Vacation Home Rentals By Owner In Annapolis, MD

Welcome to Liberty House! Tucked away in the Murray Hill section of downtown Annapolis this home is a spacious retreat for your upcoming trip. Light and airy, sparking clean with all brand new furniture and linens. The house has TWO onsite parking spots plus unlimited street parking for overflow.brWe accommodate 8 guests with 4 large bedrooms, (Please note the first floor is a pull out) and 3 large bathrooms. The front porch, covered deck, and backyard are an oasis to unwind after a day of exploring town, taking in a game or just Netflix and chill. Go Navy ! brPlease note this property is located in a quiet residential neighborhood and not suited for any kind of party groups such as weddings, Bachelor/ette events or similar.

The Liberty House- Pristine Renovation with parking,

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

$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

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

$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

$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

4

Bed

Bath

10

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

$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

Bath

Sleeps

$609.45

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

$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

$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

4

Bed

Bath

10

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

$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

Bed

2

Bath

8

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

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

Bed

Bath

Sleeps

$814.01

Welcome to Sing Second Stays, a comfortable and spacious retreat in the heart of Annapolis. Just 1.4 miles from Navy-Marine Corps Memorial Stadium, this home is ideal for Naval Academy families, alumni, and visitors looking to enjoy game days, Commissioning Week, I-Day, or a weekend exploring the charm of historic Annapolis.brbrThis home holds a special place in our hearts. I’m a Naval Academy graduate (Class of 2015) and former Navy football player, and my wife, our two children, and I lived here for four years. We walked to home games, hosted friends, and made countless memories in this house before transforming it into the welcoming rental you see today. It’s our hope that guests will feel the same warmth and connection during their stay.brbrThe location is hard to beat. We are just 2 miles from Gate 1 and 2.2 miles from Gate 8 at the United States Naval Academy. Downtown Annapolis, waterfront restaurants, historic landmarks, and boutique shopping are only minutes away. Whether you’re visiting USNA, attending a game, or simply exploring the area, this home offers unbeatable convenience.brbrParking is easy and stress-free. Our U-shaped driveway provides smooth in-and-out access with space for up to four cars—two on each side—without the need to shuffle vehicles.brbrInside, the home features a spacious split-foyer layout that works beautifully for families, groups, and multi-generational gatherings. The main level has an open-concept kitchen with modern appliances and all the essentials. The large living room includes ample seating and a 65-inch Sony TV, perfect for watching the game or relaxing after a day in town. The primary bedroom includes a king-sized bed, a full en-suite bathroom, and a 55-inch Samsung Smart TV. Two additional bedrooms, each with queen beds, share a second full bathroom on this floor.brbrDownstairs, guests enjoy a full private suite feel. There’s a bedroom with a king bed and sectional sofa, plus a large hangout room with full-over-full bunk beds, another sectional couch, and a 65-inch Vizio TV. A kitchenette includes a microwave, toaster oven, Keurig coffee maker, and mini fridge, making it easy to prep snacks or enjoy a casual breakfast. There’s also a round table ideal for dining, cards, or board games, a full bathroom, and a separate entrance. Guests will also find a washer, dryer, and utility sink on this level.brbrFor fun and relaxation, the downstairs also includes a Pop-A-Shot basketball game, a Golden Tee arcade machine, and a variety of board games and puzzles. Whether you're traveling with kids, teens, or friends, the lower level offers a great place to unwind.brbrOutside, enjoy two outdoor living areas. The upper-level deck is 40 feet by 12 feet and features a dining table for six with an umbrella, an outdoor sofa, and extra seating for relaxing or dining al fresco. Below the deck, a shaded patio area provides an additional space to gather and enjoy the fresh air.brbrSing Second Stays is pet-friendly because we understand that your furry companions are part of the family. We simply ask that pets are well-behaved and that guests clean up after them.brbrThe home is equipped with high-speed Wi-Fi, three smart TVs, and all the essentials to make your stay comfortable and convenient. Guests also have access to an air mattress and two Pack 'n Plays, making it easy to accommodate additional sleepers or young children.brbrFor your safety, the property is equipped with six exterior Eufy security cameras. These include one above the front door, two side light cameras, one covering the basement entrance, and two on the back porch. There are no cameras inside the home, and these exterior cameras are used strictly for safety and security purposes.brbrHere’s a quick look at the sleeping arrangements:brUpstairs includes a primary bedroom with a king bed and two bedrooms with queen beds.brDownstairs includes one king bedroom and a hangout room with full-over-full bunk beds.brAn air mattress and two Pack 'n Plays are available for guest use.brbrThe kitchen is fully stocked and includes a stovetop, oven, large refrigerator, freezer, Ninja coffee maker, blender, pots, pans, dishes, and utensils. Downstairs, the kitchenette provides added flexibility with a microwave, toaster oven, mini fridge, and Keurig coffee maker.brbrWe ask that guests follow a few simple house rules to keep the home enjoyable for all. Smoking or vaping is not allowed inside the home or on the back deck. Please keep noise levels reasonable and be mindful of our neighbors, especially during quiet hours. No parties or unauthorized gatherings are permitted. Pets are welcome, but we ask that guests clean up after them. The fireplaces in the home are not for guest use.brbrSing Second Stays was designed with comfort, convenience, and community in mind. Whether you’re returning to Annapolis for a reunion, celebrating with your midshipman, or simply exploring this beautiful historic town, we’d love to host you. We’re confident you’ll find our home to be welcoming, functional, and full of thoughtful touches that make your stay memorable.brbrWe look forward to welcoming you to Sing Second Stays and helping you create your own Annapolis story.

Sing Second Stays—Spacious Annapolis Home Near USNA & Navy Stadium

Annapolis, Maryland, United States

4

Bed

Bath

12

Sleeps

$534.63

This three story 1875 home is located in the Heart of Historic Annapolis. Shops, restaurants, historic sites and the City Dock are within blocks of the front door. The Main Gate of Naval Academy is just a one block walk and St John’s College is 3 blocks from the house. This 5 bedroom, 3 bathroom home can sleep up to 10. In addition to the sleeping quarters, guests have use of a kitchen, living room, dining room, sun room, sitting room, laundry facilities, and a second floor deck overlooking the courtyard garden with grill.

Heart of Historic District!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$839.61

Welcome to our Waterfront Oasis in the desirable Eastport section of Annapolis. We feature a main level open floor plan with excellent water views, 4 bedrooms and first level suite with two twins and a second living area. This home is perfectly suited to host a larger family/friend group (Please NO parties or events of any kind.) Water access out the back door, plenty of free no permit required street parking and a quick walk to downtown or USNA. Bring your kayaks/boards for our floating dock.brbrWe feature three full floors , the upstairs area has 4 full bedrooms and two full baths with an open loft/office space. The main level is a spacious open floor plan with updated kitchen and half bath . Downstairs is its own mini apartment with two entrances , laundry , sink , bar , mini fridge and Tv.brbrThe garage and slip are not for guest use. We have active cameras on all exterior access points .The home does not allow pets however the owners labs do visit numerous times throughout the year in case of pet allergies .This is NOT a party house - please read all rules before booking .brbrABSOLUTELY no events parties ( Bach / ette included ) . No smoking. 10 max people at any given time in the property . Only two cars are allowed in driveway - the rest can do street parking ( guests do not have garage access) .Please respect our neighbors and observe quiet time after 9pm. Any violation will result in additional fees and instant termination of rental contract . Property has active cameras on front and back exterior .

Waterfront Oasis in Eastport-Easy Walk to Downtown

Annapolis, Maryland, United States

5

Bed

Bath

10

Sleeps

$518.13

Be our guest at Historic 19 East Street, in the heart of the Annapolis national landmark district. Walk out the front door, look left and see the iconic Maryland State House, look right and you're less than a block from Gate One of the United States Naval Academy. St. John's College, St. Mary's, City Dock, William Paca Gardens, and Main Street are all within three blocks. Everything Historic Annapolis has to offer, from boating to restaurants to shopping to Naval Academy traditions, is yours to enjoy! brbrHistoric 19 East is the perfect location for weddings, USNA events, regattas or just a quiet getaway. The interior of this exceptionally restored 115 year old home is perfectly updated, light, friendly, and beyond comfortable with hard wood floors throughout, a large flat screen 4K TV in the living room. Gather around our large dining room table for family meals, or enjoy the very large, privately fenced bricked patio for a cook-out, brunch or cocktail after a full day of exploring the town. If you don't feel like cooking order take-out or stroll to one of the many renowned local eateries. The coffee maker is a Keurig for ease of making single cups. Our home comfortably sleeps 6 (two queens, one full, one twin) and is perfect for a family gathering, weekend getaway or a reunion among friends. It is a wonderful property in a fantastic location and we look forward to you being our guest. LIMITED PARKING: In order to help residents and visitors navigate parking downtown, a website www.AccessAnnapolis.com was created to serve as a hub for parking and transit information to help residents, businesses, employees, customers, and visitors plan their visit to downtown Annapolis. You may find more options by googling Annapolis Parking.brOnce you park your car you will be set on foot to explore all that Annapolis has to offer.brbrUSING PARK MOBILE:brNon-residents are encouraged to download the ParkMobile app (Android/Apple). After the app has been downloaded, add your vehicle tag, payment method and allowbr “location enabled services” to automatically determine ParkMobile parking zone data. Parking can also be paid by texting “PARK” to 77223. brbrTAXES: VRBO collects and pays a 6% Sales and Use Tax required by Anne Arundel County. In addition, the owners must collect and pay a City of Annapolis Hotel and Motel Tax of 7% which is listed in the rates section as a Property Fee. Please let us know if you have any questions about these taxes.brShort Term License: STR-142633brbrSuitability: Non-smoking only, wheelchair inaccessible, no pets, 25 or older please.

PERFECT LOCATION in the heart of history

Annapolis, Maryland, United States