Vacation Rentals By Owner In Annapolis, MD

This 3-bedroom, 2.5-bath single-family home mixes modern renovations with 1896 classic charm. It's been decorated with upgraded furnishings to accommodate 6 guests. You'll love the proximity to downtown Annapolis. Plus you'll have free parking for up to 3 cars in the private driveway!brbrWhy guests love staying on Lafayette Ave:brbr☼ Historic single-family home right in the heart of downtown Annapolis with natural light and upgraded features, ideal for families, romantic getaways, or a group of friends visiting historic Annapolis, Ram's Head On Stage, USNA, and other tourist sitesbr☼ Centrally located in downtown Annapolis, on historic Lafayette Ave, one block from historic West Street, within walking distance of restaurants, bars, museums, coffee shops, and morebr☼ Free parking for up to 3 cars in a private driveway (NOTE: street parking is hard to come by in this neighborhood; Gott's Court Public Garage is about 3 blocks away)br☼ Three bedrooms: Primary: king bed; Guest: 1 queen bed; Guest: 2 twin bedsbr☼ One full bathroom is on the second level with 3 bedrooms and has a tiled walk-in shower and heated floors; there is a beautiful half-bath on the main living area with heated floors; Another full bathroom is in the basement and has a tub-shower combo (NOTE: the basement full bath is best for kids and shorter adults, as the ceiling heights in the basement are about 5'10-6-feet topsbr☼ Basement has a hangout area with a Smart TV, small couch, and cushions for seating; full bathroom; and laundry (NOTE: Basement can be accessed by a narrow staircase. Basement ceilings are low - so taller adults should watch their heads. We ask that guests do not eat in the basement as to not attract bugs or other pests. This home is kept meticulously cleaned!)br☼ Kitchen with all major appliances, a drip coffee maker, Keurig, kitchen supplies and tools and morebr☼ Comfortable living room for watching movies and playing gamesbr☼ Dining room with seating for 6 and an electric fireplacebr☼ Smart TV in the living room and basementbr☼ Fresh linens, towels, toiletries & essentials providedbr☼ Professionally cleaned before each visitbrbrLook no further than this historic home in downtown Annapolis!brbrWe’ll follow up with a short online registration once you book. It’s fast, simple, and helps us prepare for your visit. Non-Airbnb guests will be asked to pay a small damage waiver OR refundable deposit.brbrFor extra flexibility, consider adding trip insurance for a nominal fee. It can cover you if you need to cancel at the last minute.brbrLafayette Ave. is managed by a small, female-owned business. We're committed to making sure all of our guests feel welcome and have the best trip ever. Book your trip with confidence that not only will this property be amazing, but the service and attention you get will be, too.

Newly renovated in DTA w parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$691.13

Our favorite part of this home is its unbeatable location in downtown Annapolis (DTA)- with private parking. You can walk everywhere:restaurants, pubs, the U.S. Naval Academy, St. John's College, Annapolis Sailing School, and more.brbrThis historic row house is ideally situated just five houses up from Ego Alley, one block from Main Street and only a short 4-minute walk to visit your Mid at the Naval Academy.brbrThe home features a fully stocked kitchen perfect for preparing a meal or Thanksgiving dinner if you decide to stay in. It's also a cozy spot to enjoy your morning coffee or unwind with a glass of wine after a day exploring Annapolis.brbrWhile rich in historic charm, the row house has been thoughtfully updated with custom bathrooms, new beds, and fresh bedding for a comfortable stay. We are excited to share our home so you can experience Historic Annapolis WITHOUT THE HASSLE OF SEARCHING FOR PARKING. brbrGREAT COMMISSION WEEK HOME!! USNA FAMILIES FAVORITE!br brThis is a licensed Annapolis Vacation Rental #STR24-145209

Walk to the Naval Academy and Historic Annapolis. Private parking at the home.

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1425.0

Chesapeake living with a view of the Bay from the lovely outdoor dining area and screened in balcony off of the huge master suite. Private patio with a furnished shed to enjoy a cup of coffee, a glass of wine, or listen to music outdoors. brWalk or bike along a mile and half of unobstructed views of the Chesapeake Bay. brbrWe are on the Bay Ridge peninsula where Lake Ogleton meets the Chesapeake. The neighborhood lends itself to life outdoors. Long walks, bike rides, kayaking and paddle boarding are the norm.brbrAfter an active day outdoors or exploring Annapolis, prepare a meal in our gourmet kitchen and enjoy the sunset while dining alfresco with a view of the Bay!brbrThis home is perfect for a group of couples! Each bedroom has it's own ensuite bath for comfort and privacy. The third guestroom & ensuite bath is located on the main level for those who want to avoid stairs.brbrStylish with modern amenities and private spaces. The perfect Annapolis getaway!brClose to the Naval Academy and downtown Annapolis yet set in the relaxing Bay Ridge neighborhood. Enjoy time with your family on our beaches, on the Chesapeake Bay and on Lake Ogleton.brbrThree beautiful bedrooms, each with a private bath plus additional sleeping for two in our den's new king sized sleeper sofa. Gourmet kitchen, comfortable living areas that allow the outdoors inside, top of the line amenities.brbrTruly, a home with charm and comforts in which to create your family memories!

Steps away from the Chesapeake Bay in the unique Bay Ridge community!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$400.56

Charming Bay Cottage just steps from a beautiful beach and the Chesapeake Bay, a short drive or walk to the crabbing and fishing pier and easy boat access at Sandy Point Park. USNA - 5 miles away and Families LOVE this house! The home is ranch style with hardwood floors, new carpeting and some new furnishings; a large screened in porch with a large table and ceiling fans. The 3rd bedroom is the den a day bed .brbr Although the house has a somewhat obstructed view of the Bay, this is a wonderful location and short drive to Historic Annapolis Downtown. If you have your own kayaks or a canoe the Little Magothy is a short walk from the house and a very calm and scenic water way. brHISTORIC ANNAPOLIS is approx. 7 miles away, and easily reached by traveling Rt. 50. The property holds 5 people comfortably and has 2 full bathrooms and an outside shower. Parking: Plenty of parking with 2 spots available in the driveway, and 2 street side. This is a non smoking home. No House parties and no parties at the private community beach. For parties and pavilion rentals please contact SANDY POINT STATE PARK approx. 4-5 miles from the house. brbrGrocery Store 1 mile from the house: Graul's Market Cape St. Claire location. brbrLong Term Rental Requests: I will not consider any long term rentals.brbrbrbr

Annapolis Bay House BOAT SHOW & USNA Families 2 Bedroom with Den sleeps 5

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$507.1

Summary:brbrThis renovated 3-bedroom home is 2 miles from Sandy Point State Park and 7 miles from Downtown Annapolis. Grill on the deck after a day at the beach, let the kids run in the fenced backyard, and spread out across 3 bedrooms and 2.5 baths. The basement has a pullout sofa for extra guests. Quiet neighborhood, free parking, and everything you need for a comfortable stay. Sleeps 8 with a king, two queens, and a pullout.brbrbrbrThe Space:brbrBEDROOMSbrbrThree spacious bedrooms with fresh linens and comfortable beds. A pullout sofa in the basement adds extra sleeping space for larger groups.brbrBATHROOMSbrbr2.5 bathrooms — clean and modern with fresh towels and essentials.brbrKITCHENbrbrFully equipped with modern appliances, cookware, dishes, and utensils. Includes refrigerator, stove, oven, microwave, and coffee maker.brbrLIVING AREASbrbrOpen living room with a large TV and comfortable seating. The basement offers a second hangout space with a large sectional that converts to a pullout bed.brbrOUTDOOR LIVINGbrbrDeck with a grill and outdoor seating — perfect for post-beach cookouts. The private fenced backyard is a peaceful retreat for relaxing or letting kids play.brbrPARKINGbrbrFree parking in the driveway and on the street.brbrLOCATIONbrbr2 miles from Sandy Point State Park and its Chesapeake Bay beach. 7 miles from Downtown Annapolis. Easy access to Route 50 and the Bay Bridge. Quiet residential area with everything you need nearby.brbrbrbrGOOD TO KNOWbrbrbrbrCheck-in: 3:00 PM / Checkout: 11:00 AMbrbrSelf check-in with smart lockbrbrFenced backyardbrbrbrbrGuest Access:brbrFront door with codebrbrbrbrThe Neighborhood:brbrQuiet neighborhoodbrbrbrbrInteraction with Guests:brbrReach out via call or text whenever

Renovated 3BR | Near Sandy Point Beach

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$551.82

Welcome to your Annapolis basecamp! Located in the private Anchorage community, we’re one block to the water and 12 minutes to downtown/USNA. This 5BR/3BA home sleeps 8 and features a chef’s kitchen with a gas range, an 8-person dining table, and dual living areas. After a day on the Bay or strolling downtown, retreat to our modern nautical oasis. Perfectly shipshape for Navy families or weekend sailors. Roomy, refined, and ready for your crew to drop anchor and relax.brbrWelcome to your home away from home in the peaceful Anchorage community of the Annapolis Neck. This spacious, updated five-bedroom retreat is perfectly situated just 10 to 15 minutes from historic downtown Annapolis and the United States Naval Academy. While the home is not directly on the waterfront, you are only one block away from the community marina and Lake Ogleton, providing a beautiful setting for morning walks or sunset strolls along the water.brbrThe interior features bright, modern living spaces designed for both comfort and connection. The main living room offers a large TV with Roku (bring your own streaming logins) and comfortable seating, while an additional upper-level sitting room provides a quiet space to relax with a book. The fully equipped chef’s kitchen is a highlight of the home, featuring a gas range, expansive counter space, and a high-top breakfast bar. For formal meals, the dining room includes a table with seating for eight guests.brbrThe home comfortably sleeps eight guests across five well-appointed bedrooms. On the upper level, the primary suite features a king bed and a recently remodeled private bathroom with a shower. This level also includes a bedroom with a full bed and TV, a third bedroom with a twin bed and a work desk, and a full hall bathroom with double sinks. The lower level offers additional privacy with a queen bedroom, a fifth bedroom with a twin bed and work desk, and a third recently remodeled bathroom with a walk-in shower. Lower level also has a washer and dryer for your convenience.brbrStep outside to a large, private fenced backyard designed for outdoor living. The space includes a dedicated dining area, comfortable seating, and a firepit for evening gatherings.brbrWhether you are visiting for a Navy event, a wedding, or a family vacation, this home offers easy access to local shops, restaurants, and Chesapeake Bay boating. For extra flexibility, we recommend adding trip insurance to cover any unexpected last-minute cancellations.brbrbrPRIMARY SUITE:br-King bed (Tempur-pedic)br-Private recently remodeled bathroom with showerbrbrFULL BEDROOM:br-Full bedbr-TVbrbrBEDROOM 3:br-Twin bedbr-Work DeskbrbrHall bathroom:br-Double sinksbr-Tub/Shower combobrbrQUEEN BEDROOM:br-Queen bedbr-TVbrbrBEDROOM 5:br-Twin Bedbr-Work DeskbrbrLower Bathroom:br-Recently remodeled bathroom with walk-in showerbrbrOther things to notebrPlease note that guests will not have access to the garage during their stay.

Port of Call: 5BR Modern Nautical Luxury

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$468.57

Welcome to the West Street Hideaway. See the best of Annapolis effortlessly when you book this 2-bed, 2-bath vacation rental! Equipped with all the essentials, boasting its own private furnished balcony, and sporting a bright modern interior, this condo is the key to an unforgettable trip. Begin your morning with a waterfront walk at Annapolis City Marina with a cup of coffee. Later visit some must-see attractions like Maryland State House and the Annapolis City Dock to soak up some knowledge.brbrOne parking spot will be provided in the private garage on the lower level of the building. The garage has a luggage trolley and direct access to the building elevator that takes you up to the condo floor for effortless unloading.brbrThe building is secured by a main door that automatically locks. Guests will be provided with two key fobs to use during your stay to unlock the door. brbrThe condo is equipped with a pull out bed that is located in the living room.

Condo

Upscale Condo in Annapolis w/Private Parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$617.5

Private 4BR, 2.5BA luxurious Gem was recently upgraded, and tastefully decorated awaits your arrival. The ranch style home is just a 5 min. car ride to the Naval Academy and downtown Annapolis to enjoy what the city has to offer. You're in close proximity to 50 West for easy access to Washington DC, and 97 North to Baltimore. This home is a rare find tucked away on an acre lot in a very quiet community. The comfort of this home includes an open floorplan with a spacious kitchen, and plenty of natural sunlight from the expansive sliders along the back of the home leading to the large deck. Come and enjoy bird watching and take in the beauty of nature from the large back deck, while relaxing on the comfortable patio furniture.

Charming Home located minutes from the Naval Academy and Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$275.46

Welcome to Fox Haven, a bright, pristine 1 Bed/1 Bath apartment that sleeps 3-4 adults comfortably and has its own separate lower-level entrance. This lovely and private single-family home is situated on a quiet, dead-end street adjacent to a wooded wildlife preserve. We provide free, unlimited parking, just on the edge of town near the Annapolis Arts District and close to the United States Naval Academy's Stadium.brbrExplore Historic Annapolis, the Chesapeake Bay, the United States Naval Academy, Washington, DC and the Eastern Shore during your stay. Numerous restaurants are located within walking distance and there's fare to satisfy any preference, including: Seafood, Mediterranean, Italian, American, Local, Thai, Asian Fusion, Small Plates, and more. Shuttle service is available from the nearby Westin Hotel to take you to the heart of downtown in just minutes to enjoy more restaurants, shopping, live music, the historic district, and our famous waterfront. brbrYour Accommodations: Designed with a mid-century vibe, this 750 square-foot guest apartment is sparkling clean and fully furnished with a well-stocked kitchen, dining/workspace, living room, smart TV, full-size sleeper sofa for an extra guest or two, a pretty bath, comfortable bed linens, and a private patio. This is truly a private oasis that will help make your stay in Annapolis comfortable and memorable.brbrYour Host: We live in the main house and maintain a quiet presence that ensures privacy during your visit. Extended stays are encouraged!brbrChildren: The apartment is not child-proofed, and the furnishings are more adult-friendly. However, families have stayed here with infants, toddlers, and young children quite easily, and they've especially enjoyed having access to the back yard and woods! Reach out to inquire about how we can meet your family's needs.brbrNumber of Guests: The maximum number of guests that can be accommodated is 4. The apartment most easily fits up to 3 adults or 2 adults and 1 to 2 children. Four adults have stayed comfortably using the full-size sleeper sofa. Plus, we provide an organic latex mattress topper and nice bed linens to enhance your comfort.brbrGetting here: Not driving BWI International Airport, Washington Reagan National Airport, Dulles International Airport and Amtrak all provide convenient ways to reach Annapolis. Once here, expand your horizons beyond Annapolis to visit Washington, DC, which is easily accessible via the Metro system's New Carrollton Station - a 25-minute drive from the apartment and Baltimore's waterfront - only a 30-minute drive.

Uptown Annapolis - Peaceful, Sparkling, 1 Bed/1 Bath Apartment, Sleeps 3-4

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$278.11

Welcome to our little oasis! We're tucked away on a beautiful residential street yet 7 minutes away from restaurants, coffee shops and all that Annapolis has to offer. 10 minutes from the coast, 30 minutes from Baltimore and 35 minutes from DC.brbrYour garden suite has a spacious kitchen complete with an oven, dishwasher and Nespresso, two bedrooms (main one comes with a TV opposite the bed, the second bedroom has a desk), a cozy tv nook, laundry and two separate entrances (one on each side of the house). Complete with high speed wifi and a private office space in the 2nd bedroom for remote work surrounded by nature.brbrThis is an in-law suite on the bottom floor of a 3-level home where tenants live on the top floor. There are no shared spaces indoors. The pool is shared. Your suite has a door opening to the side of our backyard and another door opening into the garage. We tried to stock the suite with the things we always need when we travel (spices, pots and pans for cooking, Nespresso, pour over, coffee grinder, towels for sunbathing, Netflix for chilling, etc). Nuestra casa es tu casa.brbrIn case it’s not obvious…we like plants. A lot. Please water our little ones and spritz our air plants if you stay for over a week. They’ll reward you for it!brbrGuest accessbrbrThe garden basement suite has two entrances; one in the garage leading down a flight of stairs and another via a set of stone steps that wind through our garden. The garden route is more scenic but not ideal for big suitcases!brbrPark in our driveway or in the street if you prefer. There's plenty of room.brbrOur suite is big enough for one dog, but can't accommodate multiple dogs. It's just not big enough for everyone, we've found, and a deep clean between bookings is more thorough when only one dog has been in the space.brbrPlease feel free to give the plants a spritz of water (we usually water on weekends; they'll be fine for up to a week).brbrWe are new to VRBO but have been using other hospitality sites for some time (so far we have 100% five star reviews there)! brbrWe follow an enhanced cleaning process, which is based on a cleaning handbook that was developed in partnership with experts.brbrHere are a few highlights:brbrWe sanitize high-touch surfaces, down to the doorknobbrWe use cleaners and disinfectants approved by global health agencies, and I wear protective gear to help prevent cross-contaminationbrWe provide extra cleaning supplies, so you can clean as you stay. Please do!

Annapolis Garden Suite

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$661.57

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrExperience Historic Annapolis in Comfort and Style brbrThis charming 4-bedroom home sits in the heart of Historic Annapolis, just steps from Main Street. Perfect for a weekend getaway or a special event, it offers stunning views of the Capitol from the Room with a View on the top floor. The home is ideal for entertaining with large dining spaces both inside at the dining room and outside on the large private back patio. brbr brbrHighlights: brbrSpacious Accommodations: Features oversized adult bedrooms (two King rooms, one Queen room) and a fun twin bunk room for kids. brbrModern Amenities: Upgraded kitchen, 2.5 baths, luxury linens, complimentary starter amenities, and boutique-level service. brbrOutdoor Space: Private fenced patio with dining for 6 and a grill. brbrIndoor Dining: Formal dining room table for 8 brbr brbrLocation, Location, Location: brbrStep out of the house, stroll through a charming alley (perfect for social media snaps!), and find yourself on bustling Main Street. Dine at local restaurants, shop unique boutiques, and soak up Annapolis’s vibrant waterfront scene. Just four blocks from the U.S. Naval Academy and a short drive to Washington, DC, or Baltimore, it’s ideal for exploring the area. brbr brbr**Parking is not on premises!! A dedicated parking spot at nearby garage (10-minute walk from the house) is provided. Please contact us for details. brbr brbrSleeping Arrangements (Sleeps 8): brbrKing Suite (2nd Floor): King bed, en-suite luxury shower brbrKing Guest Room (2nd Floor): King bed, shared full bath brbrBunk Room (2nd Floor): Two twin beds, shared full bath brbrRoom with a View (3rd Floor): Queen bed, skylight with Capitol views, shared 2nd-floor bath brbr brbrAdditional Features: brbrFlatscreen TV and high-speed WiFi brbrWasher & dryer brbrDedicated garage parking (0.7 miles away). brbrKeyless entry with electronic lock. brbr brbrDistances: brbrU.S. Naval Academy: 4 blocks. brbrAnnapolis Waterfront: At the end of Main Street. brbrWashington, DC: 30 miles. brbrBaltimore: 25 miles. brbr brbrHouse Rules: brbrMust be 25+ to book; no parties, smoking, or pets. brbrQuiet hours apply – please respect our neighbors. brbrCheck-in: 4:00 PM | Check-out: 11:00 AM. brbrDon’t miss out on this charming retreat—perfect for family getaways, Naval Academy events, or enjoying all that Annapolis has to offer! brbr brbr**Parking is not on premises!! A dedicated parking spot at nearby garage (10/15-minute walk) is provided. Please contact us for details.

The Heart of Annapolis at Capital Views, w Free Off-Site Parking & Patio at Historic Home

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$425.19

Life is beautiful in historic downtown Annapolis, with great restaurants, shops and romantic waterfront at your doorstep. Live like a local in a home built in 1875 but updated for today's lifestyles. This two bedroom, 1 1/2 bath home with a designated, off-street parking space -- a rare perk in this National Landmark district -- makes it easy for guests to arrive, unpack and unplug. brbrWalk down Pinkney Street to experience the restaurants and shops of downtown and see the yachts along Ego Alley. Visit the United States Naval Academy just three blocks away. Or walk up the street on brick and cobblestone sidewalks to explore the grounds of the oldest state house in continued use in America or St. John's College, dating to the 17th century. Experience the restaurants, charming antique stores and neighborhoods around State and Church Circles and beyond.brbrThis 1875 cedar shake home sits in a row of townhouses that have been updated for modern living, with hardwood floors and ceramic tile on the main floor and new carpeting in the bedrooms. Enjoy the cozy fireplace during the cold winter nights, or in the warm summer months, take your morning coffee or afternoon cocktails to the rooftop deck to enjoy views of the water, the boats and City Dock.brbrThis well-decorated house features an open floor plan with updated, fully equipped kitchen, a living room with flat-screen TV and fireplace, dining room and half bath on the first level. There is a small deck facing the courtyard and parking with space to sit and enjoy the morning sun. On the second floor, the generously sized queen bedroom features a walk-in closet, private access to a shared bath and wall-mounted flat screen television. A well-appointed guest room provides two comfortable twin beds. But the second floor also contains a hidden surprise -- a skylit ship's ladder to a widow's walk and rooftop deck with beautiful views of Ego Alley and Spa Creek. brbrAs with any luxury property, the essentials -- linens, WiFi, coffee, and toiletries -- are included.brbrHistoric Annapolis is the place to be during Naval Academy events and football games, St. John's College visits and graduation, boat shows and more. It is the perfect destination for a romantic weekend, a girls' getaway, family reunions, temporary military assignment and more. Consider making this cozy retreat on a historic street your home away from home when you come to visit Maryland's state capital.

Historic Downtown Charmer, Water Views and Parking!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$579.17

This 4-bedroom house in Annapolis is perfect for your escape to relaxation. With 4 queen beds and 3 bathrooms equipped with all the essentials, guests can unwind in a tranquil setting. The additional living room space with 2 twin beds offers tremendous flexibility for your group. You're sure to make fantastic memories with a stay at our place. Partially fenced yard, fire pit, covered patio, 2 washers and dryers, space for multiple family/friend groups. Full kitchen plus kitchenette, games, books, corn hole, easy up tent/coolers/folding tables for family tail gates.

Charming 4-bedroom house 2 blocks from the Navel Academy Stadium

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Select Dates for Price

House Boat

Annapolis Boat Life - Overnight Stays

ANNAPOLIS, Maryland, United States

Reconnect with nature at this unforgettable escape on our 44 foot Silverton. This rental comes with a full kitchen, two bathrooms with showers, two bedrooms, a couch, and dining area that convert to beds. Downtown Annapolis is easily accessible by vehicle, public transportation, water taxi, or one of our rentable kayaks.brIf you are looking for a boating experience without missing out on all the amenities of an apartment or hotel room, then this is what you have been searching for.brPerfect for large groups or families looking for weekend getaways or extended stays.

Bed

Bath

Sleeps

$412.15

Summary:brbrEscape to Annapolis in this stylish home, perfect for large groups! Enjoy a private brick patio with a fire pit dining table. Just 4 miles from the Naval Academy, this home comfortably sleeps 10 guests. Features include a fully equipped kitchen, dedicated workspace, and free parking. Your ideal base for exploring historic Annapolis or relaxing in a quiet, friendly community.brbrbrbrThe Space:brbrStep into a modern, open-concept living area designed for comfort and connection. The bright and airy space flows seamlessly from the living room to the kitchen and dining area.brbrbrbr**Key Features:**brbr• **Fully Equipped Kitchen:** A large island with seating for four, a main dining table for group meals, and a seafood pot with tools for an authentic local feast.brbr• **Comfortable Living Room:** Unwind on plush sofas after a day of exploring.brbr• **Private Outdoor Oasis:** A large, fully-fenced brick patio featuring a BBQ grill, a cozy outdoor sofa, and an 8-person fire-pit dining table for memorable evenings.brbr• **Bedrooms & Sleeping Arrangements (Sleeps 10):**brbr - **Master Bedroom (Upstairs):** Spacious retreat with a king-size bed, en suite full bathroom, and a dedicated workspace with a desk.brbr - **Second Bedroom (Upstairs):** Comfortable queen-size bed.brbr - **Third Bedroom:** One queen-size bed and a full-size trundle bed.brbr - **Living Room:** Queen-size pullout sofa bed.brbr• **Conveniences:** An in-unit washer and dryer and a Pack ’n play/Travel crib are provided for your convenience.brbrbrbrNote: 2 pets with a maximum weight of 50 pounds each permitted with a paid pet fee. No pit bulls, American bulldog, rottweilers, akitas, terriers, mastiffs, Dobermans, Great Danes, German Shepherds, huskies, chows, or wolf hybrids are permitted.brbrbrbrGuest Access:brbrGuests will have exclusive and private access to the entire house and its amenities during their stay. Relax, unwind, and make yourself at home without interruption. This includes all bedrooms, bathrooms, the kitchen, living areas, and the private outdoor patio.brbrbrbrOther Things to Note:brbrThere is plenty of street parking available (no permit required) or you can park in a non-labeled free parking spots.To park in the community parking lot- you must display the parking permit that will be provided to you at check in. brbrbrbr• For your peace of mind and compliance with local regulations, the property is fully licensed.brbr• Annapolis Short-Term Rental License: STR-145243brbrbrbrSmoking 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.brbrbrbrInteraction with Guests:brbrWe respect our guests' privacy and offer a seamless self-check-in process. While we will not be present during your stay, we are always available and happy to assist with any questions or provide local recommendations via the messaging app. Our goal is to ensure you have a wonderful and comfortable stay.

Belle By The Bay Summ

Annapolis, Maryland, United States

Bed

Bath

10

Sleeps

$698.25

Close to US Naval Academy (1.6 mi.), Navy-Marine Corps Memorial Stadium (1.1mi), and Anne Arundel Medical Center (less than 0.5 mi) with quick and easy access to Rte. 50 (0.50 mi) and I-97. brbrThis three-bedroom, 2.5-bathroom, 2-level townhome/condo with an attached one-car garage is located in the Creekside Cove community of Annapolis. The main level features a spacious open-plan living/dining, and kitchen area with hardwood floors, a gas fireplace, a covered balcony, and a half bath. On the upper level, you'll find three bedrooms and two full bathrooms, including a large primary suite that boasts a fantastic en-suite bath with a soaking tub and a separate step-in shower, along with a second bathroom in the hallway. The lower level has a storage area, garage, and parking pad.

Condo

3 Bedroom/2.5 bathroom close to Naval Academy, NMCM Stadium, and downtown.

Annapolis, Maryland, United States

Bed

2

Bath

6

Sleeps

$286.41

Your cozy getaway awaits in Annapolis at this lovely house. With two comfortable bedrooms featuring a king bed and a full bed, guests can relax and unwind easily. The bathroom offers a refreshing shower to start or end the day. Inside, the space stays comfortable year-round with heating and air conditioning. An iron is also available for guests who like to keep things neat. This soothing retreat provides a fantastic spot to recharge and explore. A great place to call homebase while you're away, we hope you enjoy your stay.

2-bedroom house in nice Annapolis with cool AC breeze

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$883.5

This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. With six bedrooms (three queen beds, two fulls and two twins) the house comfortably sleeps up to 12. Additional rooms include a pool table room, dining room, large kitchen, library and comfortable family room. The large back yard and beautiful wrap around porch are perfect for anyone looking for a little outdoor time, or for energetic kids!brbrThe convenience of this house cannot be overstated: an easy walk towards downtown you will find Carpaccio's Italian Restaurant, Ms. Shirley's Café, and the Annapolis Westin Hotel where the FREE Annapolis Circulator Trolley will pick you up and take you around the town. Additionally, the nearest grocery store is only a mile and a half away, and within two blocks of the house are a convenience store, a liquor store, and 'Paul's Homewood Cafe' on West Street! In short: if you need it, you can walk to it!brbrWe have spent many years serving our country and are happy to call Annapolis our final port of call. Please note that this is our lived-in family home, not an investment property. brbr**USNA Commissioning Week stay requires a 7 night minimum (Sat-Sat or Sun-Sun).brbrWhen you make your initial inquiry, please tell us something about yourself and the other guests with whom you will be traveling.brbr

Charming Annapolis Victorian

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$635.55

Summary:brbrThis charming 5 BR (3x true bedrooms and 2x basement rooms with bunk beds) home is conveniently located in Annapolis' Germantown neighborhood, ony two blocks from Navy's Navy-Marine Corps stadium! We've decorated it with USNA decor as well as art honoring the squadrons I've served in (HSM-51, HSM-60, HSM-40, and HSM-41)!brbr brbrPerfect for Navy sporting events and boat shows, this home is also only an 8 min drive to USNA, Downtown Annapolis (aka DTA) as well as the Annapolis Mall.brbrbrbrThe Space:brbrThis is a 3 floor property (1st floor, 2nd floor, basement) and guests have access to the entire home. The basement is partially refinished. brbrbrbrGuests will enjoy 5 bedrooms and 3.5 bathrooms. There is one bedroom on the 1st floor with a king bed included - perfect for multi-generational groups if some folks are not able to walk up a full flight of stairs to the 2nd floor. The 1st floor bathroom is unique in that the entire space becomes the shower (see photo). Upstairs guests can enjoy another king bedroom with Smart TV and ensuite bathroom. The ensuite bathroom includes a large jacuzzi bathtub - perfect for relaxing during your stay. The 2nd floor's non-primary bedroom has a queen sized bed in it with a chest of drawers - perfect for guests staying with us for more than a few days. It also has a smaller ensuite bathroom with a shower tub. There is also a full sized washer and dryer on the 2nd floor - between the two bedrooms.brbrbrbrThe basement has two rooms which we label as bedrooms since there are bunkbeds in both of them - a fully finished room and a partially finished room. The fully finished room has a sleeper sofa and twin over twin bunk beds with a smart TV and a kitchenette - a sink and a full sized refrigerator. The partially finished room has a twin over full set of bunk beds - perfect for teenagers / kids. There is also a foosball table in this room as well. It does have direct access to the yard from a door in this room. There is a powder bathroom in the basement (sink and toilet) but guests will need to walk upstairs to use the shower. Please note - guests sleeping in the partially finished room in the basement will need to walk through the fully finished room to access a restroom and the rest of the house. Basement was professionally waterproofed in summer 2025 and we haven't had any leaks/moisture since.brbrbrbrThe first floor has two dining areas separated by the kitchen. The first dining area is to the right as you walk into the house. It has two barstools and four high top style chairs on a kitchen table. There is a separate dining room table on the other side of the kitchen that seats six. The living room is next to the dining room and has a sleeper sofa that seats 3 people. There is also a desk just to the right of the stairs as you enter the property that is perfect for folks working from home! brbrbrbrThe entire property is fenced in, perfect for guests with dogs. Please ensure you clean up after your furry friends. brbrbrbrThere is a covered outdoor porch to the side of the home that makes early mornings with a cup of coffee or late evenings with a glass of wine a relaxing way to enjoy the ambiance of Annapolis. It has benches, adirondack chairs, a couch, as well as a table and chairs - perfect for outdoor dining starting for the spring through the fall! We have a propane grill and grill tools for all your BBQ needs.brbrbrbrThere is free street parking in front of the house. Spaces are usually readily available but not guaranteed. Please be respectful of neighbors when parking, especially in the event of snow. It is recommended that guests bring no more than 2 cars so that they don't block spaces in front of neighbors' houses.brbrbrbrGuest Access:brbrGuests have access to the entire house and backyard except for locked storage closets.brbrbrbrThe Neighborhood:brbrThis home is in the conveniently located in Annapolis's Germantown neighborhood off West Street, near downtown Annapolis. brbr brbrPerfect for Navy sporting events and boat shows, this home is two blocks (0.3 miles) from Navy-Marine Corps Memorial Stadium and an 8 minute drive from USNA and Downtown Annapolis. brbr brbrAnnapolis' Germantown neighborhood is wonderful! There are tons of restaurants, bars, and boutiques on West St which is two blocks away. brbr brbrWalk along the old brick sidewalks much as George Washington or Thomas Jefferson did in the days when Annapolis was the capital of the United States. Architecturally, Annapolis boasts some of the finest 17th and 18th century buildings in the country – including the residences of all four Maryland signers of the Declaration of Independence. brbr brbrAnnapolis is the home of the United States Naval Academy, founded in 1845, and of St. John's College, the third oldest institution of higher learning in the United States. brbr brbrStroll along our waterfront and enjoy the charm of our City Dock. Watch the boats as they cruise our famous Ego Alley. Sit on the seawall and watch the sailboat races as they return to the harbor and see why Annapolis is “America’s Sailing Capital.”brbrbrbrGetting Around:brbrThere isn't solid public transit in Annapolis. Guests should either rent a car or (even better) use car sharing options such as taxis or uber / lyft services.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. brbr brbrLocal Reservation Policy brbr brbrReservations under 7 nights from guests residing in the local area may be subject to cancellation at our discretion. We handle exceptions on a case-by-case basis. brbr brbrEarly Check-In & Late Check-Out Policy brbr brbrEarly arrivals and late departures are not guaranteed and must be approved in advance. If approved, the following fees apply: brbr brbr-Up to 1 hour: $100brbr-1–2 hours: $200 brbr-2–3 hours: $300brbr-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.brbrbrbr***Please note there are exterior security cameras***brbrbrbrLicense: RENT-005413-2024brbrLicense Number: RENT-003497-2024brbrbrbrInteraction with Guests:brbrWe always have a team member in the greater Annapolis area available to assist. I personally live 15-20 minutes away and can assist when in town. I have a property manager who helps me and she lives about an hour away. One of us should be available to help in case of an emergency although it could us several hours to arrive on site if we are otherwise indisposed.

Spacious 5 BR house - 5 Min Walk to N-MC Stadium!

Annapolis, Maryland, United States

Bed