cultural experience in the city.brbrNavigating from Fisher House also puts you within reach of delectable dining options. From classic seafood restaurants to trendy eateries serving diverse cuisines, you'll find a culinary delight around every corner. Don't forget to indulge in the famous Maryland crab cakes, a must-try delicacy when in Annapolis.brbrAs the day winds down, you can head back to Fisher House, reflecting on the day's adventures and planning your next outing in this charming and historic city. With its central location, Annapolis invites you to explore, discover, and create lasting memories at every turn.brbrLocation You couldn't ask for better! Just two blocks from Main Street, our home is an ideal retreat for families eager to explore the enchanting sights of Annapolis or Naval Academy families seeking proximity to the Academy. The vibrant energy of the city awaits just steps away.brbrUpon arrival, walk through the white gate on the left side of the home to enter the courtyard, and then proceed through the back door to enter the house.brbrbrbrAs you pass through the white gate onto the back patio, you’re greeted by the warm embrace of our renovated kitchen, bathed in natural light streaming through the windows. The kitchen boasts modern appliances and sleek countertops, inviting you to whip up culinary delights or simply enjoy a morning cup of coffee.brbrFrom the kitchen, step into the inviting living room, where plush chairs and a sofa bed beckon you to relax and converse. Ascend the stairway to discover two additional stories of comfort and refinement. The second floor features a king master bedroom as well as a queen bedroom, along with a full bathroom in the hallway that offers peaceful sanctuaries for rest and relaxation.brbrVenture to the third story, where the final bedroom awaits. It includes an attached bathroom with a stand up shower, a comfortable queen bed, and an additional twin bed.brbrPublic Transportation:brAnnapolis Transit:brAnnapolis Transit operates several bus routes throughout the city, including a convenient Free Shuttle loop that connects key destinations in downtown Annapolis. This shuttle is ideal for visitors, stopping at popular areas like the City Dock, historic downtown, and local parking garages. Route 94 runs through downtown Annapolis, connecting various neighborhoods. For schedules and route maps, refer to Annapolis Transit’s website or the welcome guidebook for up-to-date information.brbrPurple Shuttle:brThe Purple Shuttle is a free shuttle loop that connects major parking areas to popular downtown Annapolis destinations. It’s perfect for getting around the downtown area, with convenient stops near Market Street and key locations. The shuttle also provides easy access to Fisher House, with a drop-off directly across the street. For detailed routes and operating hours, please refer to the welcome guidebook.brbrTaxi Services:brAnnapolis Yellow Cab and A1 Taxi are local services available by phone for pickup. Taxis are commonly found in the downtown area and are a great option for traveling to nearby attractions like the Naval Academy or Westfield Mall.brbrRide-Sharing (Uber & Lyft):brBoth Uber and Lyft operate in Annapolis, with rides readily available, especially near downtown. Simply use their apps to book a ride to explore the area at your convenience.brbrWater Taxis:brWater taxis provide a scenic way to travel between various waterfront destinations, including stops along the Annapolis Harbor. This is a great option for exploring the city by water while visiting popular spots along the coast.brbrParking in Downtown Annapolis:brIf you prefer to drive, parking garages and street parking are available throughout downtown Annapolis. The nearest parking garage is just a short walk from 142 Market Street, located near the City Dock.brbr** Parking Information for Your Stay:** brWe have a dedicated parking spot for you during your stay! Parking is available at the Noah Hillman parking garage, just a 1-minute walk from the home. You can use your car's flashers while unloading your luggage, and then head to the garage once you're finished. brbrEarly Check-In & Late Check-Out PolicybrWe offer early check-in and late check-out upon request, subject to availability.brOne hour is complimentarybrHowever, a fee applies as follows:br • Early Check-In before 3pm for an additional fee of $50 to be paid before check -inbr • Late Check-Out after 12pm for an additional fee of $50 to be paid before check-outbrPlease request in advance so we can confirm availability.

Fisher House - Downtown Annapolis!

Annapolis, Maryland, United States

Bed

Bath

9

Sleeps

$829.59

Watch the sunrise on the private beach at Oh Happy Bay. The quaint two-story, cottage has a private beach on historic Bembe Beach with direct access to safe, shallow water for swimming, paddle boarding, and boating (small boat mooring). Commissioning Week families will be spoiled by the direct line of sight for the Blue Angels air show. brbrThe home is ideal for a large extended family traveling together. Enter the home into the beautifully-renovated kitchen with all new appliances and an adjoining dining room with water views and seating for 6-8. The main floor has a guest room with a Queen bed and full bath with a stand-up shower in the hall. The family room is equipped with a Full-size sleeper sofa. Head outside to the private backyard, with a deck, screened-in gazebo, lounge chairs and a picnic table for outdoor dining, cocktails or morning coffee (sampler starter pack included in your stay).brbrHead back inside and up the stairs to the large family suite with 2 bedrooms, a connecting full bath (with 2 entrances), a sitting room and access to the private 2nd floor balcony. The main bedroom has a King bed and sitting area large enough for a portable crib or air mattress. Across the hall is the guest room with the full bed. The shared bath has 2 vanities, a stand-up shower and soaking tub. Also in the hall is the full-size washer and dryer.brbrThe home has plenty of parking and space to explore with the pups and little family members. brbrLocated walking distance to Annapolis Sailing School and Capital SUP (Paddleboard lessons and rentals), the Eastport Water Taxi (with water access to downtown Annapolis). Annapolis Maritime Museum and Quiet Waters Park are just a short drive away.brbrSLEEPING ARRANGEMENTS 3 BR / 2 BA / Sleeps 8 adults:brbrUpstairs Waterfront Bedroom: br-King bedbr-Sitting roombr-Waterfront balconybr-Queen air mattress available in the closetbr-Shared bathroom with stand-up shower and soaking tubbr-Flatscreen TVbrbrGuest Bedroom across the hall from King Bedroom: br-Full bedbr-Shared bathroom with stand-up shower and soaking tubbrbrMain Floor Bedroom: br-Queen bedbr-Full hall bath in the hall with stand-up showerbrbrFamily Roombr-Full Sleeper Sofabr-Full hall bath with stand-up showerbrbrHIGHLIGHTS:br-Private beach with access to Chesapeake Baybr-Screened-in patio gazebo with dining table for 10br-Back deck with seating, picnic table and beachside seatingbr-Charcoal BBQ grillbr-Gourmet kitchenbr-Dining room table seats 6-8br-High Speed Internet and WiFi br-Big Flatscreen TVbr-Stand-Up paddle boards, life jackets, beach toys, small boat mooring (this is a mooring ball or permanent anchor system off the beach where small boats can be moored) - Available in the summer months only (May-October)br-Luxury linens, complimentary toiletries Starter Kit, and boutique-level service br-Outdoor showerbr-Parking for multiple cars in driveway and on streetbr-Full Laundry room with washer & dryer located inside the homebrbrProperty Distance to: br-Downtown Annapolis – 4 miles br-U.S. Naval Academy – 4.5 miles br-Washington, DC – 34 miles br-Baltimore - 35 milesbrbr* Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going.br* All beds are made for you with freshly-laundered sheets & towels.brbrHouse RulesbrReservations 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. Dogs allowed if $150 pet fee is paid prior to check-in. Be respectful of the house and contents, the neighbors and neighborhood.

Cottage

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$549.39

Welcome to this beautifully renovated midcentury ranch home, perfectly located just 1.5 miles from the Navy-Marine Corps Memorial Stadium and a quick 5-minute drive to Downtown Annapolis. Designed for comfort and convenience, this spacious 4-bedroom, 2-bathroom retreat offers upscale finishes and thoughtful amenities, making it the ideal choice for families, friends, or game-day getaways.brbrWhat You’ll Love:brDeluxe Suite: Relax in the luxurious suite overlooking the peaceful backyard. With a King-size bed, pull-out Full futon, en suite bath, and private wet bar (mini fridge, microwave, coffee maker), it’s your personal oasis.brSpacious King Bedrooms: Each of the three additional King bedrooms ensures restful nights for everyone, sharing a stylishly updated hall bath.brModern Living Spaces: The open-concept living room features a Smart TV, while the dining area with island seating for 8 makes mealtime a breeze.brOutdoor Perks:brStep into the private backyard and unwind around the fire pit, complete with seating for your group—a perfect spot to gather after exploring the city or cheering on your team!brbrSleeping Arrangements (4 BR / 2 BA / Sleeps 10):brDeluxe Suite: King bed, Full futon, en suite bath, Smart TV, wet bar.brKing Guestroom 1: King bed, shared hall bath.brKing Guestroom 2: King bed, shared hall bath.brKing Guestroom 3: King bed, shared hall bath.brAdditional Highlights:brbrGourmet kitchen with stainless steel appliances.brCustom workspace with desk and shelving.brDriveway parking for multiple cars.brWasher/dryer for convenience.brHigh-speed WiFi and two Big Screen Smart TVs.brLuxury linens, boutique-level service, and a complimentary starter pack of toiletries and essentials.brDog-Friendly: Bring your furry friend for a $150 non-refundable pet fee per pet.brbrPrime Location:brNavy-Marine Corps Memorial Stadium: 1.6 miles.brU.S. Naval Academy: 3 miles.brDowntown Annapolis: 5-minute drive.brWashington, DC: 30 miles.brBaltimore: 30 miles.brbrHouse Rules:brGuests must be 25+ to book; no parties, smoking, or events allowed.brQuiet hours apply—please respect our neighbors.brCheck-in: 4:00 PM | Check-out: 11:00 AM.brWhether you’re here to enjoy Annapolis’s vibrant charm, attend a Naval Academy event, or simply relax with family and friends, this home is ready to welcome you!

Modern Comfort meets Mid Century Charm at One-level home, with 4 King Beds and dog-friendly

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$898.32

Steps to the academy and downtown.brbr1 parking spot included for guests in a garage just steps from our home in the Hillman Garage, only a half a mile from the house off of main street. We pay for one parking spot for our guests on a monthly basis. There are also EV chargers in the garage.brbrThis restored three-story row home features plenty of space for relaxation – as you enter, an inviting living room and spacious dining room, separated by a restored two-way brick fireplace that feeds each room. The newly updated gas fireplace ignites with a click, providing cozy warmth and atmosphere for relaxing downtime in the front room or an intimate dinner with family and friends on the dining room side.brbrOn the second floor, a large family room dominates, with a sectional practically begging you to sink into it.brbrThis room overlooks the scene on Prince George Street below and is perfect for movie night, board games, or a quiet nap after a morning of taking in everything Annapolis has to offer. And our full-size second-floor refrigerator is just steps away for a drink or late-night snack ...brbrThe kitchen is appointed with everything you need, including stainless steel appliances, including a blender, air fryer, Instant Pot and everything in between. Whether you’re visiting for a weekend getaway, a Naval Academy event, or a relaxing retreat, our home provides the perfect balance of convenience, comfort, and charm.brbrBook your stay today and experience the best of Annapolis!.

USNA Luxury Home, parking, pet friendly

Annapolis, Maryland, United States

Bed

Bath

13

Sleeps

$257.06

Summary:brEnjoy a wonderful experience at this centrally-located apartment. 2 minute walk to Main Street and all of the attractions Annapolis has to offer - you can't beat the location! The unit has a full kitchen, living room with a queen murphy bed, sunroom with a tv/seating area/sleeper sofa, and an additional room with a daybed. It is perfect for a couple, a group of friends or a small family! Relax on the front porch or back patio with your morning coffee or an evening cocktail!

1 room with additional amazing sunroom

Annapolis, Maryland, United States

Bed

1

Bath

Sleeps

$648.46

Summary:brWelcome to our newly renovated 3BR/2BA apartment in downtown Annapolis! With two king beds, one queen bed, and a queen-sized futon, there's ample space for you and your group. Enjoy the convenience of two full bathrooms, a fully equipped kitchen, and a cozy living room area. Step outside and relax on the patio or unwind on the charming front porch. Explore the historic streets of Annapolis, just steps away from your doorstep. Your comfortable and stylish home away from home awaits you!brbrThe Space:brWelcome to our charming and newly renovated 3-bedroom, 2-bathroom rental unit located in the heart of downtown Annapolis! This exceptional Airbnb offers a delightful blend of modern comfort and historic charm, providing the perfect home away from home for your visit to this captivating city.brbrThe living room offers seating for you and your fellow guests, making it an ideal spot to gather and share memorable moments. You'll also find a fully equipped kitchen, complete with modern appliances and all the necessary amenities to unleash your culinary skills. The three bedrooms in this rental unit have been tastefully furnished to ensure a peaceful night's sleep. The two recently renovated bathrooms are sleek and modern, featuring elegant fixtures and refreshing showers. Fresh towels and essential toiletries are provided to enhance your convenience and comfort during your stay.brbrOne of the highlights of this rental is its unbeatable location. Situated in downtown Annapolis, you'll find yourself just a short stroll away from both West Street and Main Street. Immerse yourself in the vibrant atmosphere as you explore the charming boutiques, art galleries, and restaurants that line the streets. From sampling local delicacies to indulging in retail therapy, this prime location ensures you have everything at your fingertips.brbrAfter a day of sightseeing and adventures, unwind on the outdoor patio or front porch, where you can bask in the gentle breeze and enjoy a glass of wine or a cup of coffee. It's the perfect spot to savor the ambiance and reflect on your day's experiences.brbrWhether you're visiting Annapolis for a weekend getaway, a family vacation, or a business trip, this 3-bedroom, 2-bathroom rental unit is the ideal choice for a comfortable and memorable stay. Book now and make this delightful Airbnb your home base as you explore the historic charm and captivating beauty of downtown Annapolis.brbrOther Things to Note:brParking: brThere is 2 hour meter parking right outside of the building. There is also zone street parking, where non-zone cars can park for 2 hours. The closest parking garage where you can park overnight is Gott's Court Garage which is a 2 minute walk from the building!brbrFollow @the_cathedral_inn for local attractions/restaurant recs!

Downtown Annapolis Gem: 3BR/2BA

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$378.55

Summary:brNewly renovated 2 bedroom apartment in downtown Annapolis. Steps from Main Street and all that Annapolis has to offer - you can't beat the location! brThe unit has a full kitchen, living room, seating area and two bedrooms. Relax on the front porch with your morning coffee or an evening cocktail!brbrThe Space:brWelcome to our charming 2-bedroom unit, conveniently located just a 2-minute walk from the vibrant downtown of Annapolis! This historic gem, situated in a building dating back to 1905, offers a unique and authentic experience that seamlessly blends old-world charm with modern comforts. brbrThis apartment is located in a 5 unit building in historic Annapolis (contact the host if you have a larger group and wish to book any other units in the building!)brbrStep inside and be greeted by the character-filled living space, where a cozy atmosphere invites you to relax and unwind. The quaint yet stylish decor creates a warm ambiance, while the comfortable twin-sized sleeper sofa in the living room provides additional sleeping arrangements for your convenience.brbrThe well-equipped kitchen features all the necessary amenities. Whip up a delicious breakfast or enjoy a home-cooked dinner with your loved ones to share memorable moments.brbrBoth bedrooms are elegantly furnished and offer a queen-sized beds each, ensuring a comfortable and restful night's sleep. Sink into the plush bedding, and let the tranquility of the surroundings envelop you. The historic nature of the building adds an extra touch of authenticity to your stay.brbrThe small full-sized bathroom features a shower, allowing you to freshen up and prepare for your day ahead. Complimentary toiletries and fresh towels are provided for your convenience.brbrAs you step outside, you'll find yourself in the heart of downtown Annapolis, just a short stroll away from an array of shops, restaurants, and attractions. Immerse yourself in the rich history of the city by visiting the United States Naval Academy, exploring the historic landmarks, or taking a leisurely walk along the waterfront.brbrAfter a day of exploration, return to the comfort of your charming unit. Take a moment to relax on the cozy porch, where you can soak up the ambiance of the neighborhood and perhaps plan your next adventure.brbrWhether you're visiting Annapolis for a weekend getaway, a family vacation, or an extended stay, this delightful 2-bedroom unit offers a perfect blend of location, comfort, and historic charm. Experience the magic of staying in a building that tells its own story while enjoying all the conveniences of modern living. Book now and create lasting memories in this enchanting destination!brbrFollow @the_cathedral_inn for local attractions/restaurant recs!brbrOther Things to Note:brParking: brThere is 2 hour meter parking right outside of the building. There is also zone street parking, where non-zone cars can park for 2 hours. The closest parking garage where you can park overnight is Gott's Court Garage which is a 2 minute walk from the building. brbrThere are 5 units total in the building. For larger groups, contact me about renting out more than one unit for your entire clan!brbrFollow @the_cathedral_inn for local attractions/restaurant recs!

2 Bedroom Renovated Condo in Downtown Annapolis

Annapolis, Maryland, United States

Bed

1

Bath

Sleeps

$237.2

Summary:brKeep it simple at this peaceful ground floor apartment steps from Main Street and all that Annapolis has to offer - you can't beat the location! brThe unit has a full kitchen, living room, seating area and large bedroom. Relax on the front porch with your morning coffee or an evening cocktail!brbrThe Space:brOne bedroom apartment with a queen sized bed and a queen sized air mattress. This apartment is located in a 5 unit building in historic Annapolis and a 2 minute walk to downtown. brbr(contact the host if you have a larger group and wish to book any other units in the building!)brbrOther Things to Note:brParking: brThere is 2 hour meter parking right outside of the building. There is also zone street parking, where non-zone cars can park for 2 hours. The closest parking garage where you can park overnight is Gott's Court Garage which is a 2 minute walk from the building.brbrThere are 5 units total in the building. For larger groups, contact me about renting out more than one unit for your entire clan!

Lovely 1 bedroom apartment in downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Select Dates for Price

Charming & cozy, 2- level Victorian style home built in the 1920s. Well stocked w/ modern conveniences for your home away from home. The space offers 3 spacious cabins (rooms), 2 full baths & a cute backyard. The neighborhood is culturally diverse & centrally located to many major attractions, restaurants & shops. If diversity is not your thing, hakuna matata, this may not be the space for you. :Dbr2 min drive to Navy- Marine Corps Stadiumbr5 min drive to Main Stbr6 min drive to City Hallbr7 min drive to Naval Academybr10 min drive to Anne Arundel Medical Center & Annapolis MallbrThe spacebr☀ 3 bedrooms; 3 Queens, 1 sofa bedbr☀ 2 full bathroom; tub/shower combobr☀ Fully equipped kitchen and complimentary coffeebr☀ Laptop-friendly desk and free high speed WiFibr☀ 50” Smart TVbr☀ Ideal location; central with easy access to downtown and all major highwaysbrOther things to notebrFor safety and security a camera has been placed on the exterior of the home, at the entrance .brbrWe LOVE our guests. Our aim is for you to have a wonderful stay while in Annapolis; however, if you're going to be salty, please don't forget to bring the tequila! :D...

Coastal Cabins.

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$271.06

Summary:brEnjoy a stylish experience at this centrally-located apartment. 2 minute walk to Main Street and all of the attractions Annapolis has to offer - you can't beat the location! The unit has a full kitchen, living room, seating area and bedroom. Relax on the front porch with your morning coffee or an evening cocktail!brbrThe Space:brWelcome to our adorable 1-bedroom unit in the heart of historic Annapolis! Located just a delightful 2-minute stroll from downtown, this cozy retreat offers the perfect blend of convenience, comfort, and vintage appeal.brbrThis apartment is located in a 5 unit building (contact the host if you have a larger group and wish to book any other units in the building!)brbrStep into this well-preserved building, constructed back in 1905. While it may be old, its timeless charm shines through, creating an atmosphere that is both quaint and stylish.brbrAs you enter the unit, you'll find yourself in the inviting living room, tastefully furnished with a queen-sized pull-out sofa, providing additional sleeping space for extra guests. Sink into its plush cushions after a day of exploration or convert it into a comfortable bed for a peaceful night's sleep.brbrThe bedroom features a full-sized bed with soft linens and pillows. Drift off to sleep and wake up refreshed, ready to take on another day of adventures in Annapolis.brbrThe full-sized bathroom, complete with a refreshing shower, offers modern amenities while maintaining the unit's nostalgic allure. Fresh towels and essential toiletries are provided for your convenience, ensuring a pleasant and hassle-free stay.brbrWhile the unit embraces its historical roots, it also caters to modern needs. Stay connected with complimentary Wi-Fi and catch up on your favorite shows on the flat-screen TV.brbrAs for the location, it simply can't be beaten. Being a mere 2 minutes' walk from downtown Annapolis, you'll have easy access to an array of shops, restaurants, and entertainment options. Stroll along the cobblestone streets, explore the boutiques, or indulge in the local culinary delights that this vibrant city has to offer.brbrWhether you're visiting for a romantic getaway, a historic exploration, or simply to experience the charm of Annapolis, our 1-bedroom unit offers the perfect retreat in an unbeatable location. Book your stay today and immerse yourself in the rich history and captivating ambiance of this remarkable city.brbrFollow @the_cathedral_inn for local attractions/restaurant recs!brbrOther Things to Note:brParking: brThere is 2 hour meter parking right outside of the building. There is also zone street parking, where non-zone cars can park for 2 hours. The closest parking garage where you can park overnight is Gott's Court Garage which is a 2 minute walk from the building.brbrThere are 5 units total in the building. For larger groups, contact me about renting out more than one unit for your entire clan!brbrFollow @the_cathedral_inn for local attractions/restaurant recs!

Adorable 1 bedroom apartment in downtown Annapolis

Annapolis, Maryland, United States

Bed

1

Bath

Sleeps

$422.61

Amongst the allure of downtown living, lies this quant Annapolis home. This two bedroom, one and a half bath has a spacious fenced in back yard and is only steps away from the Naval Academy. The State House, great restaurants and fantastic shopping are also a close distance. Located on historic East Street, you will also find yourself surrounded by important landmarks, popular seasonal events and an all around perfectly positive Annapolis energy. Whether you're in town for an event, a football game or just having crabs with friends in the backyard; this house is the perfect quintessential Annapolis getaway. *Note: As of October 1st, 2024, we unfortunately can no longer offer a parking pass. There are several overnight parking garages guests can chose use in walking distance to our home. *

A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1040.26

Base Camp on the LakebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrExperience incredible and memorable indoor and outdoor spaces at this spacious waterfront home! Admire unparalleled Lake Ogleton views from your large backyard, which also is equipped with a fantastic dock (6.5+ depth), private hot tub, deck, and a screened porch ready for family game night and crab feasts! Private and comfortable, this home is the perfect choice for your next family adventure.brbrLovely landscaping, a luscious green lawn, a bubbly hot tub, an outdoor Ping-Pong table, a firepit surrounded by colorful Adirondack chairs, a private dock (6.5+ depth), a gas grill, and a variety of outdoor spaces for lounging and entertainment await! Fish and crab off the dock, explore the Chesapeake Bay Foundation Trail and two miles of community beaches, or try your hand at kayaking, jet skiing, boating, sailing, and biking along the lake and the Chesapeake Bay.brbrStep down from the kitchen into the large, comfy living room with large windows and sliding glass doors that lead out to the deck and offer a wall of water views. A gas fireplace and entertainment system are surrounded by comfortable and ample seating for movie night. The screened porch is actually an outdoor living room with comfy seating and a big dining table. The lower-level den provides yet another escape with a brand new loveseat and sleeper sofa, TV, games, and a full bath. The upper-level sitting area with a futon couch/bed has a window side table and two chairs plus a TV.brbrThe kitchen is modern and has been recently renovated with all the amenities and upgrades you need to prepare delicious meals and snacks for the group. Some of the great upgrades you can find include granite counters, wood floors, a Viking oven and range, beautiful cabinetry, a built-in extra large refrigerator/freezer, and two large refrigerated drink drawers. The granite kitchen bar has stool seating for four. An adjacent dining area boasts an extra long dining table for family dinners. Or you might as well take dinner out to the large screened porch off of the kitchen with comfy seating and another large dining table.brbrTHINGS TO KNOWbrbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: There is free parking available for 5 vehicles.brbrDock details: brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Lakefront home with private dock, deck, hot tub, firepit, Ping-Pong, large yard

Annapolis, Maryland, United States

Bed

Bath

16

Sleeps

$268.28

Lovely home in a great neighborhood!! Private entrance. Excellent location. Brand New 2,300 Sq. ft 3 bedroom basement apartment located on stunning property, walking distance to neighborhood private beach/children's playground. Equipped with multiple TV's, a ping pong table, bar cart and many games, this home was built to entertain. The apartment also has a gym and a dedicated work space to fulfill all your needs. 2 parking spaces included with beautiful fenced in backyard. You'll enjoy the outdoor screen in porch and deck. There is a small shopping center with a boutique, many restaurants and a grocery and liquor store 1-2 minutes from the house or drive 10-15 minutes to visit downtown Annapolis, The United States Naval Academy ,Sandy Point State Park, and about 35 miles to Washington D.C./ Baltimore. Perfect for a family getaway, teleworkers, or just a weekend getaway with plenty to do in the vicinity (great Uber/Lyft proximity for Annapolis nightlife). brbrThe spacebrTastefully decorated and furnished for comfort. Private entrance. Safe and quiet.brbrGuest accessbrbrCode is provided prior to check in. New code for new guest.

Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1302.0

Located on one of the most coveted streets in downtown Annapolis, walk to Main St. and City Dock. The Thomas Hyde House not only has beautiful views of the Maryland State House, but also has an extremely rare large parking lot adjacent to the building with at least 5 parking spaces. brbrThe building consists of two levels and a large basement. It's close proximity and walking distance to all downtown Annapolis. brbrTHERE WILL BE A SECURITY HOLD (NOT A DEPOSIT JUST A HOLD) THAT WILL BE RELEASED 3 DAYS AFTER CHECK OUT.brbrRegarding PETS: We strive to provide our guests with a space that is free from animal allergens. We are obligated to allow a genuine service animal however, be aware that the animal CANNOT BE LEFT ALONE at the home at all during your stay, not even caged. If the animal is left alone in the home you will be asked to leave immediately with no refund of unused nights.

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$551.66

Still available for Commissioning Week 2025!brbrEastport's Third Time's the Charm – Steps from Marinas, Dining, and Historic AnnapolisbrThis beautiful home is located in Eastport, just across the Spa Bridge from Historic Annapolis. Enjoy the convenience of walking to marinas, yacht clubs, restaurants, shops, and the new Eastport Brewpub. Take a stroll along the waterfront or use the water taxi to explore the harbor.brbrInterior Features:brLiving Room: Relax in the comfortable living room with hardwood floors and a flat-screen TV.brKitchen & Dining: The recently renovated open kitchen features a breakfast bar, adjacent dining area, and sliding glass doors leading to a large deck.brOutdoor Space: Enjoy the manicured backyard, complete with a private deck, patio, firepit, and cornhole set.brbrBedrooms:brTwo Queen Bedrooms, each Sleeps 2, on the second floor with luxury bedding, sharing the full bath.brAdditional Sleeping Arrangements: Queen sleeper sofa in Living roombrbrHighlights:brPrivate fenced backyard, patio deck and covered front porchbrFirepit with Adirondack chairs and cornholebrGas grill (propane included)brStainless-steel appliances including beverage fridgebrWiFi, big-screen TV, and luxury linensbrDedicated work spacebrStarter pack of toiletries, cleaning supplies, and essentialsbrWasher & dryerbrbrU.S. Naval Academy: 1.5 milesbrWashington, D.C.: 30 milesbrBaltimore: 25 milesbrbrHouse Rules:brNo smoking, parties, pets or eventsbrMust be 25+ to bookbrCheck-in: 4:00 pm | Check-out: 11:00 am

Book for CW 2025 Steps from marinas and restaurants at Eastport Third Time's the Charm

Annapolis, Maryland, United States

Bed

Bath

6

Sleeps

Select Dates for Price

The perfect place to experience amazing sunrise/sunset views on the water, beach within walking distance, restaurants, dining and nightlife. You’ll love it because of the location, the views, and the ambiance. It is a great space for couples, solo adventurers, business travelers, and families (with kids).

Waterfront Beach House with amazing views

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Select Dates for Price

Across the street from the Naval Academy Stadium. Open floor plan with stainless steel appliances, two islands, 8-10 person dining table, 3-sided fireplace & family room. Bedroom & full bath on the first floor. 4 bedrooms upstairs each with their own bathroom. Upstairs family room with large sectional tv area. Driveway has room for 2 cars and street parking permitted. Beautiful backyard outdoor seating area with comfy couches fire pit. Screened in porch with family dining table.

5 BDRM across from the USNA Stadium

Annapolis, Maryland, United States