Vacation Rentals By Owner In Annapolis, MD

$609.83

Your Annapolis Retreat near the Naval Academy and downtown

Annapolis, Maryland, United States

Welcome to our retreat in Annapolis. The place is located minutes from downtown and the Naval Academy, in the neighborhood of Cape St Claire, known for its beaches and the family-friendly atmosphere.brbrAs you enter, you are greeted from the main floor with outdoor views of the back deck. Gather with your family and friends in the kitchen for quick bites or elaborated meals to be enjoyed at the dinning table. Sit and watch your favorite shows in the living room or enjoy a conversation with loved ones while looking at the breathtaking views of the front yard. Better yet, retreat into one of three bedrooms on this floor. Each has a comfortable bed dressed with soft sheets, blankets and plenty of pillows to ensure you get plenty of rest and wake up invigorated. The master bedroom is spacious and has its own ensuite. A second full bathroom is located in the hallway.brbrAnother favorite gathering spot is the larger family room on the lower level. A third full bathroom is also on this level and is situated next to the fourth bedroom. This bedroom is the largest. It has two queen beds and a full bed. The driveway can hold up to five cars. brbrA short drive will take you to the community beach with a playground which is open during summer months. Several restaurants are located within a mile. brbrWhether you are planning a quick getaway or in town for a celebration, our home and community offer the space and amenities you need to make your stay an unforgettable experience. brbrWelcome Home! We look forward to hosting you.

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$778.67

/ Nightly

Private Vacation Home

100 5-star Reviews located in the City of Annapolis in a quiet neighborhood!

Annapolis, Maryland, United States

This is one of the most charming houses in Murray Hill! Located on a dead end street, this brick colonial with a slate roof sits on a beautiful lot just 1/2 block from Spa Creek. This beautifully updated 2449 sf home located in the City of Annapolis boasts 4 bedrooms (two bedrooms with king beds), and 3.5 baths. It was completely renovated in 2016 to become a lovely vacation rental for up to 8 guests. There are no personal belongings in the home so you are not dealing with any clutter and it was set up 100% with guests in mind to enjoy. This approach along with our ammenties has helped us earn our 94 five star reviews. brYou can park the cars in our off street driveway which is big enough to park 3 cars and walk everywhere. This means all your guests have freedom and autonomy to come and go. brThe house is located approx a 1/2 half mile from the top of Main Street. The home has hardwood floors throughout, tons of natural light, new kitchen with SS appliances, huge center island, 2 ovens, granite countertops and a family room off the kitchen with a built-in wine refrigerator. Our home is fully furnished with linens, dishes, cookware, and we provide other sundries like: coffee, sugar, Splenda, PAM, olive oil, baggies, Reynolds wrap, salt and pepper, shampoo, body wash, conditioner so there is no need to hurry up and run to the store when you get here! brbrThe home boasts 3 55-inch smart LG tv's. The master bedroom is huge (18x15) with a king bed, and a 55-inch LG tv. The master bath has a corner soaking tub, separate vanities and a luxurious shower that has 2 shower heads, 3 body sprays and a built-in bench for a spa like experience. brbrTwo additional bedrooms and one full bath are located on the 2nd floor. Bedroom #2 has a queen bed and bedroom #3 has two XL twin beds that can be put together to make a king. The 4th bedroom is located on the lower level and has its own private bath. brRelax in the screened-in porch or grab a book and either a cup of coffee or a glass of wine and walk approx 400 feet away to sit by the water's edge at Old Woman's Cove off (Spa Creek) and chill.brNote: The renter who signs the lease MUST occupy the property. There is no subletting allowed.

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$386.82

/ Nightly

Private Vacation Home

Annapolis Spacious Family Retreat

Annapolis, Maryland, United States

Summary:brbrJust minutes from Sandy Point Beach and a short 15 minute drive to the US Naval Academy, this 4 story home has everything you need to enjoy your stay. You will find a peaceful and tranquil setting to relax and unwind on either one of the decks or around the fire-pit. Relax and watch TV in multiple living room spaces or retreat to the master bedroom suite which has its own private deck. A huge bonus room on the 4th story loft area, is perfect as dedicated workspace or room for guests to stay!brbrbrbrThe Space:brbrWelcome to your home away from home! We can't wait to provide you with an unforgettable experience. Whether you seek relaxation or want to go Downtown to enjoy the views or visit the US Naval Academy, this home provides the perfect location. brbrbrbrOur 4-story home is designed for comfort and connection, comfortably accommodating up to 8 guests.brbrbrbrKey Features:brbr* Main Level: An open-concept floor plan with a fully equipped kitchen, a dining area for six, and a cozy family room with a plush couch, large Smart TV, and a warm fireplace.brbr* Lower Level: An additional living room complete with plenty of board and card games, with direct access to the outdoor fire pit.brbr* Outdoor Decks: Unwind in the private hot tub located on one of the home's decks.brbr* 4th-Story Loft: A huge bonus room that serves as a dedicated workspace or a private suite, featuring its own TV and a sleeper sofa.brbrbrbrWhere You'll Sleep:brbr* Master Bedroom (2nd Floor): A serene suite with a queen bed, large Smart TV, a spacious en-suite bathroom, and a private patio.brbr* Bedroom 2 (2nd Floor): Features comfortable and cozy bunk beds and beautiful natural light.brbr* Bedroom 3 (2nd Floor): Offers a queen bed with plenty of storage space. Bedrooms 2 and 3 share a full bathroom in the hallway.brbr* Loft (4th Floor): A comfortable sleeper sofa that opens to a queen bed.brbrbrbrbrbrPlease respect the neighbors and neighborhood. brbrNo parties or events of any kind without prior coordinationbrbrbrbrProperty Distance to:brbrUSNA: 7.1 milesbrbrNavy and Marine Corps Memorial Stadium: 7.1 milesbrbrbrbrGuest Access:brbrGuests will have private access to the entire 4-story townhouse during their stay. This includes all bedrooms, living areas, the kitchen, decks, and private hot tub.brbrbrbrAdditionally, you are welcome to use the shared community amenities:brbr* Tennis Courtbrbr* PlaygroundbrbrbrbrEntry is seamless with self check-in using a smart lock. You will receive your unique access code prior to arrival.brbrbrbrGetting Around:brbrA car is recommended for getting around the area.brbrbrbrOther Things to Note:brbrThere are two dedicated parking spaces available to you. All other parking is located on the street and is free.brbr* Security: For your safety and security, there are exterior security cameras located on the property.brbr* Check-in: This is a self check-in property. Detailed instructions and your access code will be sent prior to your arrival.brbr* Registration Number: 000794brbrbrbrInteraction with Guests:brbrWe prioritize your privacy and comfort. The home is set up for self check-in, and we will not be present during your stay. We are readily available and responsive via the messaging app should you have any questions or need assistance.

3

Bed

2

Bath

8

Sleeps

$399.0

/ Nightly

Apartment

Waterfront private In-law apartment, 10 minutes from Downtown Annapolis.

Annapolis, Maryland, United States

Boat show vendors and visitors!!! This quiet waterfront Annapolis apartment features a queen bed, double futon, Full kitchen, TV, private full bathroom, waterfront screened porch. 10 minutes to USNA and downtown Annapolis. Off street parking.brMinimum 4 nights sleeps 4brOctober 1 through October 5 and October 8th through October 12th brRent each show $1750 for 5 nights or $3000 for both shows full stay

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$199.75

/ Nightly

Private Vacation Home

Extended-Stay Annapolis Home Near USNA & Downtown

Annapolis, Maryland, United States

STR-270 - This fully furnished 4-bedroom, 3-bath Annapolis home is available for mid-term stays of 120 days or more and is ideal for relocation, military, corporate, and temporary housing needs. Located in the quiet Pendennis Mount neighborhood just across the USNA Bridge, the home offers a peaceful residential setting with easy access to downtown Annapolis, shopping, dining, commuter routes, and the Naval Academy area.brDesigned for comfortable extended stays, the home features a welcoming main living area with hardwood floors, a fireplace, and a flat-screen TV. Sleeping arrangements include a king bed in the primary suite, queen beds in two additional bedrooms, and a twin bed in the fourth bedroom. A finished basement provides another queen bed, valuable extra space for work, recreation, storage, or flexible day-to-day living.brbrGuests will also enjoy off-street parking for up to three cars, a back deck with gas grill, and a small fenced yard for approved pets. Located in the Broadneck School District, this home is a practical and comfortable option for families, professionals, and households needing furnished housing in Annapolis for several months or longer. A separate self-contained upstairs apartment at 2 Ritchie Road may also be available for additional accommodations.

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$493.8

/ Nightly

Private Vacation Home

Walk to USNA, Main St w Parking Historic Wisteria

Annapolis, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrHow many homes in Downtown Annapolis have 4 Bedrooms with 4 Baths (3 of which are en-suite) ! brbr brbrJust 1-2 blocks from the Annapolis waterfront, the State Capitol, restaurants, shopping and the Naval Academy, this cherished property is registered with the Historical Society of Annapolis (originally home to “Sam’s Grocery”—a beloved neighborhood corner-store). brbr brbrAfter Sam's Grocery closed up shop in the eighties, the building was converted into a bed and breakfast, most recently called the Chez Amis Inn. Now its a unique rental home and you have the entire place to yourself! Each of the three upstairs bedrooms has been named by the former innkeepers and they are a tribute to the State Capitol's history. On the main floor you will find the Treaty of Paris Room-a library with an en Suite bath and Full size Sleeper sofa. 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 4 BR / 4 BA / Sleeps 7 brbrThe State House Bedroom: brbr-King Size Bed brbr-En Suite Bathroom brbr-Extra Pedestal sink in bedroom brbr-Wall mounted TV brbr brbrThe Law Library: brbr-En Suite Bathroom brbr-Queen Bed brbr-Wall mounted Flatscreen TV brbr brbrThe Annapolis Room: brbr-Queen bed brbr-Private Bathroom in Hall brbr-Wall mounted Flatscreen TV brbr brbrThe Treaty of Paris Den: brbr-Multi-functional Family Den and Bedroom brbr-Full Size Sofa Bed brbr-En Suite Bathroom brbr-Wall mounted Flatscreen TV brbr*The full-size sofa bed may be tight for 2 guests. There is also a portable Twin cot located in the home. brbr brbrHIGHLIGHTS: brbrStocked kitchen with every appliance - large and small - you would need. brbr-Fully-stock Bar in the Library - BYO liquor/spirits brbr-Kitchen Coffee bar seats 2 brbr-Dining room table seats 8 brbr-Outside seating for 4 brbr-High Speed Internet and WiFi brbr-Big Screen TV in Main Floor Library (Flatscreen TVs in every Bedroom) brbr-Luxury linens, complimentary toiletries and paper product Starter Kits, and boutique-level service. brbr-Washer & dryer located inside the home. brbr-Dogs allowed with $150 non-refundable pet deposit paid prior to check-in. brbr-One Garage Parking Spot located 0.7 miles from the home. brbr-Keyless entry. Drive straight to your rental home and enter the front door with an electronic lock code. brbr brbrProperty Distance to: brbr-U.S. Naval Academy – 1 block 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. Be respectful of the house and contents - it is someone's home and the owners do come back from time to time to stay in their property. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. brbrCheck-in time: 4:00 pm brbrCheck-out time: 11:00 am

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Bath

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$731.25

/ Nightly

Private Vacation Home

Nautical Feel to This Beautiful Eastport Home

Annapolis, Maryland, United States

From the minute you walk in the door, you will feel the warmth and charm this home offers. brbrLocated on the Eastport side of Spa Creek, but only 2 blocks to the Annapolis Bridge, this well appointed home is used exclusively for vacation rentals so you are never competing with the owner's belongs tucked away for your visit. But unlike many other rental property in the area, this home is equipped to live in, and is a well stocked home with high quality amenities.brbrLocated along 'restaurant row', you are steps from some of the best restaurants in Annapolis. Or, walk the .5 miles to be in the heart of downtown Annapolis. With a two car driveway, parking is never an issue. brbrThis house was recently renovated with a light nautical feel, beautiful artwork, quality furnishings and comfort that you will want to come home to. Whether your first visit to Annapolis, or you are a frequent visitor taking advantage of Annapolis' wonderful sailing and Naval Academy, this is a home you will want to keep coming back to!

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$665.43

/ Nightly

Private Vacation Home

Waterfront Home with Private Dock, Community Beach

Annapolis, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWaterfront Oasis with Private Dock, Firepit & Kayaks brbrWelcome to the Pearl of Oyster Harbor – a tranquil waterfront retreat on the Annapolis Neck Peninsula. This charming cottage offers the best of all worlds: stunning natural beauty, water activities, and modern comforts. brbr brbrOutdoor Features: brbrPrivate dock for boating, kayaking (3 total kayaks: two adult and one youth), or paddleboarding (inflatable SUP included) brbrExpansive lawn perfect for cornhole, yard games, or simply soaking up the view brbrFirepit for cozy evenings with s'mores and stories brbrHammock for relaxing with a good book or simply enjoying nature brbrParking for 3-4 cars on the driveway brbr brbrIndoor Highlights: brbrBright, airy sunroom with harbor views for board games and family time brbrSleek, modern kitchen with large picture windows framing the waterfront brbrLiving room featuring a smart TV and gas fireplace for cozy evenings brbrSmall desk and WiFi printer for remote work convenience brbr brbrNeighborhood amenities: brbrSwimming beach brbrExercise: Beach volley ball court, 1-mile exercise circuit course, 12' climbing wall, 16' rope climb, brbrFishing pier and boat ramp brbrPlaygrounds, nature preserve, picnic areas, beach gazebos brbr brbrStarter Amenity Pack: brbrWe've got you covered with essentials to make your stay stress-free, including: brbrCoffee, sweeteners, dish soap, and paper towels brbrSoap, shampoo, conditioner, and hand sanitizer brbrFreshly-laundered sheets and towels for every guest brbr brbrSleeping Arrangements (3 BR / 2 BA, Sleeps 8): brbrFront Queen Bedroom: Queen bed, shared full bath in the hall brbrWaterfront Bedroom: Full bed, shared full bath in the hall brbrBunk Bedroom: Twin bunk beds (two twins), shared hall bath brbrLoft: Full bed above the living room brbr brbrHouse Rules: brbrFamily rentals only; one guest must be at least 25 years of age brbrNo smoking, parties, or events brbrQuiet hours from 9:00 pm to 8:00 am brbrDogs allowed with $150 per pet non-refundable fee paid prior to checkin. brbrCheck-in: 4:00 pm | Check-out: 11:00 am brbr brbrProperty Distance to: brbr-Downtown Annapolis – 4 miles (10 mins) brbr-U.S. Naval Academy – 4.5 miles (12 mins) brbr-Washington, DC – 35 miles brbr-Baltimore - 20 miles brbr brbrCreate lasting memories at The Pearl (of Oyster Harbor), where waterfront tranquility meets thoughtful amenities and outdoor fun. Book your stay today for an unforgettable Chesapeake Bay escape!

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Select Dates for Price

Private Vacation Home

Private 2BR Apartment with Parking for Corporate, Medical & Military Stays

Annapolis, Maryland, United States

STR-270 - This private 2-bedroom apartment in Annapolis is a smart choice for mid-term renters seeking a clean, comfortable, and budget-friendly stay near downtown. Well suited for corporate housing, traveling nurses, military assignments, relocations, and temporary housing needs, this second-floor apartment offers privacy, parking, and a convenient location just across the Naval Academy Bridge.brThe apartment is fully self-contained above a single-family home and features its own private entrance, sidewalk access, and off-street parking from Ritchie Road. Guests enjoy a quiet residential setting while staying close to downtown Annapolis, the U.S. Naval Academy area, major commuter routes, and local amenities.brInside, the space is organized, spacious, and easy to settle into for an extended stay. Outside, a small front yard offers room to relax, and the nearby B&A Trail provides easy access to walking, biking, and outdoor recreation.brThis is an excellent fit for traveling professionals who want dependable extended-stay housing in Annapolis without the traffic and congestion of downtown living. Pets are welcome on a case-by-case basis. The lower level of the home is available as a separate rental.

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$370.17

/ Nightly

Condo

Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek!

Annapolis, Maryland, United States

RENT-000642-2025- Experience unparalleled ease and convenience to downtown Annapolis with this exquisite top-floor corner unit boasting abundant natural light. Perfectly situated in Eastport this 1-bedroom 1-bathroom condo offers a remodeled kitchen and bathroom complemented by tasteful wall colors and crown molding throughout.--------Ideal for boat show enthusiasts or those attending commissioning week The Newport Building provides off-street parking in a secured environment with an inviting main entrance foyer and elevator access. Revel in the walkable proximity to vibrant restaurants and pubs as well as a short picturesque stroll over the Eastport Bridge to downtown Annapolis.--------Notably this property caters to comfort with a queen bed in the bedroom and a double sofa sleeper in the living room. The building strictly adheres to a no-pets policy ensuring a peaceful environment for all residents.--------As a unique highlight indulge in the breathtaking views of Spa Creek from the rooftop deck a perfect vantage point for witnessing the mesmerizing performances of the Blue Angels during commissioning week. Take advantage of additional amenities including a shared coin-operated washer and dryer on each floor.--------For added relaxation the rooftop pool is a delightful bonus open on weekends throughout the summer. Don't miss the opportunity to enjoy the perfect blend of luxury convenience and entertainment in this Annapolis gem!----

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$1405.24

/ Nightly

Private Vacation Home

Panoramic Bay Views, Wraparound Decks, 1-Minute Walk to Beach

Annapolis, Maryland, United States

STR-250 -Escape to this spacious waterfront home in Arundel on the Bay, where sweeping Chesapeake Bay views surround you on three sides. With 5 bedrooms and 3.5 baths, this coastal retreat is ideal for families and groups looking to relax, reconnect, and enjoy life by the water.brInside, the open layout offers plenty of space to gather for meals, conversation, and downtime together. The main-level primary suite features a king bed and private bath, while the additional bedrooms offer flexible sleeping arrangements for kids, couples, and extended family.brStep outside to enjoy the wraparound deck, with both screened and open-air spaces for morning coffee, outdoor dining, and evening sunsets over the bay. The large yard provides room for games and family fun, and the community beach is just a 1-minute walk away.brLocated in the peaceful waterfront community of Arundel on the Bay, this home feels private and relaxing while still being just a short drive from downtown Annapolis, with its restaurants, shops, and local attractions.brWhether you’re planning a summer vacation, a family gathering, or a quiet waterfront escape, this Chesapeake Bay home offers the space, setting, and views to make your stay memorable.--PLEASE NOTE: NO large parties or events of any kind are permitted at this home.--------

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$648.24

/ Nightly

Private Vacation Home

Location=AMAZING! Garage Parking for 1

Annapolis, Maryland, United States

STR21-145020 --------Yes! It really is the Perfect Vacation Rental in Annapolis!----Discover the perfect blend of historic charm and contemporary comfort at The Little Lighthouse. A 3-bedroom 2.5-bath vacation home ideally situated just steps from the Annapolis City Dock. Nestled in the heart of all that makes Annapolis special this home offers unparalleled convenience for those looking to explore the vibrant local scene.--------Location Location Location----Imagine waking up and strolling to the nearby bars restaurants and shops or taking a leisurely walk to the United States Naval Academy. With everything at your fingertips you'll be able to fully immerse yourself in the rich history and lively atmosphere that Annapolis is known for.--------Parking Perks----In a city where parking can be a challenge our rental includes a small garage behind a gated entrance that can accommodate up to a small SUV. This dedicated parking space is a huge bonus that should not be overlooked ensuring your stay is as stress-free as possible.--------Comfortable and Modern Living----Spread across two floors our home is designed to cater to your every need. The second floor boasts a spacious master bedroom with a king bed and an attached bathroom featuring a stall shower. Two additional bedrooms one with a queen bed and the other with two twin beds provide the perfect setup for a small family or friends traveling together.--------Perfect for Any Occasion----Whether you're visiting for the renowned boat shows Navy events or simply sightseeing in this historic town our home offers a welcoming retreat. Despite its location in the heart of the historic district the interior is fully modern and updated ensuring you have all the contemporary comforts during your stay.--------Book now and experience Annapolis like never before with the perfect home base to explore relax and enjoy all the wonders this city has to offer.

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Bath

Sleeps

$1489.52

/ Nightly

Private Vacation Home

Stunning Waterfront Retreat w/Pool, Private Dock & Sauna Near Downtown Annapolis

Annapolis, Maryland, United States

STR000259 - Just minutes from downtown Annapolis, this stunning waterfront home offers a private, upscale retreat for up to 8 guests. Located in a quiet residential neighborhood, the property combines modern design, spacious indoor living, and beautiful outdoor spaces for a memorable stay on the water.brInside, the home features soaring ceilings, light-filled living areas, and sweeping waterfront views. The gourmet kitchen is equipped with a six-burner stove, three dishwashers, and wine storage, and opens to a comfortable family room with easy access to the deck and pool area. A formal dining room provides an elegant setting for meals with family and friends.brbrThe home offers 4 spacious bedrooms, each with its own en-suite bathroom. One guest bedroom is located on the main floor, ideal for those who prefer fewer stairs. Upstairs, the primary suite features vaulted ceilings, a private balcony with panoramic water views, and a spa-like bathroom with a soaking tub, shower, bidet, and Finnish sauna. Two additional upstairs guest suites offer designer bathrooms and generous closet space.brbrGuests will also enjoy a large recreation and TV room with a pool table, piano, treadmill, Pilates machine, free weights, and balcony access overlooking the pool and water.brbrOutside, the beautifully landscaped grounds are designed for relaxing and enjoying the setting. The contemporary pool is open from Memorial Day through Labor Day and is surrounded by multiple seating areas, waterfront decks, and peaceful garden spaces. A Big Green Egg, gas grill, outdoor dining area, and copper fire pit make it easy to enjoy time outdoors from morning coffee to evening gatherings.brbrFor those who love the water, the property includes a private dock and pier, 4 kayaks, 2 paddleboards, and 2 bikes for exploring the area. Parking is available for up to 6 cars, and a full-size washer and dryer are located on the main floor for added convenience.brbrThis home is ideal for families and small groups seeking a relaxing waterfront escape with easy access to Annapolis dining, shopping, and attractions. Please note that this property is located in a peaceful residential community and is best suited for respectful guests looking to enjoy the home and surroundings.brImportant to note: This waterfront property includes a pool, dock, pier, kayaks, and paddleboards. Use of these amenities is at guests’ own risk. Children must be supervised at all times near the water and pool. There is no lifeguard or on-site supervision. No diving or jumping from the pier. Guests must use all equipment safely, inspect equipment before use, and report any damage or unsafe conditions. Use of the dock, kayaks, and paddleboards requires agreement to a separate waterfront/recreational equipment addendum before arrival.

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$473.43

/ Nightly

Private Vacation Home

Historic Annapolis 2BR En Suite Retreat- Walk to Naval Academy & Dock

Annapolis, Maryland, United States

RENT-002420-2025 -Stay in the heart of downtown Annapolis at this beautifully restored 2BR/2.5BA townhome on quiet, charming Pinkney Street. Ideal for couples, friends, or weekend getaways, each bedroom includes a private en suite bath for extra comfort and privacy.brEnjoy a welcoming living room, dining area, fully equipped kitchen, in-home washer/dryer, and a rare private enclosed courtyard perfect for morning coffee or evening wine. Walk to the U.S. Naval Academy, City Dock, Main Street dining, boutique shopping, and waterfront attractions in minutes.brWhether you're visiting for Navy games, weddings, special events, or a historic Annapolis getaway, this is the perfect home base.brPlease note: no on-site parking; nearby public garages provide easy access.

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Bath

Sleeps

$600.07

/ Nightly

Private Vacation Home

3 BR charming home sits in the heart of Annapolis with rooftop deck

Annapolis, Maryland, United States

STR-144253 Welcome to The Yellow Door on Cornhill, a beautifully restored 1800 brick home in the heart of downtown Annapolis. Blending historic character with refined modern comfort, this charming retreat is within walking distance of City Dock, shops, dining, and many of Annapolis’s most popular attractions. From the moment you arrive, the home offers a memorable stay filled with warmth, style, and classic downtown charm.brbrInside, you’ll find thoughtfully updated interiors with high-end finishes, a cozy living room with a gas fireplace and Smart TV, and a well-appointed dining space perfect for relaxed meals at home. The standout chef’s kitchen features an Aga stove, professional-grade refrigerator, and a custom butler’s pantry with a second sink, offering both beauty and function for your stay.brbrOn the second floor, the home offers two queen bedrooms, including a primary suite with an en-suite bath, plus an additional full bathroom with a walk-in shower. The third-floor loft includes a twin trundle bed and access to one of the home’s most special features: a rooftop deck with views of the Naval Academy and State House domes.brbrPlease note that, due to the home’s historic age and layout, the staircases to the upper floors are steep and narrow, so the property may not be suitable for young children or guests with mobility concerns. There is no on-site parking, and the driveway across the street may not be used, including for unloading.

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$377.69

/ Nightly

Private Vacation Home

2BR Historic District Gem w/Parking Near City Dock

Annapolis, Maryland, United States

STR21-144963 Discover a charming little gem nestled in the heart of the Historic District. It's a perfect haven for the traveler who craves the allure of downtown convenience and an affinity for antiques. This enchanting abode is adorned with timeless treasures each with its own story from generations past creating an ambiance steeped in history and character.--------The two bedrooms featuring a double bed and a 3/4 bed (larger than a twin but cozier than a double) provide a cozy retreat for up to four guests. A quaint porch thoughtfully enclosed for year-round enjoyment adds a touch of old-world charm to your stay.--------Modern amenities seamlessly blend with historic allure offering high-speed internet an updated kitchen window AC for comfort and a reserved parking space right beside the house. Immerse yourself in the captivating surroundings as this gem is strategically located close to everything inviting you to explore the vibrant energy of downtown Annapolis.--------Indulge in the proximity to Annapolis City Dock just a 4-minute stroll away and relish a 6-minute walk to the US Naval Academy. For your convenience the US Naval Academy Stadium is a mere 1.2 miles away.--------This delightful retreat not only offers a glimpse into the past with its antique charm but also ensures a cozy and convenient stay for your visit. Unwind explore and make cherished memories in this timeless abode. *Plus the sofa sleeper adds an extra layer of flexibility to accommodate your needs.----Distance from USNA: 0.3 Miles (6 Minute Walk)----Distance from USNA Stadium: 1.2 Miles----Maximum to Sleep: 4----Bedroom 1: Double ----Bedroom 2: 3/4 Bed - Larger than a Twin but smaller than a Double.----*Plus Sofa Sleeper

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$869.09

/ Nightly

Private Vacation Home

Historic 3 BR home and just forty yards from the US Naval Academy Barry Gate

Annapolis, Maryland, United States

RENT-005995-2024-The Campbell House on Prince George offers the best of downtown Annapolis with a rare blend of historic charm and modern luxury. Located just 40 yards from the U.S. Naval Academy’s Barry Gate and only a 2-minute walk to City Dock, this beautifully restored 3-bedroom, 2.5-bath home places you in the heart of Annapolis, with easy access to waterfront dining, boutique shopping, historic landmarks, and major events like Commissioning Week and the Annapolis Boat Shows.brRecognized by the Capital as Home of the Week and honored with the Historic Annapolis Preservation Project of the Year award, the home has been thoughtfully updated to combine timeless character with modern comfort. Inside, you’ll find a fully renovated kitchen with high-end appliances, inviting living spaces, and updated entertainment systems in both the living room and primary bedroom. The home comfortably sleeps 6 to 8 guests with a king bedroom, queen bedroom, two twin beds on the third floor, and a queen sleeper sofa in the living room.brOutside, enjoy a private garden patio with a gas grill, a rare bonus in downtown Annapolis. A street parking pass is also included for the duration of your stay, making it even easier to enjoy the city on foot.brSleeping ArrangementsbrPrimary Bedroom: King bed, en-suite bath with walk-in showerbrBedroom 2: Queen bedbrBedroom 3: Two twin bedsbrAdditional Sleeping: Queen sleeper sofa in living roombrPlease note: the garden patio is not available during the boat shows.

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$834.44

/ Nightly

Private Vacation Home

Steps from the Waterfront with Private Backyard at Historic Philip Clayton House

Annapolis, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrHistoric Philip Clayton House – Downtown Annapolis Retreat brbr brbrStep into Annapolis history at the Philip Clayton House, a landmark residence built in 1834. Located just one block from the City Dock, 3 blocks from the U.S. Naval Academy and the lively shops and restaurants of Downtown Annapolis, this home blends historic character with modern comforts for an unforgettable stay. brbr brbrWith nearly 200 years of stories behind its walls, the home has been thoughtfully renovated to balance original charm with modern livability. A bright family room opens to a private patio and fenced backyard—perfect for morning coffee, al fresco dining, or evenings around the fire pit. brbr brbrThere are 4 spacious bedrooms and 2.5 bathrooms, comfortably accommodating up to 10 guests. The gourmet kitchen serves as the heart of the home, featuring a large central island, top-quality appliances, and plenty of space for family meals or entertaining. brbr brbrSleeping Arrangements (Sleeps 10): brbrKing Suite (2nd Floor): King bed with ensuite full bath brbrGarden Bedroom (2nd Floor): Queen bed brbrAmericana Bedroom (2nd Floor): Queen bed brbr3rd Floor Bedroom: Two King beds brbrAdditional Baths: Full hall bath on 2nd floor + half bath on main level brbr brbrHighlights: brbrPrivate backyard with dining for 6, Adirondack chairs, and fire pit brbrPropane BBQ grill brbrMultiple dining areas in the kitchen, dining and family rooms (total seating for 16) brbrSmart TVs, WiFi, and luxury linens brbrKeyless entry and in-home laundry brbrDog-friendly ($150 per pet fee to be charged prior to checkin) brbrParking: Convenient loading zone on street in front of house with parking around the block in the easy to access Hilman garage. Daily rate $23.25. brbr brbrGuests must be 25+ or accompanied by an adult brbrNo smoking, parties, or events permitted brbrSteep staircases may not suit those with mobility issues brbr brbrNearby Attractions: brbrU.S. Naval Academy: 3 blocks brbrCity Dock & Downtown Annapolis: Walking distance brbrWashington, D.C.: 30 miles brbrBaltimore: 25 miles brbr brbrYour stay begins worry-free with a starter kit of coffee, toiletries, and household essentials. Freshly laundered linens await on every bed so you can settle in and enjoy the best of Annapolis—history, charm, and convenience all in one.

4

Bed

2

Bath

10

Sleeps

$663.16

/ Nightly

Private Vacation Home

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Annapolis, Maryland, United States

Relax at this quiet 3BR, 2BA Annapolis retreat just minutes from downtown and the waterfront. Walk to nearby shops and cafés, then unwind in the spacious living room, cozy TV den, or on the private deck. Enjoy a fully equipped kitchen and parking for up to three cars. The perfect balance of convenience and calm for your Annapolis stay.brbrThe spacebrStep into a welcoming home designed for comfort and relaxation:brbr- Bedrooms & Bathrooms -brbrBedroom 1: 1 BedbrBedroom 2: 1 BedbrBedroom 3: 1 Bedbr2 Full Bathrooms stocked with essentialsbrbr- Living & Common Spaces -brbrSpacious main living roombrCozy TV den (“TV cave”) for movie nightsbrWarm dining area for shared mealsbrFully equipped kitchenbrPrivate, serene deck for outdoor relaxationbrbr- Parking -brbrDriveway parking for up to 3 vehiclesbrbr- Location Highlights -brbrWalkable to shops and cafésbrMinutes from Annapolis waterfrontbr~10-minute drive to Downtown AnnapolisbrClose to marinas, parks, and local diningbrbrGuest accessbrYou will receive an access code to the smart lock shortly before your arrival.brbrOther things to notebrAnnapolis is a true maritime treasure—home to sailboats, harborside cafés, and centuries of nautical history. You’ll feel that energy the moment you wander through town or stroll along the waterfront.brbrAnd then you step inside the house… and you’re somewhere entirely different.brbrWe affectionately call the house “Bavaria on the Bay,” a place where old-world Europe meets coastal Maryland. The décor is inspired by the magic of Bavaria—its forests, its mountains, its fairy-tale castles. Throughout the home you’ll notice art and details that hint at that world, including pieces celebrating the iconic Neuschwanstein Castle, the model for so many storybook palaces. It’s a space where maritime Annapolis meets the romance of the Alps.brbrIf you’re curious, you can dive into the story of King Ludwig II, one of Bavaria’s most fascinating rulers and the dreamer behind these castles. His story is one of vision, beauty, and an enduring mystery: the unsolved circumstances of his final night by the lake.brbrWe’re continuously refining and adding to the décor to make the Bavarian theme even more immersive over time—so each stay offers a little something new.brbrWe care for our neighbors, so... PLEASE ALSO NOTE:brbrThis is a charming neighborhood with many families. Therefore, absolutely NO PARTIES are allowed.brbrBetween 10pm and 7am, the outside noise has to be kept to a minimum.

Bed

Bath

Sleeps

$587.74

/ Nightly

Private Vacation Home

Walkable to Main Street at Seashell in the City with 2 parking spots

Annapolis, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWelcome to this gorgeous fully-renovated home, restored to a new modern grandeur, which includes coveted parking for 2 cars on-site. Located on a quiet residential street just 2 blocks from Main Street, the home has 2 bedrooms and 2 full baths on the 2nd floor, and 2 more bedrooms on the 3rd floor. When you arrive at the home and park in the parking pad you will walk through the newly-furnished back patio up the stairs and enter through the large gourmet kitchen. The breakfast bar has seating for 3 and is fully stocked for your stay with plates, glasses, and appliances (big and small!). brbr brbrJust steps from all Annapolis has to offer, this home is located between 2 waterways: if you go out the front door to the left and walk 1.5 blocks you'll reach a dock on Spa Creek. If you walk out to the right and go 1.5 blocks, you'll be at the famous Annapolis Waterfront. This is the perfect spot for those coming in for that special Naval Academy or boat show event, or wanting to take in the sights and sounds of Greater Annapolis. Enjoy the many restaurants, historical attractions, and shops right around the corner! brbr brbrSLEEPING ARRANGEMENTS 4 BR / 2.5 BA / Sleeps 8: brbrKing Bedroom 1 at the top of the stairs: brbr- Second Floor brbr- King Size Bed brbr brbrFull Guestroom #2 on the 2nd Floor: brbr- Second Floor brbr- Full Size Bed brbr brbrQueen Guestroom #3 on the 3rd Floor: brbr-Third Floor brbr-Queen Bed brbr brbrQueen Guestroom #4 on the 3rd Floor: brbr- Third Floor brbr- Queen Bed brbr brbrHIGHLIGHTS: brbr- Furnished Back Patio with sitting area and grill brbr- Spacious kitchen brbr- Eat-in kitchen counter seats 3 brbr- Dining room table seats 8-10 brbr- WiFi brbr- Big Screen TV brbr- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service brbr- Parking for 2 cars brbr- Washer & dryer located inside the home brbr- Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations. brbr- Keyless entry. Drive straight to your rental home, park in the gravel parking pad and enter the front door with an electronic lock code. brbr brbrProperty Distance to: brbr- U.S. Naval Academy – 3 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 already made for you with freshly -laundered luxury sheets & towels. brbr brbrHouse Rules brbrReservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. brbrCheck-in time: 4:00 pm brbrCheck-out time: 11:00 am

4

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2

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8

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