308 properties available

Located in Annapolis, Washington, United States. PERFECT LOCATION in the heart of history 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! Historic 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

Located in Annapolis, Washington, United States. 7 mins away from Downtown Annapolis Come stay at our cozy house. Perfect for a group of 11people. Share beautiful memories that will last a lifetime. Close to downtown, groceries stores, mall, target, Whole Foods, gas station, restaurants, laundromat, and about a 40min drive from BWI.

Located in Annapolis, Washington, United States. Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport Welcome to our newest property in The Exclusive Maritime Eastport section of Annapolis . Just a short stroll ( half mile )or quick water taxi ride across the creek to the Historic District and USNA , Eastport has been long considered one of the best locations in our fair city . Our block has some of the finest homes in Annapolis and you will be temporary neighbors with one of the most famous baseball players ever( Go Orioles !!).... Yes it’s that exclusive ! We have 4 parking spots and plenty of unrestricted overflow for guests \ visitors . Two blocks away are the city’s best restaurants ( Blackwall Hitch , Boatyard , Carols Creek , Ruth’s Chris , Chart House , Lewnes and many more ) You will enjoy staying in the city without the hassles of the Historic District ( parking , bar noise etc ) Custom built in 2014 this property is strictly used as a short term rental - everything is top of the line built and spot

Located in Annapolis, Washington, United States. 2nd floor Spacious Downtown Getaway- Across from US Naval Academy This 2nd floor unit has all new furniture, bedding and housewares. This is 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.

Located in Annapolis, Washington, United States. Historic Downtown Union House with Free parking & private patio Enjoy Annapolis, MD in this charming Federal-style home nestled in the heart of the historic district. Spectacularly restored with attention to detail, this light-filled home will welcome you back in time with historic features like the double-sided (decorative) brick fireplace, 9’ ceilings and hardwoods floors, while you enjoy the upgraded finishes in the gourmet kitchen (i.e, Viking range, GE Monogram fridge) and bathrooms (i.e., spa tub.) Enjoy a (complimentary) bottle of wine while relaxing on the tree-shaded outdoor patio after touring the town.**Parking is not on premises!! A dedicated parking spot at nearby garage (10/15-walk from the house) is provided. Please contact us for details.Union House features 3 bedrooms and 2 baths and is a quick walk to Main Street, the waterfront, restaurants, shopping and the US Naval Academy. Catch a water taxi or launch your kayak just steps from the front door to enjoy scenic Anna

Located in Annapolis, Washington, United States. Beautifully Renovated Historic District Home Welcome to this meticulously renovated home where no detail has been overlooked. Step into the kitchen and be captivated by the cherry hardwood cabinets, stainless steel appliances, and stunning granite countertops. The gas stove and glass block tile backsplashes add a touch of sophistication, making it a dream kitchen for any gourmet chef. The heated tile floors provide a cozy atmosphere, ensuring your comfort while you prepare culinary delights.The open living area features beautiful hardwood floors, complemented by new furniture that adds a touch of elegance to the space. For additional sleeping options, there's a pull-out full sleep sofa. Convenience is key, with a half bath and a full washer/dryer available on the main level.Upstairs, you'll find two bedrooms, each with its own full bath. The master bedroom boasts a luxurious king bed, while the guest room offers a comfortable queen bed. Rest and rejuvenate in these well-appointed spac

Located in Annapolis, Washington, United States. Robert Johnson King, Historic Inns, Near Top Dining & City Attractions Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine at local restaurants - all from walkable distance!Historic Inns of Annapolis features accommodations across three distinct buildings: Maryland Inn, Governor Calvert House, and Robert Johnson House. Please note, that all guests will check in at Governor Calvert House, the address displayed on the listing.- This Room is located in Robert Johnson HousePLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of $100 /night/unit on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.- Early check-in is subject to availability upon arrival.- Following property rules, the minimum age required for check-in is 21 year

Located in Annapolis, Washington, United States. Eastport apartment with gourmet kitchen, backyard and parking This beautifully upgraded one-bedroom apartment on the 1st floor of a two-flat is just steps from local popular restaurants in Eastport. The owner has painstakingly renovated and furnished every square inch of this home which will make you feel like you're staying at a 5-Star hotel with the amenities to cook a full meal and enjoy semi-private outdoor spaces. You'll be charmed by the rocking chairs on the front porch as you enter the building. Walk inside to find the ideal layout for your stay: a spacious family room, with plenty of seating for guests and a large table that doubles as a dining table and desk, under a large flatscreen TV. When not enjoying the luxurious King bed, you'll feel spoiled in the new custom bath with a large-tiled step in shower. But it's the kitchen that will really wow you! The size and stunning finishes are more than you would expect in a one-bedroom home, with plenty of counter space to coo

Located in Annapolis, Washington, United States. Serene waterfront sunsets in this sprawling historic Annapolis home Enjoy stunning western-facing views across the river and a natural tidal pond from this sprawling historic home that sits on 1.5+ acres. The light-filled farmhouse is located on Persimmon Point, which is positioned between Harness Creek and the South River. It is a peninsula rich in local lore that includes Native American oysters mounds, pirate hideouts, tobacco farming and world champion cows. Some history: Once the home was part of the original Wimbledon Farm. From the 1930’s, Wimbledon Farm grew abundant produce and tobacco. The last magnificent tobacco barn in Annapolis is on the property next to the house. Wimbledon was also famous for their dairy. Their dairy cows and bulls attracted breeders from around the world and famously started the “Carnation” milk herd. The dairy barn was immense and the milk came into the small milk house, which is now the charming "Milkhouse Suite". Here the milk was chilled and sent o

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

Located in Annapolis, Washington, United States. Charming Charles Retreat- The perfect space for fun and relaxation! Welcome to our vacation rental nestled in the heart of Downtown Annapolis. Immerse yourself in the rich history and vibrant culture of this charming city. Our home offers unparalleled comfort and style, featuring modern amenities, cozy rooms, and tasteful décor. Step outside & find yourself in the midst of Annapolis' renowned attractions from the waterfront, shops, restaurants, and museums. Return to the comfort of your private oasis, where every detail has been curated to ensure a great stay.Our inviting 2-bedroom, 2-bathroom townhome in the picturesque city of Annapolis. Step inside and discover a cozy yet spacious retreat, thoughtfully designed to provide comfort and convenience. The open concept living area invites relaxation with its stylish furnishings and ample natural light. The fully equipped kitchen offers modern appliances and a dining area for enjoying home-cooked meals. Retreat to the tranquil bedrooms, ea

Located in Annapolis, Washington, United States. Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks 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.This 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

Located in Annapolis, Washington, United States. Perfect Home near Chesapeake Bay Escape to this bright home nestled on a quiet cul-de-sac in Eastport. Our home offers proximity to local attractions, parks, and the vibrant downtown area of Annapolis. ✔Minutes to downtown Annapolis / Navy Academy✔ En-suite bathrooms✔ Free Parking✔ Free WiFi✔ Self-check-in/out - Smart Locks Book your stay now and make lasting memories in this charming Annapolis retreat!⚠ Please note: Due to severe allergies, we regret that pets are not permitted on the premises. Thank you.TRASH AND RECYCLING DAY *Every TUESDAY, please put your trash the street side the night before. ADDITIONAL GUEST*Please make sure to indicate the correct number of guests when booking*Additional guest fees of $20 per guest, per night (after the 1st guest)LATE CHECK OUT*Sorry but we don't allow late checkouts.*If you exceed, you will be charged $30 for the first 30 minutes, and an additional hour will cost you $50.PARTIES NOT ALLOWED*Please keep noise low in the quiet hours of 9pm to 9

Located in Annapolis, Washington, United States. Nautical charmer near the City Dock with open layout, W/D, & AC Plebe's ParadiseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Decorated for a comfortable stay, from the moment you walk inside, you will feel at home. Featuring hardwood flooring, central air-conditioning, and plush furnishings - settle down on the living room's sofa and stream your favorite show. When you aren't dining out at one of the fun Annapolis eateries, the well-equipped kitchen boasts all of the necessities needed to prepare delicious dishes. Keeping chore time at bay, a dishwasher is also available for your use. Upstairs, the bedrooms ensure a good night's rest. Both of the bedrooms are ensuite with sizable bathrooms, complete with dual sinks and walk-in showers. Personal TVs in both bedrooms make streaming effortless for everyone! A private washer/dryer and round out the home's interior amenities.Historic downtown Annapoli

Located in Annapolis, Washington, United States. Your Annapolis Adventure Starts Here!! Welcome to your charming Annapolis getaway! This beautifully furnished home is the perfect retreat for your stay in this historic waterfront town.With 3 bedrooms and 2.5 bathrooms, this spacious property can comfortably accommodate 6 guest. The bedrooms are thoughtfully designed with cozy linens and ample storage space. You'll find the bathrooms well-appointed with modern fixtures and plush towels.The heart of the home is the inviting living area, where you can relax and unwind after a day of exploring Annapolis. Sink into the comfortable sofas. The open concept layout seamlessly connects the living area to the dining area. The fully equipped kitchen makes it easy to socialize while preparing meals. The kitchen features top-of-the-line appliances, ample counter space, and all the cookware and utensils you'll need.Step outside onto the private fenced-in patio offering tranquil fountains, bistro lighting and gas firepit. It's perfect for enjoying y

Located in Annapolis, Washington, United States. Fisher House - Downtown Annapolis! Welcome to our beautifully renovated historic home in the heart of Annapolis! The Fisher House was built in 1885 and named after the owner's great-grandfather, a key figure in the development of Annapolis and Academy Fire Departments. We are nestled just two blocks from Main Street, providing easy access to the city's historic sites, charming shops, delectable dining options, and of course all things Naval Academy!We are pet-friendly! Small dogs, 30lbs or less, are welcome to join your stay.Stepping out from the charming Fisher House, you find yourself two blocks from the heart of historic Annapolis, ready to explore the city's rich heritage and picturesque surroundings. Just a stone's throw away from this central location, you can begin your journey by strolling down Main Street, where a myriad of boutique shops, cozy cafes, and art galleries await.Heading east from Fisher House, you'll soon reach the majestic Chesapeake Bay, offering breathtaking vi

Located in Annapolis, Washington, United States. Boutique Historic Home just Steps from the State House! Welcome to the George Taylor House! This lovely historic home dates back to 1810 and has been recently renovated to provide guests with a comfortable and memorable experience. The house is located on one of the most picturesque streets in Annapolis, just steps from the State Capitol, the vibrant City Dock waterfront, and all that Historic Annapolis has to offer. The house consists of 3 beautifully appointed bedrooms and 2.5 bathrooms, comfortably sleeping up to 8 guests. The first floor layout includes the living room with a flat screen TV, gas fireplace and a built in bar and wine fridge, perfect for entertaining guests. The kitchen boasts stainless steel appliances, beautiful granite counter tops, a gas oven range, a microwave, a toaster oven, and all basic cooking and eating utensils. The kitchen island seats four guests, while the dining room seats eight. There is also a powder room on the main level and a rear outdoor

Located in Annapolis, Washington, United States. Historic District"Crab Cakes and Football" Welcome to Crab Cakes and Football. Enjoy Historic Downtown Annapolis with convenient walking distance to both City Dock and the Navy-Marine Corps Memorial Stadium. Private parking for 2 cars!There are seven restaurants within one block including:- Thai- Italian- Irish- Unique Annapolis FareThis is the perfect spot to enjoy all that Annapolis has to offer. People who know the area know that having 2 parking spots is almost unheard of. We are located in one of the most sought after neighborhoods in Annapolis. The neighborhood has a very peaceful, quiet feel. The property had once been a long term rental but we decided we'd rather share it with people coming here to vacation. We live 5-10 minutes from the property so you can enjoy your privacy but we are available if you need us.

Located in Annapolis, Washington, United States. Chesapeake Bay single family home Quaint community of Arundel on the Bay in Annapolis, Maryland. Spacious 4 bedroom, 3.5 bathrooms in 3000 s.f. waterfront home on the Chesapeake Bay. with a 30 ft pier for fishing and crabbing. The community has a private neighbood beach within walking distance of home. Close to shopping, restaurants and entertainment. 6 miles from the Naval Academy, 30 miles from Washington, DC and Baltimore, Maryland.

Located in Annapolis, Washington, United States. Darling 2 BR home with parking in the sought after Murray Hill section of Historic Annapolis STR22-145187THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A TEAM MEMBER WITH ADDITIONAL INSTRUCTIONS FOR BOOKING. We�re certain you will find this charming 2 BR townhouse to be the perfect home away from home. Whether you�re here for a long weekend, a special commissioning week celebration, or taking in the sights of the boat show, this lovingly restored, and beautifully decorated home is tucked into a quiet area of the historic downtown district of Annapolis. Park your car in the dedicated parking spot and walk to shops, bars, restaurants, City Dock, and of course the US Naval Academy. Enjoy your morning coffee or evening happy hour on the front porch or in the quiet, private courtyard behind the house. The gleaming hardwood floors throughout the house show the love and care the homeowners have taken to make this pl

Located in Annapolis, Washington, United States. 2 Historic Ambiance Stays Perfect for Romantic Getaways - Pets Allowed! Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine at local restaurants - all from walkable distance!Historic Inns of Annapolis features accommodations across three distinct buildings: Maryland Inn, Governor Calvert House, and Robert Johnson House. Please note, that all guests will check in at Governor Calvert House, the address displayed on the listing.- This Room is Located in Maryland InnPLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- These are BOTH separate hotel rooms. Rooms are individually unique and may not be adjoining or adjacent, allocated based on availability upon arrival. The price is for all rooms.- The property requires a damage deposit of $100 /night/unit on the credit/debit card provided. The deposit is required for EACH UNIT

Located in Annapolis, Washington, United States. Waterfront home with scenic porches, yard, grill, jetted tub, central AC, & W/D The Salty CrabOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Overlooking Chesapeake Bay, this charming Annapolis home is nestled in the serene Bay Ridge community, just steps away from a private beach. Bring the whole family together and relish watching gorgeous sunrises and sunsets and taking in panoramic bay views from both levels of this home's wraparound porches. When you aren't lounging and watching yellow, pink, and orange hues fill the sky, head for the backyard, where a patio, ample seating, and a gas grill provide the perfect space to host cookouts! The screened, first-level wraparound porch is also a prime location to host crab feasts or barbecues while looking out onto the water.Surrounded by mature landscaping, you will feel right at home when you pull into the driveway of this lovely house. Step inside and

Located in Annapolis, Washington, United States. Gem in Downtown Annapolis, close to USNA, St. John's College Comfortable stay on quiet street close to Gate 3 USNA and St. John's College. Quick walk to Maryland State House, Maryland Avenue shopping/dining, enjoy Annapolis nightlife at City Dock, Main and West Streets. Entertain on private patio. 3 queen beds, large living area with smart TV, additional living space in kitchen/lounging/dining area. Large kitchen table plus 4 eat-in seats at the bar. Navy Football and Baseball Stadiums within walking distance. Enjoy all that the Navy Yard has to offer right around the corner. Legislators welcome!

Located in Annapolis, Washington, United States. Beautiful Waterfront Townhome In Historic Annapolis This beautiful waterfront townhome with three bedrooms 3 1/2 baths, recently renovated and beautifully decorated. 5-minute walk to downtown, restaurants, shopping, bakery, and the Naval Academy. Stainless steel appliances, granite countertops, hardwood and marble flooring, gas grill on the patio. Sheets, blankets, body wash, spices/condiments are all supplied as well as two off-street parking spaces.Pool open from Memorial Day to Labor Day.Booked for 2025 Commissioning Week.*Please note- Commissioning week we ask for a 7-night minimum stay. Please feel free to contact us for more information.Sorry, no pets are allowed.