Vacation Rentals By Owner In Annapolis, MD

This is the perfect getaway home for an enjoyable and relaxing stay in Annapolis. It is conveniently located within walking distance to USNA, Navy-Marine Corps Memorial Stadium, and everything that beautiful downtown Annapolis has to offer.brBe prepared to be impressed with this exquisite and meticulously cleaned and maintained home. We invite you to stay with us for a wonderful and easy-going experience during your time in beautiful Annapolis. brThis home underwent a total renovation in the summer of 2017 with an open floor plan, amenity loaded kitchen and pantry. Features four bedrooms with comfortable furniture and beds, a spacious living room, separate TV/play room, private fenced-in backyard & fully furnished patio and a front porch with seating.

Recently Renovated Annapolis Home - Conveniently Located

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1321.26

IMMACULATE SPACE AND RARE FIND IN DOWNTOWN ANNAPOLIS SLEEPING UP TO 12! Beautifully maintained 1930's home in the middle of Annapolis. Right outside of the hustle and bustle but walking distance to everything. Added bonus of parking for 5+ on site. brbrThis is a split unit with 4BR 3 BA 1 Half Bath in the Main House and 1BR 1 BA in the Carriage House. Perfect for Wedding Parties, multi-family stays, the holidays. THE PERFECT SETUP for Commissioning Week or Reunion Weekends.*NEW* PLAN YOUR NEXT BIRTHDAY GET TOGETHER, WEDDING REHEARSAL DINNER, REUNION, HOLIDAY FUNCTION, OR NAVAL ACADEMY FOOTBALL OR ALUMNI FUNCTION AT THE CHARMER! WILL NOT FIND A PLACE THIS SIZE OR THIS IMMACULATE IN AND AROUND DOWNTON ANNAPOLIS!brbrThis beautiful early 1900’s home is the unique space to host a myriad of different events. Boasting 5 bedrooms spanned across the Main House (4 BR 2 BA 2 Half Bath) and Guest House (1 BR 1 BA) sleeping up to 21! You will not find a space this large and this immaculate in and around Downtown Annapolis!!!brbrCharming Main house - a 10-15 min walk to Navy Marine Corps Stadium / a 5 min drive from the Naval Academy and Downtown Annapolis! Perfect for families with MIDN at USNA or alums in town for a football game or reunion event. There is also ample off street parking (driveway easily fits 5 cars) at the property as well as free on street parking for large groups. Multiple level sleeping makes it great for multi-generations traveling together.brbrThe first floor has a living room and sun room, a half bath, and kitchen with a large dining space to comfortably seat 10 people. Sun room couch converts into a full size sleeper sofa.brbrThe second floor has 4 bedrooms - a master bedroom suite with ensuite bathroom. The other three bedrooms share a full non-master bathroom.brbrFinished basement is perfect for lounging and can be a separate sleeping space (sofa and keg size day bed) with half bath. brbrOutdoor includes front porch with lounge seating, covered back porch with lounge seating and string lighting perfect for dining. Propane gas grill available at the main house.brbrQuaint Guest House - First Floor entry has seating and small storage for extra bags/luggage. Up the stairs to the second floor leads to the kitchen with all amenities of home, breakfast nook seating for up to 7. brbrOff the kitchen is a covered back porch with lounge seating and string lighting. brbrLiving room has large sectional sofa, TV, and table seating for guests comfort and enjoyment. Rollout bed is available in back bedroom closet, and living room couch folds out into a full size bed.brbrEach bedroom has a king size bed and television. These bedrooms share a large oversized bathroom with double vanity. Stackable washer dryer also located in bathroom. br brOutdoor space is PERFECT for lounging, hosting a bbq or dinner (two separate gas grills), or having a private event. Large driveway and oversized backyard which includes covered second story deck with lounge seating, fans, and string lighting. Covered backyard patio area with large dining table with seating for 6 and outdoor tv for watching the game. Another uncovered concrete patio with table seating for 6, as well as a propane fire pit with lounge seating for 6 around it as well along with automatic outdoor landscape lighting to keep the event going after the sun goes down!brbr5+ parking spaces on site with free street parking on adjacent streets. Driveway and paths are lit. Guests will receive unique private code prior to check-in for use on their front and rear private entrances. Guests are able to access both front and rear porches and backyard spaces.brbrEach door is equipped with a keypad. The code will be provided day of check-in. Lighted driveway and pathways for ease of entrybrbrWe charge for additional guests above a fixed amount. This amount and additional charge varies by unit type, size, and configuration. If you input the correct guest count when you make your reservation the amount the booking site indicated as the total cost will not change (due to guest count). We ask for confirmation of guest count after you complete your booking. If you need to increase your guest count after booking confirmation due to a booking error, this could result in a price increase. Finally, we verify guest count via external cameras located on our properties. In the event that we notice a guest count at the property that is higher than reported, we reserve the right to ask for additional guest fees that would be double the amount we would have charged prior to check-in.brbrThe following additional charges may apply to late check outs/early arrivals, assuming I can offer this at all (I often can’t so please never assume this will be allowed): brbr1 hr or less early arrival or late departure: $100br1-2 hr early arrival/late departure: $200br2-3 hr early arrival/late departure: $300br3+ hr early arrival/late departure: $100/hr or the cost of an additional night’s stay, whichever is morebrbrThese fees are primarily in place to highly discourage late checkouts/early arrivals since this causes my cleaning service undue stress to prep the unit prior to your or the next set of guest’s arrival. This also increases the need for them to rush/cut corners, increasing the likelihood of them not cleaning the unit to the high standard which I hold them to.brbr***Smoking is strictly forbidden anywhere on the property - the house, front porch, back deck, or front or back yard***brbr***If we find cigar/cigarette butts of any kind on the property or evidence of smoking (ash on porch, deck, empty cigarette packs, etc.) We assess a $500 cleaning fee in addition to the regular cleaning fee***brbrWe are here to assist should you have questions. Feel free to message us!

Historic Annapolis Charmer <1Mile to NMC Stadium

Annapolis, Maryland, United States

6

Bed

Bath

20

Sleeps

Select Dates for Price

Amazing three bedroom townhome with Masters suite(with full bathroom), and 2 additional bedrooms with access to one full bathroom, 2 half bathrooms, living room, Kitchen, Patio and recreational room. High Speed WiFi included. Conveniently located in a quiet gated community, 5 min walk to eateries, boutiques, and convenient stores. A few minutes drive to Anne Arundel Medical Center, contemporary Annapolis Town Centre, Annapolis Harbour Center, the historic downtown Annapolis (restaurants, shops, museums, art, & history) and the Naval Academy.

Amazing townhome in Annapolis, near Restaurants, USNA, Shopping centers, & more

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$674.32

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrUpscale Family Retreat Near Downtown Annapolis | Resort-Style Outdoor Spaces brbr brbrThis luxury family retreat offers exceptional flexibility and can be rented as one spacious home or two separate private residences, with distinct main-level and lower-level accommodations. Newly decorated and thoughtfully furnished, the home is tucked away on a quiet cul-de-sac just minutes from Downtown Annapolis, offering a peaceful yet convenient setting. brbr brbrThe open main level features a spacious family room and cozy den—each with a flat-screen TV—alongside a beautifully equipped kitchen perfect for shared meals with three dining spaces in the dining room, at the breakfast bar and a sunny four-stop table in the family room. The main level also includes a serene King Suite with a private en suite bath and direct deck access, a comfortable Queen Guest Room with a full hall bath. brbr brbrThe lower level is perfect for extended families, offering two additional bedrooms, a full bath, a second family room, kitchenette, and laundry for added comfort and privacy. brbr brbrOutside, enjoy expansive entertaining spaces with two fire pits, a gas grill, and ample seating. With generous parking and easy access to the Naval Academy, boat shows, and Downtown Annapolis, this home is an ideal choice for family gatherings and special occasions. brbr brbrSleeping Arrangements | 4 BR / 3 BA | Sleeps 10 brbrMain Level King Suite brbrKing Bed brbrPrivate en suite bathroom with separate shower 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 sleeper sofa, linens included brbr brbrLower Level Queen Bedroom brbrQueen Bed brbr brbrLower Level Twin Bedroom brbrTwo Twin Beds brbrLower level bedrooms share a full hall bath with stand-up shower. brbr brbrHighlights & Amenities brbrOpen-concept main level with Family Room, Den, Dining Area & Kitchen brbrDining table seats 8, Breakfast bar seats 6, Four-top Table in Family Room brbrFireplace 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 brbrFull-size washer & dryer on main level, Full-size combo washer/dryer on lower level brbrParking for 3–4 cars brbrKeyless entry for easy self check-in brbr brbrDistances brbrNavy Marine Corp 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 brbrRespect the home, neighbors, and neighborhood brbrCheck-in: 4:00 PM brbrCheck-out: 11:00 AM

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

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$726.75

Experience a cozy retreat in this inviting 3-bedroom, 2-bathroom cottage, just 3 blocks from the historic Spa Creek Bridge in Eastport. Perfect for families or small groups, this home comfortably sleeps 8 and offers the ideal blend of convenience and relaxation.brbrThe Spacebrbr Bedrooms:br Master Suite with King Bed & En Suite Bath (walk-in shower, double vanity)br Guest Room with Queen Bedbr Family Room with 4 Twin Beds (perfect for kids or extra guests)brbr Bathrooms:br Master Bathroom with walk-in shower and double vanitybr Hall Bathroom with tub/shower combobrbr Living Area: Open-plan layout with a spacious family room featuring an L-shaped sectional, a dining table for 8, and a bright, white kitchen. Ideal for gatherings and creating memories.brbrKey Features:brbr Pet-Friendly – bring your furry friends!br Off-Street Parking for 3 Carsbr Spacious Yard for Outdoor Funbr Fully Equipped Kitchen for Home-Cooked Mealsbr Located just a short walk to Spa Creek Bridge and local shops, restaurants, and attractions.brbrWhether you're here to explore the charm of Eastport or simply unwind in a comfortable home away from home, this cottage offers the perfect setting for your stay.

Charm & Style in this Renovated Eastport Home

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1019.16

brbrUnique opportunity to rent an entire triplex Downtown Annapolis! One property with 3 nearly identical side-by-side units. Perfect for large families or multiple families traveling together! You’ll enjoy the best of both worlds – ample privacy for your group but plenty of space to come together. Altogether this property has 6 bedrooms and 3 sleeper sofas, comfortably sleeping 12 to 18 with private parking for 6+cars. 1 mile from the Academy and 1 mile from the stadium, you can't beat the location! Walkable to all downtown offers!brbr**Available for USNA Graduation** Please message for separate listing agreement.brbrThis listing is for 3 side-by-side townhomes in a newly renovated tri-plex! brbrEACH townhome has 2 bedrooms, 1.5 baths, its own kitchen and living room with sleeper sofa, for a total of 6 bedrooms, 3 full baths, 3 half baths, and 3 Queen sleeper sofas – space to sleep 12-18 altogether! brbrIn addition, each unit has its own private patio which can be combined to make one large entertaining space. Plus private parking lot, large yard, gas firepit, grill, yard games and much more!!brbrYour group will have private use of the whole property – huge backyard, gas-fired grill and gas firepit, patio with dining, and plenty of parking (a rarity downtown Annapolis!)This property is perfectly situated between the Academy’s campus and Navy-Marine Corps Memorial Stadium (1 mile from each)! Walking distance to anywhere and everywhere you want to be in downtown Annapolis; plenty of restaurants, shops, USNA & City Dock!

Unique Listing! Entire Downtown Triplex w/Private Parking! Sleeps 12-18. Pets ok

Annapolis, Maryland, United States

6

Bed

Bath

18

Sleeps

$485.27

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrAvailable NOW! brbr brbrNewly Managed Historic Downtown Annapolis Apartment | Dog-Friendly | Walk Everywhere brbr brbrWelcome to your home-away-from-home in this beautifully restored first-floor apartment in a historic 1857 three-flat, located in the heart of downtown Annapolis. Blending classic charm with modern comfort, this thoughtfully decorated space sits on a quiet, family-friendly street just steps from restaurants, shops, waterfront attractions, and the Main Street. brbr brbrBest of all—you’re the only unit with private backyard access, making it ideal for guests traveling with dogs. brbr brbr*Please Note: There is no on-site parking at this home. However, we can help guide to one of the many city garages just a few blocks from the home. brbr brbrCharming Living Spaces brbrWarm, inviting living room with flat-screen TV and direct access to the private backyard brbrFully equipped eat-in kitchen with all appliances and stylish finishes brbrCozy dining area with seating for four—perfect for meals, game nights, or planning your Annapolis adventures brbrFurnished front porch, ideal for morning coffee or evening relaxation brbr brbrSleeping Arrangements | Sleeps 6 brbrKing Suite: King bed with private en-suite bath featuring a stand-up shower brbrQueen Suite: Queen bed with private en-suite bath with tub/shower combo brbrLiving Room: Queen sleeper sofa (linens included) - Door closes off room for extra privacy brbrEach bedroom features its own flat-screen TV for added comfort and privacy. brbr brbrHome Highlights brbrPrivate backyard + BBQ grill with supplied propane brbrHigh-speed WiFi throughout brbrFlat-screen TVs in living room and both bedrooms brbrLuxury linens and plush towels brbrComplimentary starter toiletries, coffee, and essentials brbrKeyless entry for easy, secure self-check-in brbrIn-building coin-operated washer & dryer (2nd floor) brbr brbrUnbeatable Location brbrMain Street: 3 blocks brbrU.S. Naval Academy: 0.4 miles brbrWashington, D.C.: 32 miles brbrBaltimore: 33 miles brbr brbrPerfect for Navy visits, weekend getaways, family trips, or exploring the rich history and waterfront charm of Annapolis—all without needing a car. brbr brbrWe Provide a Curated Starter Kit brbrCoffee & sweeteners brbrShampoo, conditioner, lotion & hand soap brbrPaper towels, toilet paper, dish soap & scrubber brbrFreshly laundered linens and towels on all beds brbr brbrHouse Rules brbrMinimum age to rent: 25 brbrNo smoking, parties, or events brbrDogs welcome with $150 pet fee brbrNo unaccompanied minors brbrQuiet hours observed—peaceful residential neighborhood brbrCheck-in: 4:00 PM | Check-out: 11:00 AM

Apartment

Walk To Main St & City Dock from Historic Downtown Dog-Friendly Apartment

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$661.79

We’re a Navy + Army Family with deep ties to the Naval Academy (and West Point…sorry, Navy fans). We love Annapolis and hope you can utilize our home to create lasting memories for your family. Walk to The Naval Academy, Restaurants, Bars, Navy Football Games, and Historic Sites. Enjoy your morning coffee in Acton's Cove Waterfront Park – just steps from the front door. Don’t miss the HOME GAMES of Navy’s 36 varsity sports, and 12 club sport teams!!! We’d love to host away fans – if you are unfamiliar with Annapolis, this is the perfect location experience all of Annapolis!

Annapolis Downtown - Historic Home - Brand New Furnishings. Walk to attractions

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$934.8

BOOK YOUR ANNAPOLIS VACATION AT BURLEY CREEK HIDEAWAY!brbrCharming home owned by USNA grads.brbrLovely waterfront two-level private home (4-bed, 3-bath) on half acre lot just 5.5 miles to historic downtown Annapolis, USNA and St John’s College. Private pier for waterside fun—boating, swimming, paddling, fishing, crabbing or sunbathing. Designed around entertaining, guests will be elated with the spacious well-equipped kitchen which overlooks the family room, screened in porch and the waterfront/dock. There is a separate dining area and plenty of room for everyone to dine indoors or out. The main floor beams with natural light and western exposure to adorn guests with legendary sunsets. You will also be close enough to hear the call to colors from the Annapolis Naval Station at sunrise and sunsets each day. The perfect home for families and small groups to gather for local college events, sporting matches, boat shows, weddings, etc. Easy day trip access to Baltimore, Washington, DC and the Eastern Shore.brbr– THE PROPERTY –brbrCentrally located Burley Creek Waterfront with quick and easy access to Chesapeake Bay, downtown Annapolis, Sandy Point State Park and the eastern shore | Covered and Screened Outdoor Dining | Private Pier | Large yard for waterside games & relaxationbrbrSLEEPINGbr• Main Floor Primary Bedroom 1: King Bed with en-suite bathroombr• Main Floor Bedroom 2: Queen (access to shared main level bathroom)br• Main Floor Bedroom 3: 2 Twins (access to shared main level bathroom)br• Lower Level Bedroom 4: King + Full Sleeper Sofa (access to shared basement bathroom)brbrOUTDOOR LIVING: Screened porch overlooking the water with table, bar seating, plus sitting area. Propane grill provided. Private 65' pier for swimming, fishing, boating. Included with your stay: crab traps, 2 kayaks, SUP, canoe, cornhole, yard JENGA and yard dice.brbrINDOOR LIVING : Open layout, brick accent wall fireplace, Roku smart TV, dining table for 8brbrKITCHEN: Fully equipped, Sub-zero refrigerator/freezer, stove, ovens (2), dishwasher, microwave, Keurig coffee maker, toaster, blender, cooking basics. Seating for 5 at built-in table overlooking family room.brbrGENERAL: High-speed FIOS gigabit WiFi, linens, bath & beach towels, washer/dryer, central air conditioning/heating, ceiling fans, closetsbrbrPARKING : Large private driveway with parking for 6+ vehiclesbrbr– THE LOCATION –brbrHISTORIC DOWNTOWN: William Paca House & Garden (6.2 miles), Armel-Leftwich Visitor Center (6.4 miles), Annapolis City Dock (6.4 miles), Maryland State House (6.3 miles), Annapolis Maritime Museum (7.5 miles)brbrOUTDOOR ACTIVITIES: Burley Creek (on-site), Sandy Point State Park (5.4 miles), Annapolis City Marina (7 miles), Quiet Waters Park (10 miles), Port Annapolis Marina (14.1 miles), Herrington Harbour - Herrington on the Bay (30 miles)brSHOPPING: Groceries (4.6 miles), Liquor store (3.4 miles), Sam’s Club (8.2 miles), Costco (28.3 miles)brbrATTRACTIONS: Hammond-Hardwood House (6 miles), The Chesapeake Children’s Museum (7.1 miles), Pirate Adventures on the Chesapeake (7 miles), Top of the World Observation Level (34.8 miles), Fort McHenry National Monument & Historic Shrine (29.8 miles)brbrUS NAVAL ACADEMY: Navy-Marine Corps Memorial Stadium (5.5 miles), Alumni Hall (5.5 miles), US Naval Academy Museum (5.5 miles), Crypt of John Paul Jones (5.5 miles), Naval Academy Chapel (5.5 miles), Bancroft and Memorial Hall (5.5 miles)brbrDAY TRIPS: Baltimore, MD (30.9 miles), Washington D.C. (35.8 miles), Georgetown (40.5 miles), Rehoboth Beach, DE (89 miles), Philadelphia, PA (121 miles)brAIRPORTS: Baltimore/Washington International (BWI) (23 miles), Ronald Reagan Washington National Airport (DCA) (40.2 miles)brbr– DECOMPRESS AT BURLEY CREEK HIDEAWAY –brbrBurley Hideaway makes it easy to rest and relax with family/friends. You can find peace of mind knowing that our property will always be ready for you and that we’ll be responsive 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our home to make you feel welcome in America’s Sailing Capital.brbr– FAQs –br• Q: Can I bring my boat A: Of course! Our private pier is 65 feet long and has slips for multiple boat docking configurations. Water depth at the end of the pier is ~8', other slips range from 4-8' depending on where you dock. There is 40A service and water. Please reach out ahead of time if you plan to bring a boat.br• Q: What type of coffer maker do you have A: Both a Keurig and standard drip coffee maker. We have filters. br• Q: Do you have 'stuff' for small children (crib, plates, etc.) A: Yes, we have a pack-n-play with extra mattress and linens, high chair, baby gate, child dishware and utensils. The primary bedroom has a bathtub.br• Q: If we want to stay in, do you have games or other things to do A: We have numerous family-friendly games, lots of cards, as well as numerous books and magazines about the local area. br• Q: Can I use the kayaks/SUP/canoe Where can I go A: Two kayaks, a SUP and canoe are provided at no charge. Please wear a lifejacket. The house is a short paddle to Mill Creek and Whitehall Bay/Chesapeake Bay. Feel free to explore the local waterways - they are magical.br• Q: Are there steps in the house A: Yes, there are steps up to the front door which leads to a split foyer. If you enter in the garage, there are no steps required to get to a bathroom with shower and the large lower level suite with king bed, sitting area, and pull-out sleeper sofa. br• Q: Can I fish/crab off the pier Do you provide any equipment A: Sure can! We provide 2 crab traps. We do not provide fishing poles but you're welcome to bring your own. You'll need bait for both.br• Q: I plan to have a group of 8-10 people over for a birthday party, is that okay A: Yes. Our no-party policy is for large events where the expected number of participants is greater than allowable overnight guests (e.g. large bridal showers, graduation parties, weddings/receptions). Please be respectful of noise - the home is in a residential neighborhood. No parking in front of neighboring houses.brbr– POLICIES –brbr• Must be at least 25 years old to book (NO EXCEPTIONS)br• No smoking or vapingbr• Pets - please inquire if you require a service animal or need to bring a small pet (10 lbs).br• No events, no big parties or large gatherings (house is in residential neighborhood and loud parties will not be tolerated)brbr– WAIVERS –brbrGuests and all occupants use the pier and assume all risk associated with water activities, including on the water. Guests and all occupants swim and use the kayaks/SUP/canoe at their own risk and are responsible for ensuring they are in good condition prior to being used. Lifejackets must be worn at all times. Booking the property implies acceptance of the above and all house rules by all guests and occupants of the property who hold harmless the owners from any and all claims, liabilities and/or litigation arising from the use of the property, creek/water, kayaks, paddle board, canoe.brbrSTR Permit #000392brbrContact owners with any questions.

Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1105.72

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrBrilliantly Updated Multi-Level Retreat Walkable to Navy Stadium & Close to Historic Downtown Annapolis brbr brbrGather your family and friends for an unforgettable Annapolis stay in this beautifully updated split-level home, ideally located less than a mile from Navy-Marine Corps Memorial Stadium. Designed with multi-family and extended family travel in mind, this spacious home offers multiple living areas across four levels, so everyone can be together and have room to spread out. brbr brbrFrom Navy games and Commissioning Week to weddings and waterfront weekends, this home is the perfect home base for making lasting memories. brbr brbrDesigned for Gathering & Connection brbrInside, you’ll find bright, comfortable spaces for every part of your stay: brbrOpen main living area perfect for group gatherings brbrModern kitchen with stainless steel appliances brbrLower-level den with sectional seating—ideal for movie nights brbrMultiple levels offering privacy for multiple families brbr brbrIncredible Outdoor Living brbrEnjoy Annapolis evenings in thoughtfully designed outdoor spaces: brbrExpansive decks and patios for relaxing and dining brbrScreened porch with TV + mini fridge—perfect for crab feasts brbrFire pit for s’mores and late-night conversations brbrProfessionally landscaped yard with ambient lighting brbrFully fenced backyard (please note gaps, pets at owner’s risk) brbr brbrSleeping Arrangements brbrSleeps 13 Adults - 6 Bedrooms | 3.5 Bathrooms brbrThird Level brbrKing Suite (Sleeps 2) - King bed, Private balcony, En-suite bath with double vanity and walk-in shower brbrQueen Bedroom (Sleeps 2) - Queen bed brbr brbrSecond Floor brbrFamily Bedroom (Sleeps 3) - Queen bed, Twin daybed brbrKing Bedroom (Sleeps 2) - King bed brbrHall Bathroomm- Full bath with tub/shower combo brbr brbrTop Floor brbrFront Queen Bedroom - Queen bed brbrGarden Queen Bedroom - Queen bed brbrHall Bathroom - Full bath with stand-up shower brbr brbrLower Level Recreation Room brbrLarge sectional sofa brbrFlatscreen TV brbrRemote gas fireplace brbrSpace for queen air mattress (provided with linens) brbr brbrAmenities brbr• High-speed WiFi brbr• Multiple Smart TVs brbr• Washer & dryer brbr• Luxury linens brbr• Complimentary starter kit of toiletries, soaps, paper products & kitchen essentials brbr• Keyless entry with private side entrance brbr• Driveway parking for 4 cars + unrestricted street parking brbr• Dogs allowed with $150 non-refundable fee paid prior to checkin brbr brbrLocation brbrNavy-Marine Corps Memorial Stadium – 0.5 miles brbrU.S. Naval Academy – 2 miles brbrHistoric Downtown Annapolis / City Dock – 2 miles brbrWashington, DC – 30 miles brbrBaltimore – 30 miles brbr brbrHouse Rules brbr• Primary renter must be 25+ years old brbr• No parties, events, or smoking brbr• Quiet hours enforced – please respect our neighbors brbrCheck-in: 4:00 PM brbrCheck-out: 11:00 AM

Brilliantly Updated Multi-Level Walkable to Navy Stadium & Close to Historic Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$449.86

Welcome to this charming five-bedroom, two-bathroom escape nestled in the Hillsmere Shores neighborhood of Annapolis. Just a short 7 minute drive from downtown Annapolis, the Naval Academy and Navy-Marine Corps Memorial Stadium, our home offers the perfect blend of convenience and charm. With ample space to accommodate up to 9 guests, this retreat is perfect for families, friends or groups seeking a uniquely memorable experience. Book now for an unforgettable stay!brbrBedroom Configuration:brbrBedroom 1: Queen bedbrBedroom 2: Queen bedbrBedroom 3: Queen bedbrBedroom 4: Twin over full bunk bedbrBedroom 5: Sleeper sofa (located in the downstairs living area)brbrThe property is designed with ease and comfort in mind, beginning with the large wrap around driveway, providing ample off-street parking for 4-5 vehicles and featuring five bedrooms and two bathrooms, as well as a fully equipped kitchen, spacious back deck, and two comfortable living spaces. Each bedroom is outfitted with comfortable beds, freshly laundered, high quality bedding, and blackout curtains, ensuring that you have a restful night's sleep. brbrIndulge in two distinct living spaces, thoughtfully laid out for your enjoyment. The first living area boasts a 55-inch smart TV with surround sound, perfect for movie nights or catching up on your favorite shows. The large U-shaped couch provides ample seating for everyone to gather and unwind. brbrDescend into the lower living area, where the allure of a gas fireplace awaits. Featuring a 65-inch smart tv, large couch and lounge space, dry bar complete with a beverage fridge and high-top table - it is the ultimate space for laughter, games, and creating unforgettable memories. Watch tv/movies, listen to music, play any of the fun games provided, or use the large chalkboard to invent your own games, there is no lack of entertainment to be had in this space.brbrCook up delicious meals in the full kitchen, equipped with modern appliances, granite countertops, and a convenient breakfast bar. An electric tea kettle, Keurig coffee maker (and K-cups), 12-cup drip coffee maker (including filters and basic coffee grounds), as well as many other kitchen essentials are provided for your convenience. brbrContinue past the kitchen outside where you'll discover a spacious deck and comfortable outdoor seating. Accented with overhead string lighting and complete with a propane BBQ grill, this is the perfect spot for a cookout under the stars or happy hour with family and friends. A privacy screen ensures you can enjoy your outdoor space with tranquility.brbrThe five bedrooms offer comfortable sleeping arrangements for up to 9 guests, featuring three queen beds, a twin-over-full bunk bed, and a sleeper sofa located within the downstairs living area. And don't worry about packing too much, as the washer and dryer are at your disposal. Two of the bedrooms also offer desks and seating in the event one or more guests require a private area to work.brbrThe neighborhood offers multiple water access points and a community beach (beach requires resident parking pass). The massive Quiet Waters Park is located directly next to Hillsmere Shores and can be accessed without leaving the neighborhood. Quiet Waters Park offers many trails, overlooks, pavilions, kayak launches, art exhibits, summer concerts, and beaches - a wonderful place to take a walk, bike ride, or car ride ($6/day per vehicle. Walk-ins & bike-ins are free). Feel free to reach out to the host (or check the Quiet Waters Park website) for notable events happening during your stay.brbrWhether you're a group of friends, a family, or colleagues, our property provides the perfect blend of space, amenities, and fun to make your Annapolis trip truly memorable. With the Naval Academy and downtown Annapolis just a short distance away, you'll have endless opportunities for exploration, dining, and entertainment.brbrThe large wrap around driveway offers plenty of off-street parking for up to five vehicles, with additional street parking available as needed. brbrCheck-in is simple with keyless entry. Arrive to the property and enter your personal code into the front door smart lock. brbrThe detached garage and shed in the back yard are not available for guest use. There is a locked owner's cabinet in the laundry room. Other than that, the remaining living spaces are available to guests.brbrBasic toiletries and supplies are provided:brbrKitchenbr- Pots, pans, dishes, cups, mugs, drinkwarebr- Cooking oil, salt, pepper, old baybr- Keurig coffee maker and K-cupsbr- 12 cup drip coffee maker, coffee and coffee filtersbr- Sugar and powdered creamerbr- Tea/hot water kettlebr- Tea bagsbr- Toasterbr- Paper towelsbr- Dish soap and scrubberbr- Dishwashing detergentbrbrBathroomsbr- Shampoo, conditioner, body washbr- Toilet paperbr- Hair dryerbr- Bath towelsbr- Makeup removal towels (please use the black towels for makeup removal)brbrBedroomsbr- All beds are made with fresh laundered sheets and beddingbr- Steamer and iron & ironing boardbrbrLaundry roombr- Laundry detergentbr- Dryer sheetsbr- General cleaning suppliesbrbrALL reservations must include at least one individual that is 25 (twenty-five) years old or older. An accompanying adult must be staying in the unit with younger guests at ALL times. brbrNo pets.brbrChildren 12+ only. This property is not suitable for children under 12 years old. brbrNo smoking or parties. Please be respectful of the neighbors and neighborhood.brbrDeck/outdoor quiet hours:br- Weekdays: 9:30pm - 8:00ambr- Weekends: 10:30pm - 8:00ambr- Guests may still use the deck after hours, but please keep music and noise levels low and be respectful of the neighbors and neighborhood.brbr********************br35 minutes to Baltimorebr45 minutes to Washington, D.C.br20 minutes to the Chesapeake Bay Bridge

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$647.9

Bring your boat, your fishing gear, and your appetite for coastal charm! This 3BR/2BA Annapolis cottage offers access to a private beach, fishing pier, playgrounds, and a hot tub—all just 10 minutes from City Dock and the Naval Academy. Spacious, pet-friendly, and perfect for families, couples, or a weekend getaway.brbr2-story great room + gourmet kitchenbrPrivate beach & pier in the neighborhoodbrBring your boat, paddle boards or kayaks!brFire pit + hot tubbrRelaxed, coastal community vibebrPet-friendly and full of wildlifebrbrThe property is a short distance from Thomas PointPark, and a 10 minute drive to Annapolis City Dock, Quiet Waters Park, and the US Naval Academy. This house was made for relaxation, celebration and entertainment and has something special for everyone. Enjoy a drink on the beach, relax in the hot tub, fish/crab from the community pier, enjoy our vibrant local wildlife, make smores around the firepit or gather on the porch for a crab feast!

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Annapolis, Maryland, United States

3

Bed

Bath

8

Sleeps

$353.9

Don’t miss our unique two floor condominium in Historic Annapolis downtown with 3 bedrooms (one queen, two rooms with two singles per room), living room with 42' flatscreen tv, stereo, kitchen with stainless appliances and granite countertops, and two full bathrooms. Hardwood floors throughout. This unit requires guests to climb two flights of steps. You will be glad you did as it is an oasis in the heart of Historic Annapolis!brbrThere is a large deck with city views of the historic Maryland State House. brbrThe condo is one half block from Main Street, where coffee bars, restaurants, shops, entertainment and history awaits. The condo is within five blocks of the Naval Academy, City Dock and the harbor. Historic Annapolis is a great place to walk and enjoy the sites, the water and the entertainment, with live music, carriage rides and piano bars. There are local theatres, antique shops, boutique clothing shops and art shops all within a few blocks.brbrKeywords: Historic District - Downtown - Condominium - Two Story

Condo

Annapolis Condominium in the heart of the historic center

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$498.38

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWaterfront Condo with Spa Creek Views, Rooftop Pool & Prime Eastport Location brbr brbrExperience Annapolis from this beautifully-renovated 2-bedroom, 2-bath condo that feels like a luxury hotel suite. Nestled on a quiet Eastport cul-de-sac, this top-floor unit offers sweeping views of Spa Creek and downtown Annapolis. Guests enjoy access to a rooftop pool and terrace, marina, and off-street parking—all just a short walk to downtown, Eastport restaurants, yacht clubs, and marinas. brbr brbrThe open-concept living area features a well-equipped kitchen, dining area for 6, and a living room with water views from almost every window. The sofa converts into a Queen bed for additional guests. brbrStep onto the private furnished balcony to enjoy your morning coffee or sunset drinks overlooking the creek. brbr brbrSLEEPING ARRANGEMENTS (Sleeps 7) brbrKing Suite brbrKing bed brbrEn-suite full bathroom brbrVanity area in bedroom brbrFlatscreen TV brbr brbrGuest Bedroom brbrTwo Twin daybeds with third pull-out Twin brbrFlatscreen TV brbrFull hall bathroom with stand-up shower brbr brbrLiving Room brbrQueen sleeper sofa (linens provided) brbrAccess to full hall bathroom brbrFlatscreen TV brbr brbrAMENITIES & HIGHLIGHTS brbrRooftop terrace & pool (open late May–Labor Day; specific hours apply) brbrMarina access & water taxi nearby brbrCoin-operated laundry in building basement (bring quarters) brbrHigh-speed WiFi brbrKeurig coffee maker with starter pack brbrLuxury linens & starter toiletries provided brbr3 smart TVs brbrParking for 2 cars in lot + unrestricted street parking brbrSecure access with elevator brbr brbrPROPERTY DISTANCE TO: brbrDowntown Annapolis: 0.5 miles (10 min walk) brbrU.S. Naval Academy: 0.8 miles (15 min walk) brbrWashington, DC: 34 miles brbrBaltimore: 31 miles brbr brbrHOUSE RULES: brbrNo pets / No smoking brbrNo parties / Quiet hours: 10pm–8am brbrPrimary renter must be at least 25 years old brbrNo teen or young adult groups without accompanying adult brbrCheck-in: 4:00 PM brbrCheck-out: 11:00 AM

Condo

Prime Eastport Location - Waterfront Condo with Parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$704.58

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrThis is a unique home like none other in downtown Annapolis. Originally the Eastport Volunteer Fire Company, founded in 1864, Eastport native Art Tuers joined the company in 1949 at the age of 16. The largest fires Tuers and the dozen or so other active volunteers battled were at the Carvel Hall Hotel in 1961, in the building which was later restored as the William Paca House! brbr brbrLocated across the Annapolis harbor, the Maritime Republic of Eastport offers unique views of the Naval Academy, the Chesapeake Bay and the Annapolis Marina. Located a short walk from the home is Eastport Restaurant Row, serving up fresh seafood along with great steakhouses, it’s the perfect place to get away from the bustle of downtown. It’s also one of the only areas where you can dine right alongside the water, enjoying a great meal while catching the sun dipping behind Annapolis. brbr brbrWhen entering the home on the first floor, you will be welcomed by the original brick floors in the foyer mudroom. Take the wooden staircase up to the second floor where you will find the 9-foot ceilings over the open kitchen, dining and family room which opens onto a fully-furnished screened-in porch with a gas fireplace. In addition to the living space, the 2nd floor has 2 En Suite bedrooms: the Master features its own large balcony facing the quiet neighborhood street. To find the living sleeping space on the first floor, either walk down the spiral staircase from the family room or enter from the garage door off the 1st floor entrance. The 1st floor has a full living/bedroom space with a queen bed, sleeper sofa and full bath and a 2nd living space/rec room with a kitchenette in the garage. brbr brbrAll 3 living spaces have big-screen TVs; all bedrooms have their own TV. brbr brbrSLEEPING ARRANGEMENTS 3 BR / 3 BA / Sleeps 8: brbr brbrMaster Bedroom: brbr- Second Floor brbr- Queen Size Bed brbr- Full En Suite Bath with double vanity and large stand-up shower brbr- Flat screen TV brbr- Balcony brbr brbrBedroom 2: brbr- Second Floor brbr- Queen Size Bed brbr- Full En Suite Bath with stand-up shower (has 2nd entrance into the hallway) brbr- Flat screen TV brbr brbr1st Floor Bedroom/Living Room: brbr- Queen bed brbr- Queen sleeper Sofa brbr- Flat Screen TV brbr brbrHIGHLIGHTS: brbr- Covered balcony off the Master Bedroom brbr- Screened-in patio off the Family Room with brand new furniture brbr- Breakfast Bar seats 3 brbr- Spacious gourmet kitchen brbr- Dining room table seats 6-8 brbr-Additional furnished rec room in garage with 3rd living space, kitchenette and TV brbr- WiFi brbr- Big Screen TVs in each living and bedroom brbr- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service brbr- Parking for one car outside garage brbr- Washer & dryer located on the first floor 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 brbr brbrProperty Distance to: brbr- U.S. Naval Academy – 1.5 miles brbr- Washington, DC – 30 miles brbr- Baltimore - 25 miles 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 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 unless requested and $150 deposit paid prior to check-in. 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

Eastport Historic Firehouse with Parking, Dogs OK

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$437.45

Stay in this iconic building at the intersection of State Circle and Maryland Avenue in the Historic District of Annapolis. Walk to everything!!! Apartment is on the second floor and attic level and includes (1) queen bedroom, (1) attic bedroom with (2) twin beds, loft area with futon, new kitchen, large living area with queen sofa bed and (2) full bathrooms. Step out of the apartment onto a side porch that overlooks the State House and gardens.brThe State employees parking garage is free on weekends and evenings, and there are two additional parking garages within 6-8 minuteswalking distance. There is no off street parking available for the apartment.

Apartment

Spectacular Location: State Circle Apartment

Annapolis, Maryland, United States

Bed

Bath

7

Sleeps

$475.0

Experience an exceptional waterfront setting in the Sailing Capital of the World. This upgraded 2‑bedroom, 1‑bath cottage sleeps 4–6 guests and offers a thoughtful blend of charm and modern comfort.brThe open floor plan features hardwood floors, custom cabinetry, and granite countertops. The fully equipped kitchen includes new appliances—stove, microwave, side‑by‑side refrigerator, dishwasher, and coffee maker—and comes stocked with all essential cookware, dishes, and utensils.brThe marble‑tiled bathroom includes a spacious shower, vanity, and all the necessities for a comfortable stay. The living room offers a sleeper sofa, two plush chairs, and a large flat‑screen TV with cable. A bright dining area with seating for four provides an ideal spot for morning coffee or an intimate meal.brDouble French doors open onto a deck with seating overlooking Back Creek and the expansive backyard. Guests are welcome to relax with waterfront views or enjoy the provided kayaks.brConveniently located just minutes from Historic Downtown Annapolis, the property offers easy access to the Chesapeake Bay. Grocery stores, pharmacies, liquor stores, and excellent restaurants are all within two miles.brAs part of the marina community, guests enjoy access to seasonal pool use, a fitness center, Wi‑Fi, bicycles, and a water taxi stop just steps from the cottage. Black Market Bakers is also nearby and highly recommended for breakfast, lunch, or a sweet treat.

Stunning Waterfront Cottage in the Sailing Capital of the World!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$330.6

Walk to all Annapolis has to offer, once parked you’ll never need a car. Walk to City Dock, marinas, restaurants, pubs and pizzerias, watersports, shopping, Naval Academy and more. You will be enamoured with this quaint and charming 1920's cottage with its stylish cottage flare, cozy and comfortable interior and inviting outdoor space. We have ample room to park small RV Van up to 20' for an additional fee includes water and 30 amp electric hook-up. Monthly rentals welcomed. Sorry No children under 12 years, prior guests children damaged property.

Annapolis-Eastport Cottage Home - Walk Everywhere - RV Van Parking & Hook-up too

Annapolis, Maryland, United States

Bed

1

Bath

Sleeps

$2097.6

Wake up by the water in Annapolis. Tucked on a quiet private lane near the creeks and marinas, this light-filled home puts you minutes from Downtown, the U.S. Naval Academy, yacht clubs, and Annapolis restaurants. It’s a calm base for regattas, USNA stadium events, family trips, or a quick Chesapeake reset. Outdoors, relax in Adirondacks overlooking the water and play yard games near the fire pit after a day on the water. Beaches, boat rentals, sailing charters, and kid-friendly parks are close.

Waterfront mid-century home

Annapolis, Maryland, United States

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Bath