Vacation Rentals By Owner In Annapolis, MD

Come escape to our place at the Bay! Relax and reconnect with loved ones in this classic, family friendly cottage located in the private community of Bay Ridge. The neighborhood is great for walking, biking and relaxing on the private beach right at the end of the street. We love it here because we physically feel ourselves relax within minutes of arriving. Whether you’re relaxing indoors or exploring nearby, the amazing comfort of this cottage makes every moment special. We’ll be available to answer any questions while you stay at our place. The cottage is a 3 minute walk from the Chesapeake Bay. There is a master bedroom with a king bed and twin bunk beds. The 2nd bedroom has a queen bed. We provide sheets and towels as well as beach towels, so you only need to pack your clothes and make yourself at home. The loft area at the top of the spiral staircase has a queen air mattress for additional sleeping space. There is a pack n play for young kids as well as a baby gate and some toys. Our Bay house has been in the same family for over 60 years. Come spend some time experiencing some of our favorite things: chilling on the screened in porch with a cold beverage, walking the neighborhood to take in the amazing views, playing at the beach and in the bay and finishing the day with an evening walk to the beach to watch the sunset.

Cottage

Peaceful Escape: Bay Ridge Cottage by the Bay

Annapolis, Maryland, United States

Bed

1

Bath

7

Sleeps

$819.88

Summary:brbrTwo connected, historic row homes in the heart of Downtown Annapolis! Perfect for two families or larger groups, these houses are connected via an outdoor patio in the back. Enjoy in unit washer/dryer in both units, separate kitchens, and 3 full bathrooms. brbrHouse A: 2 full bathrooms, bedroom with loft, and 2 twin beds in a bunk room. House B offers a primary bedroom, 2 twin bedroom, with a full bath (standing shower) in the hall. Gather and grill in the outdoor spaces, entertain in house A's dining room, and house B's comfortable living room.brbrbrbrGuest Access:brbrPrivate entrancesbrbrbrbrOther Things to Note:brbrTo help ensure a smooth, secure, and enjoyable stay for all guests, please review the following important information before booking: brbr brbrCheck-In & Identity Verification Policy brbr brbrAll reservations require the primary guest (the booker) to complete a secure online check-in process prior to arrival. This includes: brbr brbr-Uploading a valid, unexpired government-issued photo ID brbr-Uploading a selfie to confirm identity brbr-Reviewing and signing our rental agreement brbr brbrThis process is similar to hotel check-in and is required because we do not typically have staff on site. Check-in instructions will only be provided once this process is complete. brbr brbrIf you would like to review the rental agreement before booking, please feel free to contact us. brbr brbrIn some cases, we may also request a security deposit and/or apply a damage waiver fee in accordance with booking channel policies. brbr brbr * It typically takes ~1 hour to screen a guest after they book this property and could take several hours if we are busy before we are able to provide them with check-in information.brbr brbrIf you make a last minute reservation, we ask you to please be patient and please do not expect to gain access to the property immediately.brbr brbrGuest Count & Occupancy Policy brbr brbrEach listing includes a maximum number of guests based on unit type and local regulations. Additional guests are welcome for an added nightly fee: brbr brbr-4 & 5+ bedroom units: $50 per guest, per night after 8 or 10 guests, respectively brbr brbrPlease ensure your guest count is entered accurately at booking. We will confirm the number of guests after reservation. If the guest count changes, pricing may be adjusted accordingly. For safety and compliance purposes, exterior security cameras are used to verify occupancy. Unreported additional guests may result in additional charges. brbr brbrPet Policybrbr brbrThis is a pet-friendly property. While our cleaning team is thorough, guests with severe pet allergies should be aware that dogs, cats, or other animals may have stayed in the space previously.brbr brbrPet fees:brbr brbr$30 per night, per petbrbr$150 per week, per petbrbr$300 per month, per petbrbr brbrPet fees are included in the accommodation rate as long as you choose the appropriate quantity of pets when completing a booking. We confirm this with all guests post booking confirmation. brbrbrbrLocal Reservation Policy brbr brbrReservations under 7 nights from guests residing in the local area may be subject to cancellation at our discretion. We handle exceptions on a case-by-case basis. brbr brbrEarly Check-In & Late Check-Out Policy brbr brbrEarly arrivals and late departures are not guaranteed and must be approved in advance. If approved, the following fees apply: brbr brbr-Up to 1 hour: $100brbr-1–2 hours: $200 brbr-2–3 hours: $300 brbr-3+ hours: $400 or the cost of an additional night (whichever is greater) brbr brbrPlease do not assume availability without confirmation. brbr brbrSmoking Policy brbr brbrSmoking is not permitted anywhere on the property, including indoor and outdoor areas. If evidence of smoking is found, an additional cleaning fee of $500 will be applied in accordance with the booking channel's cleaning and damage policies. brbr brbrSpecial Request Policy brbr brbrRequests for items such as pack-n-plays, high chairs, or other non-standard amenities should be submitted at least 7 days before check-in to ensure availability. Requests made closer to arrival will be accommodated if possible but cannot be guaranteed. brbr brbrWe understand that this is a detailed list, and we truly appreciate you taking the time to review it. These guidelines help us maintain a safe, well-cared-for property and ensure a great experience for every guest. Our goal is always for you to feel comfortable, welcome, and well taken care of during your stay.

Two Historic Rowhomes in Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$411.05

Summary:brbrExperience a beautifully restored and well appointed Greek Revival home on a calm street directly facing the U.S. Naval Academy and steps from the Navy Chapel and Gate 3. This rare property blends historic character with high-end modern updates and chic, boutique hotel-like furnishings, offering a relaxing yet central retreat in downtown Annapolis.brbrbrbrThe Space:brbrThoughtfully renovated under architectural guidance, this impeccable historic home features elegant details, abundant natural light, and a seamless layout designed for comfort and great for entertaining. brbrbrbrMain level: Gather in the living room with TV, dining room that seats 6, luxurious kitchen well-stocked for meals, coffee bar, breakfast table, and counter seating. A full bathroom with washer/dryer also on this level. Check out the outdoor patio and lovely backyard with grill and seating.brbrbrbrUpstairs: brbrBedroom 1: King bed and ensuite full bathroombrbrBedroom 2: Queen bed with TVbrbrBedroom 3: Queen bed, TV, large windows overlooking backyard, spacious patio. (elevator in this room- elevator is not for use by guests without prior approval)brbrbrbrBath 2: Ensuite for primary bedroom- standing showerbrbrBath 3: Conveniently located in the hall shared by bedrooms 2 and 3, this bathroom contains a bathtub with shower.brbrbrbrOutdoor space: Private patio/backyard with cafe table seating, 2 Adirondack chairs, and a gas grill for our guests to use!brbrbrbrLicense #: RENT-002665-2025brbrbrbrThe Neighborhood:brbrLocated on a lovely street across from the Naval Academy and just steps to all that downtown Annapolis 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 0.5 mile / 10 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, cats, or other animals may have stayed in the space previously.brbr brbrPet fees:brbr brbr$30 per night, per petbrbr$150 per week, per petbrbr$300 per month, per petbrbr brbrPet fees are included in the accommodation rate as long as you choose the appropriate quantity of pets when completing a booking. We confirm this with all guests post booking confirmation. brbrbrbrLocal Reservation Policy brbr brbrReservations under 7 nights from guests residing in the local area may be subject to cancellation at our discretion. We handle exceptions on a case-by-case basis. brbr brbrEarly Check-In & Late Check-Out Policy brbr brbrEarly arrivals and late departures are not guaranteed and must be approved in advance. If approved, the following fees apply: brbr brbr-Up to 1 hour: $100brbr-1–2 hours: $200 brbr-2–3 hours: $300 brbr-3+ hours: $400 or the cost of an additional night (whichever is greater) brbr brbrPlease do not assume availability without confirmation. brbr brbrSmoking Policy brbr brbrSmoking is not permitted anywhere on the property, including indoor and outdoor areas. If evidence of smoking is found, an additional cleaning fee of $500 will be applied in accordance with the booking channel's cleaning and damage policies. brbr brbrSpecial Request Policy brbr brbrRequests for items such as pack-n-plays, high chairs, or other non-standard amenities should be submitted at least 7 days before check-in to ensure availability. Requests made closer to arrival will be accommodated if possible but cannot be guaranteed. brbr brbrWe understand that this is a detailed list, and we truly appreciate you taking the time to review it. These guidelines help us maintain a safe, well-cared-for property and ensure a great experience for every guest. Our goal is always for you to feel comfortable, welcome, and well taken care of during your stay.

Condo

Luxe Row Home Steps to USNA Gate 3!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$526.07

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

Steps to Marinas & Shops w Parking in Eastport

Annapolis, Maryland, United States

Bed

1

Bath

6

Sleeps

$998.33

Located on one of the most coveted streets in downtown Annapolis, walk to Main St. and City Dock. The Thomas Hyde House not only has beautiful views of the Maryland State House, but also has an extremely rare large parking lot adjacent to the building with at least 5 parking spaces. brbrThe building consists of two levels and a large basement. It's close proximity and walking distance to all downtown Annapolis. brbrTHERE WILL BE A SECURITY HOLD (NOT A DEPOSIT JUST A HOLD) THAT WILL BE RELEASED 3 DAYS AFTER CHECK OUT.brbrRegarding PETS: We strive to provide our guests with a space that is free from animal allergens. We are obligated to allow a genuine service animal however, be aware that the animal CANNOT BE LEFT ALONE at the home at all during your stay, not even caged. If the animal is left alone in the home you will be asked to leave immediately with no refund of unused nights.

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$438.9

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

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

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$789.8

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

Private 4-bedroom house in Annapolis, great location!

Annapolis, Maryland, United States

4

Bed

3

Bath

11

Sleeps

$337.87

Dive into Annapolis's rich heritage, just minutes from the US Naval Academy and historic downtown. Discover state landmarks and enjoy the ease of exploration from our doorstep!brbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 300 sq. ft, equipped with complimentary toiletries, standard quality 32-inch TV, available with Standard cable.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.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 03:00 pm.brbr✦ Public or shared fitness center open from 6:00AM to 10:00PM, available in the property.brbr✦ Outdoor shared pool available from May 25 to September 5, opened from 9:00AM to 9:00PM.brbr✦ Paid parking lot – 1 space(s), available for $10 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00. 1-4 nights stay, $75 for 5+ nights staybrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Early & Late Check-outs are subject to availability for a fee.brbr✦ There's a fee for smoking in a non-smoking room. Please ask the Front Desk for locations of designated outdoor smoking areas.

Hotel

Minutes from History: 2 Relaxing Units w/ Free Breakfast Near Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

4

Sleeps

$336.68

Dive into Annapolis's rich heritage, just minutes from the US Naval Academy and historic downtown. Discover state landmarks and enjoy the ease of exploration from our doorstep!brbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 484 sq. ft, equipped with complimentary toiletries, standard quality 32-inch TV, available with Standard cable.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.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 03:00 pm.brbr✦ Public or shared fitness center open from 6:00AM to 10:00PM, available in the property.brbr✦ Outdoor shared pool available from May 25 to September 5, opened from 9:00AM to 9:00PM.brbr✦ Paid parking lot – 1 space(s), available for $10 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00. 1-4 nights stay, $75 for 5+ nights staybrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Early & Late Check-outs are subject to availability for a fee.brbr✦ There's a fee for smoking in a non-smoking room. Please ask the Front Desk for locations of designated outdoor smoking areas.

Hotel

Annapolis Adventure: 2 Cozy Units, Outdoor Pool + Easy Access to Historic Sites!

Annapolis, Maryland, United States

Bed

Bath

8

Sleeps

$436.55

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

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

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$532.16

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

Water Views - Close to Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$687.16

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

Spacious 4BR | Pet-Friendly, Sleeps 10

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1090.38

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

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

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$593.87

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrStep into Annapolis history at this beautifully restored three-story cedar home. Built in the late 18th century, this property is recognized in the Historic District’s National Registry as one that “embodies the distinctive characteristics of a period.” Over the centuries, it has served as a shoemaker’s store, an inn, and the residence of an Italian immigrant who played in the U.S. Naval Academy band. Later converted into three apartments, the home was thoughtfully restored in the 1970s and newly-renovated into the elegant single-family dwelling it is today. brbr brbrMain Level Living brbrEnter through the front door to a spacious family room, perfect for relaxing after a day of exploring downtown Annapolis. With a plush queen sleeper sofa and a large flatscreen TV, this room doubles as a cozy gathering space or extra sleeping option. Original wood floors run throughout, creating warmth and character. The Main level, and all 3 bedrooms, each have their own flatscreen TV. brbr brbrThe adjoining dining room features a restored built-in hutch and seating for six. The full kitchen is stocked with everything needed for preparing meals at home, while a convenient powder room completes the main floor. From the kitchen, step outside to the fenced-in backyard with Adirondack chairs and a propane grill—an intimate spot for morning coffee or evening cookouts. The home is located just a 2-minute walk to City Dock, Main Street, State Circle, and the Naval Academy entrance. brbr brbr**Parking is not on premises!! A dedicated parking spot at nearby garage (15-minute walk from the house) is provided. Please contact us for details. brbr brbrSLEEPING ARRANGEMENTS 3 BR / 3.5 BA / Sleeps 8: brbrTop Floor King Suite: brbrKing Bed brbrEnsuite Full Bath with double vanity, shower/bathtub combo and walk-in closet brbr brbr2nd Floor King Suite: brbrKing Bed brbrEnsuite Full Bath with stand-up shower brbr brbr2nd Floor Queen Guestroom brbrQueen Bed brbrFull Bath in the Hall with shower/bathtub combo brbr brbrMain Level brbrFull Sleeper Sofa brbrPowder room on Main Floor and shared Full Bath in the Hall on the 2nd Floor brbr brbrAmenities & Highlights brbrPrivate fenced yard with Adirondack seating and propane grill brbrFully equipped kitchen brbrDining table with seating for 6 brbrWiFi & big screen TVs in every bedroom and the Family Room brbrLuxury linens & complimentary starter toiletries brbrWasher & dryer inside the home brbrContactless check-in via coded front door entry brbrNon-smoking property brbr brbrProperty Distance to: brbr- U.S. Naval Academy – 2 blocks brbr- Washington, DC – 30 miles brbr- Baltimore - 25 miles brbr*************** brbr*Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid. brbr* All beds are ready made for you with freshly laundered sheets & towels. brbr brbrHouse Rules brbrReservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Please respect the neighbors and neighborhood. brbrCheck-in time: 4:00 pm brbrCheck-out time: 11:00 am brbr brbrBlending centuries-old charm with modern amenities, this property offers the ideal downtown Annapolis getaway—whether you’re visiting for the Naval Academy, a weekend retreat, or a family celebration.

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

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1127.01

USNA Family Stay w/Pool - Infant/Toddler Friendly!brbrEnjoy the newest addition to my “Family Friendly Staycation” home hosting experiences in Annapolis!brbrEnjoy peaceful relaxation and make priceless memories with family, friends, loved ones or unique occasion at the newest addition to my “Family Friendly” focused home stays in Annapolis! This expansive, kid friendly, amenity rich, property has everything we've ever offered at any of of 5-star super host stays and more.brbrThe space:brMom, this family friendly stay is the one you've been looking for. As a mom of 3-under-3 my home is fully equipped for multiple infants and toddlers. I have a crib, toddler bed, pack n' play with infant sleeper, bassinet(s), outlet plugs, every toy that's ever been manufactured, walkers, noisemakers (with or without the batteries!), high chairs, toddler seats, training potty/seat, infant swing, baby monitor, a jumpy jumpy thing - you name it!brbrChild Safety: All exit doors are equipped with adult height locks/bolts in addition to standard door lock. Key code access doorknobs on interior main level doors code 0123# (Laundry Room/Door to Pool Yard and Basement Door to Indoor Soft Hot Tub). Additional child safety supplies are available on-site for you ultimate peace of mind. brbrParents MUST BE ON WATCH when children are in pool yard. Life vests are not provided and are not a replacement “lifeguard”. I provide hard plastic baby pools but between my 3 children I have seen them fall straight into the pool, jump on top of it when frozen over by the 2022 winter temps (which was thankfully thick) sliding and squealing “weeeeee!” (Heart attack alert!). Children of a certain age do not “get it”, the danger or the fear. This is what happens right in front of my own two eyes!brbrPlay set in Pool YardbrResort Style Loungers Line 1 sidebrPlanning for a garden - no promises brAll bedrooms boast private wall hung smart TVs brAll rooms boast king beds except the Queen Den!brbrGrill & Fire Table - Propane Disclaimerbra.) ASSUME BOTH Require Propane Tank Fill. I stock if time/opportunity permit but time/ability varies. I offer reimbursement for a tank refill if responsibly managed and valves are turned off after use.brb.) Do a flame check on the bottle attached to both items. Turn Valve LEFT all the way (you tube clips are great guides) follow the demo before assuming empty bottle. After use or flame check turn nozzle on bottle RIGHT/TIGHT every time or the propane valve will be open and empty the bottle. brc.) If you got to use/flame check and the nozzle has been left open (left/ loose - right/tight) and can be turned right it’s likely empty. Detach bottle and swing by any local tank exchange within a stones throw. brd.) I used to guarantee stock and supply on site but without the burden of responsibility tanks were never turned off (right/tight) immediately after use. I will reimburse the cost of a bottle refill after checkout if you text me a receipt and I return to a valve check that was turned off after use. If the valve is left open and I turn it off right/tight after checkout I won’t reimburse a tank refill. bre.) I am trying to encourage personal responsibility to turn the valves OFF IMMEDIATELY AFTER USE on the tanks attached to the grill and the fire table. Not reimburse an infinity of unnecessarily wasted propane that also inconveniences the next guest that might have enjoyed and responsibly turned off the tank. brf.) My goal is to return to responsibly turned off tanks and gladly reimburse you for a fill. Not decline a valid receipt on a tank someone from the group left open. br*** Outdoor propane tank swap station in front of Sams Club 24/7, does not require membership.

USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR

Annapolis, Maryland, United States

5

Bed

3

Bath

15

Sleeps

$627.0

421 Irie brCity Of Annapolis License Number 145052brCommission weeks: 2025, 2026, 2027 are booked. SORRY!! GO Navy!! brCelebrating, I offer personal chef services!!! brbrNOTE: I LOVE my neighbors!! Please respect them. Quite times including outside pool area 9:00pm-7:30 am and a new wee one next door. :)brbrCONTACT owner, Liz 301730100 for bookingsbrbrOwner:brLiz Hopkinsonbr3017301000brEmhopkinson@icould.combrbrIrie ~ to be at total peace with your current state of being.....brAKA NO WORRIES!!!!brbrThis charming, 2 story COTTAGE was Inspired by sun-drenched island vacations and tropical shores.... ahhhh ..... The feeling of Irie!!! brbrThis 2 bedroom and 2 full bath maybe compact, (twin size Crate and Barrel sleeper chair and Half for additional guest), BUT She SURE packs a powerful punch!! TOTALLY open concept living area, caterers stocked kitchen (I’m a former catering company owner for 20 years, just trying to simplify), fully fenced in professionally landscaped yard with SO many colorful flowers, herbs and vegetables for the picking, functional and cute sunroom for additional living space amongst nature, endless entertaining, upstairs deck off of primary bedroom ... OFF STREET PARKING and Private FULL size .... YES... PRIVATE... pool in the heart of Eastport! brbrLocated in The Maritime Republic of Eastport, an easy going, Chill-Laxing community, 421 Irie is less then: br1 mile from Downtown Annapolis City Dock br1.2 miles from Maryland State Housebr1.3 Miles from the Navel Academy!! brbr421 IRIE offers you and your guests, up to five, everything!! Restaurant Row with over a dozen fabulous restaurants with-in a mile, small mom and pop shops, several yacht clubs and marinas, museums, and of course.... WATER Activities!! You say, you're on vacation and just want to chillax, just stay in and simply enjoy your new vacation home!!brbr421 Irie has it all!!!!!brbrStart your day off with your morning beverage from the built-in beverage and breakfast nook. Savior your authentic French pastry from our local bakery, Bakers and Co., a short stroll away. Enjoy your sweet or savory fare in the sunroom. If you must check in with work, we have an Ethan Allen secretary's desk off to itself. brbrFollowing breakfast you may choose to take a 10 minute stroll across Spa Creek Bridge to downtown Annapolis, City Dock, and the Navel Academy!! While in route, take time to admire the diverse number of power and sail boats in the numerous area marinas. ALL ... with-in a 10 minute stroll!! brbrYou say you do not feel like walking, the best kept secret, Annapolis Water Taxi picks up and drops off only a block away!!!! $4-$9!!! It will drop you off right at City Dock!! Want to try your hand at sailing or power boats !! There are several sailing and boating schools, YES, all with-in a 10 minute stroll!!brbrOnce you return from your adventure to this amazing 2 story cottage, relax by the glistening saltwater pool in one of the sun loungers. Or take a dip to refresh and reset the mind. You do not feel like swimming No PROBLEM!! Enjoy an adult beverage in the new (Apr. 2023) sunroom while listening to some island music, reading a book, marveling at the flower garden, watching your family or friend enjoy the pool... brAfter all, your life is IRIE when you stay with us!!brbrP.S.brIF, you do not feel like going out to dinner or cooking, for an additional fee, there are local grab and go culinary offerings, private chefs, and curbside pickup and deliveries available. brbrBeing a local, myself, I can give you a locals eye into activities and services, as well! There are quite a few adventure waiting for you, your family and friends at 421 Irie!brbrWe look forward to hosting you and your guests and making everyone’s life IRIE!!!, at least for your stay!!brbrCheers!!!brLiz Hopkinson

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Annapolis, Maryland, United States

Bed

Bath

5

Sleeps

$570.0

Beautiful Cape Code made for entertaining, this Eastport home is perfect for your next trip to Annapolis! Newly renovated kitchen has a 10x5 custom island with built in wine fridge. The open concept kitchen and living room open up to the large private backyard with patio, firepit and grill. A short walk away from Eastport’s local restaurants and pubs, and 1 mile to downtown Annapolis restaurants, City Dock, and shopping. Driveway can fit two cars, and there is plenty of street parking available.

Charming Eastport CapeCod

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$514.63

Come enjoy a relaxing stay in our coastal waterfront cottage in Epping Forest! Just steps from a community pier perfect for SUP's or kayaks with gorgeous water views that are stunning all year around and visible from the hot tub.This home is tucked into the private gated community of Epping forest, featuring a private beach with a clubhouse, swimming area and marina. brbrThe house sleeps 6 comfortably with 3 bedrooms and 2 full bathrooms. It has great outdoor seating and entertaining space and a relaxing screened in porch with a porch swing. brbrThe property is just minutes from downtown Annapolis and the Naval Academy!

Cottage

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$433.62