Vacation Rentals By Owner In Annapolis, MD

Studio, furnished apartment above detached garage on family's sprawling property. Queen-bed, with pull out full couch. Sleeps up to 4. Well-appointed and outfitted, eat-in kitchenette. Gorgeous bathroom. Vaulted ceilings. Access to our saltwater pool(seasonal) that is shared with your host family and other Oasis guests, outdoor fireplace with TV(also shared with other Oasis guests), outdoor grill and pavilion with TV and Bose system.Less than a 10 min drive to downtown Annapolis.brbrKeep reading... if you want to know more about this amazing propertybrbrThe property is equipped with everything you will need for your stay including a full-size fridge, Keurig coffee maker, teapot, stove and dishwasher. Just outside the property entrance is the gorgeous “Oasis” pool. brThis studio is PERFECT for small families or friends visiting the United States Naval Academy, Annapolis Boat Shows or any of the many Annapolis events we have going on here year-round.brbrThe property is a mere 3.5 miles away from Downtown Annapolis. brbrCovid-19 precautions-Our guests are our priority. We take every precaution when cleaning the property and make sure we meet every industry standard. We go above and beyond to ensure all surfaces and high touch areas are cleaned thoroughly and disinfected. br**No-contact check-in available upon request**brbrSLEEPING ARRANGEMENTSbrSTUDIO/1BR/1BAbrQueen size bed brPull-out couchbrFEATURESbrHeated, Saltwater pool(shared)brCovered Pavilion with ample seating and outdoor TVbrOutdoor fireplace-firewood providedbrOutdoor grill/BBQ(propane)brFull kitchen/kitchen table with seating brFree Wi-FibrLuxury Linens & towels brComplimentary sodas/water/coffee/teabrComplimentary toiletriesbrAmple parking on sitebrPerfect place to relax, reconnect and see the sites of AnnapolisbrPlease note-no washer/dryer or oven on sitebrNo smoking in this property brNo pets allowedbrThere is video surveillance on the outside peripheral aspect of the entryway of the property this is for security purposes only.brbrAMENITIESbrToo many to list! We provide at all. Just ask brSoaps, conditioners, lotions, paper towels, sodas, water, dish soap, scrubbers, wine/champagne($), even a boat ride with a licensed boat captain($)brCaptain Andy can show you all Annapolis has to offer AND can even give you a lesson on how to wakeboard/Waterski- inquire before or after you book. brbrYour comfortable bed, including the sofa bed, are made for you with freshly laundered sheets and you have bath as well as pool towels. brbrHOUSE RULESbrNo smoking. No pets. No parties/events please.brCheck in time 3:00 p.m. brCheck out time 11:00 a.m.brbrAll guests have access to the fabulous and GRAND prize winning (2022 LCA GRAND PRIZE-OUTDOOR LIVING AREA-McHale Landscape Design, Inc.) Oasis Pool and outdoor living spaces.

Apartment

Waterfront Oasis of Annapolis Star

Annapolis, Maryland, United States

2

Bed

Bath

Sleeps

$305.64

The Firefly Cottage (cute as the bug!) in beautiful Cape St. Claire.br Our cozy cottage sits on a ¼ acre of land for your exclusive use. It is conveniently located 0.4 miles (8 minute walk) from a private community beach located on the Chesapeake Bay. Shops, a grocery store, and restaurants in the Cape are ½ mile away and many more are within a short drive.brbr- We do not ask you to do chores, that is our job. We just ask you to enjoy the Cottage.brbr- Let us spoil you and your little dog too! $35 per day per dog, for up to 2 fifty-pound dogs.brbr-Breakfast included- choice of microwaveable frozen breakfast sandwiches, granola, oatmeal, cereal and milk are always included in your stay.brbr-Petit mais puissant, small but mighty. See more at Firefly-cottage.com. br- We love to customize each stay. Your gift is a reflection of your choice, if you are celebrating a special occasion we decorate and leave an extra gift for you. br- SAVE- Enjoy a 10% discount for reservations 7 days to 28 days. br- During your stay, you can delight in a short walk to the community beach, relax in the yard with hot tub, lights in the fairy garden, the herb, spices and tomatoes you pick from your private oasis in the back yard. All this and more while saving on your dream vacation. brbrSLEEPS FIVE: One queen bed, a fold-out queen bed, and a fold-out twin bed can sleep 5 people. After a perfect day at the beach or sightseeing, relax in the inviting living room with an electric fireplace, smart TV, and a table for family dining. Additionally for your convenience, there is a hair dryer, washer/dryer, and ironing board. We can also provide a Pack-n-Play.brbrSPA AND PRIVATE YARD: Stepping out into the private backyard is a hot tub and two gazebos. 2 bicycles, and helmets are provided. Enjoy comfortable chairs and tables, a barbecue grill, outdoor games, kayaks / life jackets, and a fire pit to make s’Mores. br You may host small family get togethers (10 people or less), but because the cottage is in a quiet neighborhood, music must be turned down by 9pm weeknights and 10pm on weekends. br-br-Free parking on site with a 70-foot driveway can accommodate cars, an RV, or boat. brbr- Electrical vehicle charging is available with a standard 4-prong (240V, 50amp) receptacle and a level 1 (120V, 16amp) charger by the driveway.brbr- Enjoy the garden with herbs and tomatoes (in season). Fireflies, butterflies and a few fairies and a small dragon grace the yard.brbrFULLY OUTFITTED: The fully outfitted kitchen has everything your family needs including a coffee bar for a great start to a bright morning, cereal, and milk, in addition to a complimentary gift basket customized to your preferences. brbr- Washer/dryer, iron and board, hair dryer provided.brbr- Linens, towels, bath robes provided.brbrQUIET: Enjoy the quiet, safe, residential neighborhood with beach and restaurants within walking distance. Our cottage is a quick drive to beautiful downtown Annapolis where you can delight in local cuisine, shop quaint boutiques, enjoy a harbor boat cruise, tour historic homes of some of our nation’s founding fathers, traverse a ghost tour or pub crawl, or visit the Naval Academy or St. John’s College.brbrYEAR ROUND: Annapolis Firefly Cottage of Cape St. Claire is a wonderful place to visit year round- we are centrally located near Annapolis, Washington D.C., and Baltimore, and there are many activities a short walk or drive from our cottage. Our cottage is a quick drive to beautiful downtown Annapolis where you can delight in local cuisine, shop quaint boutiques, enjoy a harbor boat cruise, tour historic homes of some of our nation’s founding fathers, traverse a ghost tour or pub crawl, or visit the Naval Academy or St. John’s College. The hot tub is operational all year round.brbr- In the Spring, shake off the winter blues as the area puts on its beautiful, spring floral cape. While visiting, you can enjoy Spring Break with your Midshipmen, Commissioning week, the Annapolis Film Festival, the Spring Boat Show, the local Strawberry Festival, the Cherry Blossom Festival in Washington, D.C., or celebrate the Naval Academy Graduation where you can watch the Blue Angels fly over while relaxing in the hot tub or just relax and sip coffee in the private backyard that’s surrounded by trees, birds, butterflies and fireflies.br- putting green, inflatable crab and frog pools and octopus sprinkler, lots of fun for for the whole family from toddlers to elder members.brbr- In the summer, you can enjoy the private community beach, take in a free concert on a Friday nights at the historic mid-18th century Goshen Farm, launch a canoe, kayak ( 2 available) stand-up paddle board launch a boat from nearby public piers, or enjoy one of the many restaurants located in the Cape. Ask to use the four person surrey bike, so much fun!brbr- The fall brings the return of Midshipmen and Navy Football, the annual Renaissance Faire, the Bay Bridge Run, ghost walks through the streets of historic Annapolis, or take in a museum or aquarium visit in nearby D.C. and Baltimore.brbr- In the winter, the Annapolis Firefly Cottage is draped in holiday cheer, warm from the electric fireplace and forced air heat. During your stay, you can delight in the holiday boat parade, visit the lights at Sandy Point, beautiful music concerts at the Academy, or take a tour of John Paul Jones Crypt and see the exquisite Naval Academy Chapel. Spent a romantic Valentine’s Day wrapped up for a walk along the beach, enjoying the electric fireplace, and an intimate dinner, attend a St. Patrick’s parade.

Cottage

Firefly Cottage at the Cape, Hot Tub, Community beach, Strawberry festival, USNA

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$453.72

A's by the Cove is ideally located in the heart of downtown Annapolis's Historic and Art Districts. It is a fully updated & detached home with historic charm and an inviting front porch. Well conceived and open floor plan to include a living room (with queen sleeper sofa), a dedicated workspace, 1/2 bath and eat in kitchen on the first floor and 2 bedrooms and a full bath upstairs. Enclosed rear yard provides an opportunity to create a lovely quiet space out our back door. brbrOne parking spot (in a nearby by public lot - less than 60 yard from the house) is included with your rental, you can walk to West street, Main Avenue or the city dock all in less than 10 min. brbrThe property is equipped with a RabbitAir Air Filtering device which allow the interior air to go through a 6-stage filtering twice every hour. it traps allergens & contaminants. It is certified Asthma & Allergy friendly.brbrA perfect location to enjoy Commissioning Week, Boat Shows and other festivals in Historic Annapolis.brbrA's by the Cove has a minimum age requirement. All adult members of your party must be 21 or older unless they are children traveling as part of a family group. Every guest must be registered and verified on your reservation. We have a strict no party or gathering policy.brbrGuest must sign Rental Agreement and provide Government ID.brbrAlthough you have access to the entire house and private backyard, there is one locked owner closet located in the living room. brbrYour arrival (and departure) are fully contactless. You will be provided with detailed check-in instructions the afternoon prior to your arrival including a code and/or mobile app to enter the home.brbrWe are here for you during your stay, but our level of interaction is entirely up to you. We are only a phone call/message away and will respond usually within minutes during extended business hours. During the overnight, we probably wont get back to you until early the next morning. If there is a life threatening emergency, please contact 911 and then call us and leave us a voicemail. We reserve the right to stop by the property at anytime but will give you at least 4 hours notice except in case of emergency.brbrThe property is equipped with video recording camera outside the home. There are 2 cameras located on the front porch and the backyard for the safety of our guests. One on the front porch looking at the front door and one on the back porch looking at the backyard. Those are used for security purpose only. Any recording is automatically deleted after 30 days. brbrThird Party Reservations (Guest not occupying the home) are strictly forbidden and again any channel policy (airbnb, VRBO, booking...). The guest who made the reservation must be an active occupant of the home for the entire duration of the reservation. Unauthorized guests will be removed from the property and the reservation will be immediately canceled. No refund will be provided regardless of the cancellation policy.

Cozy 2br home w/ parking in downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$552.62

Ideally located between the vibrant West Street and the historic Main Street, our downtown Annapolis home offers easy access to restaurants, shops, bars etc.brWe’ve carefully furnished the space to create an inviting maritime environment with 3 bedrooms and 3.5 bathrooms (en-suite) comfortably accommodating up to 7 guests. brThe high ceilings give an open and airy feel, while the inviting front porch offers a cozy east coast touch. The private backyard is perfect for the summer months .brbrWe offer an open floor pan with 3 bedrooms , 3.5 baths and five beds .. USNA family ownedbrbrUSNA family owned. We offer a paid parking space in a nearby city owned Gotts garage ( about 2 blocks away )brPopular Walking distances brWest st shopping and dining - 1 minbrParking garage - 2 minbrChurch circle - 2 minbrMain St shopping and dining - 3 min brAnnapolis City Dock- 7 minbrUSNA Gate 1- 9 min

Darling on Dean Street- Nautical home w parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$792.3

WATER, WATER everywhere! Our home is centrally located to all the water Bay Ridge has to offer.brbrOur home is located just one house away from the Bay Ridge bluff where panoramic views of the Chesapeake Bay provide a backdrop for drinking coffee or cocktail while watching all the boating action taking place on the Bay.brbrYou’ll also be one block in either direction to 2 different sandy beaches on the Bay - Severn River beach and Mayo beach. Spend the day or evening at a beach bonfire and walk home on the community bike trails offset from the road.brbrIn addition to the Bay, you're also a short walk to Lake Ogleton and the Marina. At the marina there is basketball, pickleball, lake access and of course lots of boats!brbrA one mile walk along the Chesapeake Bay/Bay Dr brings you to our hidden treasure: the Chesapeake Bay Foundation (CBF), a nonprofit dedicate to the restoration and protection of this iconic natural resource. We’ve partnered with CBF to create open spaces and trails where you are free to nature walk the beautiful grounds in peace and serenity.brbrWalk or bike the 3.5 mile perimeter of our community and take it all in: friendly neighbors, on-water activities, lemonade stands, or meditative benches with iconic views - Bay Ridge has a little bit of everything.brbrOUR HOME:brbrTwo zone central A/CbrbrHighspeed WIFIbrbrRoutine lawn carebrbr4 bed / 3 bathbrbrSleeps 6brbrBEDROOMS:- 4/3 full baths- 3 downstairs, 1 upstairsbrbrBEDROOM 1: GYM: Keiser stationary bike, full set of dumbbell weights, bands, yoga equip. Brookstone foot massager and TV. Sofa (very comfortable if sleeping needed for 7th person, sheets provided) and chair.brbrBEDROOM 2 and 3: Queen beds, guest towels, extra sheets and blankets-wrapped in dust proof bags.brbrBEDROOM 4: Master Bedroom-upstairs: Surrounded by windows, King Bed with ensuite bathroom, tub/shower, separate commode room. Vanity and mirror area with chair. Guest towels, extra sheets and blankets-wrapped in dust proof bags.brbrBATHS: 2 full baths downstairs- 1 with tub/shower, 1 with walk-in shower-can be handicap adaptablebrbrLIVING ROOM: Very large living /great room. Game bar with assorted board games, backgammon, chess, cards. 52in TV, Gas fireplace (in-op in summer). Large down sofa and loveseat. Plus a chair and a half/ ottoman in a separate reading area to read, watch boats go by or nap.brbrDINING ROOM: Seating for 6 (or 8 if needed) overlooking and open to living room.brbrKITCHEN: All Jenn-Air appliances. 5 burner gas stove, D/W, Convection/microwave and standard oven. Large double door refrigerator. Oster drip coffee maker, tea pot, double toaster, food chopper, food processor, mixer, blender, rice maker, gourmet wok. Assorted large bowls and serving platters. All you need to cook, spices, basic essentials and of course pots and pansbrbrLAUNDRY ROOM: Washer and dryer, beach towels, iron. Detergent and dryer sheets to start.brbrBREAKFAST ROOM: Buffet server, Seating for 4 or (6 if needed) surrounded by sliding glass doors to either sunporch and/or screen porch.brbrSCREEN PORCH: Beautiful views of Chesapeake Bay. Propane heater (operable in summer), seating for 4 (or 6) at table and 2brlarge cushioned chairs and ottoman. A hammock completes the relaxation on screen porch and another one outside porch under the trees to listen to birds, read or nap!brbrSUN PORCH: Weber gas grill, 2 Adirondack chairs/ ottoman in sun and 4 chairs in large completely fenced in shaded backyard.brbrPARKING: 2 driveways: Lawrence Ave has 2 spots, Barry Ave driveway has total 6 car spots. There is no parking on the roads in community. The garage is locked for owners.brbrDISTANCES: 4.5 miles to Downtown Annapolis and US Naval Academybrbr35 miles to Baltimore and Wash DCbrbrPLEASE BE RESPECTFUL OF OUR NEIGHBORS AND COMMUNITY: 25 mph in entire community, No parties, No DOGS/CATS, brPRICING:brMinimum 14 day rental maximum rental 45 days:brFirst 14 days at $695 daybrDay 15 and on at $650/ daybrNO CHILDREN UNDER 12brCleaning fee $350brMD. LICENSE# STR00686

BY THE BAY

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$339.33

This 2-bed, 1.5-bath townhome mixes modern renovations with 1900 classic charm. It's been lovingly decorated to accommodate 6 guests. You'll love the proximity to downtown Annapolis - simply walk one-half block to Main Street circle and Annapolis City Dock. You'll truly be in the middle of everything in this beautiful historic home!brbrWhy guests love staying at 20 Fleet Street:brbr☼ Historic row home right in the heart of downtown Annapolis with tons of natural light and upgraded features, ideal for families, romantic getaways, or a group of friends visiting historic Annapolis, USNA, and other tourist sitesbr☼ Centrally located in downtown Annapolis, on historic Fleet Street, just 1/2 block from the actionbr☼ Two bedrooms: Primary: king bed; Guest: 2 twin bedsbr☼ The full bathroom is on the second level with both bedrooms and has a tub-shower combo; there is a half-bath on the main living areabr☼ Kitchen with all major appliances, a drip coffee maker, kitchen supplies and tools and morebr☼ Comfortable living room for watching movies and playing games, with a sliding glass door out to a private outdoor space br☼ Two outdoor spaces - one at the ground level is fully fenced with outdoor dining and a gas grill; the other is a fenced rooftop with outdoor diningbr☼ Smart TV in the living roombr☼ Fresh linens, towels, toiletries & essentials providedbr☼ Professionally cleaned before each visitbrbrLook no further than this historic rowhome in downtown Annapolis!brbrPlease note that there is no parking on Fleet Street. Guests are encouraged to park in nearby public parking garages.brbrWe’ll follow up with a short online registration once you book. It’s fast, simple, and helps us prepare for your visit. Non-Airbnb guests will be asked to pay a small damage waiver OR refundable deposit.brbrFor extra flexibility, consider adding trip insurance for a nominal fee. It can cover you if you need to cancel at the last minute.brbr20 Fleet Street is managed by a small, female-owned business. We're committed to making sure all of our guests feel welcome and have the best trip ever. Book your trip with confidence that not only will this property be amazing, but the service and attention you get will be, too.

Naval Academy Gate 1

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$321.13

Welcome to my home! This open concept 3 (2 queens and 1 king) 2.0 full bath cottage has a large, fenced yard and backs up to the stunning Quiet Waters Park with its own access gate. Free parking for 6 cars is a quick 5-minute drive to either downtown Annapolis or Eastport. It has three (2) bedrooms on the main floor with a full bath with a fully finished downstairs with electric fireplace and additional king bed and full bath. It also has a cozy 3-season enclosed porch with views into the large yard and park.

Cottage

Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$406.6

Historic home 1.5 blocks from center of town. Easy walk to the shops, food, harbor, Naval Academy and historic attractions. Full kitchen with gas range if you decide not to partake in the plentiful dining options around town. Outside deck with BBQ a great space for entertaining. Verizon Fios Wi-Fi and central AC. Two bedrooms with full baths plus a queen sleeper sofa. Fits up to 6 guests comfortably. Water front park one block away. Perfect for siting and having your morning coffee

Historic Annapolis Home 1.5 blocks from center of town.

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$302.1

Parking included. The heart of Annapolis 1 street from the harbor, fun restaurants & backs to the Naval Academy. This 1st floor 2 bed / 1 bath condo has been fully renovated with new paint, floors, bath & kitchen. 1 Parking space included & additional paid parking on street. Queen Bed & sleeper couch is a full size. Linens included. Kitchen includes refrigerator, stove/oven, microwave, keurig, dishes silverware, pots and pans. High speed internet included & separate work area.

Condo

Annapolis steps to Harbor and Naval Academy

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$518.0

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrFamily-Friendly Coastal Retreat | Walk to Beach | Near Downtown brbrSlow down, reconnect, and make lasting memories by the Chesapeake Bay—where kids can run freely, parents can unwind, and family time comes easy. Located in the waterfront community of Arundel on the Bay, this bright and welcoming home offers access to a community beach, playground, and quiet streets perfect for biking, strolling, and exploring together. brbr brbrEasy, Comfortable Living brbrRenovated kitchen with modern appliances brbrOpen living spaces for gathering after a day in the sun brbr3 bedrooms + sleeper sofa (sleeps 9) brbrDedicated workspace for remote work brbr brbrCommunity Beach Lifestyle brbrStart your mornings with coffee by the water, spend afternoons building sandcastles or paddling along the Bay, and end your day with sunset walks through this peaceful neighborhood. brbrWalk to sandy community beach brbrPlayground and park nearby brbrQuiet, family-friendly streets brbrBeautiful water views and coastal charm brbr brbrOutdoor Space brbrLarge private backyard for kids to play brbrPropane grill for easy family cookouts brbrSpace for relaxing, dining, and evening downtime brbr brbrSleeping Arrangements (Sleeps 9) brbrPrimary Bedroom: King bed, Smart TV brbrQueen Guest Bedroom: Queen bed, Smart TV brbrBunk Room: Twin-over-Full bunk bed brbrFamily Room: Queen-size sleeper sofa brbr brbrAmenities brbrFully equipped kitchen brbrDining table for 6–8 brbrPropane grill brbrHigh-speed WiFi brbrSmart TVs brbrPrivate office workspace brbrWasher & dryer brbrLuxury linens & towels brbrComplimentary starter supplies brbrKeyless entry brbrParking for 2–3 cars brbrNo pets brbr brbrLocation Highlights brbrDowntown Annapolis – 4 miles brbrU.S. Naval Academy – 5 miles brbrWashington, DC – 35 miles brbrBaltimore – 20 miles brbr brbrHouse Rules brbrMinimum age of primary renter: 25 years brbrNo parties, pets, events, or smoking brbrNo unaccompanied minors brbrRespect the home and neighbors brbrCheck-in: 4:00 PM brbrCheck-out: 11:00 AM

Charming Coastal Retreat w Community Beach Dog-Friendly & Mins to Downtown Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$171.0

This 1920's Craftsman style bungalow is 1/2 block from the Naval Academy Stadium and within walking distance of the Historic District. Its close proximity to Baltimore, Washington DC and Maryland's Eastern Shore make it a great location for day tripping. This well appointed bright lower level suite with private entrance includes many Craftsman details including a custom quarter sawn oak wine bar and kitchen cabinets. The open floor plan includes a living room and wine bar with fridge/freezer, sink and Advantium Microwave and Ice Stone counter tops. The suite offers a bedroom with a full sized bed, full bath with tub/shower and laundry with washer/dryer. Guests are welcome to share the patio and backyard with the main house. Friendly pugs may occasionally greet guests in the backyard.

Apartment

Craftsman Bungalow Suite Near Naval Academy Stadium and Historic District

Annapolis, Maryland, United States

Bed

Bath

2

Sleeps

$489.77

NOTE: Posted rates do not apply to Holidays, Boat Shows or Commissioning Week. Theybr will be given on request. Rates are based on 8 persons in the home.brbrThis lovely upscale home in Eastport is located in a small private cul-de-sac neighborhood and offers driveway parking for 4 cars. Only 5 blocks to the Spa Creek Bridge. My Kimber Ridge home is decorated with care and has the charm of this historic town. brbrTwo full-size refrigerators and two laundry rooms make this home an excellent choice. A dream kitchen for those who like to cook. Stocked with just about everything you would need - plus some spices for cooking!brbrThe fenced-in backyard is great for families with young children. Our large deck has bench seating and patio furniture to help you enjoy outdoor dining. And don't forget the gas and charcoal grills! A Pack & Play, stroller, and highchair are an added benefit for young families.brbrPark your car in the driveway and walk to the heart of downtown Annapolis in less than 15 minutes - unless you stop on the Spa Creek bridge and enjoy the view of this great sailing community. brbrDon't forget to check out the comments on this site! brbrYou will be asked to send a copy of your Photo ID. Thank you.br brKeywords: Driveway Parking, Gas Grill, Charcoal Grill, Large Deck, Great Location, Gas Stove & Fireplace. Neighborhood curfew.

Upscale home with parking for 4 cars in driveway. Walk to downtown.

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$406.19

New to the market and just in time for Navy Football. Located at the five star Corner House. Conveniently located on the first floor of this historic Annapolis house. Suite #1 is a comfortable two bedroom Suite with the all the needed amenities to cherish this home away from home. Enjoy the full kitchen, relax in the living room and fresher up in the full bathroom with shower tub and washer dryer. Easy front and back door access to 1 parking space. brbrSmart TVs, internet and cablebrbrThis spacious and well designed Suite sleeps four very comfortably. Front bedroom has a king size bed and the back bedroom has a full size bed. Accommodations can be made for more if needed.brbrThe Corner House is a hidden gem located in the quaint President’s Hill neighborhood in historic Annapolis. This area of Annapolis is a vibrant and historically significant area that offers a mix of history, arts, culture, dining, and entertainment, making it a unique and lively part of the city. Best location for Navy football and all downtown festivities.brbrSituated just a short walk from the heart of the West Street Arts District, The Corner House is a home away from home. Enter through a white picket fence and onto a covered front porch. This is where you can enjoy your morning coffee and your afternoon tea or glass of wine when you return from your ventures. Enjoy the artwork of local and east coast regional artists that is displayed in the foyer and throughout the home.br brSuite #1 is one of three suites in this tri-gabled opulent Hill Street home offers a tranquil and comfortable vacation experience. This beautifully designed and decorated haven has two bedrooms, one bathroom and a kitchen. Includes off street parking for one vehicle. brbrMoreover, guests will enjoy easy access to a vibrant scene with nearby restaurants, taverns, galleries, and music venues. This location is conveniently situated. It has easy walking equidistance to everything uptown and downtown Annapolis, such as Maryland State House, Governor’s Mansion, Market House, Ego Alley, St John’s College, US Naval Academy, Navy-Maine Corps Memorial Stadium, historic sites, waterfront locations, and parks.brbrWest Street in historic downtown Annapolis holds significant cultural and historical importance. It is renowned for its thriving arts and culture scene. It’s home to numerous art galleries, studios, and performance venues, making it a focal point for visitors, artists, and art enthusiasts. While known for its artistic vibe, West Street also retains its historical charm with well-preserved architecture, including charming row houses and historic buildings. The street offers a diverse range of dining options, from trendy cafes to upscale restaurants. It’s also a hub for live music, with bars and venues hosting local musicians and bands. West Street features boutique and specialty shops making it a great destination for shopping for unique and artisanal items.brbrThroughout the year, West Street hosts various festivals and events, including art festivals, live music performances, and cultural celebrations fostering community and unity.brbrGuests will enjoy their quiet and serene visit at The Corner House. This is a legally licensed rental property. We strongly enforce our policies of no parties and no illicit drug use. This is a non-smoking property. Pets are not permitted. No children under the age of 12 years old.br

Apartment

Five Star Charmer! Great Location Downtown & Stadium! Parking too!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$494.74

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWalk to waterfront restaurants, hop the water taxi into downtown Annapolis, and unwind by your private fire pit—all from this charming Eastport retreat just minutes from the US Naval Academy. This professionally-decorated 2-bedroom, 1.5-bath home offers the perfect blend of comfort, location, and Eastport charm. Perfect for couples or families traveling with their pups! brbr brbrStart your day with coffee on the sunny front porch, then step into the cozy living room with a large flatscreen TV and Queen sleeper sofa. The open layout leads to a stylish dining area and a fully-stocked gourmet kitchen. Step out back to your private fenced patio and deck, complete with firepit, propane grill, and café seating for 4. brbr brbrUnrestricted street parking available. brbr brbrSleeps 7 | 2BR / 1.5BA brbrKing Bedroom (upstairs) brbrQueen + Twin Trundle Bedroom (upstairs) brbrQueen Sleeper Sofa (main floor) brbr1 Full bath upstairs, 1 Powder room downstairs brbr brbrHIGHLIGHTS brbrFenced backyard with private deck, patio, firepit & grill brbrFront porch seating brbrDining table for 4–6 brbrCafé table for 4 on deck brbrHigh-speed WiFi & large Smart TV brbrWasher & dryer inside the home brbrDog-friendly with $150 non-refundable pet fee (per pet) brbrKeyless entry – check yourself in with an electronic code brbrUnrestricted, easy street parking brbrBoutique-level service with starter amenities provided: coffee, toiletries, paper products, dish soap & more brbrAll beds are made with freshly-laundered linens & towels brbr brbrDistance to: brbrDowntown Annapolis: 1 mile brbrUSNA: 1.5 miles brbrDC: 30 miles | Baltimore: 25 miles brbr brbrHouse Rules: brbrNo smoking, parties, or events. One guest must be 25+. Quiet hours: 10pm–8am. brbrCheck-in: 4PM | Check-out: 11AM

Walk to Waterfront & USNA from Eastport Gem with Fire pit, Porch & Fenced-In Yard

Annapolis, Maryland, United States

2

Bed

Bath

7

Sleeps

$1714.59

Welcome to Ogelton Overlook. This 5 bedroom / 5 bathroom Coastal Charm sleeps 14 comfortably. This thoughtfully stylish home overlooks the Bay and is your perfect Annapolis escape. brNestled in a charming coastal neighborhood, this beautifully located home offers the perfect blend of relaxation, comfort, and classic Chesapeake Bay charm. Whether you're visiting for sailing, a weekend getaway, Naval Academy events, or simply to explore the historic waterfront, this home puts you right in the heart of it all. Step inside and feel instantly at home in a bright, welcoming space designed for comfort and relaxation. This inviting property offers the perfect setting for families, couples, and groups looking to experience Annapolis like a local.brbrGuests love the mix of comfortable living spaces perfect for relaxing after a day on the water. Thoughtfully designed interiors with coastal-inspired touchesbrPlenty of room to unwind, connect, and make memories. Whether you're enjoying morning coffee before a day of sailing or relaxing after exploring downtown, this home offers the ideal home base. Additionally, you'll have easy access to downtown Annapolis, a quiet neighborhood feel while staying close to everything and a relaxing place to unwind after a day of exploring. brbrDuring your stay you'll be minutes from; the Historic downtown waterfront full of Sailing, Marinas, and Chesapeake Bay views. The local flavor full of incredible seafood restaurants and waterfront dining. Local boutiques for shopping, town favorite coffee shops, and art galleries. Naval Academy events and campus visits. brbrSpend your day exploring cobblestone streets, watching boats glide across the harbor, or enjoying famous Maryland crab cakes before returning to your peaceful retreat.brbrWe want every guest to have a 5-star stay. You'll enjoy:brEasy self check-inbrClear communicationbrLocal recommendationsbrA clean, comfortable home prepared for your arrivalbrbrBook now and experience the charm, history, and coastal beauty of Annapolis from your own private retreat.

This thoughtfully styled home overlooks the Bay and is perfect for your Annapolis escape.

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$588.99

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrIn the shade of the Maryland Statehouse, this historic home has welcomed family, friends, and travelers for more than 175 years. Tucked on a quiet side street in the heart of Annapolis, the property blends timeless character with modern comfort—offering an ideal stay for guests who want both history and convenience. brbr brbrInside, you’ll find large rooms with flexible living spaces, hardwood heart pine floors, exposed brick, and original beams that tell the story of centuries past. The fully updated kitchen features granite countertops, a double oven, and custom cabinetry—perfect for preparing meals to enjoy at the dining table for six or outside on the private furnished patio. The sunny den opens directly to the fenced brick garden, creating a cozy indoor-outdoor flow. brbr brbrParking: Please note there is no parking on premises. A dedicated space is available at a nearby garage (approx. 15-minute walk). Contact us for details. brbr brbrSleeping Arrangements (3BR / 2BA / Sleeps 8): brbr2nd Floor King Suite: King bed, walk-in closet, en-suite Jack-and-Jill full bath with shower/tub combo brbr2nd Floor Queen Bedroom: Queen bed, access to Jack-and-Jill full bath brbrLofted King Guestroom: King bed, privacy curtains (no door), en-suite bath with stand-up shower brbrSunken Den: Sofa bed brbrMain Level Living Room: Sofa bed brbrBathrooms are modern, including a bright upstairs bath with a vintage clawfoot tub. brbr brbrAmenities & Highlights: brbrPrivate fenced patio with propane grill brbrFully equipped kitchen brbrDining room with seating for 6 and breakfast bar seating for 2 more brbrWiFi and large smart TVs brbrLuxury linens & complimentary starter toiletries brbrWasher/dryer inside the home brbrContactless check-in with coded entry brbrDog-Friendly: Bring your furry friend for a $150 non-refundable pet fee per pet. brbr brbrLocation: brbrU.S. Naval Academy – 2 blocks brbrCity Dock, shops, and restaurants – 1 block brbrWashington, DC – 30 miles brbrBaltimore – 25 miles brbr brbrHouse Rules: brbrMinimum age: 25 for primary renter brbrNo smoking brbrRespectful of neighbors and community brbrCheck-in: 4:00 pm | Check-out: 11:00 am brbr brbrWhether you’re here for a Naval Academy event, a weekend getaway, or simply to enjoy the charm of Maryland’s capital, this historic home offers the perfect balance of elegance, comfort, and unbeatable location.

Historic Annapolis Retreat – Steps from the Statehouse & City Dock with Parking and Private Patio

Annapolis, Maryland, United States

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Bath

Sleeps

$518.72

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWake up to sparkling water views and the charm of historic Annapolis right outside your window. This 3rd-floor waterfront condo offers the best of Eastport—sweeping views of Spa Creek, a private furnished balcony, and access to a waterfront pool with the best vantage point in town. Nestled on a quiet cul-de-sac, you’re steps from yacht clubs, marinas, and Eastport’s dining scene, and just a short walk across the bridge to downtown Annapolis. brbr brbrInside, the open-concept living space is designed for connection. Cook in the fully equipped kitchen, share meals at the kitchen table for two-four or the breakfast bar for four more, and unwind in the living room with a flatscreen TV—all while gazing out at Spa Creek. The highlight Stepping onto your balcony to enjoy morning coffee or sunset cocktails while yachts drift by against the backdrop of historic Annapolis. brbr brbrPlease note: the unit is on the 3rd floor and the building has no elevator. brbr brbrSleeping Arrangements (Sleeps 5): brbrWater-side King Bedroom – King bed brbrConvertible Bedroom – 1 King bed or 2 Twin beds (linens for both included) brbrLiving Room – Full sleeper sofa (linens provided) brbrFull hall bath with shower/tub combo brbr brbrAmenities You’ll Love: brbrWaterfront pool (open late May–Labor Day) brbrPrivate furnished balcony overlooking Spa Creek brbrSmart TVs in living room + bedroom brbrHigh-speed WiFi brbrCoffee maker + starter pack brbrLuxury linens & starter toiletries brbrLaundry facilities in building, not the unit (smartphone-operated) brbrSecure building access brbrAssigned parking for 1 car + free street parking brbr brbrDistances: 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 10 PM – 8 AM brbrPrimary renter must be 25+ and present during stay brbrCheck-in: 4:00 PM brbr brbrThis Eastport condo is all about waterfront lifestyle and location. Whether you’re here for a Naval Academy event, a sailing regatta, or a weekend escape, you’ll have the very best of Annapolis right at your doorstep—with Spa Creek as your backdrop.

Condo

Waterfront Suite with Views of Annapolis, Prime Eastport Location

Annapolis, Maryland, United States

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Bath

Sleeps

$522.17

Welcome to your home away from home in Annapolis! Nestled in the charming neighborhood of Eastport, this beautifully appointed 2-bedroom condo offers breathtaking views overlooking the water and the iconic Annapolis skyline. Despite its serene setting, downtown Annapolis is just a quick half-mile walk or water taxi ride across Spa Creek, allowing you to easily explore all the attractions and amenities the city has to offer.brbrStep into our newly renovated kitchen, where one of the standout features is the dark wood cabinets with stainless appliances. As you prepare your favorite meals, you'll appreciate the spacious white quartz countertops that provide ample room for all your culinary endeavors. The large opening enhances the spaciousness opening to a breakfast bar and open to the living room. Whether you're chopping vegetables, plating dishes, or enjoying a take-out meal from one of the many wonderful local restaurants, you'll find plenty of space for cooking and dining.brbrInside you'll be greeted by a welcoming atmosphere and stylish decor. The condo features a queen bedroom, and a convertible den/second bedroom with beautiful white barn doors that close the room for privacy to use as a bedroom, or open to the living room for added entertaining space. The living room sectional offers a second queen sleep sofa, providing comfortable sleeping arrangements for up to six guests. Whether you're traveling with family or friends, there's plenty of space for everyone to relax and unwind.brbrEnjoy your morning coffee on the patio as you take in the stunning waterfront views. Later, explore the historic streets of Annapolis, visit the Naval Academy, or indulge in delicious seafood at one of the nearby restaurants. Come back to the patio to take in the beautiful sunsets over a glass of wine.brbrExperience the best of both worlds during your stay in Annapolis - the peace and tranquility of Eastport's waterfront setting, combined with the convenience of being just steps away from downtown.brbrDuring your stay from Memorial Day through Labor Day you'll have access to the waterfront community pool, perfect for soaking up the sun and taking refreshing dips on warm summer days. As you lounge by the pool, enjoy the serene waterfront views that surround you, creating a truly relaxing atmosphere.brbrFor outdoor dining and gatherings, make use of the gas and charcoal grills located in the outdoor common areas. Whether you're hosting a barbecue with friends or enjoying a meal with family, the waterfront dining areas provide the perfect backdrop for al fresco dining.brbrIndoors, you're invited to take advantage of the community amenities, including the spacious party room, card room featuring a full-size pool table, and a small weight/gym room. Whether you're hosting a celebration, enjoying a game of cards, or staying active with a workout, there's something for everyone to enjoy.brbrAccessing your condo is simple and convenient with key access to the secure building and a keypad on the front door with a unique code programmed for your stay. Access information will be available after booking. And if you have any questions or need assistance during your stay, I am just 3 blocks away and ready to help.brbrParking is hassle-free with a reserved parking spot. Additionally, this section of Eastport allows street parking with no parking pass required, providing flexibility for additional vehicles.brbrWith these amenities and conveniences at your fingertips, your stay in Eastport is sure to be comfortable, enjoyable, and unforgettable. Welcome to your waterfront retreat!

Condo

Waterfront 2-Bedroom Condo on Spa Creek

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1083.0

This 4 BR, 4.5 BA house is perfect for entertaining your guests! Come into our spacious open floor plan. You feel like you are at a local pub within the comforts of your own home. Entertain with two dishwashers, large ice machine, wine refrigerator, a second mini refrigerator, and multiple trash and recyclable bins that pull out just under the six seating island bar. The great room is 22' x 28'. The wrap around deck has plenty of seating overlooking a large patio with a basketball hoop. The kids can enjoy a fenced in yard. Enjoy walking to restaurants, shopping, Navy games, and local events. brbrKeywords: 4 bedroom home with 4 1/2 baths. 2 flat screen TVS in one entertainment room. Wrap around deck with seating, basketball court, and fenced in yard,

Stunning Annapolis Home! Across from the library, walk to Naval Graduation

Annapolis, Maryland, United States

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