Vacation Rentals By Owner In Annapolis, MD

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWelcome to Your Historic Annapolis Retreat! brbrDiscover this newly-renovated and professionally-decorated gem on the prestigious King George Street, nestled in the heart of Historic Annapolis. Steps from the U.S. Naval Academy gates and a short stroll to renowned restaurants and charming boutiques, this home is a perfect blend of modern updates and timeless charm. brbrPlease note: Parking for 1 off-site garage pass (for the months of April-Nov only!) brbr brbrMain Features brbrMain Level: brbrBright and Inviting Space: An open floor plan with gleaming new hardwood floors and abundant natural light. brbrStylish Powder Room: Featuring an elegant marble sink and a crystal ceiling fixture. brbrChef’s Dream Kitchen: Fully updated with custom cabinetry, quartz countertops, a glass-mirrored backsplash, and high-end stainless steel appliances. brbr brbrOutdoor Escape: brbrStep out to the private, fenced-in patio featuring a propane grill, firepit and seating for 4—perfect for dinner parties or quiet evenings under the stars. brbr brbrUpper Levels: brbrSecond Floor: Two spacious bedrooms with king beds, flat-screen TVs, and a beautifully-updated shared full bathroom. brbrThird Floor: Ideal for younger guests, this versatile space serves as a combo bedroom, hangout area and office, featuring a queen sofa sleeper, desk and custom storage. brbr brbrWhy You'll Love It brbrPrime Location: brbr2 blocks from USNA Gate 1 brbr3 blocks to the waterfront brbrEasy drive to Washington, DC (30 miles) and Baltimore (25 miles) brbr brbrLuxurious Amenities: brbrWiFi and multiple flat-screen TVs brbrLuxury linens, complimentary toiletries, and boutique-level service brbrWasher and dryer in the home brbrKeyless entry for seamless check-in brbr brbrSleeping Arrangements brbrFront King Bedroom (2nd Floor): King bed, flat-screen TV, shared full bath brbrBack King Bedroom (2nd Floor): King bed, flat-screen TV, shared full bath brbrThird Floor: Queen sofa sleeper, flat-screen TV, shared full bath brbr brbrHighlights: brbrPrivate fenced patio with BBQ grill and firepit brbrGourmet kitchen with dining table seating for 6 brbrOutdoor dining area for 4 brbr brbrHouse Rules: brbrMust be 25+ to book brbrNo parties, pets, or smoking brbrQuiet hours observed for neighborly respect brbrCheck-in: 4:00 PM | Check-out: 11:00 AM brbr brbrDon’t Miss Out! brbrPerfect for family getaways, Naval Academy events, or soaking up the charm of Annapolis. Reserve your stay and experience all this historic treasure has to offer!

Stay in the Heart of Annapolis on King George Street Steps to USNA Gate 1 & Main Street

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1101.23

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrEnjoy stunning western-facing views across the river and a natural tidal pond from this sprawling historic home that sits on 1.5+ acres. The light-filled farmhouse is located on Persimmon Point, which is positioned between Harness Creek and the South River. It is a peninsula rich in local lore that includes Native American oysters mounds, pirate hideouts, tobacco farming and world champion cows. brbr brbrSome history: Once the home was part of the original Wimbledon Farm. From the 1930’s, Wimbledon Farm grew abundant produce and tobacco. The last magnificent tobacco barn in Annapolis is on the property next to the house. Wimbledon was also famous for their dairy. Their dairy cows and bulls attracted breeders from around the world and famously started the “Carnation” milk herd. The dairy barn was immense and the milk came into the small milk house, which is now the charming Milkhouse Suite. Here the milk was chilled and sent out to be bottled and delivered. brbr brbrToday: The house offers a special, very private family retreat just minutes to downtown Annapolis. The home was renovated to its current beauty by opening the entire back of the house to the water with windows and connecting the main house to the milk house. All of the living space, and 4 of the 5 bedrooms, are on the main floor. The lofted upstairs bedroom is perfect for the younger crowd with 3 twin beds and room to enjoy each other's company. The open floor plan, deck and terrace provide multiple living spaces inside and out. There are 2 full baths and room for 10 guests to sleep comfortably. brbr brbrEnjoy the outdoors on stone patio with fountain and dining tables, a pair of Adirondack chairs on the back deck under the shady wisteria pergola, and a BBQ grill. Inside, the dining table seats 8 with room for 3 more at the breakfast bar. Across the lush lawn, there is also a small pier on the pond for kayak launching or fishing fun for small anglers. Guests can also get away from the day by lounging on the creek side on the front porch swing. brbr brbrLocal activities: Great Frogs Winery (less than ½ mile away down the street), Quiet Waters Park (hiking trails, ice skating, SUP rentals) and kayaking or biking. brbr brbrSLEEPING ARRANGEMENTS 5 BR / 2 BA / Sleeps 10 adults (2 children): brbrMilk House Suite: brbr-Main Floor brbr-Queen Bed brbr-Living room with Full sofa sleeper brbr-Private en-suite bathroom large tile shower brbr-Private entrance and water views brbr brbrMain Floor King: brbr-King bed brbr-Private entrance to front porch brbr brbrMain Floor Queen: brbr-Queen bed brbr brbrMain Floor Twin brbr-Built-in Twin Bed brbr brbrUpstairs Loft brbr-3 Twin beds brbr brbr-Full Hall Bath with stand-up Shower and clawfoot Tub brbr brbrHIGHLIGHTS: brbr-Outdoor waterfront furnished terrace and deck - access to decks or porch from main entries brbr-Small fishing and boat launch pier on the pond brbr-Kayaks brbr-Mulitple living spaces: family room, living room and loft brbr-BBQ Gas grill (propane tank provided) brbr-Dining room table with seating for 8 brbr-Breakfast bar with seating for 3 brbr-Vermont casting gas stove brbr-High Speed Internet and WiFi brbr-Flatscreen TV's brbr-Luxury Westin Heavenly mattress in milk house, fine linens, complimentary toiletries Starter Kit, and boutique-level service brbr-Parking for multiple cars in driveway brbr-Full-size washers/dryers located on the main floor brbr brbrProperty Distance to: brbr-Downtown Annapolis – 4 miles brbr-U.S. Naval Academy – 4 miles brbr-Washington, DC – 33 miles brbr-Baltimore - 33 miles brbr-Great Frogs Winery - .4 miles brbr-Quiet Waters Park - 4.2 miles by land - closer by sea! brbr brbr*Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid. brbr* All beds are 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 house at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Be respectful of the house and contents - it is someone's home and the owners live in the home when not renting it. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind.

Serene Sunsets at Historic Waterfront Home

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$633.03

Welcome to your perfect Springtime getaway in the heart of Annapolis! This open-concept home is designed with family gatherings in mind. brbrLocationbr- 1/2 block to the USNA football stadiumbr- 5 minute drive to state circle in DTAbr- 5 minute drive to Gate 1 of USNAbr- 10 minute walk to West Annapolis (dine at delicious restaurants and shop at local boutiques)brbrParkingbr-On-site parking for up to 4 cars (2 in driveway and 2 along the curb)br-Street parking available brbrThe SpacebrbrLiving Roombr-Comfortable sectional & chair with seating for 6br-Open concept to dining room and kitchenbr-Smart TVbrbrDiningbr-Dining table with seating for 6br-Kitchen peninsula with bar stool seating for 2br-Bistro Kitchen table with seating for 2brbrKitchenbr-Pod + Drip coffee pot with ground coffee, pod decaf/regular coffeebr-Assorted decaf and caffinated teas.br-Coffee bar: creamer, sugar, sweetener, milk frothing whiskbr-Fridge: filtered water + ice maker, 6 cans of flavored seltzer water upon arrivalbr-Dishwasherbr-Electric range/ovenbr-Microwavebr-Small appliances: toaster, air fryer, blender, and griddlebr-Dishes, utensils, glasses, wine glasses, salad/mixing bowlsbr-Children's dishes and drink warebr-Pots and pans, bakeware, containers for leftoversbr-Cooking utensilsbr-knives and cutting boardsbr-basic seasonings and oilsbr-aluminum foilbrbrBasementbr-Large sectional and cushioned ottomanbr-Smart TVbr-Board games, puzzles, magnatiles, and more family fun activities located in the tv console table.brbrBedroomsbr-Memory foam king bed in first and second bedroomsbr-2 twin beds in the third bedroombr-All bedrooms have black out curtains, extra blankets, closets, luggage rack/bench.brbrBathroombr-Main floor bathroom with tub/showerbr-Basement bathroom with stand up showerbr-Public goods body wash, shampoo, and conditionerbr-Extra toiletries on hand if needed (toothbrush, toothpaste, deodorant, etc.) br-Plush towels and washcloths brbrOutdoor Spacebr-Fully fenced-in backyardbr-Weber gas grill and grilling utensilsbr-Outdoor dining table with umbrella with seating for 6br-Outdoor sectional and coffee table br-Outdoor string lights that turn on at duskbrbrExperiencebrbrLocated just minutes from Annapolis’ historic downtown, you can explore charming cobblestone streets, unique boutiques, and waterfront views. Take a stroll to the iconic Annapolis Harbor or visit the U.S. Naval Academy for a dose of local history.brbrCreate new traditions and be thankful for quality time spent in a home that feels like yours. Whether you’re hosting family dinners or enjoying the charm of this historic city, this is the perfect spot to make memories that last a lifetime.brbrWe look forward to welcoming you and ensuring your stay is both comfortable and memorable. Book your stay today and experience the the history and charm of Annapolis!brbrLicense #: RENT-001212-2024

Mins to DTA - King Beds - Parking

Annapolis, Maryland, United States

Bed

Bath

6

Sleeps

$482.58

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWelcome to the Fitzgerald Suite – Lower Level, a private apartment nestled on a quiet cul-de-sac just minutes from Downtown brbr brbrAnnapolis. This thoughtfully furnished lower level can be rented on its own or combined with the upper level of the home for larger groups, creating the full Fitzgerald Retreat experience. brbr brbrPerfect for couples, families, or small groups, this cozy space offers comfort, privacy, and convenience in a peaceful neighborhood setting close to Annapolis’ top attractions. Whether you’re visiting for a Naval Academy event, a boat show, or a weekend getaway, this space offers everything you need to feel at home. With generous parking and easy access to the area’s highlights, this is an ideal spot for family visits and special occasions. brbr brbrThe Space brbrThe lower level is designed for relaxed stays and features: brbrTwo bedrooms brbrOne full bathroom brbrComfortable family room brbrKitchenette and dining table brbrIn-unit laundry brbr brbrOutdoor Living brbrStep outside and enjoy your own private outdoor patio, complete with: brbrFire pit brbrGas grill brbrAmple seating for gathering and relaxing brbr brbrSleeping Arrangements | 2 BR / 1 BA | Sleeps 4 brbrQueen Guestroom: Queen bed brbrTwin Bedroom: Two twin beds brbrShared full hall bath with stand-up shower brbr brbrHighlights & Amenities brbrPrivate outdoor patio with fire pit brbrHigh-speed WiFi & Smart TVs brbrLuxury linens, starter toiletries & boutique-level service brbrFull-size combo washer/dryer unit brbrParking for 2 vehicles brbrKeyless entry for easy self check-in brbr brbrDistances brbrNavy–Marine Corps Memorial Stadium: 1.3 miles brbrU.S. Naval Academy: 1.5 miles brbrBaltimore: 30 miles brbrWashington, DC: 32 miles brbr brbrAdditional Details brbrA starter supply of essentials is provided, including coffee, sweeteners, paper products, soaps, and toiletries. All beds are freshly made with clean linens, and towels are provided prior to arrival. brbr brbrHouse Rules brbrMinimum age requirement: At least one guest must be 25 years or older brbrNo parties, events, smoking, or pets brbrQuiet hours: 9:00 PM – 8:00 AM brbrPlease respect the home, neighbors, and neighborhood brbrCheck-in: 4:00 PM brbrCheck-out: 11:00 AM

Private Apartment Near Downtown Annapolis with Private Outdoor Space and Parking

Annapolis, Maryland, United States

Bed

1

Bath

4

Sleeps

$603.14

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrUpscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces brbrWelcome to this newly decorated, upscale Annapolis retreat tucked away on a quiet cul-de-sac just minutes from Downtown. Thoughtfully designed for families and small groups, this beautifully furnished home offers multiple gathering spaces indoors and out, creating a private, resort-like setting ideal for relaxing and reconnecting. brbr brbr*This home can be rented separately or combined with the 2 bedroom 1 bath apartment on the lower level. brbr brbrThe open floor plan features a spacious family room and a cozy den—each with a flat-screen TV—alongside a beautifully equipped kitchen perfect for shared meals. Enjoy three dining options: a formal dining table, a breakfast bar, and a sunny four-seat table in the family room, ideal for casual meals or morning coffee. brbr brbrAfter a day exploring Annapolis, unwind in the serene King Suite with a private en suite bath and direct access to the back deck, or retreat to the comfortable Queen Guest Room with a nearby full hall bath. brbr brbrStep outside to expansive outdoor entertaining spaces featuring fire pits, a gas grill, and ample seating—perfect for evenings under the stars. With generous parking and easy access to the U.S. Naval Academy, Navy–Marine Corps Memorial Stadium, boat shows, and Downtown Annapolis, this home is an ideal choice for family gatherings and special occasions. brbr brbrSleeping Arrangements | 2 BR / 2 BA | Sleeps 6 brbrMain Level King Suite brbrKing Bed brbrPrivate en suite bathroom with separate shower and soaking tub brbrDirect access to back deck brbr brbrMain Level Queen Guest Room brbrQueen Bed brbrFull hall bath with stand-up shower brbr brbrMain Level Den brbrFull Sofabed with linens brbr brbrHighlights & Amenities brbrOpen-concept main level with Family Room, Den, Dining Area & Kitchen brbrDining table seats 8 | Breakfast bar seats 4 brbrSpacious outdoor living areas with gas grill (propane provided) brbrTwo fire pits (front patio & side deck) brbrHigh-speed WiFi & Smart TVs brbrLuxury linens, starter toiletries & boutique-level service brbrTwo full-size washers & dryers (one on each level) brbrParking for 3–4 cars brbrKeyless entry for easy self check-in brbr brbrDistances brbrNavy–Marine Corps Memorial Stadium: 1.3 miles brbrU.S. Naval Academy: 1.5 miles brbrBaltimore: 30 miles brbrWashington, DC: 32 miles brbr brbrAdditional Details brbrA starter supply of essentials is provided, including coffee, sweeteners, paper products, soaps, and toiletries. All beds are freshly made with clean linens and towels prior to arrival. brbr brbrHouse Rules brbrMinimum age requirement: At least one guest must be 25 years or older brbrNo parties, events, smoking, or pets brbrQuiet hours: 9:00 PM – 8:00 AM brbrPlease respect the home, neighbors, and neighborhood brbrCheck-in: 4:00 PM brbrCheck-out: 11:00 AM

Upscale Family Home Near Downtown Annapolis | Resort-Style Outdoor Spaces

Annapolis, Maryland, United States

Bed

Bath

6

Sleeps

$570.95

Summary:brbrCan’t beat the space and location of this property for your trip to Annapolis! Just a block away from Navy Stadium for any events, and a mile or less from other downtown amenities, restaurants, and shops! brbrbrbrPerfect house for groups- boat show, college reunions, football trips, tailgates, bachelor or bachelorette parties.brbrbrbrThe Space:brbrExperience the perfect blend of space, comfort, and an unbeatable location for your Annapolis getaway. Our home is the ideal headquarters for groups and is laid out to provide ample room for everyone to socialize and relax.brbrbrbrMain Level:brbr Features an inviting open layout connecting the kitchen, dining area, and a comfortable living room with a TV.brbr The patio door leads directly to your private outdoor oasis.brbrbrbrOutdoor Space:brbr Enjoy meals on the charming deck, complete with a dining table and grill for afternoon barbecues.brbr As evening falls, gather around the cozy brick patio's fire pit for conversation under the stars.brbrbrbrLower Level:brbr The finished basement provides a fantastic bonus area with a wet bar for crafting cocktails, comfortable lounge furniture, and a full bathroom.brbr A convenient pullout couch allows this space to easily transform into a fourth bedroom.brbrbrbrUpper Level:brbrUpstairs, you will find three comfortable bedrooms, providing restful accommodations after a day of exploring.brbrbrbrGuest Access:brbrFull home access with the exception of just one storage closet.brbrbrbrThe Neighborhood:brbrWalking distance to Navy Stadium, West Annapolis, a grocery store, bagel shop, juice bar, and more. Also walkable to Tawes Garden Park.brbrbrbrGetting Around:brbrTwo parking spots included at the property, and free parking in the neighborhood (easy too compared to the heart of downtown!). Walkable to a lot of locations, or walk to catch the free shuttle to downtown Annapolis from the Navy stadium lot!brbrbrbrOther Things to Note:brbrKeep noise to a minimum between 10:00pm and 8:00am. This is to help us maintain the peaceful atmosphere for all of the guests at the property and a peaceful presence within the neighborhood.brbrbrbrInteraction with Guests:brbrBackyard: Our private backyard is a wonderful space to relax, but please note that it is not fully fenced.brbrSecurity: For your security and the protection of the property, there are exterior security cameras installed. These cameras monitor the exterior of the home only; there are no cameras inside the property.We respect our guests' privacy and offer a self-check-in process. brbrbrbrWe will not be on the property during your stay but are readily available via the app or phone if you have any questions or need assistance.

Adorable home steps from Navy stadium!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$458.72

Summary:brbrThere's a secret downstairs - a hidden wine cellar tucked beneath this Eastport home. Upstairs you'll find 2 bedrooms, a screened porch for lazy mornings, and a full kitchen with gas stove. Out back: a fire pit, cabana, and fenced outdoor space. The basement lounge has a pullout queen, Fire TV, and laundry. You're under a mile from Eastport's restaurants, 1.3 miles from Downtown Annapolis, and 2.3 miles from USNA. Pet-friendly. Free parking under the carport. Water taxi at the nearby dock.brbrbrbrThe Space:brbrBEDROOMSbrbrTwo bedrooms on the main level. The primary bedroom has a queen bed, and the second bedroom has a double. The basement lounge adds a pullout queen for extra guests. Fresh linens provided.brbrBATHROOMSbrbrOne full bathroom on the main level with fresh towels, soap, shampoo, and a hair dryer.brbrKITCHENbrbrFully equipped with a gas stove, oven, microwave, dishwasher, Keurig, cookware, dishes, utensils, and everything you need to cook for your group.brbrLIVING AREASbrbrThe main living room has a Roku TV and comfortable seating. Downstairs, the basement lounge is a second hangout space with a large couch, pullout queen, another TV with Fire TV, and full laundry - washer and dryer.brbrOUTDOOR LIVINGbrbrStart your morning on the screened porch with coffee, then spend the evening around the fire pit out back. The cabana and outdoor seating area make this backyard feel like your own private retreat. Fenced and pet-friendly - your dog will love it here.brbrPARKINGbrbrFree parking under the carport for 2 cars plus street parking available right outside.brbrLOCATIONbrbrUnder 1 mile to Downtown Eastport - walk to Boatyard Bar & Grill, Davis' Pub, and Eastport's best restaurants. 1.3 miles to Downtown Annapolis and City Dock. 2.3 miles to the Naval Academy. About 3 miles to Navy-Marine Corps Stadium. Water taxi pickup at the nearby dock gets you downtown without driving.brbrbrbrGOOD TO KNOWbrbrbrbrCheck-in: 3:00 PM / Checkout: 11:00 AMbrbrSelf check-in with smart lockbrbrPets welcomebrbrGuests have access to the entire home including basement loungebrbrbrbrNote: During extremely cold winter nights, the basement may be cooler - extra blankets and space heaters providedbrbrbrbrGuest Access:brbrPrivate entrance. Smart lock at front door and side doorbrbrbrbrThe Neighborhood:brbrDock at the end of Springdale Ave with access to the water taxi!brbrbrbrGetting Around:brbrNeighborhood is walkable and easily accessible via vehicle. There is parking under the carport out back or right out front.brbrbrbrInteraction with Guests:brbrReach out either in the app or by text message. My cell will be given out prior to arrival through the app.

Hidden Wine Cellar | Eastport Retreat

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$659.95

Summary:brbrThis is the Annapolis home your group has been looking for. Four bedrooms, 2 baths, and room for 10 — plus a private bar and gym inside the detached 3-car garage. The fully fenced yard is perfect for dogs, kids, or post-tailgate hangouts. You're a 5-minute walk to Navy-Marine Corps Stadium and steps from West Annapolis dining: Ingrano for date night, RAR Brewery for craft beer, Always Ice Cream for dessert. Up to 4 cars on the driveway plus free street parking. Pet-friendly.brbrbrbrThe Space:brbrBEDROOMSbrbrFour spacious bedrooms with clean, modern design. Each bed is set up for a great night's sleep. The home comfortably sleeps 10 guests.brbrBATHROOMSbrbr2.5 bathrooms — two full baths stocked with fresh towels and essentials, plus a half bath on the main level.brbrKITCHENbrbrFully renovated, open-concept kitchen with stainless steel appliances, cookware, dishes, and plenty of counter space for group meal prep.brbrLIVING AREASbrbrLarge, open living room with a Smart TV. The layout is built for groups — everyone has room to spread out.brbrOUTDOOR LIVINGbrbrThe fully fenced backyard and spacious patio are perfect for BBQs, games, and hanging out. The detached 3-car garage has been converted into a private bar and gym — a unique feature you won't find anywhere else in Annapolis. Your furry friends have plenty of room to run in the fenced yard.brbrPARKINGbrbrUp to 4 cars on the driveway plus free street parking right outside.brbrLOCATIONbrbrPrime West Annapolis location. Steps from Navy-Marine Corps Stadium — walk to tailgates and games. Caddy corner to RAR Brewery Chessie's Wharf and a shopping center with Graul's Market, Naval Bagels, and Walgreens. Ingrano (fine dining) and Always Ice Cream (#1 in Annapolis) are a short walk. 1.5 miles to USNA, 1.6 miles to Downtown Annapolis.brbrbrbrGOOD TO KNOWbrbrbrbrCheck-in: 3:00 PM / Checkout: 11:00 AMbrbrSelf check-in with smart lockbrbrPets welcome — fully fenced yardbrbrAmple parking for up to 4 cars on drivewaybrbrbrbrGuest Access:brbrEntire house EXCEPT FOR the back rooms in the basement.brbrbrbrInteraction with Guests:brbrEither through the app or via cell phone. My number will be provided prior to arrival.

Pet Friendly | Park Free & Walk to USNA Stadium

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$421.77

Summary:brbrWalk out the door and you're in the center of Annapolis. This updated 2-bedroom downtown home has 2.5 baths, two separate living rooms, and a newly renovated kitchen with stainless steel appliances. The primary suite has an ensuite bath, the second bedroom has a king, and the pullout queen in the living room sleeps extra guests. Walk to the Naval Academy, City Dock restaurants, and Main Street shops without touching your car keys. Two Roku TVs, high-speed WiFi, and central AC throughout.brbrbrbrThe Space:brbrBEDROOMSbrbrTwo bedrooms on the upper level. The primary suite has a queen bed with an ensuite full bathroom. The second bedroom has a spacious king bed. A queen pullout in the living room provides additional sleeping.brbrBATHROOMSbrbr2.5 bathrooms — two full baths upstairs near the bedrooms, one half bath on the main level for guests.brbrKITCHENbrbrNewly renovated with brand-new stainless steel appliances, cookware, dishes, utensils, and all the basics for cooking at home.brbrLIVING AREASbrbrTwo separate living rooms give your group space to spread out. The main living room has a Roku TV and a queen pullout couch. The dining room also has a Roku TV, making it a flexible space for meals and entertainment.brbrOUTDOOR LIVINGbrbrPrivate outdoor space for relaxing — a nice retreat in the middle of downtown.brbrPARKINGbrbrNo dedicated parking. Overnight parking available in the Hillman Garage on Main St.brbrLOCATIONbrbrThis is as downtown as it gets. Walk to the Naval Academy, City Dock, Main Street shops, and dozens of restaurants. You're in the historic district — everything Annapolis is known for is outside your door.brbrbrbrGOOD TO KNOWbrbrbrbrCheck-in: 3:00 PM / Checkout: 11:00 AMbrbrSelf check-in with smart lockbrbrNo parking includedbrbrbrbrGuest Access:brbrEntire housebrbrbrbrInteraction with Guests:brbrText, call, email, or message in the app.

Upscale Downtown | Walk to City Dock and the Yard

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$423.42

Summary:brbrWelcome to Captains Quarters — your waterfront home in the Yacht Club Condominiums. Fall asleep to the sound of the water, wake up to views of Spa Creek, and walk to Eastport's best restaurants in minutes. Relax on the covered patio, swim in the community pool, or stroll across the Eastport Bridge to Downtown Annapolis. Two bedrooms, a full kitchen with Keurig and bean grinder, cable TV, and 2 free parking spots. Everything you need for an Annapolis stay on the water.brbrbrbrThe Space:brbrBEDROOMSbrbrTwo bedrooms, each with fresh linens and a TV. Both rooms are furnished for a restful night's sleep with views of the waterfront property.brbrBATHROOMSbrbrOne full bathroom with fresh towels, soap, shampoo, and essentials.brbrKITCHENbrbrFully equipped with all appliances, cookware, dishes, and utensils. Includes a Keurig, a drip coffee maker, and a bean grinder for the coffee lovers.brbrLIVING AREASbrbrComfortable living room with cable TV. The covered patio off the living area provides waterfront views — the best seat in the house.brbrOUTDOOR LIVINGbrbrThe covered patio overlooks Spa Creek and is furnished for dining or relaxing. Guests also have access to the community pool (Memorial Day – Labor Day), shared dock, and the waterfront common areas.brbrPARKINGbrbr2 free parking spots — a real advantage in Eastport.brbrLOCATIONbrbrSteps from Downtown Eastport. Walk to Boatyard Bar & Grill, Adam's on the 4th, and Carol's Creek Cafe. Cross the Eastport Bridge and you're in Downtown Annapolis. 1.6 miles to USNA. Under a mile to Downtown Annapolis attractions.brbrbrbrGOOD TO KNOWbrbrbrbrCheck-in: 3:00 PM / Checkout: 11:00 AMbrbrSelf check-in with smart lockbrbrNo smokingbrbrPool Hours: brbrMonday, Wednesday, Thursday 4:00 - 8:00brbrCLOSED TuesdaysbrbrFriday 3:00 - 8:00brbrSaturday/Sunday/Holidays 12:00-8:00brbrbrbrGuest Access:brbrGuests will be given a code to access the property prior to their arrival. Guests will be given the code to the lockbox outside of the property which will give them the key they need for entry into the front door.brbrbrbrInteraction with Guests:brbrCall, text, or message on the app. Whichever you prefer.

Condo

Captains Quarters | Waterfront & Pool

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$403.94

Summary:brbrBring your dog, grab a drink, and settle into this 2-bedroom Eastport home with a private fenced backyard built for hanging out. The fire pit, outdoor dining patio, and deck seating make the backyard the real star. Inside: a king and a queen bedroom, 2 full baths, Roku TV, and a full kitchen. You're in Eastport - walk to Boatyard Bar & Grill, Davis' Pub, and the Eastport Bridge to Downtown Annapolis. Two parking spots in the driveway plus free street parking. Pets welcome.brbrbrbrThe Space:brbrBEDROOMSbrbrTwo bedrooms upstairs. The primary has a queen bed, the second has a king. A cot is stored in the primary bedroom closet for extra guests. Fresh linens provided.brbrBATHROOMSbrbrTwo full bathrooms stocked with towels, soap, shampoo, and a hair dryer.brbrKITCHENbrbrFully equipped with stove, oven, microwave, dishwasher, coffee maker, cookware, dishes, and utensils. Everything you need to cook at home.brbrLIVING AREASbrbrOpen living room with a Roku TV and comfortable seating. Bright and airy main level with plenty of natural light.brbrOUTDOOR LIVINGbrbrThis backyard is why you're here. The fenced yard has a fire pit for evening hangouts, a dining patio for outdoor meals, and a spacious deck with comfortable seating — perfect for morning coffee or evening drinks. Your dog can roam freely in the fenced space.brbrPARKINGbrbrFree parking for 2 cars on the driveway plus street parking available right outside.brbrLOCATIONbrbrIn the heart of Eastport — walk to Boatyard Bar & Grill, Davis' Pub, and Carol's Creek Cafe. Cross the Eastport Bridge and you're in Downtown Annapolis in minutes. Under 2 miles to USNA, about 3 miles to Navy-Marine Corps Stadium.brbrbrbrGOOD TO KNOWbrbrbrbrCheck-in: 3:00 PM / Checkout: 11:00 AMbrbrSelf check-in with smart lockbrbrPets welcome — fenced backyardbrbrGuests have access to the entire upstairs unit and backyard. Basement is not accessible.brbrbrbrGuest Access:brbrGuests can access the entire upstairs unit A as well as the porch and backyard. Guests can park on the driveway to the left of the house. Guests will not be able to access the basement (unit B) or the small parking spot right outside of unit B.brbrbrbrThe Neighborhood:brbrQuiet neighborhood. Water Taxi Access at the end of Springdale AvebrbrbrbrInteraction with Guests:brbrGuests can call, text, or message me in the airbnb app.

Pet-Friendly Eastport | Yard & Fire Pit

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$840.6

2021 built waterfront home with sweeping views of the Chesapeake Bay located on a quiet, private road in the community of Sandy Point in Annapolis. Minutes to downtown and the Naval Academy, enjoy the wrap around decks and sunrise on the Chesapeake. Private pier is perfect for swimming, kayaking or taking in the view. Fire pit next to the seawall for relaxing and enjoying the evening navigation lights on the bay.brMaster bedroom upstairs with King bed, ensuite bath, walk-in closet and private deck. Two Queen bedrooms (up and down) with ensuite bath, walk-in closets and private balconies. Children’s bedroom has bunk bed. Bedrooms are comfortably furnished with beautiful linens, pillows and bed coverings. Downstairs family area and dining room overlook the bay. Lower deck has large table for grilling meals on the water. Owner limits gatherings to total of 15 due to limited parking and neighborhood agreement.

Newer Waterfront Home on the Chesapeake Bay

Annapolis, Maryland, United States

4

Bed

Bath

8

Sleeps

$313.5

Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private patio, and hot tub! 50 ft of waterfront make this private walk-out garden-level apartment nestled in a small wooded oasis near downtown Annapolis a gem. Walk to the marinas or the Sailing School to catch a water taxi to downtown or book a private sail or fishing tour. Walk to Port Annapolis to get some fresh baked goods at Black Market Bakery. brbrAccess the large 1000+ sf private apartment from a rear separate entrance of this owner-occupied home. There is dedicated space for 2 cars at the end of the driveway. brbrThe King bed is spacious. The Queen sleeper sofa by American Leather is the most comfortable on the market. Note that this apartment is a studio, and the bedroom is open to the living space and queen sleeper sofa. brbrEnjoy high speed internet during your stay. Watch your shows on the flat screen TV using your streaming accounts (there is no cable; bring your passwords to log in to your favorite steaming channels such as Netflix, AppleTV, Amazon Prime, YouTube, etc.). There is an XBOX and a large collection of DVDs for some old-school movie thrills.brbrIMPORTANT NOTE REGARDING INSURANCE: When you book with VRBO, you should see an option for either paying an insurance fee (flat rate ~$59) or submitting a refundable deposit. Choose whichever option best suits you. These transactions are with VRBO, not the host. br

Apartment

Bay View Studio Apartment

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$449.53

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrStay in the heart of Historic Annapolis just steps from the waterfront, shops, restaurants, and the Naval Academy. Owned by a proud multi-generational Navy family, this charming updated home blends modern comfort with patriotic décor. brbr brbrHighlights: brbr1 block to City Dock & USNA brbrPrivate brick patio w/ grill & outdoor dining brbrFully-equipped gourmet kitchen brbrStreet Parking available for one car brbrCozy living room w/ flatscreen TV + folding dining table brbrWasher/dryer + keyless entry brbrWiFi + luxury linens + starter toiletries kit brbr brbrSleeping Arrangements:2BR / 2.5BA | Sleeps 4 (+1 air mattress + sofa) brbrPrimary Bedroom (2nd Floor): Queen bed, en-suite bath, flatscreen TV brbrGuest Room (2nd Floor): Two Twin beds, en-suite bath, flatscreen TV brbrExtras: Air mattress + sofa sleeping (linens on request) brbrNote: Home has a steep staircase—guests with mobility concerns should inquire before booking. brbr brbrHouse Rules: brbrNo pets, smoking, or parties. Renter must be 25+ and present at all times. brbr brbrCheck-in: 4:00 PM | Check-out: 11:00 AM

Go Navy! Steps to USNA, City Dock & Street Parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$568.43

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrThe fully-renovated 1800 historic home is just steps from USNA’s Gate 3. Located in the heart of historic downtown on a quiet street next to the Naval Academy and St. John’s College, it’s a 5-minute walk to City Dock/Main Street. Perfect for Navy parents, Alumni, weddings, sailors, weekenders, sightseers, Legislators and Work-cationers. brbr brbrFully renovated in 2017, the kitchen is equipped with high-end stainless steel appliances (including a dual-temperature wine fridge!), granite countertops and opens up to the dining and living areas. The original hardwood floors have been re-finished, adding to the historic Annapolis charm and feel. In addition to the comfortable sleeping arrangements for 8, step out back into a massive outdoor living and dining deck with a gas grill and a fire pit. Head upstairs to the 4 bedrooms and 2 baths and relax on the private King Suite balcony. brbr brbrFor guests with cars, there are many safe, easy public parking options (some free) available within walking distance. brbr brbrSLEEPING ARRANGEMENTS 4 BR / 2.5 BA / Sleeps 8: brbrKing Suite: brbr- 2nd Floor brbr- King Bed brbr- Oversized shower walk-in shower with rain shower head and double vanity brbr- California Closets brbr- Private Balcony brbr brbrSunny Front Guest Room: brbr- 2nd Floor brbr- Queen Bed brbr- Jack-n-Jill Full Bath with Tub and Shower brbr brbrMiddle Guest Bedroom: brbr-Second Floor brbr- Queen Bed brbr- Jack-n-Jill Full Bath with Tub and Shower brbr brbr3rd Floor Bedroom/Office Combo: brbr- Two Twin beds Bed brbr- Office Desk and Chair brbr- Additional A/C unit brbr- Flatscreen Smart TV brbr brbrHIGHLIGHTS: brbr- Spacious gourmet kitchen brbr- Eat-in kitchen counter seats 2 brbr- Dining room table seats 6 brbr- Spacious outdoor living, dining and fire pit area brbr- WiFi brbr- Big Screen Smart TV's brbr- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service brbr- Washer & dryer located inside the home brbr- Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations. brbr- Keyless entry. Drive straight to your rental home and enter the front door with an electronic lock code. brbr brbrProperty Distance to: brbr- U.S. Naval Academy – Across the Street from Gate 3 brbr- Washington, DC – 30 miles brbr- Baltimore - 25 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 ready made for you with freshly-laundered sheets & towels. brbr brbrHouse Rules brbrReservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. brbrCheck-in time: 4:00 pm brbrCheck-out time: 11:00 am

Private Patio at Charming Hanover House Across from USNA Gate 3

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$401.32

Truly in the HEART of downtown we are 50 steps from Main Street, City Dock and all the action. Featuring the best front porch in town with 3 bedrooms we sleep 6 maximum. We offer an open floor plan, two full baths, kitchen and the best front porch in town. We may not be the fanciest rental in town but is a great comfortable house is an unbelievable location. Everything you need nothing you don't.brbrLocation Location location. You can't get closer to town, (without all the noise ). Owner is USNA alumni. Come see why we picked this spot in all of Annapolis to share with you.brbrParking will need to be in a city garage. Brand new AC / heat installed except middle bedroom.brbrNo parties / events . Quiet time enforced. strictly outdoors after 10 pm as we share walls with neighbors. Extra mess = extra clean fee . No parties - Bachelor / Bachelorette included. No confetti / taping on walls.

The Very Best location - 50 Steps from Main Street

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$484.57

Summary:brbrThis stylish two bedroom home is conveniently located in Annapolis' Germantown neighborhood off West Street, and two blocks (0.3 miles) from Navy-Marine Corps Memorial Stadium and an 8 minute drive to USNA and Downtown Annapolis.brbrbrbrThe Space:brbrThis is a 2-floor bungalow house and guests have access to the main floor. The basement is unfinished and not accessible to our guests.brbrbrbrThe primary (ensuite) bathroom is the only bathroom in the house with a shower. There is a powder bathroom that guests can use who are staying in the secondary bedroom. Guests staying in the secondary bedroom will need to walk through the primary bedroom to take a shower. brbrbrbrThere is a sleeper sofa in the living room for larger parties.brbrbrbrThere is a fenced in backyard that is perfect for guests with dogs. Please ensure you clean up after your furry friends. brbrbrbrThere is a covered outdoor screened in eating area that is perfect for meals in the fall and spring. There are four bar stools in the kitchen where guests can eat during inclement weather.brbrbrbrGuest Access:brbrGuests have access to the entire house and backyard except for locked storage closets and the basement lower level (not pictured). Guests staying for 7+ nights will have access to washer/dryer.brbrbrbrThe Neighborhood:brbrThis stylish two bedroom home is in the conveniently located in Annapolis's Germantown neighborhood off West Street, near downtown Annapolis. brbr brbrPerfect for Navy sporting events and boat shows, this home is two blocks (0.3 miles) from Navy-Marine Corps Memorial Stadium and an 8 minute drive from USNA and Downtown Annapolis. brbr brbrAnnapolis' Germantown neighborhood is wonderful! There are tons of restaurants, bars, and boutiques on West St which is two blocks away. brbr brbrWalk along the old brick sidewalks much as George Washington or Thomas Jefferson did in the days when Annapolis was the capital of the United States. Architecturally, Annapolis boasts some of the finest 17th and 18th century buildings in the country – including the residences of all four Maryland signers of the Declaration of Independence. brbr brbrAnnapolis is the home of the United States Naval Academy, founded in 1845, and of St. John's College, the third oldest institution of higher learning in the United States. brbr brbrStroll along our waterfront and enjoy the charm of our City Dock. Watch the boats as they cruise our famous Ego Alley. Sit on the seawall and watch the sailboat races as they return to the harbor and see why Annapolis is “America’s Sailing Capital.”brbrbrbrOther Things to Note:brbrTo help ensure a smooth, secure, and enjoyable stay for all guests, please review the following important information before booking: brbr brbrCheck-In & Identity Verification Policy brbr brbrAll reservations require the primary guest (the booker) to complete a secure online check-in process prior to arrival. This includes: brbr brbr-Uploading a valid, unexpired government-issued photo ID brbr-Uploading a selfie to confirm identity brbr-Reviewing and signing our rental agreement brbr brbrThis process is similar to hotel check-in and is required because we do not typically have staff on site. Check-in instructions will only be provided once this process is complete. brbr brbrIf you would like to review the rental agreement before booking, please feel free to contact us. brbr brbrIn some cases, we may also request a security deposit and/or apply a damage waiver fee in accordance with booking channel policies. brbr brbr * It typically takes ~1 hour to screen a guest after they book this property and could take several hours if we are busy before we are able to provide them with check-in information.brbr brbrIf you make a last minute reservation, we ask you to please be patient and please do not expect to gain access to the property immediately.brbr brbrGuest Count & Occupancy Policy brbr brbrEach listing includes a maximum number of guests based on unit type and local regulations. Additional guests are welcome for an added nightly fee: brbr brbr-2 & 3 bedroom units: $35 per guest, per night after 4 or 6 guests, respectively brbr brbrPlease ensure your guest count is entered accurately at booking. We will confirm the number of guests after reservation. If the guest count changes, pricing may be adjusted accordingly. For safety and compliance purposes, exterior security cameras are used to verify occupancy. Unreported additional guests may result in additional charges. brbr brbrPet Policybrbr brbrThis is a pet-friendly property. While our cleaning team is thorough, guests with severe pet allergies should be aware that dogs, cats, or other animals may have stayed in the space previously.brbr brbrPet fees:brbr brbr$30 per night, per petbrbr$150 per week, per petbrbr$300 per month, per petbrbr brbrPet fees are included in the accommodation rate as long as you choose the appropriate quantity of pets when completing a booking. We confirm this with all guests post booking confirmation. brbr brbrLocal Reservation Policy brbr brbrReservations under 7 nights from guests residing in the local area may be subject to cancellation at our discretion. We handle exceptions on a case-by-case basis. brbr brbrEarly Check-In & Late Check-Out Policy brbr brbrEarly arrivals and late departures are not guaranteed and must be approved in advance. If approved, the following fees apply: brbr brbr-Up to 1 hour: $100brbr-1–2 hours: $200 brbr-2–3 hours: $300brbr-3+ hours: $400 or the cost of an additional night (whichever is greater) brbrbrbr- Please note we do charge a $25/day fee for access to the laundry for parties with a 7-day or less staybrbr brbrPlease do not assume availability without confirmation. brbr brbrSmoking Policy brbr brbrSmoking is not permitted anywhere on the property, including indoor and outdoor areas. If evidence of smoking is found, an additional cleaning fee of $500 will be applied in accordance with the booking channel's cleaning and damage policies. brbr brbrSpecial Request Policy brbr brbrRequests for items such as pack-n-plays, high chairs, or other non-standard amenities should be submitted at least 7 days before check-in to ensure availability. Requests made closer to arrival will be accommodated if possible but cannot be guaranteed. brbr brbrWe understand that this is a detailed list, and we truly appreciate you taking the time to review it. These guidelines help us maintain a safe, well-cared-for property and ensure a great experience for every guest. Our goal is always for you to feel comfortable, welcome, and well taken care of during your stay.brbrbrbrLicense: RENT-005413-2024brbrbrbrCity/town permit number: STR23-145316.

Cute bungalow blocks to Stadium

Annapolis, Maryland, United States

Bed

1

Bath

6

Sleeps

$289.41

This ground floor, private entrance condo has been fully renovated w/ new paint, floors, bath & kitchen. Queen Bed & sleeper couch is a full size. Linens included. Kitchen includes refrigerator, stove/oven, microwave, keurig, dishes silverware, pots and pans. High speed internet included & separate work area. Pets case by case. Street parking included, will send details to get a free pass.

Apartment

Annapolis Escape, Steps to Harbor backs to Gate 1

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1203.2

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWelcome to your Eastport escape! brbr brbrThis newly decorated custom home has everything—Severn River views, a huge private yard, stylish interiors, and parking for 2–3 cars. Just a short mile’s walk to Downtown Annapolis, the Naval Academy, and Eastport’s best dining and shopping, you’ll be perfectly positioned for relaxation and adventure. brbr brbrMain Features brbrMain Floor brbrGourmet kitchen with high-end appliances brbrOpen dining & family room with cozy gas fireplace brbrWalk out to deck, backyard with fire pit & gas grill brbr brbrSecond Floor brbrKing suite with ensuite private bath + balcony brbr brbrKing Guest room with balcony brbrFamily bedroom: 2 Queens + 2 Twin trundles brbrShared buddy bath with double vanities, shower + soaking tub brbr brbrThird Floor brbrPrivate King suite with spa-like en-suite (shower + tub, double vanities) brbrBalcony with sweeping Severn River views brbr brbrHighlights brbrGourmet kitchen + dining for 6–8 brbrExtra dining nook (seats 4) brbrHuge outdoor lounge + dining space brbrGas grill + wood-burning fire pit (BYO firewood) brbrBalconies off back bedrooms brbrDriveway parking for 2–4 cars + free street parking brbrHigh-speed WiFi + smart TVs brbrLuxury linens & toiletries brbrWasher/dryer brbrKeyless entry + mobile app instructions brbr brbrClose to Everything brbrDowntown Annapolis – 0.9 mi brbrU.S. Naval Academy – 1 mi brbrWashington, DC – 33 mi brbrBaltimore – 33 mi brbr brbrHouse Rules brbrNo groups under 25 without adult present brbrNo smoking, pets, parties, or events brbrPlease respect the neighbors brbrCheck-in: 4:00 PM brbrCheck-out: 11:00 AM

All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis

Annapolis, Maryland, United States

Bed