Vacation Home Rentals By Owner In Annapolis, MD

$547.91

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis, Maryland, United States

Looking to explore Annapolis and live comfortably on a budget This cozy square house will be just right for you! The single family house is situated in a very convenient location! Bus stop right across the street, close to the west street, lots of restaurants and fun places, only 5 minutes drive to downtown Annapolis and Naval Academy. Relax with the whole family at this peaceful place to stay.

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$733.07

/ Nightly

Private Vacation Home

5 bedroom house with EV charger Near Downtown Annapolis

Annapolis, Maryland, United States

brExperience coastal charm and modern comfort at Voyagers’ Nest, a spacious 5-bedroom retreat near downtown Annapolis and the U.S. Naval Academy. Enjoy two living rooms, a fully equipped kitchen, and a private fenced backyard—perfect for families and groups. Your stylish home base for exploring Maryland’s historic waterfront city.brbrThis wonderful 5-bedroom gem in Annapolis features 3 king beds, 2 queen beds, 1 twin bed, 1 trundle bed. With amenities like AC, heating, and an iron, guests will have an enjoyable stay. The 2 bathrooms come equipped with a hair dryer, shower, and bathtub. Your phenomenal vacation awaits at this lovely property. We'll be available to answer any questions while you stay at our place.

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$1832.14

/ Nightly

Private Vacation Home

Spacious Converted Carriage House in Historic District near USNA

Annapolis, Maryland, United States

Relax in this updated and sophisticated house near the USNA in Annapolis with the largest garden in downtown. This tranquil retreat features 4 king bedrooms (two with baths ensuite) with 3 1/2 bathrooms offering luxurious touches like spacious showers. Dining, inside or out, accommodates all occupants. The house has good flow and can accommodate 40 for an inside buffet dinner or outside. AC and heating ensure a comfortable stay year-round. We look forward to hosting you at our place.

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$582.07

/ Nightly

Private Vacation Home

All-stop. Rental Midships.

Annapolis, Maryland, United States

Whether you have come for Commissioning Week or Boat Show, the aptly named Gatehouse is a centrally located townhome steps away from Gate One, City Dock Waterfront, and all the attractions that Historic Downtown Annapolis has to offer.brbrSettle into this spacious, well-appointed townhome in the heart of Downtown Annapolis. This detached townhome, professionally cleaned and beautifully maintained, is the perfect lodging for USNA families and events, wedding parties, and weekend explorers.brbrEnjoy your morning coffee in the quiet courtyard and, when the sun's passed the yardarm, your evening brightener on the third-floor deck, which boasts a view of the Naval Academy Chapel! If sipping a whiskey while lounging on a deep leather sofa or a Churchill armchair is more your speed, the main deck living space is the place to relax. Should you desire to escape the hustle and bustle of Randall St-tuck in and watch a movie, play a video game on the PS4, or read a book in the topside living room.brShould the inspiration to cook strike, the kitchen boasts new appliances, a chef's quality knife set, and cooking ware. In addition, groceries are just a click away from Instacart and Whole Foods Delivery through the Amazon app!brbrEventually, when the time comes to turn in, the bedrooms have taken care of your comfort needs. Down pillows, cozy comforters/quilts, and soft bathroom linens make decompressing from a long day of exploring Annapolis easy. The main bedroom has a queen bed, an ensuite bathroom, and a room-length closet for all your organization needs. The forward guest bedroom has a queen bed, a brass crib, and a separate bathroom with a combination tub/shower.brbrDue to a change in city regulations, unlimited parking passes for residential street parking can no longer be provided to guests. We provide one 24-hour pass for stays under three nights and two passes for four nights or more. However, you may pay to park on the street for up to 3 hours. In addition, the city does provide free parking from 6 PM Friday to 6 AM Monday at the Calvert Street Garage (19 St. Johns Lane). brbrYou can also park in the following garages/lots:brbr-South Street Lot (South Street, off Church Circle; $15/day; 10-minute walk to house)br-Gotts Court Parking Garage (25 Northwest Street; $15/day; 13-minute walk to house).br-CURRENTLY UNDER CONSTRUCTION, OPENING SUMMER 2023-Hillman Garage (150 Gorman Ave, entrances from Main Street or Duke of Gloucester; $20/day; 5-minute walk)br*The free Annapolis Circulator bus stops at all the city garages/lots and City Dock (closest stop to the house) and can be used to get to/from the garages. Please view the Annapolis Parking and Access Annapolis websites for further details.brbrLicense #: STR21-144994br

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$629.34

/ Nightly

Private Vacation Home

Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly

Annapolis, Maryland, United States

A serene escape awaits you at our cozy 4-bedroom, 2.5 bath retreat! We are just minutes from Historic Downtown Annapolis and nestled in a private beach community. As the sun sets, the deck comes alive under the soft glow of string lights, beckoning you to unwind in our 8-person hot tub or outdoor firepit with your worries melting away! Indulge in the culinary delights of fresh local seafood and world-renowned crabcakes just moments away. Truly indulge in our paradise getaway and experience everything Historic Annapolis has to offer! Your Annapolis Retreat Awaits! br brFeatured Amenities:brbr• 8-person Bullfrog Hot Tub br• Stunning water views from the front porch br• Fire Pit with hanging egg chairs br• Outdoor hammock br• Deck with outdoor dining under string lights br• Private Beach Community Access br• 2 paddleboards for your use (drop in within br walking distance) br• 75 smart TV with surround sound br• 4 separate bedrooms (1 king/3 Queen) brbrbrUpper-Level Amenities:brbr• 2 Bedrooms (1 Queen, 1 King), 1.5 Baths (tub)br• Full Kitchen & Dining Roombr• Cozy Living Room with Wood Burning Stovebr• Master Bedroom with Luxurious King Bed, half bath, and TVbrbrbrLower-Level Comfort:brbr• 2 Bedrooms (2 Queen Beds), 1 Full Bath (shower)br• Laundry Room for Added Conveniencebr• Spacious TV Room with small Yoga Areabr• Dedicated Office Space with Desk and Chair for Remote WorkersbrbrExperience the perfect blend of comfort, convenience, and coastal charm at our Annapolis retreat. Your unforgettable getaway starts here!

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$569.11

/ Nightly

Private Vacation Home

Steps to USNA with Large Private Patio & Free Off-Site Parking

Annapolis, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrStay in this restored historic Annapolis home, located just steps from both USNA Gates 1 and 3. The proud Navy graduate parents have kept the historic charm while updating important amenities. You'll enjoy the renovated kitchen with stainless-steel appliances, gourmet accessories and easy access to the large private backyard and patio. The serene backyard is uniquely spacious for the downtown area and is fully-furnished from the dining table with seating for 6-8, the umbrella covered sofa and chairs and even a bar top table with seating for another 4. brbr brbrBack inside, the dining room is perfect for entertaining with seating for 8-10. Relax around the comfortable furnished family room with a large flatscreen TV. Head upstairs to the second level with three bedrooms, two with queen beds, and one with a full size bed and a renovated full bathroom. There's also a dedicated work space on the 2nd floor with a desk and chair. brbr brbrThe home is perfect for families looking to visit the sites of Annapolis or Navy families who would like to be just a few blocks from the Academy. brbr brbr**Parking is not on premises!! A dedicated parking spot at nearby garage (17-minute walk) is provided. Please contact us for details. brbr brbrSLEEPING ARRANGEMENTS 3 BR / 1.5 BA / Sleeps 6: brbrSunny Queen Bedroom: brbr- Second Floor brbr- Queen Size Bed brbr brbrMiddle Guest Bedroom: brbr- Second Floor brbr- Queen Bed brbr brbrGardenview Guest Bedroom: brbr-Second Floor brbr-Full Bed brbr brbrHIGHLIGHTS: brbr- Fully furnished private back patio with dining, lounge and bar seating brbr- Full gourmet kitchen brbr- BBQ Blackstone griddle grill (propane included) brbr- Dining room table seats 8-10 brbr- WiFi brbr- Big Screen TVs brbr- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service brbr- Washer & dryer located inside the home brbr- One Garage Parking Spot located .7 miles from the home. brbr- Dog friendly-$150 non-refundable pet fee due prior to checkin. brbr- Contactless entry. Drive straight to your rental home and enter using the code we will send you prior to checkin. brbr brbrProperty Distance to: brbr- U.S. Naval Academy – 2 blocks to Gate 3; 4 blocks to Gate 1 brbr- Navy-Marin Corps Memorial Stadium - 1 mile 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. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. brbrCheck-in time: 4:00 pm brbrCheck-out time: 11:00 am

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$403.76

/ Nightly

Private Vacation Home

Pet-Friendly Cottage | Walk to USNA Stadium

Annapolis, Maryland, United States

Summary:brbrBring your pup and settle into this bright, renovated West Annapolis cottage. The screened porch is perfect for lazy mornings, and the spacious backyard gives your dog room to run. Two bedrooms, two full baths, a modern kitchen, and a finished basement with a pullout sofa and Smart TV for extra guests. Free parking in the driveway. Half a mile to Navy Stadium, under 2 miles to Downtown Annapolis, and steps from West Annapolis shops and restaurants. High-speed WiFi and central AC throughout.brbrbrbrThe Space:brbrBEDROOMSbrbrTwo bedrooms on the main level with a clean, coastal feel. The primary has a queen bed, the second has a double. Fresh linens and storage provided.brbrbrbrBATHROOMSbrbrTwo full bathrooms with bright, updated finishes. Towels and essentials stocked.brbrbrbrKITCHENbrbrFully equipped with modern appliances and everything for cooking at home.brbrbrbrLIVING AREASbrbrOpen main level with inviting decor and a dining area for gathering. The finished basement adds flexible space with a pullout sofa for extra guests and a Smart TV.brbrbrbrOUTDOOR LIVINGbrbrRelax on the screened porch — perfect for morning coffee without the bugs. The spacious backyard is surrounded by trees, creating a quiet, private retreat. Your dog will love the space.brbrbrbrPARKINGbrbrFree parking in the driveway and on the street.brbrbrbrPET POLICYbrbrPets welcome! We just ask that you clean up after your dog in the yard. Please keep dogs off the furniture and bring a bed or blanket for them to sleep on.brbrbrbrLOCATIONbrbrIn the heart of West Annapolis. Steps from shops and restaurants. Half a mile from Navy-Marine Corps Stadium. Under 2 miles to Downtown Annapolis and USNA. Near the new RAR Brewery Chessie's Wharf.brbrbrbrGOOD TO KNOWbrbr• Check-in: 3:00 PM / Checkout: 11:00 AMbrbr• Self check-in with smart lockbrbr• Pets welcomebrbr• No smoking inside home or on screened-in porchbrbrbrbrGuest Access:brbrKeypad entrybrbrbrbrThe Neighborhood:brbrQuiet residential neighborhood while also located next to shops and restaurants.

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$604.17

/ Nightly

Private Vacation Home

Escape Villa in Downtown Annapolis

Annapolis, Maryland, United States

Perfect getaway, a short stroll to West Street, the Naval Academy, Navy-Marine Corps Memorial Stadium, City Dock, and Downtown Annapolis with all its offerings -- music, dining, nightlife, shopping, and so much more.brbrIdeal for families visiting USNA midshipmen for fall football games, parents' weekends, Commissioning Week, Reunions, and Holidays.

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$392.18

/ Nightly

Private Vacation Home

Timeless Charm Meets Modern Comfort

Annapolis, Maryland, United States

This charming 3-bedroom, 2.5 bath historic duplex in downtown Annapolis offers a perfect blend of timeless character and modern amenities. Featuring hardwood floors, classic architectural details, and an updated kitchen and bathrooms, the home is within walking distance of Annapolis' vibrant waterfront, shops, and restaurants. Enjoy the convenience of city living while embracing the rich history and charm of this well-preserved gem. Ideal for those seeking comfort and style in a prime location.brbrWhy guests love staying at 215 Prince George Street:brbr☼ Historic home right in the heart of downtown Annapolis with tons of charm upgraded features, ideal for families, romantic getaways, or a group of friends visiting historic Annapolis, USNA, and other tourist sitesbr☼ Centrally located in downtown Annapolis, on historic Prince George Streetbr☼ Three bedrooms: Primary: king bed; Guest 1: 1 queen bed; Guest 2: 2 twin bedsbr☼ Two and a half bathrooms: Primary suite has a private bathroom with a walk-in shower; hall bathroom has a tub-shower combo; half bath on the main living levelbr☼ Kitchen with all major appliances, a drip coffee maker, kitchen supplies and tools and morebr☼ Comfortable living room for watching movies and playing gamesbr☼ Private outdoor space - fully fenced with outdoor dining and a gas grillbr☼ Smart TV in the living roombr☼ Fresh linens, towels, toiletries & essentials providedbr☼ Professionally cleaned before each visitbrbrLook no further than this historic home in downtown Annapolis!brbrPlease note that there is no assigned parking for this property. Guests are encouraged to park in nearby public parking garages overnight. There is short-term hourly parking on Prince George Street.brbrPlease note that parts of this home date back to 1775! So there are some charming quirks that you won't find in new builds, like a low ceiling clearance on the stairs, a step up into the primary suite, a step down and then up in the bedroom hallway, and smaller sinks in some of the bathrooms. It's truly a unique experience!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.brbr215 Prince George Street is managed by a small, female-owned business. We're committed to making sure all of our guests feel welcome and have the best trip ever. Book your trip with confidence that not only will this property be amazing, but the service and attention you get will be, too.

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$493.42

/ Nightly

Private Vacation Home

Modern Styled Home in Historic Annapolis Eastport Neighborhood

Annapolis, Maryland, United States

Built in 2021 and freshly styled in 2025 with a unique modern European touch, our family-friendly retreat offers the perfect launching pad for your Annapolis adventures. Imagine strolling through the historic downtown, discovering the local flavors of Eastport's eateries, or watching the boats gently sway in Back Creek. The iconic Naval Academy is also just moments away. Everything most people do in Annapolis is within 1.5 miles, with boat docks, water taxis, and bike routes readily available to get around without a car if desired.brbrYour Comfortable Annapolis Haven:brbr- King Master Suite (2nd Floor): Relax in your spacious retreat with a private full bathroom.brbr- Queen Bedroom (1st Floor): Enjoy a comfortable night's sleep with easy access to a shared full bathroom.brbr- Queen Sofa Bed (Living Area): Perfect for an additional guest, especially those who love to greet the sunrise!brbrWith its prime location in the heart of Annapolis and our personal touch, we invite you to experience the beauty and allure of this special town from the comfort of our Eastport gem. We hope you'll create unforgettable memories here. brbrWhen you're not there, we will be as this is our 2nd home. Welcome to our home!

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$613.9

/ Nightly

Private Vacation Home

Family and Dog-Friendly, Around the Corner from Annapolis Hot Spots with Fenced-In Yard and Parkin

Annapolis, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrStill available for Commissioning Week 2025! brbr brbrWelcome to this beautifully remodeled Victorian home in Eastport, lovingly named Around the Corner for its prime location near Annapolis' best dining, shopping, and waterfront experiences. This 2-story retreat seamlessly blends historic charm with modern conveniences, making it perfect for a memorable getaway. brbr brbrKey Features: brbrInviting Wrap-Around Porch: Begin or end your day relaxing on this quintessential Eastport feature. brbrSpacious Living & Dining Areas: Heart of pine flooring throughout creates a warm, welcoming atmosphere. brbrGourmet Kitchen: Fully updated with custom cement countertops, breakfast bar, and wine fridge. brbrOutdoor Oasis: Enjoy a private fenced-in backyard with a furnished patio, lounge chairs, and gas grill. brbrHigh-End Baths: Luxury fixtures, Restoration Hardware vanities, and boutique-level linens. brbr brbrSleeping Arrangements (Sleeps 8) brbrSunny Front King Bedroom: King bed, walk-in closet, and access to a full hall bath. brbrMiddle Queen Bedroom: Queen bed with access to the hall bath. brbrBunk Room: Twin bunk beds and built-in laundry room. brbrLiving Room: Queen sleeper sofa with access to the 1st-floor full bath. brbr brbrAmenities to Enhance Your Stay: brbrHigh-speed Fios internet (1 Gig) & WiFi brbrFlat-screen TV brbrComplimentary coffee & starter toiletries kit brbrFull-sized washer & dryer brbrLuxury linens & boutique-level service brbrKeyless entry brbrPet-Friendly: Small dogs (50lbs or less) welcome with a $150 non-refundable fee per dog brbrPrivate driveway (1 car) + unrestricted street parking brbr brbrLocation Highlights: brbrDowntown Annapolis: 0.8 miles (3 minutes) brbrU.S. Naval Academy: 1 mile (5 minutes) brbrWashington, DC: 32 miles brbrBaltimore: 30 miles brbr brbrHouse Rules: brbrAge Requirement: At least one guest must be 25 or older. brbrNo smoking brbrNo parties or events. brbrCheck-in: 4:00 pm | Check-out: 11:00 am brbr brbrReady to experience historic Eastport with all the comforts of home Book your stay at Around the Corner and immerse yourself in the beauty and charm of Annapolis!

3

Bed

2

Bath

8

Sleeps

$2014.0

/ Nightly

Private Vacation Home

Luxury Waterfront with Big Views 10 min from Downtown Annapolis

Annapolis, Maryland, United States

The perfect Commissioning Week House! Enjoy the views in this architectural gem- a modern, modified A-frame. It's a true entertainer's paradise: 4 separate deck areas with a waterfront bar, firepit and wired outdoor speakers are perfect for celebrating your grad. Help yourself to our toys- crabbing equipment, 2 kayaks, 2 paddle boards and lots of inflatables for a lazy float. brbrAll kitchen appliances are new in the past year. Main living area is open with a fireplace, large living room and kitchen great room.brbrWhen the party is over, this is also the perfect spot to just relax! Sitting waterside you can have a front-row seat to regular sailboat races and watch cruise ships come up the bay. Help yourself to a book from our extensive library and enjoy it on the outdoor hammock or curled up in the loft. brbrPrimary bedroom is very spacious with an ensuite bathroom, big screen TV and a sleep number bed. Bedroom 2 is on the ground floor with an Xbox, TV and queen bed. Bedroom 3 is also on the ground floor with a twin bed and twin trundle. Bedroom 4 with a queen bed and TV is part of a completely detached studio guest apartment for the utmost privacy. Apartment has its own kitchenette and bathroom.brbrLocation is a quiet and private residential street in the charming neighborhood of Atlantis.

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$892.67

/ Nightly

Private Vacation Home

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

Annapolis, Maryland, United States

Home is clean, spacious, and well-maintained, designed for comfort and convenience. Located in a safe residential neighborhood near shopping, restaurants, and the Chesapeake Bay. Short drive to downtown Annapolis and USNA, with easy access to Kent Island, Baltimore, and Washington, D.C. Our space is the perfect gathering spot for weddings, reunions, vacations, holidays, and sporting events. Home Features:brbrSix private bedrooms and a common area with additional beds. The home includes 4.5 bathrooms, a large open-concept kitchen with eat-in dining, a separate indoor dining room, a deck and patio with outdoor seating and dining areas, a screened porch, and a game room. The layout offers ample space for everyone to gather comfortably.brbrSleeping Arrangements:br • Master Suite: King bedbr • Bedrooms 2-6: Queen bedsbr • Common Area: 2 full beds, 1 twin bed, and a futon couch that converts to a full bedbrbrYour stay includes linens, blankets, pillows, and bed coverings to make everyone feel at home.brbrAmenities:br • Game Room: Converted garage with a billiards table, smart TV, beach gear, cards, board games, and pickleball/tennis equipmentbr • Family Room: Vaulted ceiling with skylights, two oversized sectionals, a gas stone fireplace, and a 55” smart TVbr • Kitchen: Fully stocked with dishes, utensils, pots, pans, drip coffee maker, Keurig, basic spices, and more. Opens to the family room, back deck, and screened porchbrbrOutdoor Spaces:br • Screened Porch: Oversized, with comfortable furniture and surrounded by nature—perfect for relaxingbr • Deck: Features a Weber gas grill, large wicker couch, patio table, chairs, and umbrella. Stairs lead down to a paver patio with additional tables and chairsbr • Backyard: Peaceful and private, shaded by mature trees and frequented by birds, including occasional bald eagle sightingsbrbrTech and Utilities:br • Fast, reliable Wi-Fi ideal for streaming and remote workbr • Smart TVs in bedrooms and family room with DIRECTV, MASN, and movie channelsbr • Dedicated workspace for remote workbr • Parking for up to four average-sized vehiclesbr • Washers and dryers on both upper and lower levelsbrbrNeighborhood:br • Pedestrian-friendly sidewalksbr • Paved walking and biking paths to local grocery stores, restaurants, shopping centers, and parksbr • Easy access to Sandy Point State Park, with scenic views of the Chesapeake Bay and Bay Bridge, beaches, swimming areas, grills, picnic pavilions, boat ramps, fishing spots, volleyball and basketball courts, and walking trailsbrbrEco-Friendly Features:br • LED lighting throughoutbr • Solar panels to offset electricity usebr • Recycling containers for paper, plastic, glass, and aluminumbrbrAs your hosts, we aim to provide a welcoming space that makes your stay enjoyable and memorable.

Bed

Bath

Sleeps

$568.01

/ Nightly

Private Vacation Home

Historic Renovated Home in the Heart of Downtown

Annapolis, Maryland, United States

Welcome to our listing on East Street. Located in the heart of downtown our front porch sits in the shade of the iconic Maryland State house dome. Sit and relax on one of our two porches and watch the buzz of town. Two blocks to USNA, City Dock, AYC and every main attraction in town. Our guests use one of the city pay garages to park. Go Navy!brbrIt's an updated historic home furnished by a local designer. Front porch and private backyard with screened in porch is rare in town.brbrNo Parking on site. Guests must park in a city garage.brbrQuiet hours strictly enforced after 10 pm in Historic District.brNo pets, smoking, any kind of parties or additional guests. brExtra fees required for additional cleaning or late check out.brNO GLITTER OR CONFETTI !

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$684.0

/ Nightly

Private Vacation Home

Sailor's Retreat! Perfect home for the getaway weekend. Best location!

Annapolis, Maryland, United States

Beautifully renovated home in the heart of West Annapolis. The main level has been updated to an open floor plan to accommodate modern living. This 3-story home is kept comfortable by dual-zone HVAC and smart thermostats. The yard is fully fenced in, front and back. Less than a mile and a half from downtown, 5 min walk to the USNA stadium, 2-blocks from Weems Creek water access, cafes, restaurants, and shopping.

Bed

Bath

Sleeps

$613.32

/ Nightly

Private Vacation Home

Beautiful Historic Flat next to City Dock + USNA

Annapolis, Maryland, United States

Just steps from Main Street, City Dock, and the USNA (300 ft), you'll be in the perfect location for exploring Annapolis from our historic flat. The home was built in the early 1700's and still retains its original character but was recently renovated. This charming two-level apartment has high-speed WiFi and hotel-quality mattresses and pillows.brbrParking is not available at the home, but a paid parking garage is close by (.3 miles), with a water taxi stop at City Dock to explore Annapolis by boat.brbrOur space has three bedrooms with an additional small area that can be used as a nursery or office. There is a half flight of stairs at the entrance to the home and another half flight within the apartment. Please note that there are two other units in the building, but they are completely separate and have their own entrances.brbrThe kitchen is well-equipped with essential cookware and supplies including coffee, tea, sugar, creamer, olive oil, and spices. There is a new 55 Smart TV that features Netflix, Disney, Hulu, and ESPN. We have the fastest WiFi possible and will do anything to make your stay more comfortable!

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Sleeps

$996.19

/ Nightly

Private Vacation Home

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

Annapolis, Maryland, United States

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.

4

Bed

4

Bath

14

Sleeps

$830.23

/ Nightly

Private Vacation Home

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

Annapolis, Maryland, United States

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.

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Sleeps

$521.48

/ Nightly

Private Vacation Home

Charming, Newly Renovated Historic Row Home in Downtown Annapolis

Annapolis, Maryland, United States

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

3

Bed

3

Bath

6

Sleeps

$1076.16

/ Nightly

Private Vacation Home

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

Annapolis, Maryland, United States

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.

4

Bed

2

Bath

8

Sleeps

Vacation Home Rentals By Owner In Annapolis, MD

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$521.48

$1076.16

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