Vacation Rentals By Owner In Annapolis, MD

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

$284.47

Upscale renovated units on the first floor of Yacht Club Condos. Both units A1 and C1 are available. First floor walk out decks for convenience. Walk to everything in Eastport and Annapolis. Watch the Blue Angels fly above for commissioning week. View the sunsets from the balcony.

Condo

Waterfront Condo- Eastport Annapolis- Next to Spa Creek Draw Bridge & AYC

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

$245.86

This private treehouse apartment, located above a detached garage, is nestled among the treetops on a wooded acre of land in a friendly, walkable, and quiet neighborhood. The apartment has many amenities and is only 3 miles from historic downtown Annapolis.

Apartment

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis, Maryland, United States

Bed

1

Bath

3

Sleeps

$836.72

Stunning home a short walk from Chesapeake Bay - a perfect blend of comfort and coastal charm. Stroll, jog or bike in the scenic neighborhood, and hear songbirds, see deer, and watch sailboats glide by. Open-concept design and natural light make our home ideal for entertaining, working from home, or relaxing on the spacious deck. Minutes from local eateries, and attractions in downtown Annapolis. Easy drive to DC or Baltimore. We allow one dog - max 25 lbs. Exterior security cameras on property.

Cottage

Wonderful Cottage Nestled On Chesapeake Bay

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

$421.92

Lower level furnished apartment, in one of Historic Annapolis's 10 oldest Private residences. Lovely wood, brick & ornamental ironwork throughoutbrCovered keyless entrybrKing Henredon bedbrExec desk & chairbrTV w/ Roku remotebrDecorative fireplace w/ candlesbrPorcelain claw foot tubbrBeverage station (coffee maker w/ local artisan mugs, wine/bottle openers glasses, crystal ice bucket, sterling champagne flutes)brMicrowavebrToasterbrFridge/freezerbrCutlerybrPlates & napkinsbrLaundry access upon request.brTHE SPACEbrIn this 18th century home, Circa 1770, be prepared to travel back to colonial time & become part of living history - while enjoying 21st-century conveniences.br——-brParking…brThere are several public garages within a few blocks. The closest is South Street Garage off Church Circle (closed midnight-7a)brbrPark Place Garage is discounted through the rebuild) and walk or take the shuttle. Running every 8-10 minutes.brbrThere’s also a free on-demand service for those arriving or departing after shuttle hours. M-S 7a-11p / Sun 8a-8pbrbrbrYou’re welcome to quickly drop your bags before parking. (Luggage drop off will block traffic so driver must remain with vehicle).br———brPrior to booking be aware, this is a unique space that’s over 250 years old!brSteam heat tinks, plumbing can be noisy, brick & mortar may shed, infrastructure is exposed yet tastefully painted & the bedroom ceiling maxes at 7’.brbrThe look, feel, sounds, and smells of 18th century Puritan life are bound to flood your senses & transport you back to a time when American independence remained a dream.brGuest accessbrGuests may access:brPvt ground floor entrance using personal code. Ground floor foyer, bistro dinette, kitchenette (fridge/freezer, microwave, toaster) bedroom, en-suite bath, & back patio.br*Possible laundry access upon request*brOther things to notebrIf the bedroom appears dark, assure the dimmer’s up on the wall switch.brPlease remember to be considerate of neighbors and don’t conjugate or speak loudly on Cornhill between 9pm & 8am.

Apartment

18th Cent. Charm in Historic Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$808.26

Beautifully restored 1930s cottage w/ open floor plan & vaulted ceilings provide a homey vibebrbrEnjoy having Historic Annapolis Towncenter in your backyardbrbrJack & Jill bath separates queen bedroomsbrbrHardwood floors adorn common areasbrbrGourmet kitchen w/ extensive granite countertops, breakfast bar & amenitiesbrbrDining table & chairs, extra-large comfy couch nestled between 2 chaise lounge chairs, 55 Roku tv, full daybed, electric FP, towels, linens, pvt laundry, and more!brThe spacebrPvt entrance leads through a brick terrace to your hidden cottage retreat. Personal keypad entry.brbrOpen floor plan & cathedral ceilings provide an abundance of natural light & space.brGuest accessbrGuests have exclusive cottage access and shared access to the back patio amenities including a complimentary BBQ.brOther things to notebrFriendly, well trained Dogs are welcome: $50 weekly pet fee/per dog.brbrOffsite parking …brThere are several public garages within a 5min walkbrbrIf you’re visiting during a weekend or federal holiday, Calvert Garage is an easy walk & parking’s FREE! :)brComplimentary parking is available after 6pm Fri through 6am Monday and during federal holidays.brbr(DIRECTIONS TO CALVERT GARAGE)br-From 50 E take exit 24 towards Historic Annapolis/70S/Rowe Blvd, (1.3mi)br-Turn left on Calvert Street (last light before the State House)br-Turn left on St. John's Street.br- Garage is on the left.brbrSt. John's Street also offers 9hr free Street parking.brAll street parking is free 10pm-8am.brbr(WALKING DIRECTIONS TO CORNHILL FROM ST JOHNS ST)br-Walk toward the State Housebr-Cross College Avenue onto North St (cedar shake home on L.)br-N. Street leads to State Circle.br-Take a left on the circle.br-Walk past Marland Ave (boutique shops) Harry Browns restaurant (EXCELLENT!) & The Historic Maryland Inn.br-Turn left on Cornhill Street.br-53 is the 3rd house down on the Right.brbrbrIt’s roughly a 10-minute walk.brbrMany Guests have also found Gotts garage to be easy & affordable. $15-$20/daybrbrCity Authorities recommend Park Place Garage (discounted through the Noah Hillman Garage rebuild). Easy walk or take the shuttle. Running every 8-10 minutes.brbrThere’s also a free on-demand service for those arriving or departing after shuttle hours. M-S 7a-11p / Sun 8a-8pbrbrSee the attached map to help.brbrYou’re welcome to quickly drop your bags before parking.brCornhill’s a fairly narrow one-way street. If there is no place to pull over, please be sure a driver remains with the vehicle so you don't block traffic.brbrLet me know if you have any questions and/or if there's anything I can do to make your stay better.brbrLook forward to hosting you.brJennifer

Cottage

Secluded Cozy Cottage in Historic Downtown

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

Bath

6

Sleeps

$462.52

Summary:brbrSteps away from the Naval Academy, St. John's College, State House, City Dock, Yacht Club, St. Mary's Church and local restaurants/bars/shops. This spacious, beautifully updated historic 2 story / 2 bedroom house built in 1900 offers rare private outdoor space, a lovely retreat in an ideal location with everything that Annapolis has to offer at your fingertips!brbrbrbrIt has the following must have amenities:brbrbrbr-Private outdoor patiobrbr-Updated kitchenbrbr-Cozy living roombrbr-2 full bathroomsbrbr-5 min walk to Gate 1 @ USNA and multiple restaurants around the harbor, city dock, tours, Main Street shopping and diningbrbr-In unit washer and dryerbrbrbrbrThe Space:brbr1st floor - Living room with sleeper sofa, dining room (seats 4), kitchen, full bath with stand-up shower, cozy area with lofted twin size bed and sleeping nook with twin size bedbrbrbrbr2nd floor - Primary bedroom with additional open loft with 2nd full size above, full bathroom with stand-up shower washer/dryer includedbrbrbrbrOutside- seating area on a private patiobrbrbrbr**Please note the loft (full bed) shares the same open space as the primary bedroom, and does not have a door or wall separating the two areas.**brbrbrbrGuest Access:brbrGuests have access to the entire house and outdoor area except for locked storage closets.brbrbrbrThe Neighborhood:brbrLocated on a historic street downtown Annapolis just steps to all that downtown has to offer!brbrbrbrGetting Around:brbrStreet parking in Downtown Annapolis is paid. If possible, we recommend not driving / renting a car. If you do bring a car, the Hillman Garage is the biggest parking structure in downtown Annapolis. It is a 0.1 mile / 3 min walk from the house. Additional parking info is available on the Visit Annapolis website's Parking in Downtown Annapolis page.brbrbrbrOther Things to Note:brbrTo help ensure a smooth, secure, and enjoyable stay for all guests, please review the following important information before booking: brbr brbrCheck-In & Identity Verification Policy brbr brbrAll reservations require the primary guest (the booker) to complete a secure online check-in process prior to arrival. This includes: brbr brbr-Uploading a valid, unexpired government-issued photo ID brbr-Uploading a selfie to confirm identity brbr-Reviewing and signing our rental agreement brbr brbrThis process is similar to hotel check-in and is required because we do not typically have staff on site. Check-in instructions will only be provided once this process is complete. brbr brbrIf you would like to review the rental agreement before booking, please feel free to contact us. brbr brbrIn some cases, we may also request a security deposit and/or apply a damage waiver fee in accordance with booking channel policies. brbr 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-2 & 3 bedroom units: $35 per guest, per night after 4 or 6 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 or cats may have stayed in the space previously. brbr brbrPet Policybrbr brbrThis is a pet-friendly property. While our cleaning team is thorough, guests with severe pet allergies should be aware that dogs, cats, or other animals may have stayed in the space previously.brbr brbrPet fees:brbr brbr$30 per night, per petbrbr$150 per week, per petbrbr$300 per month, per petbrbr brbrPet fees are included in the accommodation rate as long as you choose the appropriate quantity of pets when completing a booking. We confirm this with all guests post booking confirmation. brbr brbrLocal Reservation Policy brbr brbrReservations under 7 nights from guests residing in the local area may be subject to cancellation at our discretion. We handle exceptions on a case-by-case basis. brbr brbrEarly Check-In & Late Check-Out Policy brbr brbrEarly arrivals and late departures are not guaranteed and must be approved in advance. If approved, the following fees apply: brbr brbr-Up to 1 hour: $100brbr-1–2 hours: $200 brbr-2–3 hours: $300 brbr-3+ hours: $400 or the cost of an additional night (whichever is greater) brbr brbrPlease do not assume availability without confirmation. brbr brbrSmoking Policy brbr brbrSmoking is not permitted anywhere on the property, including indoor and outdoor areas. If evidence of smoking is found, an additional cleaning fee of $500 will be applied in accordance with the booking channel's cleaning and damage policies. brbr brbrSpecial Request Policy brbr brbrRequests for items such as pack-n-plays, high chairs, or other non-standard amenities should be submitted at least 7 days before check-in to ensure availability. Requests made closer to arrival will be accommodated if possible but cannot be guaranteed. brbr brbrWe understand that this is a detailed list, and we truly appreciate you taking the time to review it. These guidelines help us maintain a safe, well-cared-for property and ensure a great experience for every guest. Our goal is always for you to feel comfortable, welcome, and well taken care of during your stay.brbrbrbrPermit number: 002213-2025

Condo

Historic Row Home in Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1902.17

Newly Renovated with larger bedrooms and 2 more bathrooms!brEnjoy Annapolis with family & friends all year at this extraordinary waterfront home. With 4000 sq. ft of living space, 7 bedrooms, 6 baths, gourmet kitchen, 2 story great-room, screened-in porch, deck, balcony, hot-tub, pool, 4 deep water slips on Fishing Creek . Bring your boat, water toys & fishing gear to fully enjoy all this home has to offer. Steps from Thomas PT. Park, Close by to Dtwn Annapolis, City Dock, Quiet Waters Park, U. S. Naval Academy, great eateries, cultural events and more.

Annapolis Waterfront Oasis with Pool, Hot Tub & Piers with L2 EV Charger

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$574.94

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrEnjoy a piece of Annapolis history! Nestled at the end of a row, this circa 1879 home has the perfect blend of historic cedar shake charm on the outside combined with a surprisingly modern interior. The renovated kitchen with its exposed brick chimney, beautiful cabinets, granite countertops and breakfast bar overlooks the sunken great room with walls of windows and cathedral ceilings. Celebrate your Happy Hours on the spacious screened porch overlooking the private backyard. Back inside is a dining room with seating for 8 and bright living room in the front of the home with a new Queen sleeper sofa. There is also a powder room and full laundry room located on the main floor. brbr brbrHead upstairs to the 3 oversized bedrooms and 2 bathrooms. The 2 guest bedrooms on the 2nd floor share the unique full bath in the hall, with separate shower/bath and double vanity/toilet rooms. The third-floor suite has a Queen bed, its own private full bath and even a delightful peek-a-boo view of the Maryland State House. Located one block to the quiet waters of Spa Creek and 2 blocks to Main Street, this home is just steps away from downtown shopping, restaurants, parks and historical sites, the Naval Academy and the Maryland State House. brbr brbr***Parking is not on premises!! A dedicated parking spot at NEARBY GARAGE (10 minute walk) is provided. Please contact us for details. brbr brbrSLEEPING ARRANGEMENTS 3 BR / 2.5 BA / Sleeps 8: brbr3rd Floor Suite: brbr- Queen Bed brbr- Full ensuite bath with stand-up shower brbr brbrKing Bedroom: brbr- 2nd Floor brbr- King Bed brbr- Full bath in the hall with standup shower and soaking tub, double vanity brbr brbrFull Bedroom: brbr- 2nd Floor brbr- Full Bed brbr- Full bath in the hall with standup shower and soaking tub, double vanity brbr brbrLiving Room brbr- Main Floor brbr- Queen sleeper sofa brbr- Half bath on the main floor; shared full bath in the hall on the 2nd floor brbr brbrHIGHLIGHTS: brbr- Large Kitchen overlooking the sunny sunken den brbr- Breakfast bar in kitchen seats 2 brbr- Dining room table seats 8 brbr- Large screened-in porch brbr- Private backyard brbr- WiFi brbr- Big Screen Smart TV's brbr- 2 bicycles for guest use brbr- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service brbr- Keurig and coffee pot with starter coffee and creamers 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 code for the electronic lock on the front door. brbr brbrProperty Distance to: brbr- U.S. Naval Academy – 5 blocks 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

Historic Happy Home Steps from Main Street – Private Yard, Screened-In Porch & Parking

Annapolis, Maryland, United States

3

Bed