Vacation Rentals By Owner In Annapolis, MD

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWelcome to this gorgeous Texas-themed downtown Annapolis home. Every inch of this home has custom finishes and has been painstakingly renovated by the gracious homeowner who recently opened his home to guests. And if the interior of the home isn't enough, the outdoors are a rare gem in the city: a yard, an oversized back deck, front porch and parking for 4 cars in the driveway. brbr brbrLocated just around the corner from the Waterfront, you can see the harbor boats and all the way to the Bay Bridge from the top floor Suite. There are 2 bedrooms and 2 full baths on the 2nd floor and a third floor suite with a Queen bedroom, full bath and living room. The home's large kitchen, breakfast bar and eat-in kitchen overlook the sunny back patio. There is a large family room and dining room with seating for ten. There is also a large entry foyer and lounge with custom artwork throughout. brbr brbrThis is the perfect spot for those coming in for that special Naval Academy or boat show event, or wanting to take in the sights and sounds of Greater Annapolis. Enjoy the many restaurants, historical attractions, and shops right around the corner! brbr brbrSLEEPING ARRANGEMENTS 3 BR / 3.5 BA / Sleeps 6 adults (2 additional children): brbrKing Suite: brbr- Second Floor brbr- King Size Bed brbr- En Suite Bath with dual vanities and custom stand-up shower brbr brbrGuestroom on the 2nd Floor: brbr- Second Floor brbr- Full-Size Bed brbr- Full Bath in the Hall brbr brbr3rd Floor Bedroom Suite: brbr- Third Floor brbr- Queen Bed brbr- Full Bath brbr- Living Room with views of the Annapolis Harbor brbr brbrHIGHLIGHTS: brbr- Oversized Back Patio with sitting area, brand new furniture and gas grill brbr- Spacious gourmet kitchen brbr- Eat-in kitchen counter seats 2 brbr- Dining room table seats 8-10 brbr- WiFi brbr- Big Screen TVs brbr- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service brbr- Parking for 4 cars brbr- Washer & dryer located inside the home brbr- Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations. brbr- Touchless entry. Drive straight to your rental home, park in the driveway and enter the front door with the key from a lockbox located at the door. brbr brbrProperty Distance to: brbr- U.S. Naval Academy – 3 blocks brbr- Washington, DC – 30 miles brbr- Baltimore - 25 miles brbr brbr* Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going. brbr* All beds are already made for you with freshly -laundered luxury sheets & towels. brbr brbrHouse Rules: brbrNo smoking, pets or parties brbrMust be 25+ to rent, with an adult present at all times brbrFor your security, we have one door cameras facing the outside of the home and a noise decibel monitor that is compliant with the law. brbrCheck-in: 4:00 PM, Check-out: 11:00 AM

Parking for days at the unique Deep in the Heart of Annapolis with large private deck

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$1833.12

The Oaks Inn is a well-kept home, built in 1930 with original hardwood floors. It is nestled in the heart of Historic Downtown Annapolis and seamlessly combines timeless historic charm and original architecture with upscale furnishings and bedding. Ideally situated steps from City Dock, US Naval Academy, and the bustling ambiance of Main St., this property is also a short walk to the State Capitol. Enjoy the vibrant energy while relishing the comfort and privacy of a quaint street. The Oaks House Inn Annapolis boasts both charm and ambiance and serves as the perfect location for dining and entertaining. The spacious brick back patio provides an enchanting oasis for relaxing fun. And the lawn area is perfect for outdoor games. There is an outdoor grill, heat lamps and a firepit for your outside enjoyment.brbrThe spacebrThe Oaks Inn Annapolis is a beautiful property. Guests are presented an extraordinary opportunity to stay in one of the six bedrooms each with a King or Queen bed, one two-bedroom suite with King and Queen beds, and one suite with two double beds and a furnished rooftop deck. This location offers the epitome of convenient city adventure. Enjoy the best of both worlds with easy access to the vibrant energy of downtown Annapolis while still relishing the comfort and privacy of a quaint residential street. Step through the charming portico into back yard and side door that leads to the charming sitting room, dining area and living room to the right and game/tv room, kitchen and bar lounge area to the left. The home is thoughtfully designed to foster a harmonious flow between living spaces. The family game room and back lounge space with a bar and easy access to the spacious brick patio, garden and firepit area, serve as wonderful gathering places for entertaining guests, friends and family. On the 2nd floor, you'll find three nicely-sized bedroom suites with two full bathrooms, and one with a private balcony exuding a warm and inviting relaxed place to chill. Continue to the third floor, where three additional private bedroom suites with 2 full bathrooms await, one of which offers a rooftop deck amongst the tree tops. The fourth floor leads you to a spacious loft perfect for quiet reading, working or kids play-space. Not to be overlooked, the back patio provides an enchanting oasis for hosting gatherings, grilling, or simply relaxing amidst the beautiful surroundings. Don't miss the opportunity to visit, stay and play in the historic Oaks Inn Annapolis, as it combines the essence of Annapolis' rich history with modern elegance in one of Maryland's most coveted locations. Please note: summer A/C and CW fee applies!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$538.69

(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early.brThe house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch.brWe walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.brbrbrbrThe cottage is all yours, and its self check-in, but please reach out on the app or on Jim's cell for anything at all!brCheck-in: After 4:00 PM (early check-in when available)brCheck-out: 11:00 AM (late check-out when available)brPlease: brNo smoking brNo pets brNo parties or events brQuiet Hours 9 pm to 9 am brbrbrGroceries: Grauls, on Taylor Avenue. Go out to Ridgely Avenue, turn Right. Go about 3 blocks and Grauls is in the strip mall on the right. 8 minute walk. brbrLiquor, Beer, Wine: In the Walgreens, of all places! Same strip mall as Grauls. In the back left hand corner inside the Walgreens. Good selection of everything. Even shorter walk to Chessie's Wharf, for an amazing selection of RAR Brewing's finest drafts!brbrLocal places to eat and drink – all within 5 minute walk - turn right at the bottom of our street, on Ridgely Avenue: brBakery: Great Harvest baking – on Ridgely Avenue just a couple of hundred yards up on the left, just beyond the gas station. Go-to favorite: Mocha SconesbrbrCoffee Shop: Bean Rush Café - Annapolis St. (the next street over, take a left off Ridgely on Monterey, then right on Annapolis St. brbrBreakfast: Evelyn’s- Annapolis St. brbrDinner: In Grano, Drawing inspiration from Italy, Japan, Spain, Greece, and beyond, In Grano’s menu promises an elevated, global dining experience.brbrIce Cream: Always Ice Cream - next door to Bean Rush Café - topped Fodor's list of ice cream places in the USA! (Note: Annapolis Ice Cream Company/Always Ice Cream Named Top 12 Ice Cream Shop by Fodor's Travel!!)brbrWest Annapolis Progressive dinner: 1) round of drafts at Chessie's wharf while you wait for your table at In Grano 2) Fine Dining at In Grano (safe space for ice cream) 3) Always Ice Cream brbrPizza, Pasta: Bella Italia, in same shopping center as Grauls, at end of Ridgely Avenue (at corner of Ridgely and Taylor) brbrThe whole place. This is a stand-alone cottage. Access to private waterfront and dock. brTV / WIFI / Netflix brAir conditioning brFully Equipped Kitchen brNespresso Machine or French Press, or Drip Coffee MakerbrBeautiful Dining Nook brComfy Queen with expansive Water Views , and a Comfortable Queen sofabedbrFull Bath with all essential Amenities brHair DryerbrClothes IronbrExtra Pillows and Blankets brScreened-in Porch overlooking Weems CreekbrSerene environment brPicnic area on the dock. brFire pit on the hillsidebrPrivate Dock brUse of Stand-Up Paddle boards brUse of Canoe brUse of KayaksbrUse of 17' Boston Whaler (for experienced boaters, and at extra cost) brbr “Our stay at Jim’s place was perfect for a weekend away. We’ll definitely book again! – Steve, March 2021”brbrWe had a lovely stay at Weems Creek Cottage. It is so quaint, quiet, and thoughtful. We loved the scenery, the bedside view of the sunset over the river was stunning. We slept so well, absolute peace and immediate comfort. It’s also in a really cute area, nice little local restaurants and cafes nearby, and we enjoyed walking/driving to downtown Annapolis. Very easy to find, SO clean and very well designed, private and intimate, just really cute and charming spot. Jim was very friendly, responds immediately and provides all the information you could possibly need! We will definitely be returning in warming weather. Highly recommend! (January, 2025)brbrThe original 1910 cottage studio was fully refurbished with charming décor and your comfort in mind.brbrIn addition to the studio and screened-in porch, all of our guests have access to our waterfront backyard complete with fire pit, Adirondack chairs and fantastic views of Weems Creek: the boats, the birds and the sunsets! brbrBe sure to walk on down to the picnic area - on our private dock! There you can decide between the paddle boards, kayaking, or taking our boat out on to the Severn River or down to City Dock for a drink or a bite! (Experienced Boaters: Reach out to us about using our 17' Boston Whaler for an extra cost )brbrOver the summer, the dock picnic area is also the perfect setting for your own classic Maryland Crab Feast! For the chefs and adventurous at heart, we've got all the necessary pots and mallets to give it a go yourself. If you're not up for the mess - we can definitely tell you where to enjoy a crab feast in town.brbrBe sure to take a quick stroll through our neighborhood to grab local delicacies at the Great Harvest Bread Co, the Bean Rush Cafe and all the rest that the village of West Annapolis has to offer. Our location is pretty amazing.brbrPlus, we are only a few minutes' walk to the US Naval Academy’s Gate 8, the entrance to the historic Annapolis campus and Navy-Marine Corps Memorial Stadium!brbrFriends, we hope you will enjoy your stay with us, and please, come again!brbr“I have stayed in the cottage in all 4 seasons and each has its own unique beauty. It is a great home away from home.” – Darcy, December 2021”brbrShort walks to many things. 1.5 miles to Annapolis City Dock. Ride sharing apps. brPro tip: At City Dock, take the water taxi to Davis' Pub in Eastport, then do a progressive walking lunch or dinner on your way back to the city dock through Eastport, over the beautiful Spa Creek drawbridge - and back to the City Dock!brbr5 minutes walk to: Bean Rush Cafe/Coffee, Evelyns, Naval Bagels, RAR Brewing/Chessie's Wharf, In Grano, Positano, Always Ice Cream, Great Harvest Baking, and more. brEasy walk to the Navy stadium or St. John's College. br1.5 miles to Annapolis City Dock area or USNA Gate 1 (even closer to Gate 8)

Cottage

Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$593.64

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrThis charming 3-BR, 2.5-BA townhome is just a 1/2-block from the city dock and is a luxurious vacation getaway in the heart of the historic district of Annapolis. Built in 1881, this townhome has been completely renovated, with beautiful wood floors, an open floor plan and every modern convenience. brbr brbrEntertain in the open kitchen that flows seamlessly into the dining room and living room and out to the private back patio. There are 3 bedrooms and 2 baths upstairs, with sleeping for 5 in the 2 Queen beds and 1 Twin. The en-suite Queen bedroom also has private balcony. On the main level is room to sleep up to 2 adults or 4 more kids on the family and living room's Queen sleeper sofas. brbr brbrTake advantage of the rich culture, history, shopping and entertainment of Annapolis. The State Circle, the Annapolis Yacht Club and the Naval Academy are all within two blocks. Ego Alley and the historic William Paca, James Brice and Hammond-Harwood houses are a five-minute stroll. Park your car and experience all of downtown Annapolis within easy walking distance. Or just stay in and enjoy the three smart TVs, high-speed Wi-Fi and cable TV. Colonial charm. Rich history. Comfort and convenience. brbr brbrSLEEPING ARRANGEMENTS 3 BR / 2.5 BA / Sleeps 7-9: brbrQueen Suite (sleeps 2): brbr- Second Floor brbr- Queen Bed brbr- En-suite full bath brbr brbr Guest Bedroom (sleeps 2): brbr- Second Floor brbr- Queen Bed brbr- Full Bath in the Hall brbr brbrTwin Guest room (sleeps 1): brbr- Twin Bed brbr- Full Bath in the Hall brbr brbrFamily Room (sleeps 1-2): brbr- Main floor brbr- Queen Sleeper Sofa brbr- Full Bath in the Hall upstairs or half bath on main floor brbr brbrLiving Room (sleeps 1-2): brbr- Main floor brbr- Queen Sleeper Sofa brbr- Full Bath in the Hall upstairs or half bath on main floor brbr brbrHIGHLIGHTS: brbr- Private fenced-in back patio with gas grill (propane provided) brbr- Balcony off Queen suite brbr- Full gourmet kitchen brbr- Dining room table seats 8 brbr- WiFi brbr- Multiple Flatscreen TV's brbr- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service brbr- Washer & dryer located inside the home brbr- No pets brbr- Keyless entry. Drive straight to your rental home and enter the door with an electronic lock code. brbr brbrProperty Distance to: brbr- U.S. Naval Academy – 2 blocks brbr- Washington, DC – 30 miles brbr- Baltimore - 25 miles brbr brbr* Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going. brbr* All beds are ready made for you with freshly laundered sheets & towels. brbr brbrHouse Rules brbrReservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. brbrCheck-in time: 4:00 pm brbrCheck-out time: 11:00 am

Walk to Main Street, City Dock and USNA Gate 1 From Historic Catch 22 with Private Patio

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$344.85

This 2nd floor apt has new furniture, bedding and housewares. Extremely convenient location to downtown where there's lots to do during the daytime and at night. You'll be directly across from Gate 2 at the Naval Academy so a block in either direction and you can get onto the Yard. You'll be a short 1 block walk to Ego Alley and all of the restaurants, shops and water taxi. Eastport is a 15 minute walk. This is a beautiful location in historic downtown Annapolis that's convenient to everything that downtown has to offer and is perfect for couples with or without children, solo and business travelers.

Apartment

2nd floor Spacious Downtown Getaway- Across from US Naval Academy

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$806.66

Absolutely gorgeous downtown waterfront home. Loaded with historical significance and character, all while minutes walking distance to museums, restaurants and festivities on Main Street Annapolis. This home has a deep water slip for up to 40 feet. There are also kayaks and canoes guests may enjoy. And if you aren't up for the short walk to ego alley ... Take the water taxi, they will pick you up and bring you back to 5’s dock. This locally legendary house has had only 2 owners since 1936, each with deep ties to USNA and USMA. It is truly a family home they are happy to share. It’s not a ‘rental’ and the owners desire guests who will treat the home as their own. It is their joy to share this little gem with people who love Annapolis and it’s history.brbrThis home is the definition of tranquility as a virtually secret place in the middle of a city. Tucked away on the waterside of Southgate Ave., it is peaceful, quiet and completely private. Sleeps six adults and two children comfortably. Fully equipped kitchen. Laundry on-site. Walking distance to everything Annapolis. This home is truly one of a kind.brbrNote that there is street parking only. The photo of the driveway aims at showing the guests that the entrance to the home is down the driveway and behind 7 Southgate Avenue. This home was built in 1936 for the daughter of the then owners of 7 Southgate. Hence the legacy access. There are multiple garages that are less than .4 of a mile away if extended M-F daytime parking is needed. 2 hour weekday limit but no night or weekend parking restrictions. Both uptown and downtown Annapolis are easy walking distance from Southgate Avenue through beautiful Murray Hill.brbr

Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks

Annapolis, Maryland, United States

3

Bed

Bath

8

Sleeps

$409.66

Summary:brbrWelcome to Chapel Gate! Ideally located just outside Gate 3 of the U.S. Naval Academy and only a few blocks from City Dock, this top-floor, three-bedroom apartment offers a central home base for exploring downtown Annapolis, whether you're visiting the Naval Academy or just enjoying all that Annapolis has to offer. Enjoy the comforts of home with a comfortable living room with Roku TV, cook and dine in the lovely kitchen, and use the shared outdoor grill and patio. and enjoy in-unit laundry.brbrbrbrThe Space:brbrThe apartment spans two levels and includes three bedrooms, one bathroom, and a full kitchen. Two bedrooms and a full bath are on the main floor, and the third bedroom is on the floor above. Guests should note that stairs are required to access the unit.brbrbrbrGuest Access:brbrShared entrancebrbrbrbrGetting Around:brbrStreet parking in Downtown Annapolis is paid. If possible, we recommend not driving / renting a car. The street this home is located on is zoned for resident parking only. For weekend guests bringing a car, there is free weekend parking at at Bladen Street garage two blocks away from Friday at 6pm to 6pm Sunday. At other times, we recommend parking at the Hillman Garage which is the largest parking structure in Annapolis, about a half-mile walk. Additional parking info is available on the Visit Annapolis website's Parking in Downtown Annapolis page.brbrbrbrOther Things to Note:brbrTo help ensure a smooth, secure, and enjoyable stay for all guests, please review the following important information before booking:brbrbrbrCheck-In & Identity Verification PolicybrbrbrbrAll reservations require the primary guest (the booker) to complete a secure online check-in process prior to arrival. This includes:brbrbrbr-Uploading a valid, unexpired government-issued photo IDbrbr-Uploading a selfie to confirm identitybrbr-Reviewing and signing our rental agreementbrbrbrbrThis process is similar to hotel check-in and is required because we do not typically have staff on site. Check-in instructions will only be provided once this process is complete.brbrbrbrIf you would like to review the rental agreement before booking, please feel free to contact us.brbrbrbrIn some cases, we may also request a security deposit and/or apply a damage waiver fee in accordance with booking channel policies.brbrbrbr * It typically takes ~1 hour to screen a guest after they book this property and could take several hours if we are busy before we are able to provide them with check-in information.brbr brbrIf you make a last minute reservation, we ask you to please be patient and please do not expect to gain access to the property immediately.brbr brbrGuest Count & Occupancy PolicybrbrbrbrEach listing includes a maximum number of guests based on unit type and local regulations. Additional guests are welcome for an added nightly fee:brbrbrbr-2 & 3 bedroom units: $35 per guest, per night after 4 or 6 guests, respectivelybrbrbrbrPlease ensure your guest count is entered accurately at booking. We will confirm the number of guests after reservation. If the guest count changes, pricing may be adjusted accordingly. For safety and compliance purposes, exterior security cameras are used to verify occupancy. Unreported additional guests may result in additional charges.brbrbrbrPet PolicybrbrbrbrThis is a pet-friendly property. While our cleaning team is thorough, guests with severe pet allergies should be aware that dogs, cats, or other animals may have stayed in the space previously.brbrbrbrPet fees:brbrbrbr$30 per night, per petbrbr$150 per week, per petbrbr$300 per month, per petbrbrbrbrPet fees are included in the accommodation rate as long as you choose the appropriate quantity of pets when completing a booking. We confirm this with all guests post booking confirmation.brbrbrbrLocal Reservation PolicybrbrbrbrReservations under 7 nights from guests residing in the local area may be subject to cancellation at our discretion. We handle exceptions on a case-by-case basis.brbrbrbrEarly Check-In & Late Check-Out PolicybrbrbrbrEarly arrivals and late departures are not guaranteed and must be approved in advance. If approved, the following fees apply:brbrbrbr-Up to 1 hour: $100brbr-1–2 hours: $200brbr-2–3 hours: $300brbr-3+ hours: $400 or the cost of an additional night (whichever is greater)brbrbrbrPlease do not assume availability without confirmation.brbrbrbrSmoking PolicybrbrbrbrSmoking is not permitted anywhere on the property, including indoor and outdoor areas. If evidence of smoking is found, an additional cleaning fee of $500 will be applied in accordance with the booking channel's cleaning and damage policies.brbrbrbrSpecial Request PolicybrbrbrbrRequests for items such as pack-n-plays, high chairs, or other non-standard amenities should be submitted at least 7 days before check-in to ensure availability. Requests made closer to arrival will be accommodated if possible but cannot be guaranteed.brbrbrbrWe understand that this is a detailed list, and we truly appreciate you taking the time to review it. These guidelines help us maintain a safe, well-cared-for property and ensure a great experience for every guest. Our goal is always for you to feel comfortable, welcome, and well taken care of during your stay.

Chapel Gate 3BR Steps to City Dock & Naval Academy

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$235.17

Renovated upstairs unit two bedroom with TWO parking spots in the Historic District. Everything is high end and used exclusively as a short term rental. Private entrance, cute small custom kitchen, ceiling fans, mini split AC/ heat in every room for year round comfort. Hardwood floors, quality linens , lucid mattresses, Keurig coffee bar, toiletries. Walk to town in 10 min or less or take the free trolley to Main St, USNA, Churches, AYC. No children under 12.brbr****Must message prior to request if considering bringing a pet - one dog only with prior permission *** Our space is a wonderful couples retreat - please no parties, bach / loud groups or children under 12. It is a duplex so must be able to respect the other unit and be able to climb a flight of stairs.brVery chic and comfortable we renovated this specifically for Short term adult rental clients - no children under 12 please. Chosen as a coveted AirBnB plus listing this is our 12th short term property and the only one with on location parking in town. This is the TOP floor apartment of a DUPLEX with an open floor plan its a nice functional space. Large closets, ceiling fans, new heat AC, kitchen with gas stove. New appliances - its a true rare gem in Historic Annapolis. Only children above 12. PLEASE NOTE.... As one of the only legally licensed rentals left in town we ask that you please thoroughly read our rules before booking.brbrYou MUST message BEFORE booking with a pet. $100 pet fee = ONE DOG MAXIMUM WITH PRE APPROVAL ONLY. brNo children under 12.brPlease note It is a top floor DUPLEX and these properties are extremely popular so chances are the below unit will be rented as well.brYou will be climbing a tall staircase. Beds are generally set up as 2 kings - if you need a second king or two twins please request when booking and when you receive entry info.brTotally separate entrance with no shared spaces. If you can’t be respectful with noise issues etc to others please DO NOT BOOK. brThis is NOT a party property - 4 max adults at any time per city code. We will lose our license if this rule is broken so it is strictly enforced .brbrPet Inquiries - please send a message when booking so we can discuss. $100 pet fee - one DOG maximum. SORRY NO CATS. Only chill, NON-barking , potty trained, well behaved dogs allowed .brThis is a duplex so please be respectful to all neighbors and other rental unit.brNO children under 12 years of age .br4 Adults or acceptable age children maximum guests. Guests must request second bedroom set up if in need of specific (2 twins or king).brNo loud music, PARTIES (or Bach/ette ) or smoking of ANY KIND. Maximum 4 people at any time in the unit. Breaking this rule results in a $500 fine per city code rules .brMinimum renter age is 26brThe upstairs unit is to use front entrance only. No backyard access as that is strictly for downstairs unit only

Condo

Renovated Apt In Historic Dist w/2 Parking Spots

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$513.0

This centrally located 3-story rental is steps away from everything Annapolis offers! Whether you're in town to explore the iconic Naval Academy, catch a game at the stadium, or enjoy a craft brew at the local brewery, you’ll find it all just a short stroll from your door.brbrIndulge in unique dining at one-of-a-kind restaurants or unwind with loved ones at nearby outdoor spots. For those who love the water, bay access is just a block away. brbrMaster Bedroom:brQueen-sized bedbrAttached master bathroombrbrSecond Bedroom:brQueen-sized bedbrbrThird Bedroom:brFull-sized bedbrbrMain Living Room:brFull-sized pull-out sofa bedbrbrArea Details:brWithin walking distance, you'll find an ice cream shop, coffee shop, local brewery, fine dining, and a high-end Mexican restaurant with a cocktail bar—perfect for unwinding. For a healthier bite, there's a juice bar with fresh eats, along with a local breakfast and lunch spot. Craving pizza There's a great pizza place just around the corner, as well as a bagel shop for your morning fix. You'll also have easy access to a convenience store and grocery store for everyday needs. For unique finds, explore nearby antique stores and a high-end consignment shop. Plus, the iconic Naval Academy Stadium is just a short stroll away. If you're up for a little adventure, downtown Annapolis is just a little over a mile away, offering even more dining, shopping, and cultural attractions to enjoy.

Walking distance to Navy Stadium! No cleaning fees!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$537.7

Our renovated 3 story house is located on the peninsula of Eastport, Annapolis. We are across the street from a small marina and have views of Back Creek. With 3 bedrooms, 2 and 1/2 bathrooms, we sleep 6 adults or older children. We are an easy walk across the Spa Creek bridge into downtown Annapolis, but why bother when you can visit the excellent bars and restaurants in Eastport itself. Davis' Pub, featured on Diners, Drive-Ins and Dives, is less than 200 feet away and a variety of local and nationally known restaurants such as Chart House and Ruths Chris are a very short walk away on the small Eastport peninsula. Parking is on-street but unlike downtown Annapolis, it is easy to find a spot.brbrPlease note: this house is not suitable for young children or pets. We have steep stairs and fine rugs and furniture.br

Tastefully decorated fully-equipped Eastport Annapolis house with water views

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$531.62

Be close to everything when you stay at this centrally-located, historic townhome! Located steps from the Naval Academy, Downtown Restaurants, Bars, Shopping, and Festivals. Enjoy and relax on your large private, fenced-in patio or in your modern living room. While the restaurant scene is mouth-watering in Annapolis, you can also stay home and cook in your gourmet kitchen. Explore all that Annapolis has to offer from the comfort of your home away from home! No on-site parking but lots of off. 2 Night Minimum on weekends. Fireplace is nonfunctional.

Historic 3 Bedroom Downtown Annapolis Townhome

Annapolis, Maryland, United States

3

Bed

Bath

6

Sleeps

$766.14

Summary:brbrWelcome to our newly updated 4-bedroom home in the charming Eastport area of Annapolis! This spacious retreat is just a short walk to Downtown Annapolis, restaurants, shops, and the waterfront. Inside, enjoy bright living spaces, a large kitchen and a large primary bedroom with ensuite bathroom that offers a comfortable place to unwind. Step outside to a generous backyard—perfect for entertaining, relaxing, or gathering with friends and family after a day exploring the area.brbrbrbrThe Space:brbrWelcome to our vacation rental nestled in the heart of Eastport. Our inviting 4-bedroom, 3-bathroom home is a spacious retreat, thoughtfully designed to provide an unforgettable vacation experience. The open-concept living area invites you to relax, filled with stylish furnishings and ample natural light. Prepare meals in the fully equipped kitchen, complete with modern stainless steel appliances, before gathering around the large dining table. With easy access to Eastport’s vibrant restaurants and just a short walk to downtown Annapolis, this home is a must for those seeking both convenience and relaxation. After a day of exploration, rest and recharge in our comfortable bedrooms. brbrbrbrWhere you will sleep: brbrbrbr* Bedroom 1: The master suite features a plush king size bed for a restful night's sleep along with a large master en-suite bathroom. brbrbrbr* Bedroom 2: Queen size bed brbrbrbr* Bedroom 3: Queen size bed brbrbrbr*On the main level of the home, there is an additional bedroom/office that comes with a full size bed and includes a dedicated desk, creating a perfect workspace if needed.brbrbrbrGuest Access:brbrYou will have private access to the entire home. For your convenience, we offer seamless self check-in with a smart lock. A washer and dryer are also available for your use during your stay.brbrbrbrOther Things to Note:brbrRENT-000017-2026brbrbrbrInteraction with Guests:brbrWe respect our guests' privacy and offer a seamless self check-in process. While we won't be on-site during your stay, we are always available and happy to assist with any questions or recommendations via the app or phone to ensure you have a wonderful time.

Eastport 4 Bedroom Spacious Gem on Jefferson

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$214.32

Perfect location for all that downtown Annapolis offers. Located right across from USNA gate 2. Super convenient, park your car and walk everywhere! Lots of daytime shopping, restaurants, tours, cruises and nightlife. The apt is located on the 3rd floor. My place is perfect for couples, solo and business travelers. There is a large living room space with a full pull out couch, tv and dining table. The bedroom has a queen bed with a tv. There is a small full kitchen and updated bathroom.

Apartment

Charming Downtown 3rd Floor 1 Bedroom Apt

Annapolis, Maryland, United States

Come relax at our spacious home and enjoy our quiet neighborhood! We are located near the greatest attractions in Annapolis, but off the beaten path. Grill out with friends, enjoy the various sitting rooms, and cook great meals in the vast kitchen. Plenty of parking for larger groups of friends!brbrHome is located .7 miles from Navy Bridge, 1.1 miles from USNA, and 1.6 miles from downtown Annapolis.brbrPets allowed on a case by case basis! We will request a $100 pet fee via airbnb during your stay.

Bed

1

Bath

4

Sleeps

Select Dates for Price

Quiet home with large yard, close to Navy Bridge.

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$568.53

Welcome to our newest listing - The Coastal Cottage on Chesapeake located in the Maritime community of Eastport . This beautiful home features one level living with 3 bedrooms , 2 baths , open kitchen , front porch , large screened in porch and driveway parking for 3 cars and plenty of free off street parking. Walk to all of Eastports restaurants , Historic Downtown , AYC , EYC and USNA .

Cottage

Coastal Chesapeake cottage in Eastport

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$509.95

Summary:brbrCharming 2-bed, 2-bath cottage in West Annapolis, perfect for up to 6 guests. Features a bright, open-concept living space, a fully equipped kitchen, and a dedicated workspace. Relax on the front porch or enjoy the private backyard with a deck and fire pit. Walk to the Naval Academy stadium, local breweries, and shops. A perfect blend of comfort and convenience for your Annapolis getaway!brbrbrbrThe Space:brbrWelcome to your updated two-bedroom, two-bathroom cottage in the heart of West Annapolis! This charming home is designed for comfort and convenience, offering a bright and inviting atmosphere from the moment you step inside.brbrbrbr**Living Area:**brbr* The open-concept living area is flooded with natural light, featuring a comfortable sofa that converts to a sleeper for two additional guests.brbr* It flows seamlessly into a modern, fully equipped kitchen.brbrbrbr**Kitchen & Dining:**brbr* The kitchen features stainless steel appliances, granite countertops, and a breakfast bar for your morning coffee.brbr* It is fully equipped for preparing meals during your stay.brbrbrbr**Bedrooms & Bathrooms:**brbr* Primary Bedroom: A spacious retreat with an en-suite bathroom, a large walk-in shower, and a dedicated desk space.brbr* Second Bedroom: A comfortable and peaceful room for a great night's sleep.brbr* Second Bathroom: A full bathroom with a clean, white-tiled shower-tub combination.brbrbrbr**Outdoor Space:**brbr* Enjoy the welcoming front porch with rocking chairs.brbr* The large, private backyard is an ideal space for relaxation or fun, complete with a back deck and a fire pit for cozy evenings.brbrbrbrGuest Access:brbrYou will have private and exclusive access to the entire home, yard, and all listed amenities throughout your stay. This includes the two bedrooms, two bathrooms, kitchen, living area, front porch, back deck, and the entire private backyard with the fire pit.brbrbrbrThe Neighborhood:brbrOur West Annapolis location allows for easy access to all that Annapolis has to offer! We are a 10-minute walk to the Navy Football Stadium or the shops and restaurants in West Annapolis. Take a quick 5-minute drive to downtown “ego alley” at the Annapolis Harbor, or if you prefer, a leisurely stroll.brbrbrbrThe neighborhood is within walking distance of several local Annapolis favorite restaurants and coffee shops such as Evelyn's, Bean Rush Café, Great Harvest Bread Company and Rutabaga Juicery & Eats.brbrbrbrGetting Around:brbrA car is recommended to get around the area, but not necessary as there are many ride share options available.brbrbrbrOther Things to Note:brbr* City of Annapolis Registration Number: STR23-145279brbr* The sofa in the living room is a sleeper sofa that can accommodate two additional guests.brbr* For your convenience, a dedicated workspace is available in the primary bedroom.brbrbrbrInteraction with Guests:brbrWe respect our guests' privacy and offer a self-check-in process. We will not be on the property during your stay, but we are readily available via the app or by phone if you have any questions or need assistance.

Charming West Annapolis Cottage home

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$945.86

Renovated, charming Annapolis home on half-acre lot fronting Burley Creek. Just a short paddle to Whitehall Bay and expansive waters of the Chesapeake Bay. Four sliding glass doors overlook the water with panoramic views of evening sunsets. Home features 5 bedrooms, 4.5 bathrooms, newly renovated kitchen, huge deck overlooking the water, outdoor grill, kayaks, SUPs. Historic downtown Annapolis harbor only 15 minutes by car OR boat. Dock accommodates 40-foot boat. MLW six feet.brWaterfront with pier and sunset views. Large deck with ample seating and large dining table.brGuests will enjoy the entire two-level house situated on one-half acre on the water. Water access via the dock with paddle board and kayak available for your enjoyment.brOther things to notebrThere is a sailboat and power boat moored at the dock. During your stay someone may access the sailboat on the dock. We promise any disruption will be minimal.brbrDue to COVID 19 we ask guest to be responsible and keep risks to a minimum. We ask you follow all local, state and federal health guidelines to protect yourself, others and to prevent the spread of COVID 19. Gathering should be limited to 10 or less people. Wash hands frequently and wear a mask when social distancing is not possible. If you exhibit any signs or symptoms of Covid 19, please contact your doctor immediately for advice and instructions.brbrAt this time no parties or events are allowed at the house.brbrParties/events held at the house will need written preapproval via the Airbnb app. A party fee (depending on the scope of the event) and a party deposit fee may be applicable. Also, the cleaning fee may be adjusted based on the scope of the event.brPlease contact the host for more information, pricing and preapproval for your specific event.brLicense numberbr140873

Huge deck overlooking water

Annapolis, Maryland, United States

Bed

Bath

Sleeps

Select Dates for Price

This stunning detached home, designed by Stylish Stays, is the perfect place for a stay in THE HEART of Annapolis. This highly walkable property is located in the Arts District, w/ close by shops, restaurants, bars, waterfront, State House, and Naval Academy! brbr☞ 15+ seconds to great restaurants!br☞ 13 min walk to State Housebr☞ 15 Min walk to Navy-Marine Memorial Stadiumbr☞ 19 Min walk to City Dockbr☞ 35 Min drive to Baltimorebr☞ 40 Min drive to DCbr☞ Fenced YardbrbrEnjoy your stay with us! This space offers: br☞ Professionally Designed, Furnished, and Appointed br☞ 3 Bedrooms Comfortably Sleeping 8 (1 King, 1 Queen, 1 Full Murphy Bed, 1 Queen Sofa Bed) br☞ 2 Full Baths w/ 1 bathtub and 1 showerbr☞ High Quality Helix mattresses for a restful night's sleep br☞ Fully appointed Kitchen with electric range and convection oven, full sized microwave/dishwasher/fridge, plenty of counter and cabinet space laid out for entertaining and hosting br☞ Deck off second bedroom, Brick Patio, and fenced yard w/ full outdoor dining set and Adirondacks so you can truly set off the vibes br☞ Black out curtains in each bedroom when you want it darker br☞ 2 Story Entry Foyer for a spacious airy feel br☞ Dedicated work area with second monitor br☞ Reliable FAST Internet Connection (300mbps) br☞ Smart TVs in every living space w/ Apple TV and Chromecast br☞ Reliable WIFI throughout the homebr☞ Full Sized Laundry in unit br☞ Fully Stocked Bathrooms w/ Paya brand bath amenities br☞ Nearby Restaurants/Shops/Historical Sites/Bars/Music Venues/Markets/Parks br☞ EZ Baltimore/DC/BWI Location br☞ Mellow lighting throughout br☞ High quality sheets and towels br☞ Quiet and comfort Inside, yet Vibrant City Life outside the doorbrbrHere are some of our Past Guest comments from other properties we host: brTerrific host - very helpful and communicative. - Kelly brThe host was communicative and accommodating. Would definitely stay here again! - Ayla brbr☆☆BEDROOMS☆☆brbrThis well thought out detached home accommodates 8 guests in 3 bedrooms. The stylish primary bedroom is on the first level and is fitted with a king-size bed w/ Helix Midnight Mattress, a closet for clothing storage, and door to rear brick patio living space. The second bedroom has a queen-size bed, closet, and door to rear deck overlooking the fenced yard. The third bedroom has a Full sized murphy bed w/ Helix mattress, large closet, and a full sized desk and chair with full sized monitor. Each bedroom has an individual ductless HVAC unit to control the climate for that room, and TVbrbrThe Living Room has a sofa that converts to a queen sized pull out bed with memory foam mattress brbr☆☆BATHROOMS☆☆brbrThere are two full and bathrooms in this home, each stocked with all the essentials you need for your stay.brbrThe first level bathroom has a walk-in shower, and the full sized washer/dryer units. The second full bathroom is on the second level off the living room and has a shower/tub combo. brbr☆☆KITCHEN AND DINING☆☆brThe combined kitchen and dining area was designed for serious cooking and entertaining! Fully equipped with all appliances, utensils, cookware, and glassware you will feel right at home. With a 4-burner glass cooktop, convection oven, microwave, full sized dishwasher and refrigerator, you will thank yourself for staying with us so you have the ability to make a full Thanksgiving meal if you wanted to!brbrThere is total dining seating for 8, multiple coffee making options, and full cocktail making equipment!brbrbr☆☆OUTDOOR SPACE☆☆brThere is a large brick patio with 8 person dining table, outdoor sofa, and Adirondack chairs offering ample seating options. Enjoy the night sky in this fully fenced yard. The remainder of the yard is rubber mulchbrbr☆☆LOCATION☆☆brAnnapolis is known for being one of the oldest and most storied state capitols in the country. The surrounding neighborhoods are picturesque with historically designated homes and businesses. You are a 5 min drive from EVERYTHING Annapolis has to offer, but where this property really shines is it’s ease of walkability to everywhere. There are great restaurants starting literally 2 doors down from us!brbr☆☆Guest Agreement☆☆brFor all bookings, the guest will be required to sign a Guest Agreement. A copy of this agreement will be provided on demandbrbrFor stays over 30 nights, we include monthly spot cleaning and the first $350 of internet, electricity, and water utilities. More frequent cleanings, refills and full cleanings are available at an additional fee, which will be determined later, including the mode of payment.brbrBy booking, you are stating you give permission to the host to use a third-party to verify your identity and check criminal databases to confirm your reservation. Complete terms regarding the guest verification can be provided by the host. You may receive an email to complete your screening. Please check your spam inbox for this email and contact the host if you have any questions.brbrPlease confirm you will complete the additional guest screening via Safely, sent after booking, and if the results are unacceptable to the host, you will cancel the reservation upon request brbrWe confirm the number of guests staying in the property to your responses during the booking process and check in. We charge per guest, please make sure your guest count is accurate when booking, or update us prior to additional guests arriving.brbrEarly check-in and late checkout requests need host approval and may have extra fees. Please let us know before booking or as soon as you know if you'll be making a request. We will do our best to accommodate.brbrFees are as follows:brGuests can enjoy early check-in or late checkout for $50 per hourbrbrbr**PETS**br• There will be an additional cleaning feebr• Your pet will have to be crated if no adults are homebr• Guests will be responsible for all damage, noise, and messesbr• Guests must pick up all pet waste and properly dispose of it, while being respectful of neighbors' yards and propertybr• Poop bags should go into specified poop trash can (no loose poop bags in the large trash bins, please)br• Pets aren't allowed on the sofas/chairs/benches. They ARE allowed in beds as we can more easily clean the sheetsbr• Pets shouldn't be left unattended outsidebrbrThese rules are intended to prevent any issues with pets. Ultimately as long as there are no issues in the house from any pets, we will assume our rules were observedbrbr**PARKING**br• PLEASE NOTE PARKING IS NOT INCLUDED WITH THIS PROPERTY. br• There are three nearby pay parking garages that are a 2 and 5 mins walk, 2 hour adjacent neighborhood parking, and nearby alley (Ellington Alley) for loading/unloadingbr• As of April 2024, Overnight garage parking rates are $23 and $10 respectively, depending on the garage you park inbr• Please don’t stop in front of the property to load/unload, except at a metered spot just a few doors down.br• Side streets have a 2-hour parking limit. For more parking details, please refer to the Parking section in our House Manual.brbrbrRental Registration number #STR23-145297

Stylish & New, Pet Friendly Fenced Yard, Walkable Downtown

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$265.05

Discover the Allure of Historic Annapolis Living! brbrWelcome to your captivating 2-bedroom, 1.5-bath home nestled in the desirable Murray Hill community. This stunning retreat offers a seamless fusion of historic charm and modern upgrades, ensuring a memorable stay in Annapolis.brbr✨ Key Features:brKing beds and TVs in each roombrNewly renovated interiorsbrExpansive backyard with a beautiful flower gardenbrCustom cabinetry, granite countertops, and a gorgeous backsplash in the kitchenbrConveniently located washer and dryer in the main living areabrHardwood floors throughoutbrbrStep inside and be charmed by the heart of the home, the renovated kitchen, featuring custom cabinetry, granite countertops, and a stunning backsplash. The main living area boasts beautiful hardwood floors and includes a washer and dryer for added convenience.brbrVenture outside to the expansive backyard patio, surrounded by beautiful landscaping. The backyard flower garden is a floral paradise, showcasing hydrangeas, peonies, phlox, tulips, hyacinths, lilacs, lilies, daisies, daylilies, coneflowers, and roses - not a single spot overlooked.brbrLocated in historic Murray Hill, you'll experience the best of Annapolis living with easy access to Acton Cove, City Dock, and downtown attractions. Everything is walkable! Immerse yourself in the vibrant culture, shops, and restaurants that make Annapolis a beloved destination.brbr.5 mile to State Circlebrbr.5 mile to St. John's Collegebrbr.7 mile to City Dockbrbr1 mile to United States Naval AcademybrbrDon't miss your chance to experience historic Annapolis living. Book your stay today and make unforgettable memories in this charming home!

Historic Annapolis Home!

Annapolis, Maryland, United States