Vacation Rentals By Owner In Annapolis, MD

Summary:brbrLook no further for your next vacation home in Annapolis! Relax, unwind or entertain friends and family in this spacious, updated 4-bedroom, 4 bathroom home in the heart of Annapolis. Our home features multiple spaces for entertaining both indoor and outdoors. You can swim in the pool, cozy up by the fire place or enjoy a movie night in our theater room. When you stay here, you will find this home provides everything you need to create lasting memories and truly enjoy your time in the area.brbrbrbrThe Space:brbrNestled in a quiet neighborhood, this exquisite 4-bedroom, 4-bathroom home offers the epitome of modern living and entertainment. Boasting an array of inviting spaces designed for comfort and family gatherings, this home redefines modern living with its thoughtful design and abundance of amenities.brbrbrbrUpon entering, guests are greeted by a spacious foyer that sets the tone for the home's sophisticated ambiance. The main level seamlessly integrates spacious living areas, including a formal living room adorned with elegant furnishings and a cozy fireplace, perfect for intimate gatherings or relaxed evenings with loved ones.The heart of the home lies in its gourmet kitchen, equipped with high-end appliances, custom cabinetry, and a generous island ideal for culinary adventures and casual dining. Adjacent to the kitchen, the dining area features large windows that flood the space with natural light, creating an inviting atmosphere for memorable family meals and celebrations.brbrbrbrEntertainment is taken to new heights with the home's impressive array of recreational spaces. A theater room awaits movie enthusiasts, complete with plush seating, for an immersive cinematic experience. Whether hosting movie nights or watching the latest blockbusters, this dedicated space offers endless entertainment possibilities.For those who prefer active leisure, the recreation room provides the perfect retreat. Equipped with games, a billiard, as well as a wet bar for refreshments, this versatile space is designed for hours of fun and friendly competition. With ample room for seating and socializing, the recreation room is an ideal spot for family gatherings and casual get-togethers.brbrbrbrOutdoor living is elevated with the home's resort-style amenities, including a sparkling pool and expansive patio area. The pool area offers a tranquil oasis for relaxation and recreation. Whether lounging poolside on sunny days or hosting alfresco gatherings under the stars, the outdoor space provides endless opportunities for leisure and entertainment.brbrbrbrThe master suite serves as a luxurious retreat, featuring, a spacious en-suite bathroom with dual vanities, a soaking tub, and a separate shower. Three additional bedrooms offer comfortable accommodations for family members or guests.Throughout the home, attention to detail and quality craftsmanship that enhances comfort and convenience. brbrbrbrWhether enjoying movie nights in the theater room, hosting poolside gatherings, or simply unwinding in the comfort of home, this home has everything you need for your stay in Annapolis.brbrbrbrGuest Access:brbrGuests will have full and private access to the entire home and all its amenities during their stay. This includes all four bedrooms, four bathrooms, the main kitchen, basement kitchen, living areas, game room, home theater, office, sunroom, and the entire backyard with the private pool and hot tub.brbrbrbrOther Things to Note:brbr• Your safety is important to us. The pool and hot tub are to be used at your own risk. Please be mindful and supervise children at all times when enjoying these amenities.brbr• This property is a registered short-term rental in Annapolis. Registration Number: 000859.brbrbrbrInteraction with Guests:brbrWe respect our guests' privacy and offer a seamless self-check-in process. While we will not be present during your stay, we are always available via the messaging app or by phone if you have any questions or need assistance to ensure you have a comfortable and enjoyable visit.

The General's House-Spacious Home w/Pool & Hot Tub

Annapolis, Maryland, United States

Bed

Bath

14

Sleeps

$830.23

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrLuxury Living, Prime Annapolis Location brbrWelcome to Admiral's Quarters, a brand-new luxury townhome located in one of Annapolis’ newest communities, designed to celebrate modern style and upscale urban living. This stunning four-level farmhouse-style home features high-end finishes, designer furnishings, and thoughtful details throughout. brbrWith four spacious bedrooms, each with its own private EnSuite bath, this home offers the perfect blend of comfort, privacy, and sophistication for families, Naval Academy visits, game weekends, and group getaways. brbr brbrEnjoy the convenience of being just minutes from downtown Annapolis, the U.S. Naval Academy, and Navy-Marine Corps Memorial Stadium, with easy access to major commuter routes to Washington, D.C., Baltimore, and the Bay Bridge. brbr brbrHome Highlights brbrBrand-new construction with luxury finishes throughout brbrGourmet kitchen with stainless steel appliances brbrProfessionally designed décor and furnishings brbrPrivate entrance with four levels of living space brbrDriveway parking for 3–4 vehicles plus additional street parking (no permits required) brbr brbrSpacious Four-Level Layout brbrEntry Level: brbrWelcoming foyer, King Suite with EnSuite bath (walk-in shower), plus a flexible sleeping Nook with a King. brbr brbrSecond Level (Main Living Area): brbrBright, open-concept gourmet kitchen, dining area, and family room, plus a powder room. brbrDining table seats 8-10, breakfast bar seats 4. brbr brbrThird Level: brbrTwo additional bedroom suites, each with private EnSuite baths. brbr brbrTop Level: brbrPrivate King Suite retreat with furnished balcony and EnSuite bath (walk-in shower). brbr brbrSleeping Arrangements – Sleeps 12 brbrKing Suite (Entry Level) brbrKing in Nook (Entry Level) brbrKing Suite (Upper Level) brbrFamily Suite with Twin-over-Full Bunk + Twin Trundle brbrKing Suite with Private Balcony (Top Level) brbr brbrComfort & Convenience brbrHigh-speed WiFi brbrFlat-screen TVs throughout brbrLuxury linens and complimentary starter toiletries brbrKeyless entry for seamless check-in brbrDog-friendly ($150 non-refundable pet fee per pet) brbr brbrPrime Location brbr2 miles to Navy-Marine Corps Memorial Stadium brbr3.5 miles to the U.S. Naval Academy brbr30 miles to Washington, D.C. brbr28 miles to Baltimore brbr brbrPerfect for Commissioning Week, football weekends, Annapolis events, or exploring the region. brbr brbrHouse Rules brbrAt least one guest must be 25+ brbrNo smoking, parties, or events brbrQuiet, family-oriented community brbrCheck-in: 4 PM | Check-out: 11 AM brbr brbrBook your stay in this beautifully designed Annapolis retreat — where modern luxury meets unbeatable convenience.

New Luxury Townhome Near Downtown Annapolis with Multiple EnSuite Bedrooms and Parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$521.48

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrCharming, Newly Renovated Historic Row Home in Downtown Annapolis brbr brbrWalk everywhere in downtown Annapolis, then return home to a light-filled retreat where 1918 charm meets modern comfort. As a Naval Academy family (Go Navy!), the owners have designed this historic row home to be the perfect base for USNA families, alumni, and visitors. Tucked on a quiet side street, it offers the ideal blend of walkable convenience and peaceful relaxation. brbr brbrBright, Historic & Fully Updated; Sunlight pours through large windows, highlighting original heart-of-pine floors and clean, neutral interiors. brbrRecent professionally-designed updates include: brbrFully modern kitchen brbrBeautifully updated bathrooms brbrFresh interior paint brbrCentral A/C + heat brbr brbrCozy dining & gathering spaces designed for gathering and relaxation: brbrThe built-in banquette is perfect for morning coffee, takeout from Main Street, or game nights after a day exploring Annapolis. brbrSunny front family room with comfortable seating brbrBrand-new custom kitchen with stainless steel appliances and generous prep space brbrDining nook seating for 6 + breakfast bar for 2 brbrCozy living room opening to outdoor space brbrPrivate furnished deck with propane BBQ grill brbrFinished patio with seating around a propane fire pit brbr brbrSleeping Arrangements (Sleeps 6) 3 Bedrooms, 2.5 Bathrooms brbrKing Suite (2nd Floor): King bed, EnSuite bath with custom shower brbrKing Bedroom (2nd Floor): King bed, shared full hall bath brbrTwin Bedroom (2nd Floor): Two twin beds, shared full hall bath brbrPowder room on main level brbr brbrHome Highlights brbrFully renovated with high-end finishes throughout brbrSmart TVs + high-speed WiFi brbrBoutique-style experience with luxury linens & starter toiletries brbrFull laundry area with washer, dryer, and storage brbrKeyless entry for easy, secure check-in brbr brbrUnbeatable Location, Leave the car behind and explore Annapolis on foot: brbrAnnapolis Harbor & Main Street – 3 blocks brbrU.S. Naval Academy – 10-minute walk brbrRestaurants, shops & nightlife – within 5 minutes brbrWashington, DC – 30 miles | Baltimore – 25 miles brbr brbrHouse Rules brbrNo parties, pets or smoking brbrQuiet hours strictly enforced brbrCheck-in: 4:00 PM brbrCheck-out: 11:00 AM

Charming, Newly Renovated Historic Row Home in Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

6

Sleeps

$1076.16

Step into Annapolis history at this lovingly restored 1867 home — said to be the first subdivision of the Hammond-Harwood Gardens. Featured in Historic Preservation Society archives, this gated property blends 19th-century elegance with modern comfort, all just steps from the heart of downtown.brbrOwned and decorated by a U.S. Naval Academy graduate, the home pays tribute to Annapolis’s proud maritime heritage. The iconic wrought-iron entry gate has appeared in countless engagement and wedding photos, welcoming guests into a private brick courtyard illuminated by gas lanterns and highlighted by an English lion’s-head fountain.brbrEnjoy your morning coffee or evening glass of wine on the secluded patio off one of the guest rooms, surrounded by lush landscaping and the sound of trickling water.brbrInside, you’ll find warm, inviting spaces perfect for gathering and relaxing. The living room offers a large leather sofa, two armchairs, a game table for four, and a 65-inch TV for movie nights or big games.brbrThe renovated kitchen retains its character with hand-painted tiles and a striking stainless-steel counter and sink, paired with commercial-grade appliances and every amenity needed for home cooking. The island seats three for casual breakfasts, while the formal dining room—with an extendable table seating up to 12—is ideal for shared meals and celebrations.brbrDownstairs, a spiral iron staircase leads to the basement game room featuring a shuffleboard table, bar, and another large-screen TV — a perfect retreat for evening entertainment.brbrLocated just one block from the William Paca House and Gardens and two blocks from Annapolis Harbor, St. John’s College, and the U.S. Naval Academy, this home offers the ideal setting for Academy and St. John’s events, family getaways, or friends exploring Annapolis, Washington D.C., and Baltimore.

Submariner's Gate - Historic 4-bedroom home in charming Annapolis with parking

Annapolis, Maryland, United States

Bed

Bath

8

Sleeps

$364.2

Stylish and comfortable home in Admiral Heights, just minutes from downtown Annapolis, the waterfront & vibrant dining/shopping. Relax in a quiet neighborhood with easy access to Navy-Marine Corps Memorial Stadium, U.S. Naval Academy, downtown, and the Annapolis Arts District on West Street — perfect for game days, sightseeing, or weekend getaways. Walk or drive to local favorites, enjoy central convenience, and explore historic Annapolis & Chesapeake Bay experiences

8 Bells Bungalow - Cozy, Stylish, Prime Location

Annapolis, Maryland, United States

Bed

Bath

6

Sleeps

$473.67

Your family will be close to everything when you stay at this centrally-located place. Two blocks to Main Street, the Naval Academy, Downtown Annapolis and Historic Maryland Ave, this 1875 home has been fully renovated and updated for our guests. Boasting beautiful views of Historic Paca House and book ended by Spa Creek and St. John's College, the location is amazing.brKid friendly house with a quiet and secluded back patio for relaxing.brEntire interior (baths, kitchen, flooring and furnishing) was just renovated this year. Hotel quality linens and towels ready for your next trip to Downtown Annapolis.br

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Annapolis, Maryland, United States

Bed

Bath

8

Sleeps

$193.76

Picture yourself unwinding in a serene Annapolis retreat—designed for traveling nurses, business professionals, relocating families, and extended stays. This home offers a peaceful escape in a beautiful waterfront setting, featuring a modern stainless steel kitchen, a king-sized bed, a dedicated workspace, and an indoor ping-pong table. The home is a flexible two-bedroom layout—guests have access to both rooms, though one is unfurnished, allowing you to customize the space. Outside, relax by the private pool, which boasts a sleek black bottom and a charming waterfall feature. With a private beach, a relaxing pool, and easy access to Quiet Waters Park, historic downtown Annapolis, and Chesapeake Bay adventures, this home is the perfect balance of relaxation and productivity for your extended stay.

Apartment

Poolside Annapolis Retreat for Mid-Term Stays!

Annapolis, Maryland, United States

1

Bed

Bath

90

Sleeps

$641.25

Immerse yourself in the best that Annapolis has to offer while staying in this completely renovated, modern ranch getaway. Cozy up indoors with show or movie on the smart TVs or outdoors at the fire pit with Adirondack seating for six. Unwind and relax in any of four finely appointed, luxurious king bedrooms. The yard is partially fenced for privacy within a quiet neighborhood. The location is ideal with easy access to Navy Stadium and the Naval Academy, downtown Annapolis, Parole, and Anne Arundel Medical Center.

Modern Retreat w/ Fire Pit & Parking

Annapolis, Maryland, United States

Bed

Bath

9

Sleeps

$444.55

Unwind in Annapolis at this pleasant house perfect for groups or families. With four bedrooms, including three queen beds, guests find plenty of space to relax. The single bathroom features both a bathtub and shower, making it easy to refresh after a day of exploring. Stay comfortable year-round with heating and AC, and enjoy the convenience of an iron and hair dryer. Whether you’re lounging indoors or getting ready for a night out, this tranquil home offers a nice balance of comfort and ease. You’re sure to make fantastic memories with a stay at our place.

Spacious 4-bedroom house with AC in brilliant Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$570

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrA new home but managed by experienced hosts, iTrip Annapolis, dedicated to exceptional hospitality. Discover the perfect blend of comfort and convenience at this professionally updated, family-friendly home nestled in a peaceful cul de sac with a driveway. Located just a few blocks from the Navy-Marine Corps Memorial Stadium and minutes from the quaint shops of West Annapolis and the historic charm of downtown, this home offers an unforgettable stay. brbr brbrProperty Highlights brbrSpacious & Stylish: Recently redecorated with fresh, modern decor brbrOutdoor Oasis: Enjoy the private backyard with a cozy fire pit—perfect for family gatherings. brbrFully Equipped Kitchen: Cook meals effortlessly with stainless steel appliances. brbrAmple Gathering Spaces: Multiple levels offer room to relax and unwind. brbrPrime Location: Walkable to stadium, shops, and downtown, with easy access to Baltimore, DC, and local landmarks. brbr brbrSleeping Arrangements (4 BR / 2 BA | Sleeps 9) brbrMain Floor Suite: Queen bed, ensuite bath, and Smart TV brbr2nd Floor Navy King Guestroom: King bed, shared hall bath brbr2nd Floor Peach King Guestroom: King bed, shared hall bath brbr2nd Floor Full Guestroom: Full bed with twin trundle, shared hall bath brbr brbrAmenities brbrFully-stocked kitchen with stainless steel appliances brbrHigh-speed WiFi and multiple Smart TVs for entertainment. brbrWasher and dryer for your convenience brbrLuxury linens, boutique-level service, and a complimentary starter pack of toiletries and essentials brbrDriveway parking for multiple vehicles brbrDog-Friendly: Bring your furry friend for a $150 non-refundable pet fee per pet. brbr brbrLocation at a Glance brbrNavy-Marine Corps Memorial Stadium: 0.7 miles brbrU.S. Naval Academy: 2 miles brbrDowntown Annapolis: 2 miles brbrWashington, DC: 30 miles brbrBaltimore: 30 miles brbr brbrHouse Rules brbrGuests must be 25+ to book. brbrNo parties, smoking, or events allowed. brbrQuiet hours are enforced—please respect our neighbors. brbrCheck-in: 4:00 PM | Check-out: 11:00 AM brbr brbrWhether you're here to cheer at the Navy Stadium, explore the cobblestone streets of Annapolis, or relax with loved ones, this home offers the perfect setting for creating lasting memories.

Game Days & Family Stays at Dog-Friendly Home Near Navy Stadium w Private Fenced-In Yard

Annapolis, Maryland, United States

Bed

Bath

9

Sleeps

$505.4

Discover the beauty of Annapolis from this fantastic 5-bedroom house. With two queen beds and a peaceful bathroom featuring a bathtub and hair dryer, guests find comfort and convenience throughout their stay. The lovely space is perfect for families or groups looking to unwind and enjoy quality time together. Kick back, relax, and enjoy everything Annapolis and our house has to offer.

Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$698.25

Enjoy a stylish experience at this centrally-located and newly-built (2022) Eastport Annapolis townhome. Spacious two living areas with a separate dining room, screened in porch and backyard. Each bedroom offers an en-suite bathroom, and you could not be more centrally-located to all that Eastport has to offer - step outside to famous Boatyard Bar & Grill and Forward Brewing directly across the street. Convenient street parking out front - walk to downtown Annapolis and USNA.brThe spacebrWhere you will sleep:brMaster bedroom - King Bedroom Suite with two walk-in closets, upscale and modern en-suite bathroom with oversized shower featuring rain shower and multiple jets, towel warmer for that extra touch.brbrFront bedroom - King Bedroom Suite with office desk/chair for workspace. En-suite bath with full tub.brbrMiddle bedroom - Queen Bedroom Suite with en-suite bathroom.brbrAll bedrooms upstairs. Washer and Dryer in hallway closet space upstairs. All amenities are top-line and well stocked.brbrMain level features a front living room with queen sleeper sofa, dual-sided gas fireplace that opens to an 8-person dining room on the other side. Open concept Chef's kitchen with waterfall island and seating for four - two beverage fridges for entertaining. Cozy living room with oversized sectional that leads to a backyard screened in porch with private backyard.brGuest accessbrEntire townhousebrOther things to notebrWe want you to feel that every detail has been thought of and that you can walk in, relax and enjoy with friends. This open concept floor plan allows for both comfort and ease and is the perfect location for walking to all that Eastport and Annapolis have to offer.

MODERN 2022 NEWLY BUILT TOWNHOME

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Select Dates for Price

Apartment

Anchor's Away in the Heart of Eastport!

Annapolis, Maryland, United States

Downtown in the heart of Eastport Annapolis, this first floor studio condo boasts high ceilings with lots of natural light and ample closet space. Fully remodeled with new floors, tile and stainless steel appliances, as well as a pull-down Murphy bed that is home to a comfy tempur-pedic mattress. Cozy electric fireplace below a 58” 4K television. Basement houses additional storage and full-size W/D. Grill area shared by the 3 units in this building with on-street parking. Please note that MD assesses a 7% occupancy tax which will be invoiced after your booking is completed and collected through VRBO. This tax is in addition to the 6% sales/occupancy tax collected by VRBO upon initial booking.

Bed

Bath

Sleeps

$641.48

1930's Single family home on adorable cul-de-sac downtown Annapolis with off-street parking! Located off West Street in downtown's Arts District, we are conveniently located in walking distance to City Dock, USNA, Navy Stadium, or to the many restaurants and shops Annapolis has to offer. Private driveway so parking is never a problem. Great fenced in backyard and patio for entertaining! 3 bedroom, 2.5 bath, with additional sleeping options in the finished basement (queen murphy bed) and a pull out sofa in the living room (queen). This home checks all the boxes for a memorable stay in Annapolis.brbrSorry, we are already booked for '22, '23, & '24 Commissioning Weeks.

***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$332.44

Stay just one block from historic Downtown Annapolis in this charming, character-filled 3BR retreat. Perfect for up to 6 guests, it offers a bright and comfortable space inside a unique, historic building. Enjoy a kitchen with all the basics for easy meals, cozy living area with TV, and the convenience of in-unit washer/dryer. Fresh linens, towels, and essentials are all provided so you can settle in stress-free. The location can’t be beat—walk to shops, dining, and waterfront.brbrWelcome to your cheerful Annapolis getaway—just one block from the heart of downtown! This light-filled 3-bedroom, 1-bath home on a hill is tucked inside a historic brick building full of character, offering comfort and convenience for up to 6 guests.brbrEach bedroom is thoughtfully furnished with a queen bed, dresser, and closet so you’ll have plenty of storage during your stay. The bathroom features a tub-shower combo. There is also a queen sofa bed in the living room.brbrThe living room invites you to unwind with a cozy sofa, Smart TV for streaming your favorites, and a decorative fireplace that adds a touch of historic charm. Gather for meals in the dining room, which seats six comfortably, or enjoy a casual breakfast at the kitchen bar with stools. The fully equipped kitchen includes a gas stove, oven, fridge with ice maker, dishwasher, and all the essentials you’ll need for cooking at home. For your convenience, there’s also an in-unit washer and dryer.brbrGuests will have to walk up a flight of steps to get from the street to the home, and again up a half flight of steps to get to the unit, but once inside, everything is on a single level—bright, airy, and easy to enjoy.brbrStep outside and you’ll find yourself in one of the most charming neighborhoods in Annapolis. Within a short stroll, you can explore the U.S. Naval Academy, City Dock, Maryland State House, and the many boutique shops, galleries, cafés, and restaurants that line the historic downtown streets. Stroll the waterfront, take a boat tour of the harbor, or enjoy the lively nightlife—all just minutes from your door.brbrPaid street and garage parking are available nearby, making it easy to come and go. Whether you’re here for history, sailing, dining, or simply soaking in the energy of this vibrant city, this home is the perfect home base for your Annapolis getaway.brbrWe’ll follow up with a short online registration once you book. It’s fast, simple, and helps us prepare for your visit. Non-Airbnb guests will be asked to pay a small damage waiver OR refundable deposit.brbrFor extra flexibility, consider adding trip insurance for a nominal fee. It can cover you if you need to cancel at the last minute.

Apartment

Prime Spot Stay–Simple Comfort, Perfect Location

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$841.25

This clean, peaceful, 5 BR, 4 BA house features a waterfront view from 2 spacious decks in a quiet community. Perfect for families or small groups, like book clubs or reunions!brBEDROOMS: 5 BRs w 4 queens and 1 full-over-full bunk bed sleep up to 10 guests. Denver Mattress Company mattresses & soft Supima cotton sheets comfort you, every night. BR 1 & BR 2 have private BAs. BR 1, BR 2 & BR 3 have private sliding doors leading onto the lower deck with its water front view. BR 4 (full-over-full bunk bed) & BR 5 (queen bed) front a quiet, single lane road.brATTRACTIONS: 15-min drive to Naval Academy & downtown Annapolis. 8-min drive to Quiet Waters Park. 5-min drive to a Giant grocery, Starbucks, restaurants & a pharmacy. 5-min walk to historic Highland Beach & the Chesapeake Bay.brDINING AREA: Perfect for cooking & eating together! Dining table with 8 chairs and 4 bar stools nearby at the counter. Deck chairs & a foldable table make deck meals a convenient option.brKITCHEN: Top floor, NUT-FREE, well-stocked, well-equipped kitchen has plenty of chef’s items in the pantry, new electric range & granite countertops. The sink has an Instant Hot and an under-the-sink reverse osmosis water system. The Bosch dishwasher is so quiet that you’ll barely hear it cleaning for you.brTOP FLOOR: Open floor design to maximize waterfront view. Regulation-size ping pong table, TV, games & puzzles are available. Top floor has a bright, gourmet kitchen, full BA & home office/fitness room. Half-covered upper deck for outdoor relaxation.brNEIGHBORHOOD: Scenic, low-traffic street popular with joggers. 5-min walk to Chesapeake Bay & to the historic Highland Beach community. brVIEW: 100-ft waterfront view with a Living Shoreline and a wildlife critical area. Turtles or ducks may visit at high tide. Hummingbirds, butterflies & more may visit the pollinator-friendly garden. Either deck or large backyard are ideal for family games, meditation, yoga or tai chi. Postcard sunset! No pier.brWATER: All household water arrives filtered and drinkable from the well. The kitchen has an under-the-sink reverse osmosis system and an Instant Hot. brWIFI: Free to our guests & provided by Verizon.brEXTRAS: hair dryer, iron & ironing board, deck chairs & garage use. Generous driveway & street parking accommodate 5 cars.brNOTE: Due to a child's allergy, this is a NUT-FREE VACATION HOUSE. Do not bring nuts inside, please.

Cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$367.02

The Corner House – Quaint and Cozy 2 Bedroom Suite with ParkingbrThe Corner House is a hidden gem located in the quaint President’s Hill neighborhood in historic Annapolis. New to the market, this suite is a cozy nook nestled on the third floor of this historic house. It is one block from West Street. This area of Annapolis is a vibrant and historically significant area that offers a mix of history, arts, culture, dining, and entertainment, making it a unique and lively part of the city.brbrSituated just a short walk from the heart of the West Street Arts District, The Corner House is a home away from home. Enter through a white picket fence and onto a covered front porch. This is where you can enjoy your morning coffee and your afternoon tea or glass of wine when you return from your ventures. Enjoy the artwork of local and east coast regional artists that is displayed in the foyer and throughout the home.br brKnown as “Cunningham’s Retreat”, this loft-style suite boasts both a nautical character and coastal charm. One of three suites in this tri-gabled opulent Hill Street home offers a tranquil and comfortable vacation experience. This beautifully designed and decorated haven has two bedrooms, one bathroom and a kitchen. Includes off street parking for one vehicle. brbrMoreover, guests will enjoy easy access to a vibrant scene with nearby restaurants, taverns, galleries, and music venues. This location is conveniently situated. It has easy walking equidistance to everything uptown and downtown Annapolis, such as Maryland State House, Governor’s Mansion, Market House, Ego Alley, St John’s College, US Naval Academy, Navy-Maine Corps Memorial Stadium, historic sites, waterfront locations, and parks.brbrWest Street in historic downtown Annapolis holds significant cultural and historical importance. It is renowned for its thriving arts and culture scene. It’s home to numerous art galleries, studios, and performance venues, making it a focal point for visitors, artists, and art enthusiasts. While known for its artistic vibe, West Street also retains its historical charm with well-preserved architecture, including charming row houses and historic buildings. The street offers a diverse range of dining options, from trendy cafes to upscale restaurants. It’s also a hub for live music, with bars and venues hosting local musicians and bands. West Street features boutique and specialty shops making it a great destination for shopping for unique and artisanal items.brbrThroughout the year, West Street hosts various festivals and events, including art festivals, live music performances, and cultural celebrations fostering community and unity.brbrGuests will enjoy their quiet and serene visit at The Corner House. This is a legally licensed rental property. We strongly enforce our policies of no parties and no illicit drug use. This is a non-smoking property. Pets are not permitted. No children under the age of 12 years old.br

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$785.71

Complement your next outing to the Annapolis area with a stay at our beautiful waterfront home primely situated on the Chesapeake Bay! Featuring a well-equipped modern kitchen, deck with outdoor dining area, separate comfortable outdoor seating area, an outdoor fire pit, and dock with 4 adirondack chairs to enjoy the sunsets with a beverage of your choice. Stroll through Sandy Point State park and visit the Colonial Annapolis Historic District and the Annapolis Maritime Museum.brbrOur Bay Home has three bedrooms, a large kitchen with island and dining, two living areas, wood burning fire place, multiple outdoor areas, an outdoor fire pit, and dock. brbrThe upper level bedrom is the largest with its own bathroom complete with soaking tub and seperate shower, double sinks and closet area. The large capacity washer and dryer are in the closet area. Off the principle bedroom is your private deck with 2 loungers and a beautiful view of the bay. You might even see a bald eagle or osprey looking for their next fish to catch. brbrThe other two bedrooms are located on the main level and share a full bathroom. The Queen Bedroom has a four poster bed, TV, closet, and french doors with a view of the bay. The double-bunk-bed room has a large closet and shelves. Both bedrooms have blackout blinds. brbrAt the end of the hall is a large TV/Exercise/Game room. There is an 85` TV, cozy couch and lounge chair to relax in or close the door and have the kids hang out in there while the adults are in the main area of the home. There are games, a pelaton, rowing machine, hand weights, yoga mats and a ping pong table. brbrThe kitchen-living-dining area share the same space. There is a large L-shaped island with a five burner gas stove with oven, a microwave, prep and serve areas, bar stools and book shelves with our favorite cookbooks. There is a hand powered Italian meat slicer for the adventurous charcuterie maker. The large velvet couch with big pillows is a great place to enjoy the fire place and watch the weather and birds outside. The dining table has four chairs and the bar has four bar stools. brOut the door to the right side of the kitchen is a the grilling area with a ceramic charcoal grill. It takes about thirty minutes to warm up and then its ready to grill all your favorite foods. To the back of the house is a large deck going the full width of the house with a large outdoor couch and chairs, and a 10 person dining table and pizza oven. brbrTo the left of the house is a screened in porch area with a fan, two chairs and a cafe table. We like to go out there and watch the rain storms come in and go by. brbrIn the back yard, is a fire pit with seating for six people and a huge Sycamore tree. Its a great space for playing bocci ball. The dock is one of our favorite place to enjoy coffee while watching the sun come up and a different beverage for watching the magnificent sunsets. The four adorondack chairs make this time quiet comfortable. Fishing from the dock can be quite promising as well!brbrThe front yard is long and flat with the driveway flanking the one side. There is a large garden on the other side with many Crape Myrtle trees. The driveway leads to the round parking area in front of the house. br brWe are located about 15 minutes from downtown Annapolis in a quiet, one street, neighborhood with tons of large trees and wildlife sightings daily.brbrWe are 15 minutes from most places around Annapolis and so a car is the best option for accessing our property.brbrFor general questions: please contact Joel and for emergencies contact Evelyn.brbrOur home is located in a `one street` neighborhood with wonderful neighbors walking their dogs daily.

Bay Home in Annapolis with Private Dock

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$952.86

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWalk to Everything Ideal for Families & Groups brbr brbrWelcome to your Eastport escape! Stay in this stunning, professionally decorated Craftsman-style home just steps from the waterfront and all the shops, restaurants, and charm of downtown Annapolis. With three levels of beautifully appointed living space, this 4-bedroom, 3.5-bath home offers everything you need for a relaxing weekend getaway or an extended stay with family and friends. brbr brbrHighlights brbrFully-equipped Gourmet Kitchen with modern appliances, ample counter space, and seating for everyone: brbrDining table seats 10 brbrKitchen table seats 5 brbrBreakfast bar seats 4 brbr brbrMultiple Gathering Areas: brbrMain living room with gas fireplace & flatscreen TV brbrLower-level rec room with 85 TV, bar seating, gas fireplace, arcade machine, foosball, board games, and Queen pull-out sofa brbrCozy backyard with furnished deck, grill, and Solo Stove fire pit brbr brbrOutdoor Spaces: brbrCovered front porch brbrPrivate balcony off King Suite, perfect for sipping your morning coffee brbrFully-fenced yard with Adirondack chairs, dining table, with outdoor games and yard toys brbr brbrSleeping Arrangements (Sleeps 12): brbrKing Suite (2nd Floor) brbrKing bed, Private balcony, Flatscreen TV & electric fireplace brbrWalk-in closet brbrSpa-like ensuite with dual vanity, soaking tub & custom shower brbr brbrQueen Bedroom (2nd Floor) brbrQueen bed + Twin trundle brbrDesk brbrShares buddy bath with Bunk Room brbr brbrBunk Room (2nd Floor) brbrTwin over Queen bunk brbrShares buddy bath brbr brbrQueen Bedroom (Lower Level) brbrQueen bed brbrAdjacent full hall bath brbr brbrRec Room (Lower Level) brbrQueen sleeper sofa, Full bath access brbr brbrEntertainment, Comfort & Work Stations: brbr3 Smart TVs | Strong WiFi throughout brbr3 Gas fireplaces brbrWood-burning Solo Stove in backyard (BYO firewood & s’mores supplies) brbrArcade machine, foosball table, and board games for family fun brbrFast WiFi throughout the house, with cheerful work area in lower-level den and a desk in one of the upstairs bedrooms brbrWasher & dryer in-home brbrAll bedrooms have individual charging stations brbrProfessionally laundered linens and bath towels provided brbrStarter pack of toiletries & household essentials included brbrA portable crib and booster seat are also available for your littlest guests. brbr brbrWalkable to: brbrDavis Park Dock – 0.1 mi brbrEastport restaurants & shops – 0.2 mi brbrDowntown Annapolis – 0.7 mi brbrU.S. Naval Academy – 0.9 mi brbrEasy access to Washington, DC (30 mi) and Baltimore (25 mi) brbr brbrHouse Rules: brbrNo pets, parties, or smoking brbrPrimary renter must be 25+ and present during stay brbrExterior doorbell camera & legal decibel monitor for safety brbrOther things to note brbrPlease note that we may collect additional information from you after confirming your booking (usually an email address) in order to comply with local regulations and to provide the best possible experience. brbr brbrThis home is the perfect blend of luxurious comfort and unbeatable location. Whether you’re planning a weekend filled with waterfront adventures, a midweek work-from-home escape, or a festive family gathering, you’ll love calling this Eastport gem your home base in Annapolis.

Steps to Downtown Annapolis & Spa Creek from Stunning Craftsman with Game Room, Parking and Backyard

Annapolis, Maryland, United States

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