Vacation Home Rentals By Owner In Annapolis, MD

STR21-145020 --------Yes! It really is the Perfect Vacation Rental in Annapolis!----Discover the perfect blend of historic charm and contemporary comfort at The Little Lighthouse. A 3-bedroom 2.5-bath vacation home ideally situated just steps from the Annapolis City Dock. Nestled in the heart of all that makes Annapolis special this home offers unparalleled convenience for those looking to explore the vibrant local scene.--------Location Location Location----Imagine waking up and strolling to the nearby bars restaurants and shops or taking a leisurely walk to the United States Naval Academy. With everything at your fingertips you'll be able to fully immerse yourself in the rich history and lively atmosphere that Annapolis is known for.--------Parking Perks----In a city where parking can be a challenge our rental includes a small garage behind a gated entrance that can accommodate up to a small SUV. This dedicated parking space is a huge bonus that should not be overlooked ensuring your stay is as stress-free as possible.--------Comfortable and Modern Living----Spread across two floors our home is designed to cater to your every need. The second floor boasts a spacious master bedroom with a king bed and an attached bathroom featuring a stall shower. Two additional bedrooms one with a queen bed and the other with two twin beds provide the perfect setup for a small family or friends traveling together.--------Perfect for Any Occasion----Whether you're visiting for the renowned boat shows Navy events or simply sightseeing in this historic town our home offers a welcoming retreat. Despite its location in the heart of the historic district the interior is fully modern and updated ensuring you have all the contemporary comforts during your stay.--------Book now and experience Annapolis like never before with the perfect home base to explore relax and enjoy all the wonders this city has to offer.

Location=AMAZING! Garage Parking for 1

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$600.07

STR-144253 Welcome to The Yellow Door on Cornhill, a beautifully restored 1800 brick home in the heart of downtown Annapolis. Blending historic character with refined modern comfort, this charming retreat is within walking distance of City Dock, shops, dining, and many of Annapolis’s most popular attractions. From the moment you arrive, the home offers a memorable stay filled with warmth, style, and classic downtown charm.brbrInside, you’ll find thoughtfully updated interiors with high-end finishes, a cozy living room with a gas fireplace and Smart TV, and a well-appointed dining space perfect for relaxed meals at home. The standout chef’s kitchen features an Aga stove, professional-grade refrigerator, and a custom butler’s pantry with a second sink, offering both beauty and function for your stay.brbrOn the second floor, the home offers two queen bedrooms, including a primary suite with an en-suite bath, plus an additional full bathroom with a walk-in shower. The third-floor loft includes a twin trundle bed and access to one of the home’s most special features: a rooftop deck with views of the Naval Academy and State House domes.brbrPlease note that, due to the home’s historic age and layout, the staircases to the upper floors are steep and narrow, so the property may not be suitable for young children or guests with mobility concerns. There is no on-site parking, and the driveway across the street may not be used, including for unloading.

3 BR charming home sits in the heart of Annapolis with rooftop deck

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$377.69

STR21-144963 Discover a charming little gem nestled in the heart of the Historic District. It's a perfect haven for the traveler who craves the allure of downtown convenience and an affinity for antiques. This enchanting abode is adorned with timeless treasures each with its own story from generations past creating an ambiance steeped in history and character.--------The two bedrooms featuring a double bed and a 3/4 bed (larger than a twin but cozier than a double) provide a cozy retreat for up to four guests. A quaint porch thoughtfully enclosed for year-round enjoyment adds a touch of old-world charm to your stay.--------Modern amenities seamlessly blend with historic allure offering high-speed internet an updated kitchen window AC for comfort and a reserved parking space right beside the house. Immerse yourself in the captivating surroundings as this gem is strategically located close to everything inviting you to explore the vibrant energy of downtown Annapolis.--------Indulge in the proximity to Annapolis City Dock just a 4-minute stroll away and relish a 6-minute walk to the US Naval Academy. For your convenience the US Naval Academy Stadium is a mere 1.2 miles away.--------This delightful retreat not only offers a glimpse into the past with its antique charm but also ensures a cozy and convenient stay for your visit. Unwind explore and make cherished memories in this timeless abode. *Plus the sofa sleeper adds an extra layer of flexibility to accommodate your needs.----Distance from USNA: 0.3 Miles (6 Minute Walk)----Distance from USNA Stadium: 1.2 Miles----Maximum to Sleep: 4----Bedroom 1: Double ----Bedroom 2: 3/4 Bed - Larger than a Twin but smaller than a Double.----*Plus Sofa Sleeper

2BR Historic District Gem w/Parking Near City Dock

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$869.09

RENT-005995-2024-The Campbell House on Prince George offers the best of downtown Annapolis with a rare blend of historic charm and modern luxury. Located just 40 yards from the U.S. Naval Academy’s Barry Gate and only a 2-minute walk to City Dock, this beautifully restored 3-bedroom, 2.5-bath home places you in the heart of Annapolis, with easy access to waterfront dining, boutique shopping, historic landmarks, and major events like Commissioning Week and the Annapolis Boat Shows.brRecognized by the Capital as Home of the Week and honored with the Historic Annapolis Preservation Project of the Year award, the home has been thoughtfully updated to combine timeless character with modern comfort. Inside, you’ll find a fully renovated kitchen with high-end appliances, inviting living spaces, and updated entertainment systems in both the living room and primary bedroom. The home comfortably sleeps 6 to 8 guests with a king bedroom, queen bedroom, two twin beds on the third floor, and a queen sleeper sofa in the living room.brOutside, enjoy a private garden patio with a gas grill, a rare bonus in downtown Annapolis. A street parking pass is also included for the duration of your stay, making it even easier to enjoy the city on foot.brSleeping ArrangementsbrPrimary Bedroom: King bed, en-suite bath with walk-in showerbrBedroom 2: Queen bedbrBedroom 3: Two twin bedsbrAdditional Sleeping: Queen sleeper sofa in living roombrPlease note: the garden patio is not available during the boat shows.

Historic 3 BR home and just forty yards from the US Naval Academy Barry Gate

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$834.44

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrHistoric Philip Clayton House – Downtown Annapolis Retreat brbr brbrStep into Annapolis history at the Philip Clayton House, a landmark residence built in 1834. Located just one block from the City Dock, 3 blocks from the U.S. Naval Academy and the lively shops and restaurants of Downtown Annapolis, this home blends historic character with modern comforts for an unforgettable stay. brbr brbrWith nearly 200 years of stories behind its walls, the home has been thoughtfully renovated to balance original charm with modern livability. A bright family room opens to a private patio and fenced backyard—perfect for morning coffee, al fresco dining, or evenings around the fire pit. brbr brbrThere are 4 spacious bedrooms and 2.5 bathrooms, comfortably accommodating up to 10 guests. The gourmet kitchen serves as the heart of the home, featuring a large central island, top-quality appliances, and plenty of space for family meals or entertaining. brbr brbrSleeping Arrangements (Sleeps 10): brbrKing Suite (2nd Floor): King bed with ensuite full bath brbrGarden Bedroom (2nd Floor): Queen bed brbrAmericana Bedroom (2nd Floor): Queen bed brbr3rd Floor Bedroom: Two King beds brbrAdditional Baths: Full hall bath on 2nd floor + half bath on main level brbr brbrHighlights: brbrPrivate backyard with dining for 6, Adirondack chairs, and fire pit brbrPropane BBQ grill brbrMultiple dining areas in the kitchen, dining and family rooms (total seating for 16) brbrSmart TVs, WiFi, and luxury linens brbrKeyless entry and in-home laundry brbrDog-friendly ($150 per pet fee to be charged prior to checkin) brbrParking: Convenient loading zone on street in front of house with parking around the block in the easy to access Hilman garage. Daily rate $23.25. brbr brbrGuests must be 25+ or accompanied by an adult brbrNo smoking, parties, or events permitted brbrSteep staircases may not suit those with mobility issues brbr brbrNearby Attractions: brbrU.S. Naval Academy: 3 blocks brbrCity Dock & Downtown Annapolis: Walking distance brbrWashington, D.C.: 30 miles brbrBaltimore: 25 miles brbr brbrYour stay begins worry-free with a starter kit of coffee, toiletries, and household essentials. Freshly laundered linens await on every bed so you can settle in and enjoy the best of Annapolis—history, charm, and convenience all in one.

Steps from the Waterfront with Private Backyard at Historic Philip Clayton House

Annapolis, Maryland, United States

4

Bed

Bath

10

Sleeps

$663.16

Relax at this quiet 3BR, 2BA Annapolis retreat just minutes from downtown and the waterfront. Walk to nearby shops and cafés, then unwind in the spacious living room, cozy TV den, or on the private deck. Enjoy a fully equipped kitchen and parking for up to three cars. The perfect balance of convenience and calm for your Annapolis stay.brbrThe spacebrStep into a welcoming home designed for comfort and relaxation:brbr- Bedrooms & Bathrooms -brbrBedroom 1: 1 BedbrBedroom 2: 1 BedbrBedroom 3: 1 Bedbr2 Full Bathrooms stocked with essentialsbrbr- Living & Common Spaces -brbrSpacious main living roombrCozy TV den (“TV cave”) for movie nightsbrWarm dining area for shared mealsbrFully equipped kitchenbrPrivate, serene deck for outdoor relaxationbrbr- Parking -brbrDriveway parking for up to 3 vehiclesbrbr- Location Highlights -brbrWalkable to shops and cafésbrMinutes from Annapolis waterfrontbr~10-minute drive to Downtown AnnapolisbrClose to marinas, parks, and local diningbrbrGuest accessbrYou will receive an access code to the smart lock shortly before your arrival.brbrOther things to notebrAnnapolis is a true maritime treasure—home to sailboats, harborside cafés, and centuries of nautical history. You’ll feel that energy the moment you wander through town or stroll along the waterfront.brbrAnd then you step inside the house… and you’re somewhere entirely different.brbrWe affectionately call the house “Bavaria on the Bay,” a place where old-world Europe meets coastal Maryland. The décor is inspired by the magic of Bavaria—its forests, its mountains, its fairy-tale castles. Throughout the home you’ll notice art and details that hint at that world, including pieces celebrating the iconic Neuschwanstein Castle, the model for so many storybook palaces. It’s a space where maritime Annapolis meets the romance of the Alps.brbrIf you’re curious, you can dive into the story of King Ludwig II, one of Bavaria’s most fascinating rulers and the dreamer behind these castles. His story is one of vision, beauty, and an enduring mystery: the unsolved circumstances of his final night by the lake.brbrWe’re continuously refining and adding to the décor to make the Bavarian theme even more immersive over time—so each stay offers a little something new.brbrWe care for our neighbors, so... PLEASE ALSO NOTE:brbrThis is a charming neighborhood with many families. Therefore, absolutely NO PARTIES are allowed.brbrBetween 10pm and 7am, the outside noise has to be kept to a minimum.

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$587.74

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWelcome to this gorgeous fully-renovated home, restored to a new modern grandeur, which includes coveted parking for 2 cars on-site. Located on a quiet residential street just 2 blocks from Main Street, the home has 2 bedrooms and 2 full baths on the 2nd floor, and 2 more bedrooms on the 3rd floor. When you arrive at the home and park in the parking pad you will walk through the newly-furnished back patio up the stairs and enter through the large gourmet kitchen. The breakfast bar has seating for 3 and is fully stocked for your stay with plates, glasses, and appliances (big and small!). brbr brbrJust steps from all Annapolis has to offer, this home is located between 2 waterways: if you go out the front door to the left and walk 1.5 blocks you'll reach a dock on Spa Creek. If you walk out to the right and go 1.5 blocks, you'll be at the famous Annapolis Waterfront. This is the perfect spot for those coming in for that special Naval Academy or boat show event, or wanting to take in the sights and sounds of Greater Annapolis. Enjoy the many restaurants, historical attractions, and shops right around the corner! brbr brbrSLEEPING ARRANGEMENTS 4 BR / 2.5 BA / Sleeps 8: brbrKing Bedroom 1 at the top of the stairs: brbr- Second Floor brbr- King Size Bed brbr brbrFull Guestroom #2 on the 2nd Floor: brbr- Second Floor brbr- Full Size Bed brbr brbrQueen Guestroom #3 on the 3rd Floor: brbr-Third Floor brbr-Queen Bed brbr brbrQueen Guestroom #4 on the 3rd Floor: brbr- Third Floor brbr- Queen Bed brbr brbrHIGHLIGHTS: brbr- Furnished Back Patio with sitting area and grill brbr- Spacious kitchen brbr- Eat-in kitchen counter seats 3 brbr- Dining room table seats 8-10 brbr- WiFi brbr- Big Screen TV brbr- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service brbr- Parking for 2 cars brbr- Washer & dryer located inside the home brbr- Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations. brbr- Keyless entry. Drive straight to your rental home, park in the gravel parking pad and enter the front door with an electronic lock code. brbr brbrProperty Distance to: brbr- U.S. Naval Academy – 3 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 already made for you with freshly -laundered luxury 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. No parties, events or smoking of any kind. brbrCheck-in time: 4:00 pm brbrCheck-out time: 11:00 am

Walkable to Main Street at Seashell in the City with 2 parking spots

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$662.62

Summary:brbrWalk to Navy-Marine Corps Memorial Stadium from this 2,400 sq ft renovated home with a finished 930 sq ft basement. Chef's kitchen with GE Café appliances and quartz island, master suite with spa-like marble bath, and a basement with full bath, laundry, and extra sleeping. Three bedrooms, 3.5 baths - ideal for game-day groups, USNA families, or Annapolis weekends.brbrbrbrThe Space:brbrThe main level flows from a welcoming entryway seating area into the open-concept kitchen and living space. Just off the kitchen, an enclosed living room with a sectional and TV provides a quieter hangout spot.brbrbrbrThe chef's kitchen is the centerpiece: GE Café appliances, a large quartz island with seating, white shaker cabinetry, and coastal clam shell chandeliers that set a warm tone for the whole floor.brbrbrbrUpstairs, the master suite has soaring ceilings, a spa-like marble bathroom with a 72-inch double vanity, and a desk nook for remote work. Two additional queen bedrooms share the second floor, each with its own closet and quality linens.brbrbrbrThe finished 930 sq ft basement adds a full bathroom, laundry, additional sleeping, and a flexible space for games, movies, or overflow guests. With 3.5 baths total, morning bottlenecks aren't an issue even with 10 people.brbrbrbrGuest Access:brbrGuests will have access to the home by keypad entry. The code changes with every guest.brbrbrbrThe Neighborhood:brbrWith the Naval Academy only 2 miles away and Navy Stadium just a short stroll from your door, you'll be at the center of the action! Plus, enjoy access to a community pool and the serene surroundings of Heineman Park and Harts Cove. With privacy and direct water access for kayaking or paddle boarding, this home is your gateway to an unforgettable stay. Please note that kayaks located at the community dock are privately owned by residents and are not available for guest use.brbrbrbrGetting Around:brbrPublic Bus Service:brbrAnnapolis Transit:brbrRoute 70: This route connects Annapolis to nearby areas, including Eastport and Edgewater. It can be convenient for getting to downtown Annapolis, the Annapolis Mall, and City Dock.brbrRoute 91: A local route connecting Annapolis to the neighborhoods of Edgewater, providing access to various parts of the city.brbrFree Shuttle Loop: A free shuttle that operates within downtown Annapolis, stopping near popular spots like the City Dock, the State House, and Historic District. It's great for visitors who want to explore the downtown area without worrying about parking.brbrPurple Shuttle:brbrThe Purple Shuttle is a free service that connects major parking areas in Annapolis to popular downtown destinations. While it doesn’t directly serve Dewey Drive, it's a useful option once you’re in the downtown area for getting around between parking areas and key locations.brbrMTA Commuter Bus Service:brbrRoute 920 (Annapolis to Washington, D.C.): If you need to travel further, the Maryland Transit Administration (MTA) operates commuter buses to Washington, D.C., from the Annapolis Park & Ride station. These buses run during peak commuting hours and provide a quick way to access D.C. from Annapolis.brbrRoute 301 (Annapolis to Baltimore): This service connects Annapolis to Baltimore, making it an option for getting to and from the city. Buses are typically available during business hours.brbrRide-Sharing (Uber/Lyft):brbrBoth Uber and Lyft are readily available in Annapolis, especially in the downtown area. You can use either service to get around the city or travel to nearby regions like Washington, D.C., or Baltimore. These rides are generally affordable and can be a quick option when you need to travel short distances.brbrWater Taxis:brbrWater Taxis operate throughout the Annapolis Harbor, providing a scenic and fun way to travel between waterfront destinations. These taxis stop at key locations like City Dock, Eastport, and nearby marinas, allowing visitors to see Annapolis from the water. It’s a unique way to travel, especially during the warmer months.brbrMetro and Rail (for longer trips):brbrNew Carrollton Metro Station: About 30 minutes by car from 311 Dewey Drive, the New Carrollton Metro Station is a major transit hub for Metrorail (serving the Orange, Green, and Yellow Lines) and Amtrak trains. It provides easy access to Washington, D.C. and beyond.brbrBWI Airport: About 30 minutes by car, BWI Airport is another great option for traveling outside the Annapolis area. You can access Amtrak or MARC commuter trains from BWI to reach Washington, D.C., Baltimore, or other parts of the region.brbrParking in Downtown Annapolis:brbrIf you plan to drive, there are multiple parking garages and street parking options in downtown Annapolis, especially near the City Dock and other key attractions. The Park Annapolis garage is one of the larger parking facilities in the downtown area, located near the City Dock, making it an ideal option for those visiting the waterfront or historic districts.brbrbrbrOther Things to Note:brbrSmoking 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.brbrbrbr**Early Check-In & Late Check-Out Policy**brbrWe 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. Thank you!brbrbrbrThe dock shown in the photos is a neighborhood dock shared with other residents and is not private to the homebrbrbrbrInteraction 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.

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$354.34

Perfect for groups of 4 wanting to be near Annapolis and the Chesapeake Bay, but far enough away for peace, quiet, and easy parking. brThis 2-bedroom, 2-bathroom home has been thoughtfully decorated with comfortable and cozy amenities. brPrimary suite features a queen bed, TV, full bath with stand-up shower and beautiful views from large windows.brSecond bedroom features two twin beds and a TV. Bathroom has a tub-shower combo. brPlentiful light and everything you need for a wonderful trip!brbrWhy guests love staying at Ellis Road:brbr☼ Recently renovated cottage 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 Oyster Harbor - 5 miles/15 min drive to downtown Annapolis, 32 min to BWI airport, 43 minutes to Baltimore, 51 min to Washington DCbr☼ 1/2 a block to the Chesapeake Bay, with a private community beachbr☼ Two bedrooms: Primary: queen bed, TV, skylight, large private bathroom with standup shower; Guest: 2 twin beds, TV, skylight and large windows, hall bath with tub-shower combobr☼ The primary bathroom is truly unique and provides an elevated experience - with floor-to ceiling windows (with privacy screens, of course). br☼ Kitchen with all major appliances, a drip coffee maker, kitchen supplies and tools and morebr☼ Large dining table in the 4-seasons sunroom with space for 6br☼ Comfortable living room for watching movies and playing gamesbr☼ Smart TV's in living room and bedroomsbr☼ Private driveway parkingbr☼ Private fenced-in backyard with patio and outdoor furniturebr☼ Fresh linens, towels, toiletries & essentials providedbr☼ Professionally cleaned before each visitbrbrLook no further than this cozy cottage in Oyster Harbor in Annapolis!brbrPlease note that there is a section of the home that is blocked off from guest use with a locked door. This listing accurately describes all that is available to guests. Additionally, there is a covered car in the driveway that is not available for guest use. The water at this property is well water with a water softening system, so the water may feel softer than what you are used to at home, but rest assured, it is of a high quality. 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.brbrEllis Road 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.

Cozy Cottage with Beach Access

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$429.81

Welcome to our elegant stand alone charming home on Charles Street in Historic Annapolis. This 3 bedroom 2.5 bath is just a short stroll from Main Street , USNA , Yacht Clubs and Event venues. Plenty of room to relax with a large private outdoor space.brbrStately 3 bed 2.5 bath stand alone home in the Historic District .brbrThe city does not allow street parking for short term rentals . Our guests use of the numerous city garages - The closest is one block away . Fireplaces are for decorative use only.

Charming on Charles Street

Annapolis, Maryland, United States

3

Bed

Bath

6

Sleeps

$463.32

Cute and comfortable home in the heart of the HISTORIC DISTRICT of DOWNTOWN Annapolis. Park the car (a spot is included) and walk everywhere!brbr❤️❤️ New kitchen, 2 system central AC and Heat, parking spot, master bath and deck installed in 2021. New patio in Spring 2021 to include a Solo stove for more outdoor enjoyment. ❤️❤️brWe welcome you to our cute historic row house in one of the most coveted areas in all of the Historic District !You will be delighted by this one of a kind home located right in the heart of Downtown Annapolis. We have been a full time vacation rental since 2011 and have loved hosting hundreds of groups, families and friends coming to visit the city that I'm proud to call my hometown. We now have rented out a coveted personal parking spot one block away. 99% of properties in town do not have parking and cannot provide street passes so this is a real selling point if you're looking for convenience. City garages are $25 a day and local hotel valet starts at $40.... Parking is at a premium in our little city so we are thrilled to be able to offer this to our guests!!br Built in 1845 and renovated in 2008 (while keeping our period touches in order to stay on Historic Register ) and freshly painted ( exterior and interior with new flooring And furniture in 2019 ) this home retains much of its original charm while having all of the needs of modern day living and designed to be a clean comfortable affordable home away from home for an affordable price . One of the most photographed homes in town, it is located two blocks from the Main st , City dock , and USNA . Charles is an exclusive, QUIET , one way residential only street. Recently chosen as the location for filming of a special for The History Channel ( May 2012) we have also been chosen as one of the select Capital Newspapers 'Homes of the Week' (Oct 8, 2011) as well as one of the exclusive properties for The Historic Foundations ' Candlelight Tour ' Our home has a great location without all of the noise from traffic or the late night bar scene yet you and your guests can absolutely walk to everything you want or need from this property. Spend the day at the private park at the end of the street and watch the sailboats cruise by or walk to town for some sightseeing, shopping, a Navy game,sailing or one of the numerous award winning restaurants. You may even meet some famous people on your walk home-our house is right around the corner from TV personality Greta Van Susteren and across the creek from famous director Barry Levinson. Last summer baseball star Cal Ripken was spotted numerous times paddle boarding down at the park as he is also renting a house very nearby! brLocated directly in the middle of all of the historic churches, this home is an ideal option for out of town wedding parties and guests. Once you compare hotel rates in town you will find that renting a full house is a wonderful alternative-this is your chance to be an Annapolitan! (Yes, that is a real term for a local :) brAfter a full day you will be sure to enjoy your downtime when you arrive home. Wide plank wood floors, a copper tin ceiling and period reclaimed wood doors are only some of the interesting period features you will admire. Decorated by a local art dealer and gallery owner this home contains many unusual, one of a kind pieces by artists you might recognize . The custom made dining room table is large enough to accommodate all of the house guests or you may choose to grill ( brand new summer 2021 ) outside on the very private deck Relax after dinner on our outdoor set - If you're lucky maybe the neighborhood ducks will swing by for a visit. It's a great quiet spot with great neighbors . Please note we do have a shared wall so this is not a party property or a good fit for loud groups , Bach events etc . We host couples , couple groups and families . We are pet friendly ( one dog max - no kitties etc ) with an additional fee - please message us first before requesting a pet.brThis home sleeps six very comfortably and we are a certified rental property through the City of Annapolis . The first floor master suite has a queen bed and desk while the two upstairs guest bedrooms contain a king and two extra long twin beds with totally empty closet space and drawers. As we are a year round rental you will not be inconvenienced by having to squeeze your luggage and things among owners jeans, toys and old prom dresses :) In the kitchen we have a large welcome book along with local maps and menus to get you acquainted to our lovely town. If you have and specific concerns, questions or requests please don't hesitate to call or shoot me an email. We have been locals here for many many years and should be able to answer just about anything!brWe have been a full time vacation rental for over ELEVEN ( Wow - time flies )years and have had the pleasure of renting our home for countless special events such as reunions, couples get -away weekends, weddings,St Johns College events, Navy games and Commissioning week, parent weekends, boat show ,sailing regattas and Maryland state legislators. We are booking up extremely quickly for next year. Please check our calendar for pricing and availability and we hope you consider our property for your next stay in Annapolis. brWe reserve the right to have three night or week minimums for special events such as Navy games , Commissioning week and Sailboat show.brbrThe owner is a lifelong Annapolitan and local business owner with multiple short term rentals in town. The property next door is under ongoing renovation. Work is done during only within city allowed hours of construction but wanted to note for guests .brbrNo Smoking of any kind. No parties, ( Bach / Ette included ). We have shared walls - quiet time after 10pm. Dogs only, (1 dog max and absolutely no barkers) allowed but you MUST let us know ahead of time - $100 extra cleaning fee required to be paid by cash/check separately to me. Pets (if accepted and one max), are not to be left unattended at ANY time unless crated or allowed any furniture. Any noise complaint/violation will result in immediate cancel of reservation with no refund.

Charming Renovated Historic Home Downtown wParking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$385.25

Brand new home with comfortable beds, open floor plan with kitchen excellent for entertaining, and fully equipped. All furniture is brand new. Located on quiet dead end street with large yard. A 5-minute walk to Quiet Waters Park, Hillsmere shopping center with restaurants (such as Annapolis Smokehouse and Grumps Cafe), the Dark Horse Bar, and Giant. A 10-minute drive to downtown Annapolis. Also nearby is Thomas Point Park. Ideal for boaters mooring at Bembe Beach Rd Yacht clubs or visiting family at Bay Woods Assisting Living or Naval Academy. Comfortable getaway at a much better value than hotels!brbrbrThe home is brand new built in 2023, on a quiet private residential lot. Living space is on the second floor, reached by an outside staircase. The front door opens into an open floor plan kitchen and living room excellent for entertaining. The living room has a chair that folds out to a single sized bed. The couches recline, have phone holders that charge, and lights on the bottom that illuminate at night. The kitchen is fully equipped with fridge, microwave, stove, oven and dishwasher. There is a coffeemaker with a fully equipped coffee station with to go cups for those on a busy schedule. All lights and fans throughout the home are remote controlled, and in the kitchen, guests have the option to change the color of the lights to create a different ambiance. The closet in the kitchen contains a stackable washer and dryer equipped with laundry detergent, softener and dryer sheets. Down the hallway are 2 bedrooms and 1 bathroom. The bedrooms offer comfortable queen sized beds, plenty of closet space with felt hangers, and TVs. Each room has mini split allowing for separate climate control from rest of house. All linens, sheets, towels, bedding, soap, shampoo are provided. The grounds are well maintained with a gravel walkway leading up to the stairs of the house. The driveway is paved and boasts ample off-street parking for 3-4 vehicles. House has an outdoor ring security camera and multiple motion lights. Nautical touches throughout house.

Bay Ridge house by Quiet Waters Park, Thomas Point Park

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$837.9

Beautifully renovated home in Eastport one of Annapolis’s sought after neighborhoods. Two blocks from the Spa Creek Bridge and an easy walk to downtown, City Dock, restaurants, shops, and USNA.brFeaturing a custom kitchen, two comfortable bedrooms, and two modern bathrooms. The lower-level family room includes a large tv, wet bar and beverage fridge. The standout screened porch offers true indoor-outdoor living and dining with a cozy seating area & gas fireplace to be enjoyed in any season. And a driveway that holds 2 cars!brbrThis thoughtfully updated home comfortably sleeps up to 4 guests ( and features:br2 private bedrooms (queen and double beds)br2 full bathrooms with walk-in tile showersbrAdditional sleep sofa in the lower-level family roombrOutstanding custom kitchen with modern finishes and high-end appliancesbrBright, open living spaces ideal for relaxing or entertainingbrbrOne of the home’s standout features is the exceptional indoor/outdoor living space in the screened in porch:brHuge screened-in porch with a large dining table — perfect for meals and gatherings (seats 8-10!)brPatio living room with fireplace, ideal for cool eveningsbrPeaceful setting to unwind after a day exploring AnnapolisbrbrAmenitiesbrNew custom renovation throughoutbrFully equipped kitchenbrFast Wi-FibrSmart TVbrTwo-car private drivewaybrWasher & dryerbrCentral heating & air conditioningbrbrLocationbrbrLocated over the Spa Creek Bridge on the Eastport side of Annapolisbr2 blocks to Spa Creek bridgebrEasy walk to Downtown Annapolis, City Dock, Naval Academy areabrClose to restaurants, coffee shops, marinas, and waterfront parksbrEastport offers a relaxed, local vibe while keeping you steps away from all the action.brbrPerfect For:brWeekend getawaysbrNavy or Naval Academy visits including Commissioning WeekbrBoat shows and local eventsbrCouples, families, and small groupsbrbrOther Things to Note:brPrivate home in a residential neighborhoodbrNo parties or eventsbrQuiet hours respected

Newly Renovated 2-Bedrom Eastport Home - Park in the Drive and Walk to Downtown

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$332.49

Summary:brbrEscape to our charming 2-bed, 2-bath cottage in Annapolis Town Center! Newly updated, this cozy retreat comfortably fits 4 guests. Features a fully equipped kitchen, dedicated workspace, and a private yard. Just a 10-minute trip to historic downtown and the Naval Academy. Perfect for families and friends seeking a stylish Annapolis getaway with free parking.brbrbrbrThe Space:brbrStep inside to a bright and airy open-concept living space, where modern style meets cozy comfort. This newly updated home is the ideal retreat for your Annapolis visit.brbrbrbr* **Living Area:** Relax on comfortable leather sofas after a day of exploring.brbr* **Kitchen:** A fully equipped kitchen is ready for you to prepare everything from a quick breakfast to a family dinner.brbr* **Master Bedroom:** Features a comfortable queen-size bed, a private en-suite bathroom, and direct access to the backyard.brbr* **Second Bedroom:** Also offers a queen-size bed with plenty of room for your belongings.brbr* **Dedicated Workspace:** A convenient desk area is available for those needing to catch up on work.brbr* **Private Yard:** Step outside to a quiet, private yard to enjoy a morning coffee or an evening breeze.Where you will sleep: brbrbrbrThe master bedroom comes with a queen size bed and a master bathroom. There is also direct access to the back yard area. brbrbrbrThe second bedroom comes with a queen size bed and plenty of room for clothing storage. brbrbrbrRENT-002091-2025brbrbrbrGuest Access:brbrGuests will have full and private access to the entire home for the duration of their stay. This includes both bedrooms, both bathrooms, the living area, the kitchen, and the private front and back yards. Make yourself completely at home!brbrbrbrOther Things to Note:brbrThe driveway in front of the home fits 2-3 vehicles (depending on size).brbr* City of Annapolis Rental License: RENT-002091-2025brbrbrbrInteraction with Guests:brbrWe respect our guests' privacy and offer a self-check-in process. We will not be on the property during your stay but are readily available via the app or phone if you have any questions or need assistance.

Annapolis Town Center Cottage

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$393.3

Welcome to your perfect Annapolis escape — a beautifully appointed, fully furnished cottage where every detail has been thoughtfully taken care of so you can simply arrive and enjoy.brNestled on a peaceful, serene street, you’re just steps away from it all: the historic downtown, the prestigious U.S. Naval Academy, and the Navy and Marine Corps Stadium. Walk everywhere, stress-free.brInside, the cottage wraps you in warmth and comfort. Relax on the tranquil screened front porch, gather in the inviting living and dining areas, and sleep soundly across two beautifully furnished bedrooms — a queen and a room with two twin beds — with all bedding and fresh linens provided. The lower level offers a cozy full-size futon and a dedicated office area, perfect for those who need to stay connected.brTwo well-stocked bathrooms with essentials and a hair dryer, a spacious fully equipped kitchen — fridge, stove, toaster, microwave, coffee maker, and dishwasher — plus in-unit washer and dryer, central AC, high-speed Wi-Fi, and three smart TVs with Roku and Fire TV make this cottage as practical as it is charming.brStep outside to your private garden oasis — fire up the BBQ grill, unwind at the patio set, and enjoy two complimentary private parking spots, a rare find in the area!brLooking for a longer stay Ask about weekly and monthly discounts, and last-minute bookings. We’d love to host you!

Charming Annapolis Cottage-Steps from Naval Academy & Downtown with parking.

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$540.09

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrEnjoy Annapolis, MD in this charming Federal-style home nestled in the heart of the historic district. Spectacularly restored with attention to detail, this light-filled home will welcome you back in time with historic features like the double-sided (decorative) brick fireplace, 9’ ceilings and hardwoods floors, while you enjoy the upgraded finishes in the gourmet kitchen (i.e, Viking range, GE Monogram fridge) and bathrooms (i.e., spa tub.) Enjoy a (complimentary) bottle of wine while relaxing on the tree-shaded outdoor patio after touring the town. brbr brbr**Parking is not on premises!! A dedicated parking spot at nearby garage (10/15-walk from the house) is provided. Please contact us for details. brbr brbrUnion House features 3 bedrooms and 2 baths and is a quick walk to Main Street, the waterfront, restaurants, shopping and the US Naval Academy. Catch a water taxi or launch your kayak just steps from the front door to enjoy scenic Annapolis from Spa Creek. This is an ideal location for those coming to town for that special Naval Academy or boat show event, or looking to experience the sights and sounds of Greater Annapolis and the Chesapeake Bay. brbr brbrSLEEPING ARRANGEMENTS 3 BR / 2 BA / Sleeps 6: brbrPrimary Bedroom: brbr- Second Floor brbr- Queen Bed brbr brbrQueen Guest room: brbr- Second Floor brbr- Queen Bed brbr brbrDouble Twin Guest room: brbr-Second Floor brbr-Twin over Twin Trundle brbr brbrHIGHLIGHTS: brbr- Beautiful Fenced-In Back Patio with dining table for 6, bar with seating for 4 and gas grill brbr- Gas grill with propane provided brbr- Sonos Ray sound brbr- Spacious gourmet kitchen with stainless steel appliances brbr- Dining room table seats 6 brbr- WiFi brbr- Smart TV brbr- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service brbr- Washer & dryer located inside the home brbr- One Garage Parking Spot located .7 miles from the home. brbr- Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations. brbr- Keyless entry. Enter the front door with an electronic lock code. brbr brbrProperty Distance to: brbr- U.S. Naval Academy - 4 blocks brbr- Main Street and shopping - 2 1/2 blocks brbr- Spa Creek - 1 1/2 blocks brbr- City Docks - 4 blocks brbr- Washington, DC - 30 miles brbr- Baltimore - 25 miles brbr brbr*Amenity & Supplies starter pack: coffee, sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid. brbr* All beds are already made for you with freshly-laundered luxury 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. No parties, events or smoking of any kind. brbrCheck-in time: 4:00 pm brbrCheck-out time: 11:00 am

Historic Downtown Annapolis Union House with Private Patio & Free Off-Site Parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$533.52

Kick back and relax in this calm, charming newly renovated coastal farmhouse waterfront two-story home with private pier & boat lift! Can sleep 8 guests comfortably. Gorgeous sunrises! Experience fresh Maryland Crabs or fish caught from your private pier & enjoy the peace, serenity and bay breezes from your furnished enclosed porch and green space. Enjoy true nature and explore Meredith Creek on the Chesapeake Bay by land or water! Super clean with water views from dining, living room, kitchen and primary bedroom!

Annapolis Charm Waterfront Private Fishing Dock Pier Near Beach & Naval Academy

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$669.64

In this lovely home in a quiet neighborhood in Cape St. Claire, Annapolis, MD, you are a short 12-minute car ride from the US Naval Academy and downtown Annapolis with great restaurants to choose from. Walk along the Little Magothy River and perhaps visit the very nearby playground and small beach. In season, relax in the private pool, or sit by the pool and private dock and watch the ospreys flying in and out of the nest. Enjoy the cozy fireplace on chilly evenings or hang with your friends or family in the downstairs game room, complete with a ping pong table. Or mellow by the new updated “smart tv’s” installed in late 2025. brbrStay connected with the high-speed WiFi; manage laundry with the in-house washer and dryer; and enjoy the full kitchen featuring the stove, oven, refrigerator, and tools needed you to whip up delicious meals, not to mention the propane grill by the pool. brWith 2 full bathrooms, air conditioning, and ample parking, this property offers all the comforts of home during your Annapolis getaway. Time and time again, we receive feedback that the house and property provide a wonderful place to unwind.brThe spring, summer, and fall 2026 schedule is posted. Feel free to reach out if you have questions brIf you are interested in Commissioning Week 2027 or 2028, feel free to reach out with questions.

Waterfront Annapolis w/swimming pool & pier - A Perfect place to Unwind

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$562.52

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrOriginally built in 1857, this fully-restored home has a rich history that's been documented from it's original purpose as a Horse Barn and later became a popular hotel, due to its location in the center of the City, along with the neighboring townhouses on the block. As part of the larger City Hotel complex, this row house block is a rare example of early 19th century commercial domestic architecture which retains a high degree of integrity and contributes significantly to the pivotal intersection of Duke of Gloucester and Conduit streets. In 1900 the rowhouse block was sold independently in 1903 to Weems and Grafton D. Ridout, in whose family the building remained until the mid twentieth century. brbr brbrWhen entering the home, you will be greeted by both the historic charm and all of the upgraded amenities that make for a modern experience. Walk through the impeccably-decorated living and dining rooms into the stunning kitchen with all stainless steel appliance and beautiful granite kitchen counters. Even the breakfast bar seating is an example of the owners' attention to beautiful decor. Head out the glass door in the kitchen to the private fenced-in back patio with lounge chairs and a BBQ. Also on the main floor is a European-inspired full bath with a small stand-up shower. brbr brbrUpstairs are 2 bedrooms and 1 full bath, the 2nd full bath is located on the first floor (and is a small European-style bath). There's a King bed in the Main bedroom, a Queen in the guest room and the sofa in the Den that pulls out to a full bed. There's also a flatscreen TV and sunny desk space in the Den. brbr brbrWalk Score 100 - When you're ready to explore Annapolis, you are just 1/2 a block to the shops and restaurants on Main Street, 2 blocks to the waterfront and 3 blocks to the Naval Academy! While the home does not have dedicated parking, it is conveniently located, via walkway, to the Hillman garage. brbr brbrSLEEPING ARRANGEMENTS 2 BR / 2 BA / Sleeps 6: brbrMain King Bedroom: brbr- 2nd Floor brbr- King Bed brbr- Full Bath in the Hall or downstairs brbr brbr Guest Bedroom: brbr- 2nd Floor brbr- Queen Bed brbr- Full Bath in the Hall or downstairs brbr brbrUpstairs Den brbr- 2nd Floor brbr- Full Sofa Bed brbr- Flat Screen TV brbr- Full Bath in the Hall or downstairs brbr brbrHIGHLIGHTS: brbr- Private Patio fenced in the back yard with propane BBQ grill brbr- Full gourmet kitchen brbr- Breakfast bar seats 4 brbr- Dining room table seats 4 brbr- WiFi brbr- Big Screen TV's brbr- Double-facing decorative fireplaces brbr- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service brbr- Washer & dryer located inside the home brbr- Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations. brbr- Keyless entry. Drive straight to your rental home and enter the door with an electronic lock code. brbr brbrProperty Distance to: brbr- Main Street Annapolis - 1 block brbr- U.S. Naval Academy – 3 blocks; 8 minute walk brbr- Washington, DC – 30 miles brbr- Baltimore - 25 miles brbr brbr* 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. 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. No parties, events or smoking of any kind. brbrCheck-in time: 4:00 pm brbrCheck-out time: 11:00 am

Downtown Gem! Stay in a Historic Carriage House Steps from Main Street, City Dock & USNA

Annapolis, Maryland, United States

Bed