Vacation Home Rentals By Owner In Annapolis, MD

$1203.2

All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis

Annapolis, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWelcome to your Eastport escape! brbr brbrThis newly decorated custom home has everything—Severn River views, a huge private yard, stylish interiors, and parking for 2–3 cars. Just a short mile’s walk to Downtown Annapolis, the Naval Academy, and Eastport’s best dining and shopping, you’ll be perfectly positioned for relaxation and adventure. brbr brbrMain Features brbrMain Floor brbrGourmet kitchen with high-end appliances brbrOpen dining & family room with cozy gas fireplace brbrWalk out to deck, backyard with fire pit & gas grill brbr brbrSecond Floor brbrKing suite with ensuite private bath + balcony brbr brbrKing Guest room with balcony brbrFamily bedroom: 2 Queens + 2 Twin trundles brbrShared buddy bath with double vanities, shower + soaking tub brbr brbrThird Floor brbrPrivate King suite with spa-like en-suite (shower + tub, double vanities) brbrBalcony with sweeping Severn River views brbr brbrHighlights brbrGourmet kitchen + dining for 6–8 brbrExtra dining nook (seats 4) brbrHuge outdoor lounge + dining space brbrGas grill + wood-burning fire pit (BYO firewood) brbrBalconies off back bedrooms brbrDriveway parking for 2–4 cars + free street parking brbrHigh-speed WiFi + smart TVs brbrLuxury linens & toiletries brbrWasher/dryer brbrKeyless entry + mobile app instructions brbr brbrClose to Everything brbrDowntown Annapolis – 0.9 mi brbrU.S. Naval Academy – 1 mi brbrWashington, DC – 33 mi brbrBaltimore – 33 mi brbr brbrHouse Rules brbrNo groups under 25 without adult present brbrNo smoking, pets, parties, or events brbrPlease respect the neighbors brbrCheck-in: 4:00 PM brbrCheck-out: 11:00 AM

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$464.03

/ Nightly

Private Vacation Home

Cozy Stay in Downtown Naptown -Located in the heart of Annapolis - 3BR, 2 BA

Annapolis, Maryland, United States

Welcome to 17 Lafayette Ave—your charming retreat in the heart of historic Annapolis! Just steps from downtown, the U.S. Naval Academy, shops, and waterfront dining. This cozy home blends modern comfort with historic charm, featuring a full kitchen, fast Wi-Fi, and private outdoor space. Perfect for couples, families, or business travelers looking to explore the best of Annapolis on foot. This delightful property features 1 king bed and 2 queen beds, perfect for a peaceful night's sleep. Guests can relax and unwind. Enjoy the cozy living room with a sofa bed for extra space. Fall in love with Annapolis and enjoy the magic it has to offer.

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$741.0

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Private Vacation Home

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

Annapolis, Maryland, United States

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.

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$1127.46

/ Nightly

Private Vacation Home

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

Annapolis, Maryland, United States

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.

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$2878.5

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Private Vacation Home

Nantucket on the Chesapeake Heated Pool

Annapolis, Maryland, United States

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

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$558.6

/ Nightly

Private Vacation Home

Cozy Townhome in Downtown Annapolis

Annapolis, Maryland, United States

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

2

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2

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4

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$494.92

/ Nightly

Private Vacation Home

Annapolis Blue and Gold Haven

Annapolis, Maryland, United States

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.

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$383.84

/ Nightly

Private Vacation Home

Annapolis Baystone House

Annapolis, Maryland, United States

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!

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Bath

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$397.86

/ Nightly

Private Vacation Home

Charming 1926 Four Bedroom Home w Ample Parking

Annapolis, Maryland, United States

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.

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$1206.77

/ Nightly

Private Vacation Home

Clean, Spacious Family House

Annapolis, Maryland, United States

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.

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Sleeps

$1259.74

/ Nightly

Private Vacation Home

Oasis by the Bay - Waterfront Heated Pool Hot Tub!

Annapolis, Maryland, United States

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.

Bed

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$1000.86

/ Nightly

Private Vacation Home

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

Annapolis, Maryland, United States

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.

Bed

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Sleeps

$2257.2

/ Nightly

Private Vacation Home

Cool 1870's home anchored in the Historic District with modern amenities.

Annapolis, Maryland, United States

Our century-and-a-half-old, five bedroom and three bath home with 3,000 square feet centrally situated in the heart of the Annapolis Historic District downtown. brbrYou'll be 3-4 blocks from the Naval Academy, Main Street shops, food and the historic State Capital. brbrOurs is a Federal style, circa 1870's, three story brick row home which was partially upgraded in 2017. Renovation included gutting both the kitchen and the English basement bedroom. brbrEnjoy a screened porch overlooking a private garden surrounded by an eight foot tall brick wall. There is plenty of space throughout the home with hideaways where you can relax and get away from it all.brbrThere are three full baths - the second floor has a walk in shower. The master bathroom has a claw foot tub combination shower. The renovated English Basement, which is the fifth bedroom, has the third full bath with a walk in shower. Although we permit up to ten guests, there are five beds: a California King, a queen, a sleeper sofa queen in the English basement and two double beds on the second floor. There are two queen inflatable’s stored in the English basement.brbrThe rear bricked patio has a Weber gas grill and a Solo fire pit and it is surrounded by an 7-8 foot high brick wall. The rear screened porch behind the kitchen is our favorite go to space for sharing pleasant weather or streaming to the the overhead TV screen.brbrWith its walk-to-everything coordinates, creaky heart pine floors, tall ceilings and upgraded amenities, you'll feel a warm coziness throughout our old brick home. brbrThe English Basement bedroom has three entrances including a rear door to the brick walled patio.brbrYou can come and go from the English basement bedroom through the interior stairs or through the lower level front door which takes you up the brick steps directly to Prince George Street. brbrThere is a small laundry on the second floor and two large capacity LG laundry machines in the English Basement.brbrNon-smokers only. This is our 'real' home, we live here when not renting. Our home is for mellow family events. brbrNo on site parking - Calvert Street Garage at 19 St. Johns St. is free on weekends and after 6pm daily. Hillman Garage at 150 Gorman St. has 24 hr parking @ ~$30 daily. br(rev July 27, 2025)

Bed

Bath

Sleeps

$396.41

/ Nightly

Private Vacation Home

Charming Charles -Walkable Downtown Annapolis Home

Annapolis, Maryland, United States

Summary:brbrEscape to your private oasis in this stylish 2-bed, 2.5-bath townhome in the heart of Downtown Annapolis. This historic yet modern retreat features a fully equipped kitchen and a charming private patio. Perfectly located, you're just a short walk from the historic district, waterfront, and renowned restaurants. Ideal for a weekend getaway or Naval Academy event, experience the best of Annapolis from this perfect home base.brbrbrbrThe Space:brbrWelcome to our inviting 2-bedroom, 2-bathroom townhome in the picturesque city of Annapolis. Step inside and discover a cozy yet spacious retreat, thoughtfully designed to provide comfort and convenience. The open concept living area invites relaxation with its stylish furnishings and ample natural light. The fully equipped kitchen offers modern appliances and a dining area for enjoying home-cooked meals. brbrbrbrRetreat to the tranquil bedrooms, each boasting plush beds and tasteful decor, ensuring a restful night's sleep. The townhome features 1 half bathroom on the main level and two full size bathrooms, each featuring contemporary fixtures and complimentary toiletries. brbrbrbrOutside, a charming patio awaits, perfect for sipping your morning coffee or unwinding in the evening breeze. Situated in a desirable neighborhood, you'll find yourself in close proximity to Annapolis' renowned attractions, including the historic district, waterfront, and shopping destinations. Whether you're here for a weekend getaway, Naval Academy event or an extended stay, our 2-bedroom townhome provides a comfortable haven for exploring all that Annapolis has to offer.brbrbrbrKey Features:brbr* **Living Area:** Open-concept with stylish furnishings and historic exposed brick.brbr* **Kitchen:** Fully equipped with modern appliances and an adjacent dining area, perfect for home-cooked meals.brbr* **Bedrooms:** Two tranquil bedrooms, each boasting plush beds and tasteful, coastal-inspired decor.brbr* **Bathrooms:** Two full en-suite bathrooms with contemporary fixtures and complimentary toiletries, plus a convenient half-bathroom on the main level.brbr* **Outdoor Space:** A charming, private brick-paved patio, an ideal spot for sipping your morning coffee or unwinding in the evening breeze.brbrbrbrRENT-000713-2025brbrbrbrGuest Access:brbrGuests will have private and exclusive access to the entire townhome throughout their stay, including the private patio. Enjoy the comfort and privacy of having the whole space to yourselves.brbrbrbrThe Neighborhood:brbrDowntown Annapolis is a historic and charming neighborhood. It is nestled along the shores of the Chesapeake Bay and is known for its picturesque streets lined with beautifully preserved colonial buildings. The area offers a blend of maritime heritage, boutique shops, restaurants, and lively waterfront activities. With its cobblestone streets and iconic landmarks like the Maryland State House and the United States Naval Academy, downtown Annapolis is a popular destination for both tourists and locals alike. The vibrant atmosphere, rich history, and scenic waterfront make it a delightful place to explore and immerse yourself in the city's maritime culturebrbrbrbrGetting Around:brbrOnce you get settled in the home, there are several places to explore and visit within walking distance. There are also several ride share options available.brbrbrbrOther Things to Note:brbrDue to a change in city regulations, guest parking passes for the residential street can no longer be provided for your stay. You may park on the street for up to 2 hours in any other open space. brbrbrbrThe city does provide free parking from 6PM Friday to 6AM Monday at the Calvert Street Garage (19 St. Johns Lane) or you can also park in the following garages/lots: Hillman Garage (150 Gorman Ave - entrances from Main St or Duke of Gloucester) South Street Lot - South Street off Church Circle, Gotts Court Parking Garage – (25 Northwest Street) Knighton Parking Garage – (1A Colonial Avenue), Park Place - 5 Park Place (just off West St ). brbrbrbrThe free Annapolis Circulator bus stops at all the city garages/lots and the city dock and can be used to get to/from the garages. Please see the Annapolis Parking website for further detailsbrbrbrbrInteraction with Guests:brbrWe respect our guests' privacy and offer a self-check-in process for your convenience. While we will not be present during your stay, we are always available via the messaging app or phone if you have any questions or need assistance.

Bed

Bath

Sleeps

$421.8

/ Nightly

Private Vacation Home

Charming 3-bedroom house in Annapolis Eastport! Beautifully furnished home

Annapolis, Maryland, United States

Beautifully furnished 3 bedroom, 2 bath home, available for short or long term rental in Eastport Annapolis! 4 minutes uber to ego alley, 15/20 minutes walk to all Eastport restaurants and shops. Naval Accademy less than 2 miles away. Perfect for families heading out to Naval Accademy functions, graduation, or the Annapolis boat shows! Also perfect for graduate student waiting for move, or for a vacation spot in the heart of Eastport Annapolis. Please contact home owner for all inquiries. Kane 513-748-6823. Stay comfortably in Annapolis at this 3-bedroom house. Marvelous bedroom setup includes 2 full beds and 1 bunk bed. Enjoy the convenience of WiFi, heating, and AC. With 2 bathrooms equipped with a hair dryer, guests will feel right at home. We hope you enjoy what our place and Annapolis has to offer.

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Bath

Sleeps

$733.0

/ Nightly

Private Vacation Home

DISCOUNTED FOR USNA COMMISSIONING WEEK 2024 and 2025! Short term and weekends.

Annapolis, Maryland, United States

Beautiful, remodeled 3 BR home with stunning great room addition, 20' x 20' screened, covered porch with newly added outdoor deck allows you to BBQ on a propane weber grill while you socialize. A marbled wall entrance with compass rose floor inlay greets your arrival. Six ceiling fans grace cathedral and standard ceilings, providing an airy retreat. Screened in porch with couch, glass top dining table and eight cushioned chairs provides relaxation. Three full baths are remodeled with marble walls and floors. Three bedrooms with two King beds and one double. Trundle bed in separate, semi-private area opens to two twin beds. Sleeps 8 with current beds and up to 10 with the Queen air mattress provided by homeowner. Linens (sheets, towels), fresh bars of soap, paper towels, TP, dish soap, etc are provided to ensure you enjoy your time in Annapolis and you don't need to run to the store for staples.brbrThree HDTVs, DVD player, surround sound and wifi are some of the amenities. Two HVAC units allow you to adjust temperature to your comfort.brbrWell behaved, house broken, adult dogs are considered for a $180 non refundable pet / cleaning fee. Certain breeds or chewers may not be approved. Please contact homeowner to discuss pets. No cats, please! :) Anchorage Community about 2 miles from USNA Stadium and walking distance to Bay Ridge views.brbrKeywords: Gorgeous, remodeled Annapolis home. 2-3 mi from downtown Annapolis. Ideal for Boat Shows, Naval Academy Graduation and events, Sailing, sightseeing, water sports, antiquing, and more. brbrBeautifully landscaped yard and relaxing 20 x 20+ screened in porch with glass deck table, chairs, and hammock. Screened in porch has door to outside deck with gas grill. Established community with pool/water privileges/Lake Ogleton, Visitors are encouraged to enjoy scenic 5 miles walk/bike ride round trip around Bay Ridge with stunning views of the Chesapeake and Severn River.brbr3 night minimum

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Bath

Sleeps

$640.59

/ Nightly

Private Vacation Home

Beautiful Annapolis Home Near the Beach with a fitness room

Annapolis, Maryland, United States

Enjoy luxury coastal living perfect for families and friend groups in this newly remodeled Annapolis retreat. Located in peaceful, walkable Cape St. Clair with access to the private beach. Relax by the outdoor fireplace, host movie nights in the home theater, or grill outdoors. With a gym, office, and short drive to the Naval Academy and downtown, comfort and convenience meet by the bay.brbrThe home features 4 bedrooms (2 queen beds, 1 full bed, 2 bunk beds) with smart TVs in the two queen bedrooms and full bedroom. Enjoy 3 full bathrooms stocked with hand soap, body wash, shampoo, and conditioner.brbrEntertainment is easy with a home theater (4K projector, surround sound, wireless streaming), a pool table, board games, and a home gym with a stationary bike and multi-function utility machine offering 40+ workouts. A selection of books, complimentary coffee and tea, and smart check-in/check-out make your stay effortless.brbrOutdoors, relax under the pergola by the fireplace, dine at the outdoor table, or enjoy the balcony with a coal grill and cozy seating. Guests also have access to the private Cape St. Clair community beach, just a short walk away.brbrIdeal for family vacations, friend getaways, or peaceful escapes by the water, this home blends comfort, style, and entertainment for an unforgettable Annapolis stay.

4

Bed

3

Bath

11

Sleeps

$626.48

/ Nightly

Private Vacation Home

Quiet Woodland Lodge w Community Beach Access & Large Private Deck

Annapolis, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWelcome to The Woodland Lodge brbrTucked at the end of a quiet cul-de-sac in the water-privileged community of Annapolis Roads, this 4-bedroom, 3-bath home offers privacy, comfort, and coastal charm. Surrounded by a beautifully landscaped yard, enjoy a spacious furnished deck perfect for relaxing or dining outdoors. Inside, the bright, open layout flows into a stunning two-story family room with soaring ceilings, natural light, and a cozy pellet stove fireplace. brbr brbrLocated just 10 minutes from downtown Annapolis, with access to a community beach and playground, this home is the perfect Chesapeake Bay retreat. brbr brbrSleeping Arrangements - 4 Bedrooms, 3 Baths, Sleeps 8 brbrThird-Floor Suite brbrCalifornia King bed brbrEn suite luxury bath with double vanities, Jacuzzi tub, and stand-up shower brbrPrivate Loft overlooking family room brbrFlat-screen TV brbr brbrFront Queen Bedroom (Main Floor) brbrQueen bed brbrShared full bath with combo bathtub/shower brbr brbrBackyard-Facing Queen Bedroom (Main Floor) brbrQueen bed brbrShared full bath with combo bathtub/shower brbr brbrLower Level Bedroom brbrQueen Bed brbrFull bath with shower in the hall brbrAccess to back patio and yard brbr brbrHighlights brbrLarge Private furnished deck with table with seating for 4 brbrSmoker grill and wood-burning Solo Stovefire pit brbrDining room table for 6 plus seating for 2 at the breakfast bar brbrLofted office on the second floor brbrCommunity amenities include: beach, playground, fire pit and launching pier brbrHigh-speed internet and WiFi brbrFull house back-up power generator brbrFlat-screen TVs in every bedroom and all of the living spaces brbrLuxury linens, starter toiletries, and boutique-level service brbrDriveway and cul-de-sac parking for 4-5 cars brbrFull laundry room with washer and dryer brbrDogs allowed with $150 non-refundable fee due prior to checkin. brbrKeyless entry for a seamless check-in experience brbr brbrDistances brbrDowntown Annapolis: 3 miles brbrU.S. Naval Academy: 3 miles brbrWashington, DC: 33 miles brbrBaltimore: 32 miles brbr brbrIncluded Amenities brbrStarter pack with coffee, sweeteners, soap, shampoo, conditioner, lotion, hand sanitizer, paper towels, toilet paper, dish soap, and dishwasher detergent brbrFreshly laundered, ready-made beds with clean towels brbr brbrHouse Rules brbrThe primary guest must be at least 25 years old. brbrQuiet hours must be respected in this family-friendly neighborhood. brbrNo parties, events, or smoking of any kind. brbrCheck-in: 4:00 PM | Check-out: 11:00 AM brbr brbrWhether you're visiting for a relaxing getaway or a special gathering, this Annapolis Roads retreat offers everything you need for a memorable stay.

Bed

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$663.64

/ Nightly

Private Vacation Home

Adorable cottage! Walking distance to USNA & downtown! (VRBO only)

Annapolis, Maryland, United States

Listing will never be posted on Craig's list - VRBO only **Adorable 1930's cape cod, located in the historic Murray Hill neighborhood. Off street parking and walking distance to great restaurants, bars, shows and US Naval Academy and stadium. Cute, cozy and fun, decorated in vintage mid century style to match when the home was built. Super cute backyard and patio - a romantic oasis covered with twinkling lights, an amazing venue for a small family gathering, wedding, or party (additional fee would apply, contact owner). (VRBO ONLY* THIS LISTING WILL NEVER BE ON CRAIGS LIST*)

Bed

Bath

Sleeps

$849.3

/ Nightly

Private Vacation Home

Annapolis -Eastport - -3 Bedroom- 3 bath with parking

Annapolis, Maryland, United States

Delightful Arts and Crafts/ Coastal style home. Main Level is open space concept with 9 ft ceilings and plenty of natural light, walk out to large yard and patio for grilling entertaining. brSecond floor Master Suite and two Guest bedrooms each with walk in closet and full bath. 1/2 mile walk to Naval Academy Gate 1 and Downtown brAnnapolis HarborbrOpen concept is great for relaxing and entertaining..

3

Bed

3

Bath

8

Sleeps

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