Vacation Rentals By Owner In Annapolis, MD

A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area. Kitchen has large sliding picture window with outdoor service shelf to pass food and drinks onto the patio. Full sized fridge with ice maker and plenty of pantry and cabinet space. Two burner induction cooktop. Microwave / Convection Oven. Gas grill outside. Room darkening privacy shades. Appointed with basic cooking and serving tools. Electric griddle. Blender. On demand, continuous hot water heater. Plenty of clothes-hanging and storage space for vacation-length stays. Wall mounted flat screen Smart TV on swivel. WiFi. Two person indoor dinette on wheels. Outdoor dining table. 15,000 BTU HVAC, ceiling fan, whole home circulating fan, and attic exhaust fan. Very well insulated and quiet. Bluetooth speaker. Additional outdoor shower on back of main home available for any who desire to use it. One parking space dedicated to VRBO guests.

Guest House

A Serene Tiny Home Experience

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$741.0

Peaceful house on a quiet street two blocks from the Navy Stadium with easy access to downtown Annapolis via the stadium shuttle or a pleasant 1.5 mile walk/bike. With three bedrooms plus a queen-sized sleeper couch, there's room for the whole crew. The location strikes a perfect balance of convenient access to downtown Annapolis with easy in/out access from the highway/grocery stores/etc. without the chaos that is downtown. When you're trying to get away from all the crowds downtown, enjoy the well-equipped kitchen and large deck with grill. Two driveway parking spaces plus plenty of on-street parking. Third bedroom (not yet pictured) has a twin-sized futon and twin bed.

Charming 3-bedroom house in Annapolis two blocks from the Navy Stadium

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$439.89

Unique accommodations on a comfortably equipped 43 foot Hatteras yacht, just a 5 minute drive to historic downtown Annapolis and the Naval Academy. 15 minute drive to the Navy Stadium, 15 minutes drive to Rt 50. THIS LISTING IS FOR ACCOMODATIONS ONLY! THE BOAT MAY NOT BE DRIVEN!brForward cabin has bunk beds. Aft cabin has a queen bed. Fully equipped galley (kitchen) with 2-burner cook top, microwave/oven, fridge, toaster oven and Keurig. Boat has WIFI, heat, AC and hot water!

House Boat

Welcome Aboard the Kathleen Marie!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$422.75

A stunning home, “Circa 1885” is a restored piece of Annapolis history. Sitting at one of the two major gateways that lead into downtown, our beautifully renovated home sits on the corner of King George and Randall Streets. A distinctive yellow PRIVATE entry door off of Randall Street leads to this rental apartment that boasts 2 large bedrooms (K, Q), family room with a cozy pull out sofa (F), 1 bath with antique claw foot tub/shower, beautiful eat-in kitchen, and beautifully restored original pine flooring throughout. Everything you need in Annapolis is within an easy walk: US Naval Academy (directly across the street), Navy-Marine Corps Memorial Stadium, Maryland State House, restaurants, shopping, City Dock, Market Place, Eastport, William Paca House & Gardens, museums, boat supplies, as well as the perfect seat to enjoy the 4th of July fireworks! An abundance of options to enjoy boating adventures on the bay or taking the Annapolis Water Taxi to dinner are all located just 2 blocks from our home. Excellent for small groups and a wonderful place to experience Historic Downtown Annapolis.brbrOther things to note:br*Suitable for children 6 & upbr*Please no big parties or large eventsbr

Apartment

CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$473.86

HISTORIC ANNAPOLIS/ART’S DISTRICT brbrBuilt in 1898, “John Stevens House” in sought-after neighborhood of President’s Hill “Arts District”. This charming, light-filled 2-level unit of a duplex features a cozy living room, full bath & fully equipped eat-in kitchen, 2 bdrms/4 beds & driveway brbrEnjoy your morning coffee on the porch or a walk a block to coffee shop, local dining & boutiques. Short walk to Naval Academy, City Dock & Navy Stadium or go by Water Taxi/free Trolley.brbrWashington DC, Baltimore Harbor, Convention Ctr, Camden Yards & Ravens Stadium - 30 mi.brbr* SINGLE NIGHT BOOKINGS CASE BY CASE. PLEASE MESSAGE ME. brbr*PETS CASE-BY-CASE WITH NON-REFUNDABLE PET DEPOSIT. PLEASE MESSAGE ME. brbr*COMMISSIONING WEEK CANCELLATIONS LESS THAN 6 MONTHS PRIOR TO STAY ARE NON-REFUNDABLE.

Cottage

Walk to Everything - Historic Art’s District

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1127.46

The location is ideal - one short block to USNA Gate 3, and just 4 blocks to the downtown waterfront. Home has a private driveway for up to three vehicles. brbrEnjoy the elegance, yet comfort of this completely renovated home!brbrA perfect home to enjoy time in Annapolis! Located on King George Street, walking distance to the Academy or downtown, available year round with a private driveway for up to three vehicles.brbrThis stunningly appointed home offers you an at-home setting in the heart of Annapolis, 1 block from the Academy Gate 3 entrance and 4 blocks to City Dock. The 2005 renovation took it down to the studs and rebuilt as a new house with every amenity. The gourmet kitchen is a cook (or caterer's!) delight with six burner gas stove, double oven, warming drawer, double dishwasher and granite counter-tops on an 11 foot center island. Dining table expands to comfortably seat 12. Downstairs enjoy a fully finished recreation area with pool table, wet bar and entertainment area, with exterior access to the back patio from the lower level. This level can also be used for sleeping two on the queen sleep sofa.brbrThree bedrooms have their own full bath with custom tile showers, plus an additional bedroom (without in-suite bath). The master and both guest rooms all have queen beds. The third floor suite holds both a twin bed, full bed and full shower, and private outdoor roof deck with stunning views of the Academy Chapel.brbrEnjoy this home for any visit to Annapolis!brbrCOMMISSIONING WEEK: Rented for USNA Commissioning Week 2025, 2026, 2027. Available for 2028 and beyond. brbrThis house is conveniently located for any Annapolis events. Walking distance from the Academy, downtown and under a mile to the stadium, this is an easy house to just park your car and walk. It is located just 4 blocks to the waterfront and the entrance to the October Boat Shows.brbrWhere you will sleep...brbrBedroom 1 - Queen Bed, Full bath with shower and separate jetted tub.brBedroom 2 - Queen Bed, en suite full bath.brBedroom 3 - Queen BedbrBedroom 4 - Full bed, Twin bed, en suite full bath with private balconybrBasement - Queen pullout couchbrbrGuest accessbrYou will be given a keypad code prior to your arrival, and no interaction will be required. We live locally in the Annapolis area, Property Manager lives in Eastport.

Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$2878.5

Enjoy comfort and convenience in this beautifully-appointed home! Nantucket on the Chesapeake has an old-world feel yet has all of today’s modern conveniences. This beautiful 100 year old waterfront home just 4 miles from the U. S. Naval Academy offers incredible, wide-open water views in the Bay Ridge area of Annapolis.brbrGroup rentals will not be honored or renting to anyone under 30 years old.brbrWeddings and special events of any kind are not permitted at this property.brbrThe Pool house is the owners office and not part of the rental. It is not utilized by the owner during a rental. Pet Policy: Pets Not Permitted

Nantucket on the Chesapeake Heated Pool

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$558.6

Modern Downtown Annapolis Retreat – Walk to EverythingbrbrWelcome to 222 West Street – Unit A, a thoughtfully designed private retreat located in the heart of downtown Annapolis. Whether you’re visiting for a weekend getaway, a sailing regatta, a Naval Academy event, or a longer stay, this space offers the perfect blend of comfort, convenience, and style.brbrPrime LocationbrbrStep outside and you’re just minutes from:brbrHistoric Downtown AnnapolisbrbrCity Dock and the Annapolis HarborbrbrU.S. Naval AcademybrbrRestaurants, cafés, boutiques, and nightlife on West Street and Main StreetbrbrNo car required — everything Annapolis is known for is right at your doorstep.brbrThe SpacebrbrUnit A is a private, ground-level residence designed for relaxation after a day exploring the city. The layout is efficient yet comfortable, ideal for couples, solo travelers, or professionals.brbrFeatures include:brbrComfortable sleeping accommodations with quality linensbrA modern, fully equipped kitchenettebrStylish bathroom with updated finishesbrSmart TV and high-speed Wi-FibrHair DrierbrIron and Ironing BoardbrBaby Pack and PlaybrClimate control for year-round comfortbrThe interior is clean, modern, and calm — a quiet escape while still being in the center of the action.brThoughtful ComfortsbrFresh towels and essentials providedbrCoffee and tea setup for easy morningsbrSelf check-in for convenience and privacybrbrPerfect For:brbrWeekend getawaysbrNaval Academy visits and graduationsbrSailing events and boat showsbrBusiness travelersbrExtended stays in AnnapolisbrbrWhy Guests Love It:brbrWalkable locationbrQuiet, private unitbrClean, modern designbrEasy check-inbrClose to everything Annapolis has to offer

Cozy Townhome in Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$383.84

Summary:brOur newly updated 4-bedroom, 3.5-bathroom home in Annapolis offers spacious living just 15 minutes from downtown. Featuring an open-concept design, gourmet kitchen, and sunlit living areas, this home is perfect for entertaining. The primary suite boasts a luxurious ensuite and walk-in closet. A finished basement adds extra living space, while the backyard provides a private retreat. Conveniently located near shopping and dining, this home combines comfort and convenience for everyone!

Annapolis Baystone House

Annapolis, Maryland, United States

4

Bed

3

Bath

8

Sleeps

$494.92

Summary:brbrCharming 2-BR Annapolis townhome, perfect for your coastal retreat! Steps from Navy-Marine Corps Memorial Stadium & minutes to the U.S. Naval Academy. This modern, light-filled space comfortably sleeps up to 7 guests. Enjoy a fully equipped kitchen and a prime location for exploring historic downtown Annapolis. Ideal for families, groups, and Naval Academy visitors.brbrbrbrThe Space:brbrWelcome to your inviting home away from home! Step inside this two-story townhome and discover a cozy yet spacious retreat, thoughtfully designed with a clean, modern coastal theme and filled with ample natural light.brbrbrbrThe open-concept living area invites you to relax on the comfortable sofa and enjoy a movie on the wall-mounted TV. The fully equipped kitchen features classic wooden cabinets and modern white appliances, perfect for preparing home-cooked meals to enjoy at the adjacent dining area.brbrbrbrWhen it's time to rest, retreat to one of the two tranquil bedrooms:brbr* Bedroom 1: Features a Queen Bed.brbr* Bedroom 2: A spacious room with one Full Bed and one Single Bed.brbr* Living Room: The sofa converts into a Queen Bed for additional guests.brbrbrbrThe home includes one full bathroom with a convenient shower-tub combination.brbrbrbrGuest Access:brbrYou will have private and exclusive access to the entire two-story townhome during your stay. Make yourself comfortable and enjoy all the amenities our home has to offer, including both bedrooms, the bathroom, kitchen, and living area.brbrbrbrOther Things to Note:brbrPlease note that this is a two-story townhome and access to the bedrooms requires using a staircase. The home is professionally cleaned and sanitized before every stay to ensure your health and comfort.brbrbrbrInteraction with Guests:brbrWe prioritize your privacy and comfort. While we will not be present at the property during your stay, we are readily available via phone or the messaging app should you need any assistance or have questions. We're happy to provide local recommendations to make your trip memorable.

Annapolis Blue and Gold Haven

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$283.9

Welcome to our charming Annapolis retreat! Nestled in a quiet community on the Chesapeake bay, Barefoot Cottage offers a perfect blend of comfort and convenience. Enjoy a stroll around iconic landmarks, savor local cuisine, or unwind with a walk on the beach. Thoughtful interiors and modern amenities, Barefoot Cottage promises a memorable stay for your solo trip, couples romantic getaway, sailing enthusiasts or USNA visitor. Book now for an unforgettable experience in this historic maritime city!brbrYour home in Annapolis! Barefoot Cottage is a 1-bedroom apartment nestled along the shores of the Chesapeake Bay, perfect for a solo quiet retreat, couples retreat, and anyone visiting the fun events happening in and around town! As you step inside, you'll be greeted by a charming interior adorned with coastal decor and soothing hues reminiscent of the nearby waters. The bedroom features a plush queen-sized bed, promising restful nights after days of exploration. The living area offers a choice of comfortable seating to unwind with a glass of wine, watch a movie or cozy into the corner lounge chair with a good book. Laundry area is tucked away under a handmade live edge wood and epoxy countertop. Whip up a delicious meal in the fully-equipped kitchen, complete with all the essentials for a delightful cooking experience. brbrWith access to a private beach close by, you can spend your days lounging in the sun, enjoying a picnic lunch or strolling along the bay. Feeling outdoorsy Included with your stay you will find 2 folding bicycles and 2 inflatable paddle boards!brbrWhether you're seeking relaxation or adventure, our Chesapeake Bay retreat offers the perfect haven for a memorable visit to Annapolis's rich maritime history and vibrant culture.brbr**There is a steep staircase with 13 stairs leading up to the second floor**brbrOur cleaners take every precaution when cleaning Barefoot Cottage. All high touch surfaces are thoroughly disinfected (including light switches, knobs, handles, remotes etc.) using Seventh Generation cleaning products. All throw pillows have removable covers and are washed after every guest. All Free and Clear laundry detergent for our towels and bedding which are washed on the Bedding/Hygiene cycle in our HE washer and dryer. Guests have self check-in with no physical interaction with anyone.brbrSLEEPING ARRANGEMENTS 1BR/1BA/Sleeper Sofa comfortably sleeps 2 adults, 2 adults/2 children or up to 3 adults:brbrPrimary Suitebr- Queen Bedbr- Sitting Areabr- Flat-screen t.v.brbrLiving Roombr- Full sleeper sofabr- Flat screen t.v.br- Reading nookbrbrHIGHLIGHTSbrPrivate entrance and parking for one vehicle brHigh Speed Internet and WI-FIbrFull-size washer and dryerbrEat in kitchenbrChesapeake Bay oriented community with private beach and parkbrNon-smokingbrService animals welcomebrPets welcomebrKeyless entry with personal lock code for the duration of your stay.brbr********************brbrDistance to local attractions:brbrWater Taxi - 3 milesbrbrDowntown Annapolis - 4 milesbrbrU.S. Naval Academy - 5 milesbrbrWashington, DC - 35 milesbrbrBaltimore, MD - 20 milesbrbr*******************brbrHouse RulesbrbrCheck-in 4:00 p.m.brCheck-out 11:00 a.m.brbrParking for ONE vehicle only!brbrLicense Numberbr000618

Guest House

Summer on the Bay | Near USNA | Private Retreat

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$397.86

A centrally located home that exceeds all needs and comfort or your family. Both cozy and spacious from well thought out additions, modifications. Maintains its original 1926 feel and Annapolis stylings with tasteful upgrades. Large private off-street parking court, spacious yard and gardens. It will feel like home the moment you arrive.brbrThe home was originally built in the `Four Square` style in 1926 on a larger than average neighborhood lot. It has been recently enlarged and renovated with original details kept where possible and replicated with the new construction. The floorplan has been modified to a more open-air design.brHouse has 1 master bedroom with private bath, 2 charming bedrooms and the loft bedroom. There is a hall bath and a powder room for these rooms. brThe front door opens to an open floorplan of foyer, living room and dining room with the power room just down a short hallway. The hallway and dining room open into the kitchen/sitting area passing a large pantry and coffee nook on one side and an alcove with side door on the other. The kitchen is spacious with an L shaped island with barstools, and plenty of cabinets and counter space. The room has almost all glass along the walls which makes you feel like you`re in the gardens. The sitting area in the kitchen feels like a sunroom. Back to the front foyer...the open `L` shaped stairs take you to the second floor where two of the bedrooms are right at the top of the stairs along with the hall bath. Also on the second floor is the laundry room, an office nook and the master bedroom. Spiral stairs take you to the spacious loft, which is alsothe third room . I left the wall sheathing of the original house exposed in the spiral stairwell which acts as both an accent wall as well as exposing past framing techniques. brThe grounds are well maintained with brick patio, flagstone and brick walks and gravel driveway. The yard and gardens are quite lush, especially during the prime seasons. There is an old garage nestled into the gardens in the rear of the property.brWe are in a most charming neighborhood with sidewalks and streetlights and has an eclectic mix of homes and mature trees. The sidewalks have been recently repaired and the streets resurfaced. brThe neighborhood is the most centrally located area in Annapolis being just minutes from the historic district in one direction and major shopping district in the other while right among a full variety of shops and restaurants, as well as a brand-new library and the Navy stadium which has a paved trail of approximately four miles. Tawes Gardens with a manmade but naturalized pond and gardens are a block over from the stadium. Eastport and West Annapolis also very close, both are communities with interesting shops and charming homes.brFrom our neighborhood of Homewood, there are multiple means of access in and out of the community, close access to roads in and out of Annapolis and easy access to all the points of interest in town. brAnd lastly, there is the charming wooden front porch to relax, surrounded by variety of shrubs and perennials, where you can and enjoy the quiet and to say hello to the dog walkers, bicyclists, joggers and immediate neighbors.brbrYou have access to the house, yard. and driveway. The garage and basement would be private since it’s mostly storage anyway. The house will hopefully feel like it’s your space. The back of the house on the first floor is a kitchen and sunroom combination with a lot of windows, a panoramic view with gardens surrounding you. The master bedroom is quite large with a full bath. The house feels both cozy and spacious.brbrMy main goal is for guests to enjoy their time at the house. So I’ll tend to leave you be and I’ll be around to do upkeep and maintenance on the house and gardens. My intent is for the house to be your space so I would announce if I need to come inside the house for any reason. Feel free to approach me when you see me and I’ll also be available by phone. I’d love to share with you what I know of Annapolis, places to eat, things to see.brbrThe neighborhood is an eclectic mix of homes going back as far as the end of the 1800s, with most of the homes built in the early to mid 1900s. It is a quiet neighborhood with a bike trail created from an old train route. The Naval Academy stadium is at the north end of our street and we are just four houses down from the stadium. West Street is at the south end of our street and is the main corridor running from the historic district to the east and the main shopping distric to the west. Wide variety of shopping, restaurants and services along West Street as well.brbrThere is always ample street parking in front of the house. Even though there is a driveway, there are also numerous vehicles and trailers so please park in the street to avoid blocking anyone in. There is bus shuttle, Uber, taxi and electric cart shuttle service available from our neighborhood. Walking from house to the historic district waterfront could take about 20 minutes or so, and with shops and restaurants along the way.brbr- The neighborhood is and has been quite safe, you will see a lot of walkers, joggers, dogs, bicyclists, etc.br- Annapolis in general has always struggled with parking BUT this neighborhood has available street parking all the time and you have one of the largest private driveway in the community.br- I won`t be on the premises all the time, I don`t want you to feel any unnecessary intrusion. I won`t enter the house without announcing myself via text or knocking unless there is an emergency. I will be on and off the premises for lawn mowings, yard maintenance, etc. I also will also have free access to the basement and garage. Feel free to approach me anytime I am around. I will send you my mobile number so you can reach me any time.br- Self check in and self check out. I will send texts with information related to check in, check out, keys for front door, etc.br- Please don`t make any assumptions if something is unclear, contact me first. br- Please confirm any texts I send, that will let me know you got the information so I can relax.br- The house will be clean with fresh linens on the beds. I won`t be doing house cleaning during your stay, that will be up to you to wash linens and clean as you care to. I will have a cleaning outfit come in after check out. Let me know if you`d like to pay for additional cleanings throughout your stay.br- Let me know of anything you need, I`ll help if I can.

Charming 1926 Four Bedroom Home w Ample Parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1206.77

5 bedrooms (sleeps 9). First-floor wheelchair accessible bedroom with ADA compliant bathroom. Entertaining kitchen and porch/deck with grill - great for family gatherings. 1.9 miles from downtown and USNA - easy walk or Uber ($10). One block to grocery/shopping, restaurants. Plenty of parking, quiet neighborhood in the middle of Everything-Annapolis. FULL WEEK (5+ NIGHTS) ONLY BOOKINGS FOR USNA COMMISSIONING WEEK.

Clean, Spacious Family House

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1259.74

Summary:brbrLocated only 5 miles from Annapolis, this newly updated, 3-story home with great views of the Chesapeake Bay is perfect for your next family getaway! It is located on an inlet of the lower Severn River which connects directly to the Chesapeake Bay.brbrbrbrRelax in the heated pool (open late April - late September) and the hot tub year round! Enjoy three levels of patio and balconies! The lower-level walk-out patio is home to the six-person hot tub, the second-level large deck opens from the living room with lounge chairs and dining for four, and the third-level large balcony opens from the primary bedroom with seating for two. The beautiful in-ground private pool is surrounded by comfortable lounge chairs. The green lawn ends with a cozy firepit area for evening S'mores and storytelling. Take advantage of the poolside built-in grill available for warm-weather barbecues with your loved ones.brbrbrbrThe Space:brbrThere are many areas to enjoy family time or sneak away to enjoy a book waterside. An extra-large waterside living room with a fireplace opens out to the large, main floor deck. The living room features large, comfy couches and digital projection TV for a comfy family movie night. A large rec room with a wet bar and seating opens to the waterside patio, where you can find the hot tub and grill, and venture out to the yard. On the lower level, the in-law suite has a cozy and warm sitting room. A great spot to hide with a good book - feel free to read historical novels from the homeowners' private library.brbrbrbrThe spacious kitchen is complete with plenty of storage and fully equipped with amenities. You will never say 'there are too many cooks' in this kitchen! Granite countertops all around, ending at a large kitchen bar with stools plus a table and chairs for four. The open dining room with an extra-large table offers enough seating for your full family. Or you might as well dine alfresco on the back deck with a table and chairs seating for four. All in all, this home has stellar interior and exterior entertaining space for your family gatherings.brbrbrbrParking notes: This home has a driveway that can ONLY accommodate up to 4 standard-size vehicles.brbrStreet parking is not allowed in the neighborhood. Parking on the street may result in your car being ticketed and/or towed. Paid parking is available at locations 15+ min from this property.brbrWe highly recommend limiting your party to no more than 4 cars at a time, regardless of how many people stay at the property.brbrbrbrGuest Access:brbrGuests have access to the entire house and backyard except for locked storage closets and a wine fridge in the basement.brbrbrbrThe Neighborhood:brbrThis is a quiet residential neighborhood on the Chesapeake Bay that is a 15-20 min drive to downtown Annapolis / the US Naval Academy.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-4 & 5+ bedroom units: $50 per guest, per night after 8 or 10 guests, respectively brbr brbrPlease ensure your guest count is entered accurately at booking. We will confirm the number of guests after reservation. If the guest count changes, pricing may be adjusted accordingly. For safety and compliance purposes, exterior security cameras are used to verify occupancy. Unreported additional guests may result in additional charges. brbr brbrPet Policybrbr brbrThis is a pet-friendly property. While our cleaning team is thorough, guests with severe pet allergies should be aware that dogs, cats, or other animals may have stayed in the space previously.brbr brbrPet fees:brbr brbr$30 per night, per petbrbr$150 per week, per petbrbr$300 per month, per petbrbr brbrPet fees are included in the accommodation rate as long as you choose the appropriate quantity of pets when completing a booking. We confirm this with all guests post booking confirmation. 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: $150brbr-1–2 hours: $300 brbr-2–3 hours: $450 brbr-3+ hours: $600 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: 002213-2025brbrbrbrCounty permit number: STR-00031brbrbrbrYou must be 25 years or older to rent this property.brbrbrbrInteraction with Guests:brbrIf I am in town and available I will help you out if needs be! I also have a property manager who lives in Annapolis who may be able to help if I'm not available.

Oasis by the Bay - Waterfront Heated Pool Hot Tub!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1000.86

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrHistoric Charm Across from the Naval Academy brbrNestled in the heart of Downtown Annapolis, this spacious 5-bedroom, 4.5-bath historic brick row home is a rare gem. Located directly across from the U.S. Naval Academy's Gate 3, this home combines the charm of historic Annapolis with modern conveniences like on-site parking for 2-3 cars, a private patio, and generous living spaces. brbr brbrFeatures You'll Love: brbrNavy-Inspired Elegance: Thoughtfully designed with nautical decor and a welcoming ambiance brbrAmple Space to Relax: Enjoy the spacious dining, living, and kitchen areas, perfect for entertaining family and friends brbrConvenient Parking: 2 Private parking spots behind the home make exploring Downtown Annapolis a breeze brbrOutdoor Oasis: Unwind on the private patio deck with dining for six, lounge chairs, and a BBQ grill. brbr brbrInquire about discounted extended stays! brbr brbrSleeping Arrangements (5 BR / 4.5 BA / Sleeps 10): brbrAnne Arundel Suite (2nd Floor): Queen bed, en-suite full bath brbrAcademy Room (2nd Floor): Queen bed, full hall bath brbrCapital View Room (3rd Floor): Queen bed, en-suite full bath brbrCollege Walk Room (3rd Floor): Queen bed, shared hall bath brbrCompass Rose Room (3rd Floor): Full bed, shared hall bath brbr brbrAdditional Highlights: brbrGourmet kitchen with ample counter space brbrDining table seats 10-12 for large gatherings brbrBig screen Smart TVs and high-speed WiFi for entertainment brbrLuxury linens, starter toiletries, and boutique-level service brbrEasy keyless entry for a seamless check-in experience brbr brbrPrime Location: brbrU.S. Naval Academy Gate 3: Just across the street! brbrAnnapolis Waterfront: A short walk to shops, restaurants, and sights. brbrWashington, DC: 30 miles away. brbrBaltimore: 25 miles away. brbrHouse Rules: brbr brbrGuests must be 25+ to book; no parties, pets, or smoking allowed. brbrQuiet hours must be observed to respect neighbors. brbrCheck-in: 4:00 PM | Check-out: 11:00 AM. brbr brbrThings to Note: brbrNo Washer/Dryer: Plan accordingly for extended stays. brbrSteep Staircases: Guests with mobility challenges may want to consider alternative accommodations. brbrOwner's Suite: The locked-off private basement suite may be used by the owner on occasion but is not part of the rental space.

On-Site Parking, Steps to USNA Gate 3 and Private Patio at Historic Gatehouse

Annapolis, Maryland, United States

5

Bed

4

Bath

10

Sleeps

$264.53

Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites such as the United States Naval Academy, Maryland State House, and St. John's College. Explore the beautiful Chesapeake Bay area for day trips to Washington DC or a sailing adventure along the coast.brbrThis listing is for a room within a hotel.brbr✦ Your room is 275 sq. ft, equipped with complimentary toiletries, high definition 42-inch TV, available with Standard cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm, and is flexible afterwards. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid valet parking – 1 space(s), available for $50.33 per day.brbr✦ Shuttle service is available upon request for free.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $30 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $34.20 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. for a $150/stay fee + $20/night cleaning feebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Refundable security deposit is charged per night on a valid credit card.brbr✦ Pet Policy: Max 2 dogs/room up to 50lbs eachbrbr✦ Credit card are subject to a surcharge of 2.5 percent.brbr✦ Free Shuttle within the area(Based on Availability)

Top Location | Close to Annapolis Historic Sites | Pets Allowed & Free Shuttle

Annapolis, Maryland, United States

Bed

Bath

2

Sleeps

$264.53

Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites such as the United States Naval Academy, Maryland State House, and St. John's College. Explore the beautiful Chesapeake Bay area for day trips to Washington DC or a sailing adventure along the coast.brbrThis listing is for a room within a hotel.brbr✦ Your room is 275 sq. ft, equipped with complimentary toiletries, high definition 42-inch TV, available with Standard cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm, and is flexible afterwards. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid valet parking – 1 space(s), available for $50.33 per day.brbr✦ Shuttle service is available upon request for free.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $30 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $34.20 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. for a $150/stay fee + $20/night cleaning feebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Refundable security deposit is charged per night on a valid credit card.brbr✦ Pet Policy: Max 2 dogs/room up to 50lbs eachbrbr✦ Credit card are subject to a surcharge of 2.5 percent.brbr✦ Free Shuttle within the area(Based on Availability)

Governor Calvert Historic King at Historic Inns of Annapolis | Pet-Friendly

Annapolis, Maryland, United States

Bed

Bath

2

Sleeps

$385.27

Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites such as the United States Naval Academy, Maryland State House, and St. John's College. Explore the beautiful Chesapeake Bay area for day trips to Washington DC or a sailing adventure along the coast.brbrThis listing is for a room within a hotel.brbr✦ Your room is 200 sq. ft, equipped with complimentary toiletries, high definition 42-inch TV, available with Standard cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm, and is flexible afterwards. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid valet parking – 1 space(s), available for $50.33 per day.brbr✦ Shuttle service is available upon request for free.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $30 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $34.20 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. for a $150/stay fee + $20/night cleaning feebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Refundable security deposit is charged per night on a valid credit card.brbr✦ Pet Policy: Max 2 dogs/room up to 50lbs eachbrbr✦ Credit card are subject to a surcharge of 2.5 percent.brbr✦ Free Shuttle within the area(Based on Availability)

Rare Antique Gem | Steps to State House | 0.3 Mi to Naval Academy

Annapolis, Maryland, United States

Bed

Bath

4

Sleeps

$255.36

Conveniently located in the center of Maryland's famous capital city, our inns are within easy walking distance to sites such as the United States Naval Academy, Maryland State House, and St. John's College. Explore the beautiful Chesapeake Bay area for day trips to Washington DC or a sailing adventure along the coast.brbrThis listing is for a room within a hotel.brbr✦ Your room is 280 sq. ft, equipped with complimentary toiletries, high definition 42-inch TV, available with Standard cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm, and is flexible afterwards. If you expect to arrive later, please let us know as soon as possible to make the necessary arrangements.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid valet parking – 1 space(s), available for $50.33 per day.brbr✦ Shuttle service is available upon request for free.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $30 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $34.20 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. for a $150/stay fee + $20/night cleaning feebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The maximum number of days that you may book per reservation is only 28 days.brbr✦ Refundable security deposit is charged per night on a valid credit card.brbr✦ Pet Policy: Max 2 dogs/room up to 50lbs eachbrbr✦ Credit card are subject to a surcharge of 2.5 percent.brbr✦ Free Shuttle within the area(Based on Availability)

Right Where History Is | Just Across Maryland State House

Annapolis, Maryland, United States

Bed