Vacation Home Rentals By Owner In Annapolis, MD

Friends! We are a USNA family (‘92) and love this town! Walk to bottom of Fleet Street and you are at the docks. Walk to the top and you are at State Circle. Small car garage parking now with EV! Although this blue Carriage House is from the 1800's, you will love all the modern touches including bluetooth speaker, smART tv with local artist paintings, newer kitchen appliances and a Brand New Deck! People watch right outside our door at one of Annapolis’ most photographed murals. Go Navy Beat Army!!brSTR22-145194brThe spacebrPrimary Bedroom- king bed with Novaform mattress. Sconce lights for bedroom readers. Fan with remote and ensuite bathroom.brbrBedroom 2 - Queen custom bed with comfy mattress. Everyone says how comfortable it is.brbrPullout Queen/full CouchbrPlease inquire if you plan to park in the garage. It is very narrow and walls are not straight. Please check your car size. EV charger in garage.

Downtown on Fleet St. desirable home with garage parking and EV Walk everywhere

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$622.47

Welcome to the Restriction Retreat, where trouble checks in. Treat yourself and your family to five-star amenities, an unbeatable location, and indulge with modern comforts. Get the “real” R & R experience located steps from downtown Annapolis. A 2 bed / 2.5 bath home with a living space, dining area, and relaxing patio with a fire-pit. A king and queen bedrooms, and queen pullout sofa, it can sleep up to 6 adults.brbrOur home is not your ordinary Airbnb, it’s a piece of history. Built in 1900, we have designed it with elegance and hospitality first, but don’t take my word for it, experience it yourself. The Restriction Retreat reflects the luxury and charm of historic Annapolis. brbrBetween the aesthetics and the amenities, you’ll have everything you need to relax, recharge, and enjoy your time in downtown Annapolis. Voted one of the most beautiful towns in America by Conde Nast Traveler. You’ll quickly see why we fell in love with it!brbrRestriction Retreat has been carefully designed to reflect the history of the capital of Maryland. Rich with traditions from the Naval Academy and local experiences. While the home has been updated, we tried to maintain some historical details which makes it unique and reflects the character and history of Annapolis. brbrWe combined luxury and vintage with amenities of today. If you love to cook, we welcome you to our chef’s kitchen to whip up an amazing meal for your family. brbrFollow us on IG @Restriction.Retreat to view more photos of the space and check out upcoming events.

Restriction Retreat - Relax & walk to Main St

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$706.23

Annapolis Bungalow Home that is professionally cleaned and is a full time short-term rental. I have been a Superhost with other listings for over 10 years. Walking distance to Navy Stadium and to Park Place where you can jump on the trolley and take a ride through town.There is a kayak/paddle launch at the bottom of the street. Enjoy the spacious backyard deck and yard. Bring your kayaks and store on our rack and walk it down to the launch. No recording devices are inside the home, strictly outside and in sight so that we can monitor who is coming inside the home as per VRBO policy. One doorbell camera and one backyard camera.

Chesapeake Comfort, Annapolis.

Annapolis, Maryland, United States

Bed

2

Bath

6

Sleeps

$393.3

Settle in by a cozy wood fire, walk the beaches at sunrise, visit Historic Annapolis museums, restaurants, and vibrant nightlife. The house sleeps 6 or 7 and is fully set up with fresh linens, fluffy towels, a soaker tub, and filled with good books and original art. The private backyard is fully fenced, surrounded by bamboo, two fish ponds and a life-size Buddha statue. Grill something delicious and eat on the back deck, enjoy the birdsong and the fragrant wisteria arbor. It's one of the original 1940s cottages built in the Bay Ridge resort community, renovated for comfort while keeping the charm.

Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1505.54

Summary:brbrThis 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.brbrbrbrThe Space:brbrUpon 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.brbrbrbrWhere you will sleep: brbrbrbrThe 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. brbrbrbrOn 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. brbrbrbrOn the third floor you will find a bedroom that comes with three beds, ample closet space and a full size bathroom.brbrbrbrGuest Access:brbrYou will have private access to the entire home. For your convenience, we offer seamless self check-in with a smart lock. A washer and dryer are also available for your use during your stay.brbrbrbrThe Neighborhood:brbrHistoric cobblestone sidewalks are a captivating feature found around the neighborhood. Walking on these cobblestone sidewalks is like stepping back in time, as they have been part of the urban landscape for centuries. They add a touch of nostalgia and character to historic districts, enhancing the overall ambiance and charm of the area.brbrbrbrGetting Around:brbrThe driveway of our home can accommodate up to 2 vehicles if parked behind each other. A car is not needed, but there are several parking garages close to the house. The city does provide free parking from 6PM Friday to 6AM Monday at the Calvert Street Garage (19 St. Johns Lane) or you can also park in the following garages/lots: Hillman Garage (150 Gorman Ave - entrances from Main St or Duke of Gloucester) South Street Lot - South Street off Church Circle, Gotts Court Parking Garage – (25 Northwest Street) Knighton Parking Garage – (1A Colonial Avenue), Park Place - 5 Park Place (just off West St ). The free Annapolis Circulator bus stops at all the city garages/lots and the city dock and can be used to get to/from the garages. Please see the Annapolis Parking website for further detailsbrbrbrbrInteraction with Guests:brbrWe respect our guests' privacy and offer a seamless self check-in process. While we won't be on-site during your stay, we are always available and happy to assist with any questions or recommendations via the app or phone to ensure you have a wonderful time.

Downtown Annapolis Duke's House

Annapolis, Maryland, United States

4

Bath

9

Sleeps

Exceptional(20)

$948.1

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.

Beautiful Blend of Restoration and Renovation in this Downtown Home

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$634.95

Welcome to Sea La Vie Annapolis 2069, a stunning newly built vacation rental nestled in the Bestgate area of Annapolis, just 3 miles from the historic United States Naval Academy. This spacious four-bedroom, five-bathroom home offers a perfect blend of modern comfort and charming ambiance, making it an ideal retreat for families or groups of up to nine guests.brbrAs you step inside, you'll be greeted by a bright and airy living area that seamlessly flows into a well-equipped kitchen, perfect for preparing meals together. The home features two luxurious king bedrooms, a cozy queen bedroom, and a unique rooftop bedroom with daybeds that convert to a double bed and a twin, ensuring ample sleeping arrangements for everyone. Connecting the bedroom to the rooftop bar, there is a wet bar center with a mini-fridge, sink, microwave and coffee bar.brbrEnjoy the serene garden view from the rooftop patio, where you can unwind with a glass of wine or coffee utilizing the convenient Coffee and Wine Bar. The property is pet-friendly, allowing you to bring your furry companions along for the adventure. With a garage and four parking spaces, convenience is at your fingertips.brbrAdditional amenities include an EV charger, ensuring your electric vehicle is always ready for your next outing. Located in a popular area in West Annapolis, Sea La Vie Annapolis 2069 is close to local attractions, dining, and shopping, making it easy to explore all that Annapolis has to offer.brbrDon't miss the chance to experience this exceptional property—book your stay at Sea La Vie Annapolis 2069 today and create unforgettable memories!brbr3 miles to United States Naval Academy & St. John's Collegebr2 miles to Navy-Marine Corps Memorial Stadiumbr3 miles to Annapolis Historic District:br2 miles Annapolis Mall and Annapolis Town Centerbr1 mile to Trader Joes, Sam's Club and many other favoritesbr1 mile to Anne Arundel Medical Centerbr22 miles to Baltimore/Washington Airportbr25 miles to Washington, D.C. brSTR License 001172 with an expiration date of 01/15/2028

Parking. Short Uber Ride. Townhouse in Annapolis! 3 Miles from USNA and Downtown

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$741.57

Summary:brbrHistoric 1885 row home two blocks from Main Street and steps from the U.S. Naval Academy. Three bedrooms across three floors with a king master, two queens, and a twin - sleeps 9. Pet-friendly (dogs under 30 lbs welcome) with covered off-street parking half a block away. Walk to Annapolis' restaurants, shops, and waterfront without ever moving your car.brbrbrbrThe Space:brbrEnter through the white gate to a private back patio, then into the renovated kitchen - modern appliances, sleek countertops, and natural light from every window. The living room is just beyond, with plush seating and a sofa bed for extra sleeping.brbrbrbrSecond floor: king master bedroom and a queen bedroom share a full hallway bathroom.brbrbrbrThird floor: queen bed, twin bed, and its own attached bathroom with stand-up shower - great for a family with kids or guests who want more privacy.brbrbrbrThe home was built in 1885 and is named for the owner's great-grandfather, a founding figure in Annapolis' fire departments. You'll feel that history in the architecture while enjoying fully modern finishes throughout.brbrbrbrGuest Access: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.brbrbrbrThe Neighborhood: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.brbrbrbrGetting Around:brbrPublic Transportation:brbrAnnapolis Transit:brbrAnnapolis 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.brbrbrbrPurple Shuttle:brbrThe 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.brbrbrbrTaxi Services:brbrAnnapolis 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.brbrbrbrRide-Sharing (Uber & Lyft):brbrBoth 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.brbrbrbrWater Taxis:brbrWater 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.brbrbrbrParking in Downtown Annapolis:brbrIf 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.brbrbrbrStepping 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.brbrbrbrHeading 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.brbrbrbrTo 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.brbrbrbrIf 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.brbrbrbrFor 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.brbrbrbrNavigating 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.brbrbrbrAs 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.brbrbrbrOther Things to Note:brbr** Parking Information for Your Stay:** brbrWe 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. brbrAdditional Parking: If you have an additional vehicle, you may purchase an extra parking spot in the same garage before parking. A QR code is available in the garage for payment instructions. Vehicles parked without payment or in unauthorized areas may receive a ticket or be towedbrbrbrbrSmoking is strictly prohibited on the property; if any evidence of smoking is found that requires additional cleaning or remediation, the associated costs will be charged to the responsible party.brbrbrbrbrbrEarly Check-In & Late Check-Out PolicybrbrWe offer early check-in and late check-out upon request, subject to availability.brbrOne hour is complimentarybrbrHowever, a fee applies as follows:brbr • Early Check-In before 3pm for an additional fee of $50 to be paid before check -inbrbr • Late Check-Out after 12pm for an additional fee of $50 to be paid before check-outbrbrPlease request in advance so we can confirm availability.brbrbrbrInteraction with Guests:brbrOur 24/7 dedicated support team is always available to ensure your stay is smooth, comfortable, and five-star-worthy. If there’s anything you need—questions, recommendations, or assistance—please don’t hesitate to reach out. We're just a message away and happy to help.

Historic Annapolis Home | 2 Blocks to Main St

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1054.78

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrElegant Historic Home with Private Parking in the Heart of Downtown Annapolis brbr brbrWelcome to your beautifully restored retreat—once two separate homes, now thoughtfully combined into one expansive and stylish residence in the heart of Historic Annapolis. Enjoy the rare convenience of two private and secure parking spaces, and settle into a home that blends character, comfort, and location. brbr brbrMain Living Spaces brbrOn the main floor, guests will find multiple areas to relax and gather: brbrFormal dining room for celebratory meals brbrComfortable living room perfect for conversation or quiet moments brbrOpen-concept kitchen and family room with ample seating and direct access to the covered patio and fenced-in backyard brbrStep outside to a covered patio with lounge furniture, and enjoy evenings in your private backyard oasis, complete with stone pavers and a charming front porch swing. brbr brbrSleeping Arrangements (Sleeps 7 adults + 1 infant | 3 Bedrooms | 2.5 Baths): brbrKing Suite (2nd Floor): King bed, oversized en-suite bath with jacuzzi tub, walk-in shower, dual vanities, and a custom walk-in closet brbrQueen Bedroom (2nd Floor): Queen bed, shares access to a full hall bath brbrBunk Room (2nd Floor): Twin over Full bunk bed, full-size crib, and shared full hall bath brbr brbrHome Highlights brbrGourmet kitchen with generous prep space and modern appliances brbrTwo secure parking spaces (The garage height has 7 foot clearance; width may limit larger SUVs) brbrDining table seats 10–12—ideal for large family meals or entertaining brbrSurround sound speakers for immersive music and movie nights brbrSmart TVs and high-speed WiFi brbrMain level extra large laundry room with full-size refrigerator washer, dryer, drying racks, and storage brbrLuxury linens and starter toiletries provided for a boutique-level experience brbrKeyless entry for seamless and secure check-in brbr brbrLocation, Location, Location brbrAnnapolis Harbor & Main Street – 3 blocks away brbrU.S. Naval Academy – 10-minute walk brbrRestaurants, boutiques, and bars – All within a 5-minute stroll brbrWashington, DC – 30 miles | Baltimore – 25 miles brbr brbrNo parties or smoking permitted. brbrQuiet hours must be observed to respect the neighborhood. brbrCheck-in: 4:00 PM | Check-out: 11:00 AM brbr brbrWhether you’re here to explore Annapolis’ historic charm, celebrate with friends, or attend a Naval Academy event, this spacious and well-appointed home is the perfect downtown base.

Spacious Historic Home with Private Parking in the Heart of Downtown Annapolis

Annapolis, Maryland, United States

Bed

2

Bath

8

Sleeps

$819.88

Summary:brbrTwo connected, historic row homes in the heart of Downtown Annapolis! Perfect for two families or larger groups, these houses are connected via an outdoor patio in the back. Enjoy in unit washer/dryer in both units, separate kitchens, and 3 full bathrooms. brbrHouse A: 2 full bathrooms, bedroom with loft, and 2 twin beds in a bunk room. House B offers a primary bedroom, 2 twin bedroom, with a full bath (standing shower) in the hall. Gather and grill in the outdoor spaces, entertain in house A's dining room, and house B's comfortable living room.brbrbrbrGuest Access:brbrPrivate entrancesbrbrbrbrOther 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 brbr * It typically takes ~1 hour to screen a guest after they book this property and could take several hours if we are busy before we are able to provide them with check-in information.brbr brbrIf you make a last minute reservation, we ask you to please be patient and please do not expect to gain access to the property immediately.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. brbrbrbrLocal 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.

Two Historic Rowhomes in Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$526.07

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrEastport's Third Time's the Charm – Steps from Marinas, Dining, and Historic Annapolis brbrThis 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. brbr brbrInterior Features: brbrLiving Room: Relax in the comfortable living room with hardwood floors and a flat-screen TV. brbrKitchen & Dining: The recently renovated open kitchen features a breakfast bar, adjacent dining area, and sliding glass doors leading to a large deck. brbrOutdoor Space: Enjoy the manicured backyard, complete with a private deck, patio, firepit, and cornhole set. brbr brbrBedrooms: brbrTwo Queen Bedrooms, each Sleeps 2, on the second floor with luxury bedding, sharing the full bath. brbrAdditional Sleeping Arrangements: Queen sleeper sofa in Living room brbr brbrHighlights: brbrPrivate fenced backyard, patio deck and covered front porch brbrFirepit with Adirondack chairs and cornhole brbrGas grill (propane included) brbrStainless-steel appliances including beverage fridge brbrWiFi, big-screen TV, and luxury linens brbrDedicated work space brbrStarter pack of toiletries, cleaning supplies, and essentials brbrWasher & dryer brbr brbrU.S. Naval Academy: 1.5 miles brbrWashington, D.C.: 30 miles brbrBaltimore: 25 miles brbr brbrHouse Rules: brbrNo smoking, parties, pets or events brbrMust be 25+ to book brbrCheck-in: 4:00 pm | Check-out: 11:00 am

Steps to Marinas & Shops w Parking in Eastport

Annapolis, Maryland, United States

2

Bed

1

Bath

6

Sleeps

$998.33

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

$438.9

Comfortable stay on quiet street close to Gate 3 USNA and St. John's College. Quick walk to Maryland State House, Maryland Avenue shopping/dining, enjoy Annapolis nightlife at City Dock, Main and West Streets. Entertain on private patio. 3 queen beds, large living area with smart TV, additional living space in kitchen/lounging/dining area. Large kitchen table plus 4 eat-in seats at the bar. Navy Football and Baseball Stadiums within walking distance. Enjoy all that the Navy Yard has to offer right around the corner. Legislators welcome!

Gem in Downtown Annapolis, close to USNA, St. John's College

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$789.8

Your home away from home in Annapolis with 4 bedrooms. Under 2 miles to the Naval Academy!brThis spacious home is located in a quiet, walkable, wooded neighborhood on 2 acres of land. Ample parking available on driveway and street! First floor has a large updated kitchen, spacious dining room, living room, and sunroom overlooking the private, shaded backyard.brbrTwo First floor bedrooms:brMaster King Bed with Private BathbrGuest Queen Bed with Full Bath brbrTwo Second Floor bedrooms:brTwin Bunk Room- 2 bunks (sleeps 4)brTwin Bedroom - 3 Twins (sleeps 3) OR can be 1 KING and 1 TwinbrHallway full bath shared by both roomsbrbrBasement rec-room has a pool table and plenty of toys for young ones. Back porch and yard space are great for hosting outdoor parties. Trampoline for kids to jump. Upper landing has a large desk area great for reading or working from home.brNo pets please.

Private 4-bedroom house in Annapolis, great location!

Annapolis, Maryland, United States

4

Bed

Bath

11

Sleeps

$436.55

Custom home with inlaid floor, wood counters, hand made cabinets, and artistic touches. Beautifully landscaped large private yard. Badminton net and croquet available. Enjoy the outdoors bug free in the large screened-in porch while listening to the sounds of falling water and bullfrogs from the koi pond. Master king suite with vaulted ceiling, private patio with fire pit, and large walk-in shower. 52” tv in main room with video and music library in basement. Kitchen is well appointed with almost any small kitchen appliance (toaster, coffee maker, keurig, blender, crockpot, and more) you may need during your stay. Pour a glass of wine in the premium bar ware while storing your new wine finds from local Maryland wineries in the wine fridge in the kitchen. High quality pots and pans are available to whip up dinner to enjoy on the porch or in the dining room overlooking the pond. brRelax in the sitting room with 2 sided stacked stone gas log fireplace (only available for use in winter months). Guest rooms (1 double, 1 twin) have access to the hall full bath with a tub and shower. For larger families who need to spread out the finished basement includes a media room with TV and DVD, pull out queen couch, and a third full bathroom. Washer and dryer also available for use during your stay. High chair seat, baby gate, and bassinet available if little ones are joining you. Legos, board games, puzzles, cards are also available if you want to stay in enjoying the home. brSituated in a quiet neighborhood. Easy walk to Navy Stadium providing access for football games and other events. Less than 2 miles from downtown including Naval Academy, St. John’s, Ego Alley, shopping and more. brbr

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$532.16

Come enjoy an Annapolis getaway. Perfect for vacations, and enjoying the Chesapeake Bay, and Maryland's capital city only 15 minutes away. The house has views of Fishing Creek and the boat launch is at the end of the street to kayak or boat by Thomas Point, the Chesapeake Bay and have views of the Thomas Point Lighthouse. The neighborhood is quiet and friendly and is great for walks and runs. You can walk 6 blocks to a small beach or one block to the crabbing dock.brbrThis 5 bedroom home sleeps 12-14 in 3 king sized beds, 1 queen bed & a bunk room. Main bedroom upstairs with King bed, private bath, and two closets. Two King bedrooms (up and down) have ample space. Queen bedroom upstairs. Bunk bedroom sleeps 4-5 with double bunk beds. Bedrooms are comfortably furnished with beautiful new crisp linens, pillows and bed coverings. brbrDownstairs family area and dining room have water views. Plus there is a game room featuring a 50” smart tv, Golden Tee, poker chips/cards, and dart board, games and puzzles.brbrEnjoy the large backyard with a fire pit for relaxing and enjoying the evening on the bay or sit on the back deck for outside eating and views of the sunset! There is a gas grill ready for you to cook up some good eats to enjoy on the patio.brbrYour stay includes Wi-Fi, parking for 3 cars, fully stocked kitchen, and a washer/dryer.brbrLicense number STR-271

Water Views - Close to Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$687.16

Summary:brbrSpread out in this spacious 4-bedroom Annapolis home — room for 10 with an open layout, updated finishes, and a fully fenced backyard where dogs can roam. The renovated kitchen has stainless steel appliances, and the large living room is built for groups. About 10 minutes to Downtown Annapolis, close enough to explore but tucked into a quiet neighborhood with plenty of space. Free parking, high-speed WiFi, Smart TVs, laundry, and a half bath on the main level.brbrbrbrThe Space:brbrBEDROOMSbrbrFour spacious bedrooms with modern design and comfortable beds. The home sleeps 10 guests across multiple rooms.brbrBATHROOMSbrbr2.5 bathrooms — two full baths with fresh towels and essentials, plus a half bath on the main level.brbrKITCHENbrbrFully renovated with stainless steel appliances, cookware, dishes, utensils, and plenty of space for cooking group meals.brbrLIVING AREASbrbrLarge, open living room with a Smart TV. The layout flows naturally and gives groups room to be together without being on top of each other.brbrOUTDOOR LIVINGbrbrFully fenced backyard with a spacious patio — perfect for grilling, hanging out, or letting dogs run. A peaceful retreat after a day exploring Annapolis.brbrPARKINGbrbrFree parking on the driveway and street.brbrLOCATIONbrbrAbout 10 minutes from Downtown Annapolis. Quiet residential neighborhood with easy access to the city. Close to local parks and the waterfront.brbrbrbrGOOD TO KNOWbrbrbrbrCheck-in: 3:00 PM / Checkout: 11:00 AMbrbrSelf check-in with smart lockbrbrPets welcome — fully fenced backyardbrbrbrbrGuest Access:brbrEntire house other than the locked storage closet in the garage.brbrbrbrInteraction with Guests:brbrText or call is preferred if serious or immediate attention needed. Otherwise app communication is fine.

Spacious 4BR | Pet-Friendly, Sleeps 10

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1090.38

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWelcome to Modern Elegance in Historic Annapolis brbrStep into this fully-renovated 1900s home, where modern sophistication meets timeless charm. Lovingly restored, this home offers parking for two cars (or one SUV)—a rare luxury in the heart of downtown Annapolis. Owned by four Naval Academy graduates—three U.S. Marines and one Navy nuclear surface warfare officer—this property stands as a tribute to the enduring bond they forged as members of the Academy's 14th Company and their decade of service to our nation. You’ll feel their legacy of camaraderie and commitment the moment you arrive. brbr brbrNestled on one of Annapolis's most picturesque streets, the home is just a block from the Naval Academy's main entrance. The inviting front porch is the perfect perch to soak in the vibrant energy of historic downtown Annapolis, creating a seamless connection between the home and the community’s storied past. brbr brbrThe interior boasts an elegant Great Room with a custom entertainment bar, open dining area, and Naval Academy-inspired decor that sets the tone for your stay. The gourmet kitchen is a chef’s dream, with seating at the breakfast bar for casual gatherings. With spacious accommodations for up to 11 guests, including a stunning top-floor suite, the home caters to families and groups seeking both comfort and style. brbr brbrWhether visiting for a Naval Academy event, the boat show, or simply to explore Greater Annapolis, this home puts you steps away from local attractions, restaurants, and shops. From relaxing mornings on the front porch to evenings exploring the waterfront, your stay promises to be unforgettable. brbr brbrSleeping Arrangements: 4 BR / 2 BA / Sleeps 11 brbrMain Bedroom 1 (2nd Floor): Queen Bed brbrMain Bedroom 2 (2nd Floor): Queen Bed brbrGuest Bedroom (2nd Floor): Two Twin Beds brbr3rd Floor Suite: Open sleeping/living space with 5 Twin Beds brbr brbrHighlights brbrFront Porch: New furniture for lounging and enjoying the lively neighborhood views brbrCustom Bar: Seats 4-5 for entertaining brbrGourmet Kitchen: Fully equipped with seating for 4 at the breakfast counter brbrDining Area: Accommodates 6-8 guests brbrModern Amenities: WiFi, smart TVs, luxury linens, and a boutique-level starter kit brbrConvenience: Keyless entry, laundry facilities brbrParking: Space for 2 cars or 1 SUV brbrImportant Notes brbrGuests must be 25+ years of age or accompanied by an adult. brbrNo smoking, pets, parties, or events are allowed. brbrThe steep staircase may not suit guests with mobility issues; please inquire if needed. brbr brbrDistance to Nearby Attractions brbrU.S. Naval Academy: 1 block brbrWashington, D.C.: 30 miles brbrBaltimore: 25 miles brbr brbrAmenities & Services brbrStart your stay worry-free with our complimentary starter pack, including coffee, toiletries, and household essentials. All beds come pre-made with freshly laundered linens, ready to welcome you home. brbr brbrThis home promises the perfect blend of history, luxury, and convenience, making it an ideal retreat for your Annapolis adventure.

Prime Location! Modern Comfort 1 Block to Gate 1 w/ Parking & Walkability

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$593.87

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrStep into Annapolis history at this beautifully restored three-story cedar home. Built in the late 18th century, this property is recognized in the Historic District’s National Registry as one that “embodies the distinctive characteristics of a period.” Over the centuries, it has served as a shoemaker’s store, an inn, and the residence of an Italian immigrant who played in the U.S. Naval Academy band. Later converted into three apartments, the home was thoughtfully restored in the 1970s and newly-renovated into the elegant single-family dwelling it is today. brbr brbrMain Level Living brbrEnter through the front door to a spacious family room, perfect for relaxing after a day of exploring downtown Annapolis. With a plush queen sleeper sofa and a large flatscreen TV, this room doubles as a cozy gathering space or extra sleeping option. Original wood floors run throughout, creating warmth and character. The Main level, and all 3 bedrooms, each have their own flatscreen TV. brbr brbrThe adjoining dining room features a restored built-in hutch and seating for six. The full kitchen is stocked with everything needed for preparing meals at home, while a convenient powder room completes the main floor. From the kitchen, step outside to the fenced-in backyard with Adirondack chairs and a propane grill—an intimate spot for morning coffee or evening cookouts. The home is located just a 2-minute walk to City Dock, Main Street, State Circle, and the Naval Academy entrance. brbr brbr**Parking is not on premises!! A dedicated parking spot at nearby garage (15-minute walk from the house) is provided. Please contact us for details. brbr brbrSLEEPING ARRANGEMENTS 3 BR / 3.5 BA / Sleeps 8: brbrTop Floor King Suite: brbrKing Bed brbrEnsuite Full Bath with double vanity, shower/bathtub combo and walk-in closet brbr brbr2nd Floor King Suite: brbrKing Bed brbrEnsuite Full Bath with stand-up shower brbr brbr2nd Floor Queen Guestroom brbrQueen Bed brbrFull Bath in the Hall with shower/bathtub combo brbr brbrMain Level brbrFull Sleeper Sofa brbrPowder room on Main Floor and shared Full Bath in the Hall on the 2nd Floor brbr brbrAmenities & Highlights brbrPrivate fenced yard with Adirondack seating and propane grill brbrFully equipped kitchen brbrDining table with seating for 6 brbrWiFi & big screen TVs in every bedroom and the Family Room brbrLuxury linens & complimentary starter toiletries brbrWasher & dryer inside the home brbrContactless check-in via coded front door entry brbrNon-smoking property brbr brbrProperty Distance to: brbr- U.S. Naval Academy – 2 blocks brbr- Washington, DC – 30 miles brbr- Baltimore - 25 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/no pets. Please respect the neighbors and neighborhood. brbrCheck-in time: 4:00 pm brbrCheck-out time: 11:00 am brbr brbrBlending centuries-old charm with modern amenities, this property offers the ideal downtown Annapolis getaway—whether you’re visiting for the Naval Academy, a weekend retreat, or a family celebration.

Boutique Historic Cedar Home 2 blocks from the Waterfront, USNA and Main Street

Annapolis, Maryland, United States

Bed