Vacation Home Rentals By Owner In Annapolis, MD

ALL NEW!brJust minutes from USNA Stadium, downtown Annapolis and US Naval Academy, MBA Homes' Nautical Oasis is perfect for families, groups and couples. Enjoy the spa shower with multiple jets, relax on luxurious bedding, and unwind in the private backyard with a fire-pit.brMonthly rentals also welcome! Book now for a memorable stay!brbrbrThe spacebrWelcome to MBA Homes' Nautical Oasis – Your Group/ Family-Friendly Retreat in Annapolis!brbrProperty Details:br• 3 Bedrooms / 2 Bathroomsbr• Private, fenced-in yard with fire pitbr• Modern, fully equipped kitchenbr• Open-concept living & dining areasbr• Luxurious bedding and spa-style showerbr• High-speed Wi-Fi and Smart TVsbr• Washer & dryer in unitbr• Conveniently located near:br- U.S. Naval Academy Stadiumbr-Downtown Annapolis shops and diningbr- US Naval Academybr- Anne Arundel Medical CenterbrbrbrbrOur charming 3-bedroom, 2-bathroom, single-level home offers the perfect blend of luxury, comfort, convenience, accessibility, and privacy. Whether you’re attending a game at the U.S. Naval Academy Stadium, visiting midshipmen at the Naval Academy, attending an appointment at Anne Arundel Medical Center, or exploring historic downtown Annapolis, our home is ideally located for all your needs.brbrLOCATION:br• 1 mile/3 min drive/22 min walk to USNA Stadiumbr• 1.6 miles/5 min drive to AAMC Hospitalbr• 2 miles/5 min drive to Downtown Annapolisbr• 3 miles/11 min drive to the Naval AcademybrbrLIVING AREA & KITCHENbrEnter into an open floor plan that creates a warm, welcoming atmosphere. The living room features comfortable seating and a 65 flat-screen TV—perfect for movie nights or catching up on your favorite shows. It flows seamlessly into a dining area with a table ideal for family meals. The fully equipped kitchen includes modern appliances, ample counter space, and all the cookware you’ll need to prepare your favorite dishes.brbrBEDROOMS & BATHROOMSbrThe master suite boasts a luxurious king-sized bed with high-end linens and a memory foam mattress for a restful night’s sleep. The en-suite bathroom features a spa shower, ideal for unwinding after a busy day. The second and third bedrooms are equally cozy, with plush beds and quality linens. Both bathrooms are well-appointed with modern fixtures and everything you’ll need.brbrOUTDOOR SPACEbrThe private, fully enclosed backyard is a highlight of the home. Relax on the deck with outdoor seating, enjoy time by the fire-pit, or let the kids play safely. This peaceful space is perfect for morning coffee, evening meals, or unwinding in the fresh air.brbrFAMILY-FRIENDLY AMENITIESbrWe understand that traveling with children requires extra care. Upon request, we’re happy to provide a playpen/travel crib, high chair, and children’s plates and cutlery to ensure a comfortable stay for your little ones.brbrLOCATION ADVANTAGESbrThis home’s location couldn’t be better. Just minutes from the U.S. Naval Academy Stadium, it’s easy to catch a game or event. The Naval Academy is also just a short drive away, making it easy to explore this historic institution. AAMC Hospital is nearby for family visits or medical appointments. Downtown Annapolis is just a short drive, with charming shops, restaurants, and historic sites to explore.brbrbrWhether you're here for a weekend getaway, an extended stay, or visiting midshipmen at the Naval Academy, everything you need is within reach. We’re confident that Nautical Oasis will be the perfect base for your Annapolis adventure. Book now to secure your stay, and feel free to reach out with any questions – we can’t wait to welcome you!

Family/Group Retreat Near USNA stadium & Downtown Annapolis; Private yard

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$448.4

brbrCharming Eastport Cottage just 3 blocks from restaurants and bars (Ruth's Chris, Boatyard, O'leary's, Carol's Creek, to name a few) and less than .5 mile from Historic Downtown Annapolis. Enjoy a weekend (or longer stay) away where everything you need is in walking distance. Start your mornings with a 2 block walk for coffee and pastries, or breakfast on the porch or deck, then wander through Eastport and Downtown Annapolis while you enjoy seasonal weather (there is always something going on), and end your day by going out to eat, or grilling on the back deck overlooking a beautiful garden and patio space at your getaway 'home'. Enjoy coffee (which is provided) or cocktails on the front porch and watch the folks and their pets stroll by!

Eastport Cottage .5 mi from Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1178.0

This lovely 4-bedroom home boasts 3 full bathrooms and room to comfortably sleep up to 12 people. With its spacious and well-appointed layout, it provides all the convenience and comfort you need. Please note the loft bedroom is accessible by a narrow spiral staircase. brbrAnnapolis Boat Show Weeks:brFor boating enthusiasts, this property is strategically located for Annapolis Boat Show Weeks. You'll find yourself in close proximity to all the action and have a comfortable space to unwind after a day of exploring the latest marine innovations.brbrNavy Sporting Events:brIf you're here to support the Midshipmen at Navy sporting events, you'll appreciate the property's proximity to the Naval Academy. After cheering on the team, return to a welcoming space that can accommodate your group and relive the excitement.brbrExploring Downtown Annapolis:brWhen you're ready to explore the heart of Annapolis, you're in luck! Downtown Annapolis is just minutes away. Stroll along cobblestone streets and explore the city's rich history and charming shops. Visit the United States Naval Academy, tour the historic Maryland State House, and enjoy delicious dining at local restaurants.brbrEntertaining by the Firepit:brThe backyard is a true gem of this property, featuring a delightful firepit, making it perfect for evening gatherings. Share stories, laughter, and marshmallows around the fire with plenty of seating for your group.brbrUSNA Commissioning Week:brFor families and friends celebrating the accomplishments of U.S. Naval Academy graduates during Commissioning Week (full week required for booking) and other big USNA weekends, this home offers the space and comfort you need. With room for up to 12 guests, everyone can stay together and enjoy the celebrations. We kindly require at least a 7-night stay for the entirety of Commissioning Week.brbrWhether you're attending special events like the Annapolis Boat Show, Navy sporting events, or USNA Commissioning Week, or simply seeking a relaxing getaway, 507 Schley Road is the ideal choice. Book your stay now to make the most of your time in Annapolis, enjoy the convenience and comfort of a spacious 4-bedroom vacation rental with 3 full bathrooms, and take advantage of vibrant downtown Annapolis just minutes away, offering history, culture, and culinary delights.

Spacious Annapolis Abode: 507 Schley Rd Vacation Rental, Minutes from Downtown!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$545.91

Hello and Welcome to Annapolis! You are going to love this home.brbrIMPORTANT: if you are inquiring about USNA Commissioning week please send us a message request. USNA Commissioning current base rates are $12,000 for a 7-night minimum stay.brbrWe purchased this home January 2010 and lived here for 6 happy years with our 3 boys. We are fully licensed as a short term rental home by the City of Annapolis. Located in the heart of the Historic District, and steps away from the US Naval Academy and the Maryland State Capital, our home was built in 1890, and renovated in the 1920s, 1990s, and again in 2010!brbrThe Navy Marine Corps football stadium is 1 mile away, and a pleasant walk on a nice day (and much faster than driving through the game day traffic!). Popular wedding destinations (William Paca House, Annapolis Yacht Club) are a short stroll from the front door, and an easy walk to Main Street and the City Dock with all its restaurants, shops, and tour boats make this the perfect in-town location.brbrWe've decorated and furnished the home with a nod to the historic character of the architecture. There are built-ins, hidden compartments, detailed moldings, a double staircase, a sun porch looking onto King George Street and a fully stocked Cook's kitchen. The formal dining room is adjacent to the kitchen and features an antique dining table from the 1920's. Though not entirely historic the house does also include wireless internet, basic cable, a DVD player, and a large flat screen TV.brbrUpstairs, the Master suite was designed with a more modern feel and features a large bathroom (which was featured in Annapolis Home Magazine) and second floor sun porch overlooking the back yard with views towards State Circle. The 2nd bedroom has a queen bed and the third bedroom has a pair of twin beds with a view of the Navy Chapel dome! There is also another another recently renovated full bathroom on the 2nd floor.brbrWe have 2 off-street parking spots and a beautifully landscaped backyard with a patio and grill, shady trees and plenty of room for a backyard get together. An additional 2 parking spaces may be reserved by request (seasonal fees may apply).brbrMature groups only. This is not a party house. Ideal for families, Navy parents, history buffs, and parents of the bride or groom. We look forward to speaking with you!brbrSTR# RENT-002617-2025brKeywords: House

Sophisticated Charmer with Parking & Views of the USNA Chapel Dome

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$507.78

Take it easy at this unique and tranquil getaway in historic Eastport. This 4-bedroom, 3-bathroom home has plenty of space for up to 8 guests. Enjoy the beautiful, fenced backyard, free parking, and excellent location.brbrCharming 1920s Bungalow in Eastport – Walk to Downtown AnnapolisbrbrAbout the Space:br-Unique, restored bungalow in the heart of Eastport’s maritime districtbr-Just one mile to Downtown Annapolis, City Dock, Naval Academy, and the State Housebr-Historic charm meets modern comfort with wood floors, antique decor, and nautical touchesbr-Ideal for families, small groups, or those seeking a cozy getawaybrbrLiving Spaces:brMain Room:br-Filled with maritime-themed decor and eclectic characterbr-Drum set for music loversbr-Futon sofa and armchairbrbrbrSecond Living Room:br-Perfect for reading or intimate gatheringsbr-Desk with maps and books for explorationbr-Flows into the dining room and fully equipped kitchenbrbrOutdoor Oasis:br-Sliding door from the kitchen leads to a large, private fenced-in yardbr-Organic garden with fig and pawpaw treesbr-Two small ponds (one in the front)br-Patio with a grill, chiminea, lawn furniture, and shade treesbr-Eco-friendly landscaping for a sustainable retreatbrbrBedrooms & Bathrooms:brFirst Floor:br-Queen bedroom with attached bathroom and showerbrSecond Floor:br-Three bedrooms, each with a queen bedbr-Hall bathroom with a stand-up showerbr-Primary suite has a queen bed and private bathroom with a large soaking tub and hand-held showerhead brbrEco-Friendly Features:br-Rooftop solar panels for sustainable energybr-Permeable gravel driveway for environmental benefitsbr-Energy-efficient tankless water heater means you'll never run out of hot water!br-Composting and recycling encouragedbrbrAmenities & Conveniences:br-One off-street parking space; free on-street parking availablebr-Ceiling fans, central AC, and complimentary WiFibr-Two smart TVs for entertainmentbr-Two office spaces with desks and chairs – great for remote workbr-Books on sailing and local culture for curious mindsbrbrPet Rulesbr-Guests must disclose pets at the time of booking. br-Guests may bring up to 2 dogs who weigh 60 lbs or less each.br-Guests must keep dog(s) leashed when outside of the home or yard.br-Dog(s) are not permitted on beds/couches/chairs.br-Guests must clean up pet waste.brbrGetting Around:br-Most Annapolis attractions within walking distancebr-Water Taxi Nearby:br-Just a 3-minute walk to the South Annapolis Yacht Center pickup spot (750 Boucher Ave.)br-A scenic ride to Annapolis City Dock with optional dockside pickups along the waybr-Ask your Water Taxi Captain for local tips and recommendations!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.

Unique and central in Eastport

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$505.92

Summary:brThe Pinkney house is a 2 bedroom, 2.5 bath town home boasts an unparalleled location within close proximity to the Naval Academy and the bustling energy of Downtown Annapolis. Whether attending events, visiting loved ones, or simply savoring the rich heritage of the area, you will find yourself immersed in the vibrant culture and history of Annapolis. In the heart of Downtown Annapolis, where parking can be a premium, having 1 dedicated parking spot ensures both convenience and peace of mind.brbrThe Space:brWelcome to our 2-bedroom, 2.5 bathroom townhome in the picturesque city of Annapolis. Step inside and discover a cozy yet spacious retreat, thoughtfully designed to provide comfort and convenience. The open concept living area invites relaxation and ample natural light. The fully equipped kitchen offers modern appliances and a dining area for enjoying home-cooked meals. brbrRetreat to the tranquil bedrooms, each boasting plush beds and tasteful decor, ensuring a restful night's sleep. The townhome features 1 half bathroom on the main level and two full size bathrooms on the second floor each featuring complimentary toiletries. brbrEscape to the patio located on the roof of the house, perfect for sipping your morning coffee or unwinding in the evening breeze while taking in the downtown water views. You'll find yourself in close proximity to Annapolis' renowned attractions, including the historic district, waterfront, and shopping destinations. Whether you're here for a weekend getaway, Naval Academy event or an extended stay, our townhome provides a comfortable haven for exploring all that Annapolis has to offer.brbrbrSTR24-145388brbrGuest Access:brYou will have access to the entire home during you stay.brbrThe Neighborhood:brDowntown Annapolis is a historic and charming neighborhood. It is nestled along the shores of the Chesapeake Bay and is known for its picturesque streets lined with beautifully preserved colonial buildings. The area offers a blend of maritime heritage, boutique shops, restaurants, and lively waterfront activities. With its cobblestone streets and iconic landmarks like the Maryland State House and the United States Naval Academy, downtown Annapolis is a popular destination for both tourists and locals alike. The vibrant atmosphere, rich history, and scenic waterfront make it a delightful place to explore and immerse yourself in the city's maritime culturebrbrGetting Around:brOnce you get settled in the home, there are several places to explore and visit within walking distance. There are also several ride share options available.brbrOther Things to Note:brDuring your stay you will have access to 1 parking space behind the house free of charge. If you have more than 1 vehicle, you may park on the street for up to 2 hours in any other open space. brbrThe 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 ). brbrThe 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 detailsbrbrInteraction with Guests:brI am available to assist you via Airbnb message, phone or text

Downtown Pinkney House w/Parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$327.21

Welcome to this vibrant downtown Annapolis oasis—a unique purple parallelogram with a parking spot. From the front door, admire the State Capitol view; from the rear fence, enjoy Ego Alley. Just a short walk to the Naval Academy and St. John's College. This 1-bedroom, 1.5-bath home features a full kitchen, spa-like bathroom with a tub (perfect for your little ones) washer/dryer, and an outdoor patio. Immerse yourself in Annapolis' culture and history from this remarkable, centrally located gem.

Historic Home with Parking Steps From Capital & USNA

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$383.04

Welcome to this spacious and fully furnished home, designed to be your comfortable home away from home. Spanning three levels, the layout offers the perfect balance of together time on the main floor and private time in the finished basement.brbrWhether you are here for a family vacation or a remote-work trip, you’ll find plenty of space to relax and recharge.brbrTop Features at a GlancebrPremium Sleep: Super comfortable beds with crisp cotton sheets.brbrEntertainment Hub: Finished basement with a 65” Smart TV.brbrRemote-Work Ready: Dedicated desk with lamp & comfortable chair.brbrRoom for Everyone: 3 levels of living space to spread out.brbrChef’s Kitchen: Fully equipped with dishwasher, blender, and coffee maker.brbrThe LayoutbrUpstairs: Rest & Recharge (3 Bedrooms) We know a good night's sleep is the most important part of your stay. That's why we prioritize super comfortable beds, topped with soft, high-quality cotton sheets, plush pillows, and extra warm blankets.brbrBedroom 1: Queen BedbrbrBedroom 2: Queen BedbrbrBedroom 3: Bunk Bed (Perfect for 2 kids or young adults)brbrFull Bathroom: Features a tub/shower combo, fresh towels, and a toilet with a bidet for added comfort.brbrMain Floor: Gather & Dine The heart of the home! Since there are no bedrooms or baths on this level, it is 100% dedicated to quality time.brbrLiving Room: A cozy space to play board games, watch TV, or relax while dinner simmers.brbrKitchen: A spacious, functional design equipped with a stove, oven, microwave, fridge, and dishwasher. We provide all the pots, pans, and kitchenware you need—plus a blender, water kettle, and coffee maker for your morning routine.brbrCleaning Essentials: We’ve stocked the pantry with Windex, Clorox, dish soap, and laundry detergent for your convenience.brbrDownstairs: Work & Play (Finished Basement) The ultimate bonus space! Perfect for sending the kids to play or getting some work done in peace.brbrSleeping: Full-size foldout sleeper couch (Sleeps 2).brbrEntertainment: Massive 65” TV for movie nights.brbrWorkspace: A dedicated desk with a lamp, ottoman, and comfy chair.brbrConvenience: Easy access to the downstairs bathroom.

Annapolis Charm –Bright 3BR in Downtown

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$719.98

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrStay right in the heart of Historic Annapolis, just 2 blocks from Main Street. This 2-unit property offers the opportunity to stay together while each having your own apartment. The Historic building, once a grocery store and the residences of the store, is the perfect blend of convenience and comfort in the two well-appointed spaces, each with their own full kitchen, bedrooms and bathroom. brbrMain Sail on the main floor: 2 bedroom/1 bath, sleeps 6 brbrThe Jib on the 2nd floor: 1 bedroom/1 bath, sleeps 4 brbr brbrProperty Highlights: brbrCentral Location: Walk to all the attractions of Historic Annapolis, including Main Street, just 2 blocks away, and the U.S. Naval Academy, another 2 blocks away. brbr brbrSleeping Arrangements : brbrMain Sail, main floor (Sleeps 6) brbrKing Bedroom: King Bed, Full-size Sleeper Sofa (linens provided) brbrTV brbrQueen Bedroom:Queen Bed brbrShared Bathroom: Full bath in the hall with stand-up shower brbr brbrThe Jib, 2nd floor (sleeps 4) brbrKing Bedroom: King Bed brbrTwin futon (plus 2 more Twin futons in the closet; linens provided) brbrFull Bathroom in the hall with combo bathub/shower brbr brbrAdditional Features: brbrModern Amenities: High-speed internet and WiFi, two flat-screen TVs brbrDining: Full kitchens with seating for 4-6 guests in each unit brbrLuxury Linens: Luxury bed and bath linens, complimentary toiletries Starter Kit, and boutique-level service brbrConvenience: 2 Full-size washer and dryers - one in the 1st floor unit, the 2nd in the main entrance of the 2nd unit brbrEasy Access: Keyless entry; Walk into the building's lower level then up to the 2nd floor where there will be a lockbox on the wall with the key to the unit. brbrConvenient Parking: Parking for one car on driveway behind home brbrDog-Friendly - available after payment of $150 per dog is made prior to checkin brbr brbrProperty Distance to: brbrMain Street: 2 blocks brbrU.S. Naval Academy: 4 blocks brbrWashington, DC: 32 miles brbrBaltimore: 31 miles brbr brbrAmenity & Supplies Starter Pack: brbrIncluded: A starter set of coffees, sweeteners, soap, shampoo, conditioner, lotion, hand sanitizer, paper towels, toilet paper, dish soap, sponge, and dishwashing liquid brbrFresh Linens: All beds are made with freshly-laundered sheets, and towels are provided in the baths. brbr brbrHouse Rules: brbrAge Requirement: At least one member of the party must be 25 years of age. brbrNo Smoking brbrRespect: Be respectful of the house, contents, neighbors, and neighborhood. No parties. brbrCheck-in/Check-out: Check-in time is 4:00 pm, and check-out time is 11:00 am.

Experience Historic Annapolis — Stay in This Unique Dual-Suite Home with On-Site Parking

Annapolis, Maryland, United States

Bed

2

Bath

10

Sleeps

$519.12

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrGreen on Fleet – Historic Annapolis Rowhouse (c.1885) One Block to City Dock & the U.S. Naval Academy brbr brbrStay in this beautifully renovated historic home in the heart of downtown Annapolis, just one block from City Dock, the U.S. Naval Academy, the State House, shops, and restaurants. Step outside onto a charming cobblestone street and experience the city’s historic district at its best. brbr brbrBuilt between 1885–1887, this classic Annapolis worker’s rowhouse has been part of the Fleet Street neighborhood for more than 130 years. Originally rented to working families connected to the city’s busy waterfront, homes like this formed the heart of Annapolis’ historic maritime community. Around 1910, the house was home to a Chesapeake Bay oysterer, whose story inspired the artwork above the bar. brbrToday, Green on Fleet blends historic character with modern comfort—offering guests a cozy retreat with curated interiors and a private brick patio just steps from the waterfront. brbr brbrPlease Note: No on-site parking is provided. brbr brbrSleeping Arrangements (Sleeps 4 | 2BR / 1.5BA) brbr brbrPrimary Bedroom (2nd Floor) brbr• California King bed brbr• Hall full bath brbr brbrGuest Bedroom (2nd Floor) brbr• Queen bed brbr• Hall full bath brbr brbrHighlights brbr• Gourmet kitchen with stainless appliances & granite countertops brbr• Private brick patio with seating & BBQ grill brbr• Dining table for 6 + convertible bar brbr• WiFi & Smart TV in family room brbr• Washer & dryer brbr• Keyless entry brbr• Luxury linens & starter supply kit included brbr brbrDistance to: brbr• U.S. Naval Academy – 1 block brbr• Washington, DC – 30 miles brbr• Baltimore – 25 miles brbr brbrHouse Rules brbr• Primary renter must be 25+ and present during stay brbr• No parties, pets, events, or smoking brbr• Respect neighbors and quiet hours brbr• Check-in: 4 PM | Check-out: 11 AM

Historic Annapolis Renovated Rowhouse (c.1885) One Block to City Dock & the U.S. Naval Academy

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$430.03

Incredible location in the Historic District of Annapolis. Walking distance to the Naval Academy, St. Johns College, and Annapolis waterfront. This 100+ year old charming row house offers a scenic front porch and beautiful backyard English garden w/brick patio where you enjoy the sounds of the extraordinary USNA Chapel. The home has 3 bedrooms upstairs, 1 full/1 half baths, living room, separate dining room, and kitchen. brbrThis home is open year round with a two night minimum stay.brbr RENT FOR COMMISSIONING WEEK, WEDDINGS, AND ALUMNI REUNIONS, OR A FAMILY VACATION:brbrThis home is conveniently located for any Annapolis events; and will surely make for a memorable stay in Maryland’s capital city. br

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$663.45

Welcome to our custom Craftsman in the exclusive Maritime Eastport section of Annapolis. Surrounded by the city's best restaurants (Ruth's Chris, ChartHouse, Vin 909 and many, many others) as well as home to some very famous neighbors it's one of the most desirable locations in town. A short stroll across a quaint drawbridge and your downtown for shopping and USNA. Very spacious home with 4 bedrooms 4 baths, parking for 4 cars and a pool table. Truly a million plus dollar property!brbrCustom built in 2014 it's one of a kind and spotless. Ideal for two families with 4 full bathrooms and two living areas and a large walkout basement with a pool table . First floor master suite , 3 bedrooms upstairs with a pull out in threefold living room area. Pool table , sofas and full bathroom in walk out basement . Fantastic water views of AYC , USNA , Spa Creek and downtown. We back up to the brand new exclusive South Annapolis Yacht Center where all the mega yachts dock.brbrThe back area leads to a the exclusive South Annapolis Yacht Center that is getting renovated and rebuilt as of March 2019. Construction is finished behind us and further down the peninsula . Great Spa creek water views of The Bridge downtown AYC and USNAbrbrMessage first about pets - no instant booking . Extra pet fee required . We have a service animal in our family and are not required to accept . Please Inquire first . No parties - Bach / Ette included . No confetti / taping on walls . Noise complaints will end reservation .

Eastport Haven House

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1378.87

Welcome to Fair Winds DTA (Downtown Annapolis): a beautiful, spacious, and sunlit historic home on gorgeous Prince George Street in the heart of downtown Annapolis. Less than a minute walk from both the vibrant waterfront and the Naval Academy’s Gate 1, this home’s location quite simply cannot be beat. It’s perfect for Naval Academy families and Annapolis visitors alike!brbrBlending coastal elegance with warm hospitality — we invite you to unwind and enjoy an authentic Annapolis stay.brbrAnnapolis License: RENT-002655-2025brbrThis beautifully restored historic home sits right in the heart of downtown Annapolis and waterfront bustle. Featuring five spacious bedrooms and 3.5 baths, it blends timeless charm with modern luxury. Every room is thoughtfully appointed with high-end finishes and authentic architectural details. Enjoy morning coffee or evening cocktails on the oversized patio overlooking the town — the perfect balance of history, elegance, and coastal serenity.

Historic Downtown Luxury • USNA • Waterfront

Annapolis, Maryland, United States

5

Bed

Bath

10

Sleeps

$1138.41

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWelcome to All Decked Out, your dream escape in the waterfront Oyster Harbor Community of Annapolis, a tranquil retreat on the Annapolis Neck Peninsula. This beautifully renovated 4-bedroom, 3-bath home blends modern elegance with timeless coastal charm. With sweeping water views, a private pier, multiple decks, and seamless Chesapeake Bay access, this home is perfect for boating enthusiasts, families, and anyone craving tranquility by the water. brbr brbrSpacious Coastal Living brbrThe open concept layout is designed for gathering and relaxation. brbrExpansive windows framing serene waterfront views brbrWaterfront dining room with seating for 6 brbr brbrChef’s Kitchen brbrA true entertainer’s kitchen featuring: brbrLarge island with breakfast bar seating for 4 brbrNew stainless steel appliances brbrAmple prep space brbrFully stocked with cookware and dinnerware for 12 guests brbrCoffee bar in the kitchen (plus a second coffee bar in the Dining Room and a third in the King Suite) brbr brbrSleeps 12 brbrMain Level brbrDouble Queen Suite (sleeps 4) with en-suite bath with dual access to Living room brbr brbrSecond Level brbrWaterfront King Suite with luxury bath, sitting room, coffee bar & deck access brbrWaterfront Double Queen Bedroom (sleeps 4) with deck access brbrFull Bedroom brbrFull Hall bath with shower brbr brbrOutdoor Living brbrPrivate dock brbrCovered deck + upper waterfront deck brbrWaterfront patio with built-in grill & outdoor kitchen brbrWater views from multiple rooms brbrBring your boat, kayak, or simply enjoy sunset views from the dock. brbr brbrCommunity Perks brbrGuests enjoy access to Oyster Harbor’s beach, fishing pier, boat ramp, playgrounds, nature trails, and exercise course. brbrDog-Friendly - $150 non-refundable fee per pet (paid prior to check-in). brbr brbrIdeal Location brbr10 minutes to Downtown Annapolis brbr12 minutes to USNA brbrEasy access to DC & Baltimore (33 miles) brbrParking for 2-4 SUVs/cars in the circular driveway (garage parking not included) brbr brbrPerfect for family gatherings, Navy visits, or peaceful waterfront retreats. brbr brbrLocation Highlights: brbrNestled in the quiet Oyster Harbor community, this property is minutes from downtown Annapolis, shopping, dining, and entertainment.

Newly-Remodeled Stunning Waterfront Luxury Home w Private Pier in Annapolis, Dog-Friendly

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$403.99

SPECIAL OFFER!!! Receive 10% more as discount when you book from N0V 21st - NOV23! brRelax and recharge in our peaceful beachside home—just minutes from downtown Annapolis and top local attractions. Nestled in a quiet wooded enclave within the Cape St. Claire Private Beach Community and near the pristine shores of Sandy Point Beach, this refined escape offers a harmonious blend of upscale comfort with Chesapeake charm. Enjoy easy access to scenic beaches, tranquil nature, and the perfect setting for a restful getaway.brInside, enjoy a bright, open living space with plush seating, smart TV, and large windows. The fully equipped kitchen includes a dishwasher, coffee maker, microwave, and all the essentials for home-cooked meals. The dining area seats 8 comfortably and is perfect for meals or entertaining.brbrThere are three bedrooms including a primary suite with queen bed, walk-in closet, and ensuite bath with soaking tub, plus two additional queen bedrooms and a half bath. Crib available upon request.brStay connected and productive with high-speed Wi-Fi, a dedicated workspace, and full laundry amenities. Pet-friendly for up to 2 well-trained pets, and there’s off-street parking including 2 reserved spaces.brbrOutside, relax on the private deck with wooded views or follow the walking trail to the Little Magothy River. You’re just a 15-minute walk or 4-minute drive to Sandy Point State Park, a public beach ideal for a full day by the water or catching sunrise over the Bay.brbrPlease note: Cape St. Claire’s private beach, known for its quiet shoreline and great crab cakes, is only 8 minutes away but reserved exclusively for residents. While guests won’t have access to this beach, Sandy Point Beach offers a fantastic and accessible alternative just around the corner.brbrNearby Attractions & Essentials:br• Sandy Point State Park – 15 min walk / 4 min drivebr• Downtown Annapolis / U.S. Naval Academy (USNA) – 12–15 min drivebr• Maryland State House & City Dock – 13 minbr• Chesapeake Bay Bridge – 6 min / 1.5 miles from the propertybr• Cape St. Claire Community & Shops – 8 minbr• Bay Hills & USNA Golf Club – short drivebr• Jonas Green & Quiet Waters Parks – nearbybr• Anne Arundel Community College – short drivebr• Anne Arundel Medical Center – short drivebr• Graul’s Market, cafés & restaurants – 7 min drivebr• Conveniently located off Hwy 50 East/West for easy access to the entire region.brbrbrYou will have full access to the entire home during their stay. This includes all three bedrooms, 2.5 bathrooms, the spacious living and dining areas, a fully equipped kitchen, private deck with wooded views, in-unit washer and dryer, and dedicated parking spaces.brbrYou’ll also enjoy easy access to nearby nature trails and a community path that leads to the waterfront. Entry is self-check-in via a secure smart lock—details will be shared prior to your arrival for a smooth and convenient check-in experience.

Charming Pet-Friendly Stay - Near Bay & Beaches.

Annapolis, Maryland, United States

Bed

2

Bath

8

Sleeps

$380.76

We offer a 10% military discount upon request! A cozy home away from home in Eastport located within 1.5 Miles of Historic Downtown Annapolis and 2 miles from US Naval Academy. Conveniently located near numerous restaurants and shopping centers. Plenty of room for indoor and outdoor comfort and activities!brThe spacebrComfortable beds, fully stocked kitchen, and spacious outdoor area with dining table and fire pit! All three bedrooms are located on the second level. Our home offers a king bedroom, queen bedroom, and a full bedroom. We also keep a pack-n-play available for guests to use as needed! Washer and dryer available on site in the basement as well! Note: there is an additional toilet located in the unfinished basement and is not enclosed but still fully functional!brbrGuest accessbrGuests will have access to the entire home during their stay!brbrOther things to notebrWe want to mention we have backyard chickens, but you’ll have no responsibilities to visit or take care of them! They are in a coop/run and stay there!

Restful and Charming Home in Eastport

Annapolis, Maryland, United States

Bed

1

Bath

6

Sleeps

$695.4

Consider this house your home away from home while you visit Annapolis. This charming retreat features three bedrooms, including two king beds and a cozy twin bed, perfect for families or groups. Guests enjoy a terrific bathroom with a relaxing bathtub and a handy hair dryer. The space stays comfortable year-round with heating and air conditioning. Whether you’re unwinding after a day of exploring or planning your next adventure, this awesome house offers a welcoming spot to recharge. We look forward to hosting you at our place.

Elegant 3-bedroom house with EV charger in Downtown Annapolis

Annapolis, Maryland, United States

Bed

1

Bath

6

Sleeps

$1050.43

The Timberpeg N. California Douglas Fir Post and Beam construction with Finnish Spruce ceilings is a beautiful stunning design. The open floor plan offers thrilling vistas out onto Martins Cove, a tributary of the Chesapeake Bay. Take advantage of the side screened in porch, front deck on the waterfront and large waterfront screened in porch. Grill and eat outdoors or inside. Enjoy the wildlife and if you are lucky catch a glimpse of a bald eagle soaring across the Cove. You have use of 4 bedrooms and 4 full baths with queen beds in the main house. Basement au pair apartment with full kitchen and full bath.The separate studio above the garage has a double bed and full bath and wet bar and microwave/refrig. The house has non-toxic finishes, sealers and paints. The entire house layout is handicap accessible with main floor accessible with no steps. Grab bars throughout. Kayak, canoe, crab and fish off the dock. Funfor all.

GREENNEST is an ENVIRONMENTALLY FRIENDLY Waterfront home close to Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1252.39

About this spacebrStunning Contemporary Home with private beach! House has been listed on another site receiving five star reviews from all previous guests. House was recently renovated on the Severn River with magnificent views of the Chesapeake Bay Bridge, a private dock & gorgeous sand beach w/ games, fire pit & hammock. Just minutes to downtown. Water views from all rooms, two propane fireplaces, designer kitchen, wine unit, electronic blackout shades, private office, screened-in porch, front patio w/grill & fire bowl. Master bedroom w/stand-alone tub & walk-in closet. Private road w/room for 3 cars. Spectacular Sunrises.brThe spacebrThis gorgeous house sits at the mouth of the Severn River. The Severn River/Chesapeake Bay sits on the front side of the house and Chase pond (connects to the Bay) sits on the backside of the house. Water views from every room! The rooms have large expanses of glass to enjoy the views. Truly a unique setting.brbrThe site is perfect to watch the fireworks on the 4th, watch the blue angels during Naval Academy graduation weekend (they fly over the house and dock multiple times during their show), stay during the Annapolis boat shows, or a vacation/getaway with family or friends any time of the year. We have recently decided to list the house during Christmas and New Year's Eve. A wonderful spot to enjoy the holidaysbrbrWe are located in Annapolis. The location is ideal...3 miles to downtown Annapolis so you can visit but return to a peaceful location on the water.brbrThe beach is a perfect place to set up games. We have several games for the beach. If you have little ones, they will love to play in the sand. There is a fire pit on the beach with plenty of wood stacked if you wish to make a bonfire. Roasting sticks are in the kitchen. There are six beach chairs and beach towels. You can swim from the sandy beach or from the end of the dock. Gorgeous sand bottom at the end of the dock and shallow. We have a tree hammock next to the beach. This house owns well over half the private beach and another home owns the smaller portion of the private beach.brbrAt the end of the dock, the average depth is 2.5 feet. If you have a boat with a similar draw, please bring it and tie up. We have a launching site in the neighborhood. If you have jet skis, you are welcome to bring those too. Four large Adirondack chairs are affixed to the end of the dock. Please note, the water below the dock is shallow so do not dive. There is a ladder at the end of the dock that you can lower yourself into the water. All sand bottom at the end of the dock. brbrGreat sunrises and electronic blackout shades in each bedroom if you want to sleep in. Bedding in two rooms is by Restoration Hardware and the master bedroom has a custom made duvet cover and shams. All beds have down duvets and extra pillows are available in each room. All bathrooms have Restoration Hardware towels. The master bedroom has two super soft Restoration Hardware bathrobes and the other two bedrooms each have one bathrobe.brbrEnjoy the sunrises or sunsets from the dock. While enjoying the beautiful sunrises, you have the choice of enjoying a cup of coffee from the Nespresso Machine, the coffee press, and/or the coffee maker. We have a grinder too. There is an instant-hot tap if you would rather a cup of tea.brbrThe patio facing the Bay has a large grill with wonderful views of the Bay Bridge. We have comfortable Adirondack chairs on the patio. A wonderful place to enjoy the sunrise/sunset, your company while grilling and/or simply at the end of the evening.brbrThe designer kitchen has a sub-zero refrigerator/freezer, propane top 4 burner, 2 ovens, a built-in microwave and a dishwasher. Pots, pans, knife set, dishware, and glassware are new. With the open floor plan, you are able to enjoy your family or guests in the dining area or great room while preparing meals. We always have sugar, flour, olive oil for your convenience. There are also 3 bar stools at the kitchen counter. If you don't feel like cooking, I have a great list of restaurants.brbrThere is a beautiful office with built-in cabinets, a business chair, and large windows and glass doors with access to the back deck. If you need to get some work done, this is a great spot! Perfect for the business traveler.brbrThere are two propane fireplaces; one in the Great Room and one in the Master Bedroom. They will click on with a remote.brbrA generator, in case of a power outage, will kick on automatically and runs parts of the home.brbr4 smart TV's throughout the house.brbrWe are located in a quiet neighborhood at the end of a cul de sac/private drive.brbrThis is a smoke-free and pet free home. No exceptions.brNo parties, events, weddings and/or receptions allowed at the house. No Exceptions. The property is only for the guests approved and booked for the stay.brbrWe have many suggestions for fun activities in Annapolis. Once you book, please contact me via text or call if you would like suggestions on restaurants and/or help to pre-plan activities in Annapolis.brbrThree parking spots available.brbrPlease note: Any lighting of the fire pit and grill are at your own risk.brAny swimming or activities in the Bay are at your own risk. Do not swim in the pond.brDo not dive or jump from the dock; the water is shallow.brGuest accessbrAble to access entire house except for the garage. Room for 3 cars.br

Luxury Waterfront Annapolis home with your very own Private Beach & Dock

Annapolis, Maryland, United States

Bed