Home Vacation Rentals By Owner In Annapolis, MD

Showing 40 Of 436 Vacation Rentals
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Exceptional(4)

$814.01

/ Nightly
Private Vacation Home

Sing Second Stays—Spacious Annapolis Home Near USNA & Navy Stadium

Annapolis, Maryland, United States

Welcome to Sing Second Stays, a comfortable and spacious retreat in the heart of Annapolis. Just 1.4 miles from Navy-Marine Corps Memorial Stadium, this home is ideal for Naval Academy families, alumni, and visitors looking to enjoy game days, Commissioning Week, I-Day, or a weekend exploring the charm of historic Annapolis.brbrThis home holds a special place in our hearts. I’m a Naval Academy graduate (Class of 2015) and former Navy football player, and my wife, our two children, and I lived here for four years. We walked to home games, hosted friends, and made countless memories in this house before transforming it into the welcoming rental you see today. It’s our hope that guests will feel the same warmth and connection during their stay.brbrThe location is hard to beat. We are just 2 miles from Gate 1 and 2.2 miles from Gate 8 at the United States Naval Academy. Downtown Annapolis, waterfront restaurants, historic landmarks, and boutique shopping are only minutes away. Whether you’re visiting USNA, attending a game, or simply exploring the area, this home offers unbeatable convenience.brbrParking is easy and stress-free. Our U-shaped driveway provides smooth in-and-out access with space for up to four cars—two on each side—without the need to shuffle vehicles.brbrInside, the home features a spacious split-foyer layout that works beautifully for families, groups, and multi-generational gatherings. The main level has an open-concept kitchen with modern appliances and all the essentials. The large living room includes ample seating and a 65-inch Sony TV, perfect for watching the game or relaxing after a day in town. The primary bedroom includes a king-sized bed, a full en-suite bathroom, and a 55-inch Samsung Smart TV. Two additional bedrooms, each with queen beds, share a second full bathroom on this floor.brbrDownstairs, guests enjoy a full private suite feel. There’s a bedroom with a king bed and sectional sofa, plus a large hangout room with full-over-full bunk beds, another sectional couch, and a 65-inch Vizio TV. A kitchenette includes a microwave, toaster oven, Keurig coffee maker, and mini fridge, making it easy to prep snacks or enjoy a casual breakfast. There’s also a round table ideal for dining, cards, or board games, a full bathroom, and a separate entrance. Guests will also find a washer, dryer, and utility sink on this level.brbrFor fun and relaxation, the downstairs also includes a Pop-A-Shot basketball game, a Golden Tee arcade machine, and a variety of board games and puzzles. Whether you're traveling with kids, teens, or friends, the lower level offers a great place to unwind.brbrOutside, enjoy two outdoor living areas. The upper-level deck is 40 feet by 12 feet and features a dining table for six with an umbrella, an outdoor sofa, and extra seating for relaxing or dining al fresco. Below the deck, a shaded patio area provides an additional space to gather and enjoy the fresh air.brbrSing Second Stays is pet-friendly because we understand that your furry companions are part of the family. We simply ask that pets are well-behaved and that guests clean up after them.brbrThe home is equipped with high-speed Wi-Fi, three smart TVs, and all the essentials to make your stay comfortable and convenient. Guests also have access to an air mattress and two Pack 'n Plays, making it easy to accommodate additional sleepers or young children.brbrFor your safety, the property is equipped with six exterior Eufy security cameras. These include one above the front door, two side light cameras, one covering the basement entrance, and two on the back porch. There are no cameras inside the home, and these exterior cameras are used strictly for safety and security purposes.brbrHere’s a quick look at the sleeping arrangements:brUpstairs includes a primary bedroom with a king bed and two bedrooms with queen beds.brDownstairs includes one king bedroom and a hangout room with full-over-full bunk beds.brAn air mattress and two Pack 'n Plays are available for guest use.brbrThe kitchen is fully stocked and includes a stovetop, oven, large refrigerator, freezer, Ninja coffee maker, blender, pots, pans, dishes, and utensils. Downstairs, the kitchenette provides added flexibility with a microwave, toaster oven, mini fridge, and Keurig coffee maker.brbrWe ask that guests follow a few simple house rules to keep the home enjoyable for all. Smoking or vaping is not allowed inside the home or on the back deck. Please keep noise levels reasonable and be mindful of our neighbors, especially during quiet hours. No parties or unauthorized gatherings are permitted. Pets are welcome, but we ask that guests clean up after them. The fireplaces in the home are not for guest use.brbrSing Second Stays was designed with comfort, convenience, and community in mind. Whether you’re returning to Annapolis for a reunion, celebrating with your midshipman, or simply exploring this beautiful historic town, we’d love to host you. We’re confident you’ll find our home to be welcoming, functional, and full of thoughtful touches that make your stay memorable.brbrWe look forward to welcoming you to Sing Second Stays and helping you create your own Annapolis story.
Bed 4

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Bath 3

Bath

Sleep 12

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Exceptional(92)

$839.61

/ Nightly
Private Vacation Home

Waterfront Oasis in Eastport-Easy Walk to Downtown

Annapolis, Maryland, United States

Welcome to our Waterfront Oasis in the desirable Eastport section of Annapolis. We feature a main level open floor plan with excellent water views, 4 bedrooms and first level suite with two twins and a second living area. This home is perfectly suited to host a larger family/friend group (Please NO parties or events of any kind.) Water access out the back door, plenty of free no permit required street parking and a quick walk to downtown or USNA. Bring your kayaks/boards for our floating dock.brbrWe feature three full floors , the upstairs area has 4 full bedrooms and two full baths with an open loft/office space. The main level is a spacious open floor plan with updated kitchen and half bath . Downstairs is its own mini apartment with two entrances , laundry , sink , bar , mini fridge and Tv.brbrThe garage and slip are not for guest use. We have active cameras on all exterior access points .The home does not allow pets however the owners labs do visit numerous times throughout the year in case of pet allergies .This is NOT a party house - please read all rules before booking .brbrABSOLUTELY no events parties ( Bach / ette included ) . No smoking. 10 max people at any given time in the property . Only two cars are allowed in driveway - the rest can do street parking ( guests do not have garage access) .Please respect our neighbors and observe quiet time after 9pm. Any violation will result in additional fees and instant termination of rental contract . Property has active cameras on front and back exterior .
Bed 5

Bed

Bath 3

Bath

Sleep 10

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$518.13

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Private Vacation Home

PERFECT LOCATION in the heart of history

Annapolis, Maryland, United States

Be our guest at Historic 19 East Street, in the heart of the Annapolis national landmark district. Walk out the front door, look left and see the iconic Maryland State House, look right and you're less than a block from Gate One of the United States Naval Academy. St. John's College, St. Mary's, City Dock, William Paca Gardens, and Main Street are all within three blocks. Everything Historic Annapolis has to offer, from boating to restaurants to shopping to Naval Academy traditions, is yours to enjoy! brbrHistoric 19 East is the perfect location for weddings, USNA events, regattas or just a quiet getaway. The interior of this exceptionally restored 115 year old home is perfectly updated, light, friendly, and beyond comfortable with hard wood floors throughout, a large flat screen 4K TV in the living room. Gather around our large dining room table for family meals, or enjoy the very large, privately fenced bricked patio for a cook-out, brunch or cocktail after a full day of exploring the town. If you don't feel like cooking order take-out or stroll to one of the many renowned local eateries. The coffee maker is a Keurig for ease of making single cups. Our home comfortably sleeps 6 (two queens, one full, one twin) and is perfect for a family gathering, weekend getaway or a reunion among friends. It is a wonderful property in a fantastic location and we look forward to you being our guest. LIMITED PARKING: In order to help residents and visitors navigate parking downtown, a website www.AccessAnnapolis.com was created to serve as a hub for parking and transit information to help residents, businesses, employees, customers, and visitors plan their visit to downtown Annapolis. You may find more options by googling Annapolis Parking.brOnce you park your car you will be set on foot to explore all that Annapolis has to offer.brbrUSING PARK MOBILE:brNon-residents are encouraged to download the ParkMobile app (Android/Apple). After the app has been downloaded, add your vehicle tag, payment method and allowbr “location enabled services” to automatically determine ParkMobile parking zone data. Parking can also be paid by texting “PARK” to 77223. brbrTAXES: VRBO collects and pays a 6% Sales and Use Tax required by Anne Arundel County. In addition, the owners must collect and pay a City of Annapolis Hotel and Motel Tax of 7% which is listed in the rates section as a Property Fee. Please let us know if you have any questions about these taxes.brShort Term License: STR-142633brbrSuitability: Non-smoking only, wheelchair inaccessible, no pets, 25 or older please.
Bed 3

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Bath 2

Bath

Sleep 8

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Exceptional(23)

$829

/ Nightly
Private Vacation Home

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis, Maryland, United States

Annapolis Beachfront w/Bay Bridge view - Wake up to a beautiful view of the sunrise over the Chesapeake Bay. Go to sleep with the bright moonlight over the water. View of the water and Bay bridge from the kitchen, dining and living room. Deck over-looking sandy beach area. Swimming or wading in 2-5ft water for approx. 50 yards. Close proximity to grocery stores, restaurants and shopping. Home accommodates 4 cars. 7 steps to enter home. One level living area. Kitchen, dining, living room, 3 bedrooms, 2 baths. Interior with hardwood floors and carpeted bedrooms. Beautiful kitchen with granite island countertops with built-in cooktop/oven. Marbled bathroom floors. Quiet safe neighborhood for walking, biking, jogging. Children friendly -- sandy beach in front of home, or a short walk to gated beach area with swimming, playground, gazebo and pier for fishing. Community boat ramp for launching boats and jet-skis. Four miles to downtown Annapolis historical district, museums, nightlife, shopping, restaurants, Naval Academy, State Capitol, Senate and House buildings and much much more! Paddle boards, and rafts on the premise available with the exception of jets skis are available for use. Summer months allow for a private day at the beach without leaving the premise. You will have the pleasure of enjoying a private beachfront area to relax, listen to the waves, tan, take a swim, lounge on a floatable, or just enjoying the view of the Chesapeake Bay Bridge. Winters months are just as beautiful.
Bed 3

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Bath 2

Bath

Sleep 6

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Exceptional(44)

$351.9

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Cottage

Waterfront Annapolis Cottage: Fire Pit & Pier

Annapolis, Maryland, United States

Located on Meridith Creek, this charming vacation rental features a large yard, fishing pier, and an outdoor space with dining, furniture, and a fire pit. Inside this 3-bed, 1-bath cottage, cozy furniture decorates the open living area. During your stay at this lovely cottage, stroll through the quaint Annapolis Historic District, visit the US Naval Academy, or take a day trip to D.C. and Baltimore. It is the perfect home base for your next Maryland getaway on the water!brbr-- THE PROPERTY --brbrSTR Permit #142832 | Meredith Creek Access | Crab Traps Provided | Covered Outdoor Dining | DockbrbrBedroom 1: Queen Bed | Bedroom 2: Full Bed | Bedroom 3: Twin Bunk BedbrNote: The top bunk is intended for children's use only.brbrOUTDOOR LIVING: Patio, covered dining table, fire pit, patio furniture w/ cushions, yard, double BBQ pit, swimming dock, fishing pier, Meredith Creek access, on-site crabbing (traps provided)brINDOOR LIVING: Open layout, stone accent wall, couch & reclining chairs, flat-screen satellite TV, dining tablebrKITCHEN: Fully equipped, refrigerator, stove/oven, dishwasher, microwave, 1-cup coffee maker, teapot, cooking basicsbrGENERAL: Free WiFi, linens & towels, laundry machines, central air conditioning, ceiling fans, closets, landlinebrFAQ: Pet fee (paid pre-trip)brPARKING: Driveway (2 vehicles)brbr-- THE LOCATION --brbrHISTORIC DOWNTOWN: William Paca House & Garden (7.9 miles), Armel-Leftwich Visitor Center (8.0 miles), Annapolis City Dock (8.1 miles), Maryland State House (8.1 miles), Annapolis Maritime Museum (9.3 miles)brOUTDOOR ACTIVITY: Meredith Creek (on-site), Sandy Point State Park (2.3 miles), Annapolis City Marina (8.8 miles), Quiet Waters Park (14.2 miles), Port Annapolis Marina (15.0 miles), Herrington Harbour - Herrington on the Bay (26.0 miles)brATTRACTIONS: Crypt of John Paul Jones (7.2 miles), Hammond-Hardwood House (7.3 miles), The Chesapeake Children’s Museum (9.8 miles), Pirate Adventures on the Chesapeake (10.0 miles), Top of the World Observation Level (35.4 miles), Fort McHenry National Monument & Historic Shrine (36.7 miles)brUS NAVAL ACADEMY: Navy-Marine Corps Memorial Stadium (7.3 miles), Alumni Hall (7.5 miles), US Naval Academy Museum (7.6 miles), Naval Academy Chapel (7.7 miles), Drydock Restaurant (8.2 miles), Memorial Hall (8.2 miles)brDAY TRIPS: Baltimore, MD (31.7 miles), Washington D.C. (36.7 miles), Rehoboth Beach, DE (85.8 miles), Philadelphia, PA (117 miles)brAIRPORT: Baltimore/Washington International Thurgood Marshall Airport (23.9 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- Pet friendly with $50 fee (+ fees & taxes, 1 dog max)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr-Note: The top bunk is intended for children's use only.
Bed 3

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Bath 1

Bath

Sleep 5

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Exceptional(10)

$622.47

/ Nightly
Private Vacation Home

Restriction Retreat - Relax & walk to Main St

Annapolis, Maryland, United States

Welcome to the Restriction Retreat, where trouble checks in. Treat yourself and your family to five-star amenities, an unbeatable location, and indulge with modern comforts. Get the “real” R & R experience located steps from downtown Annapolis. A 2 bed / 2.5 bath home with a living space, dining area, and relaxing patio with a fire-pit. A king and queen bedrooms, and queen pullout sofa, it can sleep up to 6 adults.brbrOur home is not your ordinary Airbnb, it’s a piece of history. Built in 1900, we have designed it with elegance and hospitality first, but don’t take my word for it, experience it yourself. The Restriction Retreat reflects the luxury and charm of historic Annapolis. brbrBetween the aesthetics and the amenities, you’ll have everything you need to relax, recharge, and enjoy your time in downtown Annapolis. Voted one of the most beautiful towns in America by Conde Nast Traveler. You’ll quickly see why we fell in love with it!brbrRestriction Retreat has been carefully designed to reflect the history of the capital of Maryland. Rich with traditions from the Naval Academy and local experiences. While the home has been updated, we tried to maintain some historical details which makes it unique and reflects the character and history of Annapolis. brbrWe combined luxury and vintage with amenities of today. If you love to cook, we welcome you to our chef’s kitchen to whip up an amazing meal for your family. brbrFollow us on IG @Restriction.Retreat to view more photos of the space and check out upcoming events.
Bed 2

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Bath 2

Bath

Sleep 6

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Exceptional(1)

$1505.54

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Private Vacation Home

Downtown Annapolis Duke's House

Annapolis, Maryland, United States

Summary:brbrThis newly renovated 4-bedroom, 3.5 bathroom home is perfectly situated in the heart of historic downtown Annapolis, making it the ideal retreat for those looking to experience the charm and excitement of the city. Modern elegance featuring high-end finishes, designer furnishings, and thoughtful touches throughout. The home also offers the convenience of on-site parking for 2 vehicles and is within walking distance to the USNA, Annapolis’ best restaurants, shops, and waterfront attractions.brbrbrbrThe Space:brbrUpon entering, you’re greeted by an open-concept living space with abundant natural light, sleek hardwood floors, and a cozy yet sophisticated ambiance. The gourmet kitchen boasts top-of-the-line stainless steel appliances, quartz countertops, and a spacious island that’s perfect for entertaining. The dining area is surrounded by ample natural light and seating. There is also an additional office space and sitting room.brbrbrbrWhere you will sleep: brbrbrbrThe master suite is a serene oasis with a king-sized bed, a spa-like ensuite bathroom with a walk-in shower, and ample closet space. brbrbrbrOn the second floor, there are two additional bedrooms are equally inviting, each with plush bedding, tasteful decor, and easy access to a stylish shared bathroom. brbrbrbrOn the third floor you will find a bedroom that comes with three beds, ample closet space and a full size bathroom.brbrbrbrGuest Access:brbrYou will have private access to the entire home. For your convenience, we offer seamless self check-in with a smart lock. A washer and dryer are also available for your use during your stay.brbrbrbrThe Neighborhood:brbrHistoric cobblestone sidewalks are a captivating feature found around the neighborhood. Walking on these cobblestone sidewalks is like stepping back in time, as they have been part of the urban landscape for centuries. They add a touch of nostalgia and character to historic districts, enhancing the overall ambiance and charm of the area.brbrbrbrGetting Around:brbrThe driveway of our home can accommodate up to 2 vehicles if parked behind each other. A car is not needed, but there are several parking garages close to the house. The city does provide free parking from 6PM Friday to 6AM Monday at the Calvert Street Garage (19 St. Johns Lane) or you can also park in the following garages/lots: Hillman Garage (150 Gorman Ave - entrances from Main St or Duke of Gloucester) South Street Lot - South Street off Church Circle, Gotts Court Parking Garage – (25 Northwest Street) Knighton Parking Garage – (1A Colonial Avenue), Park Place - 5 Park Place (just off West St ). The free Annapolis Circulator bus stops at all the city garages/lots and the city dock and can be used to get to/from the garages. Please see the Annapolis Parking website for further detailsbrbrbrbrInteraction with Guests:brbrWe respect our guests' privacy and offer a seamless self check-in process. While we won't be on-site during your stay, we are always available and happy to assist with any questions or recommendations via the app or phone to ensure you have a wonderful time.
Bath 4

Bath

Sleep 9

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Exceptional(20)

$948.1

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Private Vacation Home

Beautiful Blend of Restoration and Renovation in this Downtown Home

Annapolis, Maryland, United States

Welcome to this newly updated rental home, a stunning blend of renovation and restoration located in the heart of the Historic District. As you step through the front door, you'll be greeted by a beautifully appointed interior that seamlessly blends modern amenities with historic charm.brbrLocated just steps away from Main Street, this home is situated on a quiet street that offers the perfect balance of convenience and tranquility. You can easily explore all the attractions and amenities that the town has to offer while enjoying the peace and quiet of your own private sanctuary.brbrEvery detail of the home has been carefully curated to create an unforgettable vacation experience. From the stylish decor to the luxurious bedding and linens, you'll feel pampered and comfortable throughout your stay.brbrEnjoy the privacy of the backyard - a beautiful oasis that provides a perfect place to relax and unwind. Or, relax on the front porch with a book or a glass of wine in the comfortable deep cushion wicker chairs and watch Annapolis saunter by. brbrFour bedrooms - king, two queens and two twins offer you a variety of sleeping options for you and your guests. And three and a half baths, and full washer/dryer give you all the comforts and amenities you expect.brbrIf you're looking for a vacation rental home that offers the perfect blend of modern convenience and historic charm, look no further than this beautifully appointed home in the heart of the Historic District.
Bed 4

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Bath 3

Bath

Sleep 8

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Exceptional(41)

$1076.64

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Cottage

Beachfront Home Minutes to Downtown Annapolis Dogs OK

Annapolis, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWatch the sunrise on the private beach at Oh Happy Bay. The quaint two-story, cottage has a private beach on historic Bembe Beach with direct access to safe, shallow water for swimming, paddle boarding, and boating (small boat mooring). Commissioning Week families will be spoiled by the direct line of sight for the Blue Angels air show. brbr brbrThe home is ideal for a large extended family traveling together. Enter the home into the beautifully-renovated kitchen with all new appliances and an adjoining dining room with water views and seating for 6-8. The main floor has a guest room with a Queen bed and full bath with a stand-up shower in the hall. The family room is equipped with a Full-size sleeper sofa. Head outside to the private backyard, with a deck, screened-in gazebo, lounge chairs and a picnic table for outdoor dining, cocktails or morning coffee (sampler starter pack included in your stay). brbr brbrHead back inside and up the stairs to the large family suite with 2 bedrooms, a connecting full bath (with 2 entrances), a sitting room and access to the private 2nd floor balcony. The main bedroom has a King bed and sitting area large enough for a portable crib or air mattress. Across the hall is the guest room with the full bed. The shared bath has 2 vanities, a stand-up shower and soaking tub. Also in the hall is the full-size washer and dryer. brbr brbrThe home has plenty of parking and space to explore with the pups and little family members. brbr brbrLocated walking distance to Annapolis Sailing School and Capital SUP (Paddleboard lessons and rentals), the Eastport Water Taxi (with water access to downtown Annapolis). Annapolis Maritime Museum and Quiet Waters Park are just a short drive away. brbr brbrSLEEPING ARRANGEMENTS 3 BR / 2 BA / Sleeps 8 adults: brbr brbrUpstairs Waterfront Bedroom: brbr-King bed brbr-Sitting room brbr-Waterfront balcony brbr-Queen air mattress available in the closet brbr-Shared bathroom with stand-up shower and soaking tub brbr-Flatscreen TV brbr brbrGuest Bedroom across the hall from King Bedroom: brbr-Full bed brbr-Shared bathroom with stand-up shower and soaking tub brbr brbrMain Floor Bedroom: brbr-Queen bed brbr-Full hall bath in the hall with stand-up shower brbr brbrFamily Room brbr-Full Sleeper Sofa brbr-Full hall bath with stand-up shower brbr brbrHIGHLIGHTS: brbr-Private beach with access to Chesapeake Bay brbr-Screened-in patio gazebo with dining table for 10 brbr-Back deck with seating, picnic table and beachside seating brbr-Charcoal BBQ grill brbr-Gourmet kitchen brbr-Dining room table seats 6-8 brbr-High Speed Internet and WiFi brbr-Big Flatscreen TV brbr-Stand-Up paddle boards, life jackets, beach toys, small boat mooring (this is a mooring ball or permanent anchor system off the beach where small boats can be moored) - Available in the summer months only (May-October) brbr-Luxury linens, complimentary toiletries Starter Kit, and boutique-level service brbr-Outdoor shower brbr-Parking for multiple cars in driveway and on street brbr-Full Laundry room with washer & dryer located inside the home brbr brbrProperty Distance to: brbr-Downtown Annapolis – 4 miles brbr-U.S. Naval Academy – 4.5 miles brbr-Washington, DC – 34 miles brbr-Baltimore - 35 miles brbr brbr* Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going. brbr* All beds are 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. Dogs allowed if $150 pet fee is paid prior to check-in. Be respectful of the house and contents, the neighbors and neighborhood.
Bed 3

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Bath 2

Bath

Sleep 8

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Exceptional(1)

$634.95

/ Nightly
Private Vacation Home

Parking. Short Uber Ride. Townhouse in Annapolis! 3 Miles from USNA and Downtown

Annapolis, Maryland, United States

Welcome to Sea La Vie Annapolis 2069, a stunning newly built vacation rental nestled in the Bestgate area of Annapolis, just 3 miles from the historic United States Naval Academy. This spacious four-bedroom, five-bathroom home offers a perfect blend of modern comfort and charming ambiance, making it an ideal retreat for families or groups of up to nine guests.brbrAs you step inside, you'll be greeted by a bright and airy living area that seamlessly flows into a well-equipped kitchen, perfect for preparing meals together. The home features two luxurious king bedrooms, a cozy queen bedroom, and a unique rooftop bedroom with daybeds that convert to a double bed and a twin, ensuring ample sleeping arrangements for everyone. Connecting the bedroom to the rooftop bar, there is a wet bar center with a mini-fridge, sink, microwave and coffee bar.brbrEnjoy the serene garden view from the rooftop patio, where you can unwind with a glass of wine or coffee utilizing the convenient Coffee and Wine Bar. The property is pet-friendly, allowing you to bring your furry companions along for the adventure. With a garage and four parking spaces, convenience is at your fingertips.brbrAdditional amenities include an EV charger, ensuring your electric vehicle is always ready for your next outing. Located in a popular area in West Annapolis, Sea La Vie Annapolis 2069 is close to local attractions, dining, and shopping, making it easy to explore all that Annapolis has to offer.brbrDon't miss the chance to experience this exceptional property—book your stay at Sea La Vie Annapolis 2069 today and create unforgettable memories!brbr3 miles to United States Naval Academy & St. John's Collegebr2 miles to Navy-Marine Corps Memorial Stadiumbr3 miles to Annapolis Historic District:br2 miles Annapolis Mall and Annapolis Town Centerbr1 mile to Trader Joes, Sam's Club and many other favoritesbr1 mile to Anne Arundel Medical Centerbr22 miles to Baltimore/Washington Airportbr25 miles to Washington, D.C. brSTR License ​​​​​​​001172 with an expiration date of 01/15/2028
Bed 4

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Bath 4

Bath

Sleep 9

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Exceptional(17)

$741.57

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Private Vacation Home

Historic Annapolis Home | 2 Blocks to Main St

Annapolis, Maryland, United States

Summary:brbrHistoric 1885 row home two blocks from Main Street and steps from the U.S. Naval Academy. Three bedrooms across three floors with a king master, two queens, and a twin - sleeps 9. Pet-friendly (dogs under 30 lbs welcome) with covered off-street parking half a block away. Walk to Annapolis' restaurants, shops, and waterfront without ever moving your car.brbrbrbrThe Space:brbrEnter through the white gate to a private back patio, then into the renovated kitchen - modern appliances, sleek countertops, and natural light from every window. The living room is just beyond, with plush seating and a sofa bed for extra sleeping.brbrbrbrSecond floor: king master bedroom and a queen bedroom share a full hallway bathroom.brbrbrbrThird floor: queen bed, twin bed, and its own attached bathroom with stand-up shower - great for a family with kids or guests who want more privacy.brbrbrbrThe home was built in 1885 and is named for the owner's great-grandfather, a founding figure in Annapolis' fire departments. You'll feel that history in the architecture while enjoying fully modern finishes throughout.brbrbrbrGuest Access:brbrUpon arrival, walk through the white gate on the left side of the home to enter the courtyard, and then proceed through the back door to enter the house.brbrbrbrThe Neighborhood:brbrLocation You couldn't ask for better! Just two blocks from Main Street, our home is an ideal retreat for families eager to explore the enchanting sights of Annapolis or Naval Academy families seeking proximity to the Academy. The vibrant energy of the city awaits just steps away.brbrbrbrGetting Around:brbrPublic Transportation:brbrAnnapolis Transit:brbrAnnapolis Transit operates several bus routes throughout the city, including a convenient Free Shuttle loop that connects key destinations in downtown Annapolis. This shuttle is ideal for visitors, stopping at popular areas like the City Dock, historic downtown, and local parking garages. Route 94 runs through downtown Annapolis, connecting various neighborhoods. For schedules and route maps, refer to Annapolis Transit’s website or the welcome guidebook for up-to-date information.brbrbrbrPurple Shuttle:brbrThe Purple Shuttle is a free shuttle loop that connects major parking areas to popular downtown Annapolis destinations. It’s perfect for getting around the downtown area, with convenient stops near Market Street and key locations. The shuttle also provides easy access to Fisher House, with a drop-off directly across the street. For detailed routes and operating hours, please refer to the welcome guidebook.brbrbrbrTaxi Services:brbrAnnapolis Yellow Cab and A1 Taxi are local services available by phone for pickup. Taxis are commonly found in the downtown area and are a great option for traveling to nearby attractions like the Naval Academy or Westfield Mall.brbrbrbrRide-Sharing (Uber & Lyft):brbrBoth Uber and Lyft operate in Annapolis, with rides readily available, especially near downtown. Simply use their apps to book a ride to explore the area at your convenience.brbrbrbrWater Taxis:brbrWater taxis provide a scenic way to travel between various waterfront destinations, including stops along the Annapolis Harbor. This is a great option for exploring the city by water while visiting popular spots along the coast.brbrbrbrParking in Downtown Annapolis:brbrIf you prefer to drive, parking garages and street parking are available throughout downtown Annapolis. The nearest parking garage is just a short walk from 142 Market Street, located near the City Dock.brbrbrbrStepping out from the charming Fisher House, you find yourself two blocks from the heart of historic Annapolis, ready to explore the city's rich heritage and picturesque surroundings. Just a stone's throw away from this central location, you can begin your journey by strolling down Main Street, where a myriad of boutique shops, cozy cafes, and art galleries await.brbrbrbrHeading east from Fisher House, you'll soon reach the majestic Chesapeake Bay, offering breathtaking views and a refreshing breeze. If you're in the mood for a leisurely walk, the scenic Annapolis City Dock is the perfect destination. Here, you can admire elegant sailboats and dine at waterfront restaurants, savoring delicious seafood dishes while soaking in the maritime atmosphere.brbrbrbrTo delve deeper into Annapolis' history, venture north from Fisher House to visit the Maryland State House, the oldest state capitol still in continuous legislative use. Marvel at its grand architecture and explore the nearby Maryland State House Square, where you can learn about the city's colonial past through informative plaques and exhibits.brbrbrbrIf you're looking to further immerse yourself in Annapolis' maritime culture, consider taking a boat tour from the Annapolis Harbor. Discover the city's maritime traditions, lighthouses, and scenic beauty as you glide along the waterways, providing a unique perspective of the city.brbrbrbrFor those interested in the arts, the Arts District of Annapolis, located to the west of Fisher House, boasts numerous galleries and theaters. You can spend hours appreciating local artworks and catching live performances, enriching your cultural experience in the city.brbrbrbrNavigating from Fisher House also puts you within reach of delectable dining options. From classic seafood restaurants to trendy eateries serving diverse cuisines, you'll find a culinary delight around every corner. Don't forget to indulge in the famous Maryland crab cakes, a must-try delicacy when in Annapolis.brbrbrbrAs the day winds down, you can head back to Fisher House, reflecting on the day's adventures and planning your next outing in this charming and historic city. With its central location, Annapolis invites you to explore, discover, and create lasting memories at every turn.brbrbrbrOther Things to Note:brbr** Parking Information for Your Stay:** brbrWe have a dedicated parking spot for you during your stay! Parking is available at the Noah Hillman parking garage, just a 1-minute walk from the home. You can use your car's flashers while unloading your luggage, and then head to the garage once you're finished. brbrAdditional Parking: If you have an additional vehicle, you may purchase an extra parking spot in the same garage before parking. A QR code is available in the garage for payment instructions. Vehicles parked without payment or in unauthorized areas may receive a ticket or be towedbrbrbrbrSmoking is strictly prohibited on the property; if any evidence of smoking is found that requires additional cleaning or remediation, the associated costs will be charged to the responsible party.brbrbrbrbrbrEarly Check-In & Late Check-Out PolicybrbrWe offer early check-in and late check-out upon request, subject to availability.brbrOne hour is complimentarybrbrHowever, a fee applies as follows:brbr • Early Check-In before 3pm for an additional fee of $50 to be paid before check -inbrbr • Late Check-Out after 12pm for an additional fee of $50 to be paid before check-outbrbrPlease request in advance so we can confirm availability.brbrbrbrInteraction with Guests:brbrOur 24/7 dedicated support team is always available to ensure your stay is smooth, comfortable, and five-star-worthy. If there’s anything you need—questions, recommendations, or assistance—please don’t hesitate to reach out. We're just a message away and happy to help.
Bed 3

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Sleep 9

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$750.08

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Condo

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Annapolis, Maryland, United States

Indulge in a fully remodeled 1-king bedroom Eastport condo by the water featuring rooftop pool & terrace, marina on spa creek, and 2 free parking spaces. Walk 0.3 mi to downtown Annapolis, enjoy nearby restaurants, boutiques, the harbor, 0.5 mi to the Naval Academy, and 1.9 mi to Navy Stadium. Perfect for couples, small families, or anyone seeking a sophisticated waterfront retreat with style and comfort.brbrWe’re here to make your stay smooth, comfortable, and stress-free. During your reservation, we’re readily available by message and respond quickly to questions, recommendations, or anything that comes up during your stay. Whether you need help with the apartment, have a question about the area, or want a local recommendation—we’re just a message away. While we respect your privacy and won’t be on-site unless needed, you can expect:brPrompt, friendly communication, support throughout your stay, from check-in to check-out, clear instructions and quick help if something isn’t working as expected. If there’s ever an urgent issue, we prioritize immediate response and resolution. Our goal is for you to feel well taken care of, without being interrupted—so you can relax and enjoy Annapolis with peace of mind.brbr 0.3 miles to Historic Downtown Annapolis br 1 mile to the U.S. Naval Academy br 1.9 miles to Navy-Marine Corps Memorial StadiumbrbrTop Places to Eat (All Walkable!):brEastport – 5-Minute WalkbrBoatyard Bar & Grill – Fresh seafood, legendary crab cakes, and nautical charm right on the water.brBlackwall Hitch – Upscale coastal cuisine, creative cocktails, and a lively atmosphere.brForward Brewing – Craft beer brewed onsite with casual bites and a relaxed local vibe.brDowntown Annapolis – Less than 10-Minute WalkbrIron Rooster – Famous breakfast spot with homemade pop tarts and comfort food classics.brOsteria 177 – Elegant Italian dining perfect for date nights.brCarrol's Creek Café – Romantic waterfront dining with beautiful harbor views.brMain Street – Charming brick-lined street filled with boutiques, galleries, and cafés.brEgo Alley – Watch boats cruise through this iconic harbor inlet—classic Annapolis scenery.brbrMust-See Attractions:brU.S. Naval Academy – Walk the historic Yard, visit the Chapel, and explore one of Annapolis’s most iconic landmarks.brMaryland State House – The oldest state capitol still in legislative use.brEastport Bridge – Cross into downtown on foot for stunning harbor views, especially at sunset.brbrWaterfront & Outdoor Fun:brAnnapolis Sailing School – Book a sailing lesson or private charter.brWatermark Boat Tours, Charters, and Cruises – Spend the day on the water or enjoy a romantic sunset ride.brSpa Creek – Perfect for kayaking or paddleboarding.brQuiet Waters Park – A short drive away for walking trails, picnics, and serene waterfront views.brbrExclusive Building Amenities:brPrivate Waterfront Dock – Relax on Adirondack chairs, sip your morning coffee, or enjoy sunset drinks. Perfect for soaking in the Annapolis vibe or arriving by boat.brRooftop Terrace – Start your day with the Star-Spangled Banner at 8 a.m., then wind down at sunset with Taps over the harbor. A truly unique Annapolis experience.brbrDuring your stay, you’ll have access to the following areas and amenities:brThe entire remodeled private 1-bedroom (King) apartment, living room with Queen pull-out memory foam sleeper sofa, electric fireplace & TV, fully equipped kitchen, spa like bathroom with rainfall shower, dedicated workspace, in-unit lighting, TVs, Wi-Fi, and all provided amenitiesbrbrBuilding & Shared Amenities:brRooftop terrace with panoramic views of downtown Annapolis and the Naval Academy, rooftop seasonal pool (open Memorial Day through Labor Day), Hours and rules are posted on-site and must be followed. brBuilding’s private waterfront dock - Access requires a code (provided before arrival), adirondack chairs available for guest use. brbrAccess Notes:brBuilding Entry, Elevators & Stairs: brEntering the Building & Unit: To access the unit, you’ll enter through the main entrance of the building. A navy blue key box is located directly in front of the building at eye level along the brick wall. The unit number is labeled on the lockbox. We’ll provide the lockbox code closer to your arrival. Use the key from the lockbox to enter the building. Once inside, you can reach the unit in either of the following ways:brElevator: Located to the right of the main hallway. Stairs: Located behind the first door labeled “Elevator Room” in the main foyer. Take the elevator or stairs to the 3rd floor, where our unit is located. The unit itself is equipped with a smart lock, and we’ll send you the entry code prior to arrival.brRooftop Terrace & Pool Access (Important)brPlease note: the rooftop terrace and pool are NOT handicap accessible. To access the rooftop amenities: Take the elevator to the 5th floor. Exit the elevator and locate the door directly across from it. Enter the stairwell and walk up one flight of stairs to the rooftop. The elevator does not go to a “6th floor.”brIf you have any questions about accessibility, arrival, or navigating the building, feel free to reach out—we’re always happy to help!brbr**Please be respectful of shared spaces and other residents when using common areasbrbrOff-Limits AreasbrFor everyone’s safety and privacy, the following areas are not accessible to guests: Any locked closets, cabinets, or storage spaces, building maintenance areas or mechanical rooms, and areas marked “Residents Only” or otherwise restrictedbrbrHouse Rules (Important)brTo maintain a comfortable environment for all guests and residents:brNo parties or eventsbrNo smoking or vaping anywhere inside the apartment, on the terrace, or in common areasbrNo pets allowedbrRegistered guests only—no unapproved visitorsbrPlease follow all posted building, pool, dock, and rooftop rulesbrFailure to follow these rules may result in fines, early termination of the stay, or loss of access to amenities.brbrQuestions brIf you have any questions about access, amenities, or what’s included during your stay, just send us a message—we’re happy to help and want you to enjoy everything this property has to offer.brbrThis fully renovated luxury apartment in the heart of Eastport, Annapolis is thoughtfully designed to combine upscale comfort, modern convenience, and cozy, boutique-hotel details. Every inch of the space has been curated to make your stay feel effortless, relaxing, and elevated.brbrThe home includes:br☀ 1 stylish bedroom with a plush King memory foam bed and luxury linens and pillowsbr☀ 1 spa-inspired bathroom with a rainfall shower, plush towels & premium toiletriesbr☀ Cozy living area with a comfortable sofa + queen pull-out memory foam sleeper + glider chair + coffee table + throw blanketsbr☀ 2 flat-screen 55” Smart Roku TVs (living room + bedroom)br☀ Fully stocked kitchen that includes brand new spices and cookware (oven, microwave, toaster, air fryer, mini fridge, freezer, and Brita water pitcher)br☀ Coffee station (drip, keurig, and espresso)br☀ Dedicated workstation with desk, lamp, leather rolling chair, fast Wi-Fi & ample outletsbr☀ Electric fireplace for cozy nights indoorsbr☀ Record player with vinyl records and bluetooth speaker to connect smart phonebr☀ Bar cart with wine & whiskey glasses (Corkcicle to-go cups for rooftop happy hour)br☀ Large windows with beautiful sunset views & blackout curtains for slow morningsbr☀ Shared rooftop terrace with sweeping city skyline & Naval Academy views br☀ Seasonal shared rooftop pool (open Memorial Day–Labor Day)br☀ Private building dock access with Adirondack chairs (code required)br☀ 2 dedicated free parking spotsbrbrBedrooms + BathroombrThe home features one beautifully appointed King size bedroom and a spa-style bathroom. The bedroom is elegantly designed with comfort and relaxation in mind. Sink into the king-sized memory foam bed, dressed in luxurious linens, and wake up refreshed and ready to explore Annapolis. There is a clothing rack with plenty of hangers, a full size dresser, and 55 inch Smart Roku tv. The bathroom offers a rainfall shower, modern finishes, plush towels, and premium toiletries (shampoo, conditioner, body wash, hand soap, toilet paper, hand towels) —perfect after a day on the water or exploring the historic district.brbrKitchen & DiningbrThe thoughtfully designed, fully stocked kitchen includes modern appliances and everything needed to prepare meals with ease:brFull-size ovenbrMicrowave, air fryer, toaster, mini fridgebrCoffee station with Keurig, drip coffee maker, and espresso potbrbrWhether you’re cooking breakfast, enjoying takeout from a local favorite, or pouring a glass of wine at night, the space blends function with style.brbrLounge Spaces brThe inviting living area features a luxury sofa with a queen pull-out memory foam sleeper bed, a large flat-screen Roku TV, and a sleek electric fireplace that adds warmth and ambiance—creating the perfect place to relax after a day exploring downtown or enjoying the waterfront. A Victrola record player with your choice of vinyl, stylish bar cart, and cozy lighting add a special, memorable touch. brbrRooftop, Pool &, Dock Waterfront AccessbrGuests enjoy access to:brA shared rooftop terrace with panoramic city and Naval Academy views, a seasonal rooftop pool (open Memorial Day–Labor Day), the building’s private waterfront dock, featuring Adirondack chairs and peaceful water views. brbrFamily-Friendly ExtrasbrTraveling with children We provide:br4moms Pack-n-play crib brA toddler hiccapop inflatable mattress (upon request)brbr★ Book Now & Experience Elevated Comfort in Annapolis! ★
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Bath 1

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