94,639 properties available

Located in Annapolis, Washington, United States. Eastport Classic Charm House Nestled in the charming neighborhood of Eastport, Annapolis, this spacious 4-bedroom, 3.5-bathroom home offers the perfect blend of modern comfort and classic charm and is conveniently located within walking distance to Downtown Annapolis. When you enter, you will be welcomed by an open-plan living room featuring hardwood floors, large windows that allow ample natural light, and a cozy fireplace, creating an inviting space for relaxation. The living room is adjacent to the gourmet kitchen which is equipped with stainless steel appliances, granite countertops, and a large island that doubles as a breakfast bar. The dining room is perfect for hosting dinner parties, with elegant fixtures and easy access to the outdoor entertaining area. The expansive backyard is an entertainer's paradise, featuring a large patio area, perfect for barbecues and outdoor dining. Lush landscaping provides a serene and private environment. A spacious deck extends from the back of

Located in Annapolis, Washington, United States. Quiet dog-friendly suburban home with patio, grill, yard, kitchen, & Pack-N-Play Admiral's GlenOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located on a quiet and peaceful suburban street, you will have an unforgettable trip to this personal slice of paradise! Perfectly situated in the gorgeous Homewood neighborhood, you'll be just a short walk/bike ride from downtown Annapolis, where a series of amazing attractions await you and your family. Check out the variety of dine-in restaurants and historic sites right at your fingertips. Treat the family to a football game at the Navy-Marine Corps Memorial Stadium, or take a day trip to the local cities of Baltimore or Washington D.C. With so many parks close by, you'll be primed for some much-needed outdoor recreation.Head back to this beautiful tree-lined street and walk up the steps and into your new home away from home. It's inside that you'll find

Located in Tracys Landing, Maryland, United States. Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub Spacious 5-bedroom (4 full- and 2 half-baths) waterfront getaway built along the natural topography of Fairhaven Cliffs. All 5 bedrooms have the same five-star/A+ view of the Chesapeake Bay! Watch the sun rise over Poplar Island and the Eastern Shore in the distance. This property was designed for family fun: You'll have a private pier on the Chesapeake Bay, just below your own 35-foot pool. Sit on the pier, in the hot tub, or on the pool-side deck and enjoy the peaceful views of Herring Cove (a protected section of the Chesapeake that is a sailing favorite), while the kids play on the new play structure just next to the pool. Or sit in the waterside hammock and be lulled to sleep by the splashing of the waves. If you want to enjoy the water, descend the 5-step swim ladder off the dock and swim in the Bay! (Or walk in the Bay....the water is only a couple of feet deep, even a hundred yards out.....in the winter the

Located in Annapolis, Washington, United States. All-stop. Rental Midships. Whether you have come for Commissioning Week or Boat Show, the aptly named Gatehouse is a centrally located townhome steps away from Gate One, City Dock Waterfront, and all the attractions that Historic Downtown Annapolis has to offer.Settle into this spacious, well-appointed townhome in the heart of Downtown Annapolis. This detached townhome, professionally cleaned and beautifully maintained, is the perfect lodging for USNA families and events, wedding parties, and weekend explorers.Enjoy your morning coffee in the quiet courtyard and, when the sun's passed the yardarm, your evening brightener on the third-floor deck, which boasts a view of the Naval Academy Chapel! If sipping a whiskey while lounging on a deep leather sofa or a Churchill armchair is more your speed, the main deck living space is the place to relax. Should you desire to escape the hustle and bustle of Randall St-tuck in and watch a movie, play a video game on the PS4, or read a book in the

Located in Annapolis, Washington, United States. Contemporary waterfront 4BR home close to downtown Annapolis - stunning water views w/private dock/pier/ private pool and kayaks. STR259 - THIS 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.Please note: If you request to book this property, your reservation is not confirmed until you are contacted by Annapolis Accommodations to complete your booking and payment. Ultra Contemporary waterfront home very close to downtown Annapolis with stunning views of the South River and private dock/pier and kayaks. Four bedrooms, huge master bedroom suite, sleeps 8 + large play room.Beautifully appointed with all designer kitchen and baths, interior decorator curated space with artwork and sculpture, Persian rugs tastefully incorporated in every room, Brazilian hardwood floors throughout the first floor, carpeted upstairs. First floor: Entry hall way with gorgeous art, large livi

Located in Annapolis, Washington, United States. Walk everywhere . . .just minutes to historic Annapolis, Updated. A modern historic gem in a 10 unit building in Eastport or as the locals call it the Maritime Republic of Eastport or "MRE". The 1880s building has been fully renovated to capture the old world charm with the exposed factory brick but updated with hard word floors, plantation shutters, granite countered open kitchen concept, living and dining area, double vanity granite master bath, and a private garden area with dining and grill. This is our home with very few rentals as we want others to treat it like it is their own. This means it is very clean and well equipped with modern conveniences such as central air-conditioning, cable and WiFi. Unrestricted street parking and convenient self entry / door code access . We do not allow pets due to allergies of our own and those who are interested in staying with us.

Located in Tracys Landing, Maryland, United States. Private Waterfront Retreat with Pool, Hot Tub and Game Room Family Rental only!This brand new custom home was built with stunning views of the Chesapeake Bay and all the bells and whistles, including a large private pool (open late April-end of Oct), hot tub (available year round) and game room on a semi-private beach. The four-season screened-in porch naturally stays warm in the winter from the sun and cools from the bay breeze with the windows open. The home is a perfect retreat for one or more large families traveling together on a private resort-like getaway.Upon entering the home, you will be wowed by the fully-loaded great room, complete with a flatscreen TV, electric fireplace, designer furniture and views of the waterfront landscape. The gourmet kitchen has luxury appliances, a breakfast bar, a dining table for 8 and high-end stainless-steel appliances. Before heading upstairs, check out the private office, which doubles as another bedroom with a Queen sleeper sofa, located o

Located in Annapolis, Washington, United States. Fully Furnished 4 Bedroom/3 Bathroom Single Family Home in Annapolis just a few minutes from downtown STR-270 - THIS 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.Daily, weekly, monthly rates. Pets considered. This fully furnished home is located in Pendennis Mount and part of the Broadneck School District. 4 Bedroom/3 Bathroom Single Family Home in Annapolis just across the USNA bridge. King bed in master. Queen beds in 2 bedrooms and a single in 4th bedroom. There's a fireplace, hardwood floors, finished basement and a flat screen tv in the living room. Off street parking for 3 cars, small yard and small back deck for grilling with the gas grill. (Separate self-contained apartment unit upstairs with the address of 2 Ritchie Road offered separately for rent.)

Located in Annapolis, Washington, United States. Cozy Maryland Retreat Near Sandy Pointe State Park Discover the best of Annapolis with ease from this updated 3-bedroom, 1-bathroom home! The vacation rental has all the essentials for a stress-free stay, including a laptop-friendly workspace, free WiFi, and in-home laundry. Plus, you’ll be near the best shops, restaurants, and nightlife! Spend your days cruising on the Severn River or cheering on your team at Navy-Marine Corps Memorial Stadium! End the day with a home-cooked meal, or keep the night going with a drink on West Street.-- THE PROPERTY --Annapolis Short-Term Rental License: STR23-145239 | Off-Street Parking | In-Home Laundry | Walkable LocationBedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Twin Bed | Living Room: Sleeper SofaHOME FEATURES: Smart TV, board games, dining table, laptop-friendly workspaceKITCHEN: Dishwasher, stove/oven, refrigerator, microwave, cooking basics, dishware & flatware, Keurig, air fryer, toaster, blender, spices, trash bags & paper towels

Located in Annapolis, Washington, United States. Waterfront 2-Bedroom Condo on Spa Creek 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.Step into our newly renovated kitchen, where one of the standout features is the contrasting white and aqua cabinets which adds a vibrant pop of color. As you prepare your favorite meals, you'll appreciate the spacious granite countertops that provide ample room for all your culinary endeavors. 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.Inside you'll be greeted by a welcoming atmosphere and

Located in Annapolis, Washington, United States. Newly-renovated Lighthouse Inn with game room parking, private backyard, walk to downtown Stay in this stunning Craftsman home, just steps from the water and everything Eastport/Annapolis has to offer. Enjoy 3 levels of this professionally-decorated 4 bedroom, 3.5 bath home with multiple family gathering spaces, both indoors and outdoors. The home features a modern open kitchen with all the necessary amenities for entertaining, from the appliances and finishes to the space for a large family plus their guests. There is seating at the dining room table for 10 guests, plus 4 more at the breakfast bar and 5 at the kitchen table. Sip your morning coffee on King Suite's 2nd floor private balcony. Head to the recreation room and spread out on the sectional sofa, with bar seating, and a gas fireplace to watch the games on the 85” flatscreen TV. The kids can play on the arcade machine, foosball table or with one of the many board games in the lower-level den. (The sectional sofa in the rec r

Located in Annapolis, Washington, United States. 2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace Harrison HallOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Looking for the perfect retreat for a memorable stay-cation with your beloved groups? Then, look no further than this two-story, family-friendly home located just a mile from the heart of the forever charming Annapolis! The extensive enclosed backyard provides a private space where you and your guests can hang out and create everlasting memories - gather around the firepit under the starry night sky or host a warm-weather barbecue on the deck, equipped with a propane grill, a six-person dining table, and a cushy swing. Upon entering the first floor of this darling home, guests will first come across a beautifully appointed foyer with vintage music-scene decor. As you continue the tour, an astonishing dining room will appear before your eyes. This space is furnis

Located in Annapolis, Washington, United States. Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W/D The Ship's BridgeOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Featuring the most sought-after Chesapeake Bay view, this luxurious newly built waterfront Annapolis retreat is ready for you and your family and friends! The porch and balcony are where you will spend most of your time on the rocking chairs or comfy outdoor couch taking in the Chesapeake Bay. The back patio and gardens offer alfresco dining with a gas grill and a beautiful teak umbrella table with seating for six.The warm living area looks out to the Bay with a large comfy couch, swivel chairs, and a gas fireplace. Spend relaxing evenings on the amazing stone porch with Adirondack rockers - take in the famous Annapolis sailboat races from there and the second-floor balcony! The lower-level rec room has a big couch that converts to a queen sleeper, two comf

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

Located in Annapolis, Washington, United States. Nautical-themed home with four bedrooms, bright interior, deck, W/D, and AC The Robins NestOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Delightfully adorned with nautical charm and soft furnishings, this centrally-located Annapolis home is well-prepared to host you and yours! Nestle down in absolute comfort when you sit on the oversized sofa in the living room and stream your favorite TV shows and movies. When hunger hits, head for the home's full kitchen where you'll be greeted by turquoise cabinetry, wooden countertops, and stainless steel appliances. Your culinary creations will be easily prepared in this space and can be further enjoyed at the formal dining table. A bedroom and full bathroom are also available on the main level of the home. Upstairs, you'll discover a separate washer/dryer (perfect for refreshing your vacation garb), three spacious bedrooms, and a large bathroom. With high-qu

Located in Annapolis, Washington, United States. Waterfront Estate Annapolis - Beautiful Views - Dock & Boat Slip - Pet Friendly Brand New Construction with over 8000 sf finished October 2023 in a private family subdivision at the end of an exclusive neighborhood. A home built with our large grown family in mind and provided with every detail for any family to enjoy together. This is a non-smoking, pet friendly house. 8 miles from downtown Annapolis.Pets welcomed with their own pet room on first floor, complete with dog shower, commercial ice machine, washer and dryer, and pet friendly floors with dutch door. Large private office area off main living room with desk, computer and starlink internet access. 5 Full bedrooms with ceiling fans, each with their own private en suite bathrooms. One Free Room upstairs with an oversized John Michael Designs Double Fluff Monster couch for TV viewing or sleeping. Master Bedroom has an entire extra room perfect for crib area, large walk in closet, private patio overlooking river, laundry room

Located in Annapolis, Washington, United States. "Around the corner" from everything with private fenced-in yard and parking *Flexible Commissioning Week Cancellation Policy*Welcome to this charming remodeled Eastport Victorian home "Around the Corner" from some of the best spots in Annapolis. Combining beautiful appointments with the best of historic significance and modern touches, you and your guests will feel spoiled! You'll be greeted by the inviting wrap-around front porch, the perfect way to end or begin your day. When entering the newly-decorated 2-story home, you'll find a very spacious living room that opens up to the large dining area, updated kitchen and heart of pine flooring throughout. There is also a full bath on the main floor. Enjoy complimentary coffee at the breakfast bar, and at the end of the day, grab a bottle of wine from the wine fridge and head outside to the fantastic patio and backyard. Head upstairs to the 3 bedrooms and 2nd full bath with new high end fixtures and a Restoration Hardware vanity. The back

Located in Annapolis, Washington, United States. Spacious home with an outdoor pool, screened porch, washer/dryer & central AC Thomas Point TranquilityOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Nestled in a family neighborhood between Fishing Creek and the South River, this Annapolis vacation home is great for groups with children, thanks to the various children's sleeping options. It offers a large heated, saltwater pool, and quality furnishings, while is just minutes outside downtown Annapolis. A quick stroll down the street takes you to Thomas Point Park.This private retreat offers a large new deck, screened porch, fenced saltwater pool, and a sprawling yard for your enjoyment.Step inside to an open and light-filled space. The home features a large updated kitchen and spacious living and dining areas accented with a gorgeous stacked stone fireplace. A seated breakfast bar, lots of counter space, and quality appliances provide you with ever

Located in Riva, Maryland, United States. Cheerful 3 bedroom home with ample space and parking on premise Find your next home away from home in our “Mini Manor”.Enjoy room to spare with 3 bedrooms, two bathrooms, a kitchen with everything you need, and ample parking, plus a fully covered back porch with a BBQ. Great wifi coverage make it an optimal remote work site. Private river access is just a short walk through the peaceful neighborhood.In addition to great spots like Mike’s Crabhouse and the Old Stein Inn, Riva has ample parks and trails and is only 20 minutes from beautiful Annapolis

Located in Annapolis, Washington, United States. Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience This new 4 bed / 3 bath modern luxury home sleeps 10 and is located in a quiet neighborhood near the Westin Hotel. Once you walk in the door you will know you made the right choice deciding to stay in this gorgeous home. THE SPACE:-The first floor has 10ft ceilings, an open floor plan, gourmet kitchen with upscale appliances, full bath (walk in shower), 1 bedroom (queen), and large laundry room.-The second floor has 3 large bedrooms (1 - king, 2 - queen, 3 - 2 queens) to easily accommodate a larger family or group. -All 3 bathrooms are spacious and each has a double vanity. -All hardwood floors throughout the homeLOCATION:The house is conveniently located 1.5 blocks to the Westin hotel, 2 blocks to many restaurants (Fado's, Carpaccio's, Miss Shirley's, Paul's Homewood Cafe), 1 block to a convenience store and 2 blocks to a liquor store. This house is walking distance to downtown and 2 blocks to Park Place w

Located in Severna Park, Maryland, United States. Multiple family spaces both inside and out 13 mins to USNA From the moment you walk into this lovely home, you will feel the presence of the long serving navy family, ship captain, naval historian/USNA grad. There are reminders throughout of the hard work and loyalty this family have to each other and the comfort they have found in the many gathering spaces in the home. Looking for a family resort-like stay, bring the family bikes, and hop on the B&A Trail just block from the home, and head less than a mile into the quaint Severna Park town to Big Bean Coffee, Froyo House and Squisito Pizza!Enjoy the 3 outdoor spaces, 2 of which have fire pits; a large 4-seasons room, perfect for enjoying a Maryland Crab Feast! On the main floor, spread out to watch the flatscreen TV in the large family room with a wood-burning fireplace, or enjoy the owners impressive collection of books in the living room. The 4 spacious bedrooms upstairs, plus the kids bunk space and hangout space in the basement,

Located in Crownsville, Maryland, United States. Deep water private pier and Minutes to Annapolis from renovated waterfront home with Prepare to be spoiled at this custom-renovated luxury waterfront home. This beautifully-detailed home features serene waterfront views from two of its four bedrooms and the open floor plan kitchen and great room on the first floor. Sitting on a private lot on the Severn River, the backyard has a large gathering space with a lounge area, dining table and deep water private pier. Included in your stay is use of the owner's kayak, stand-up paddle board, canoes and a gas grill.Inside, the spacious home has all the bells and whistles! The brand new gourmet kitchen has an oversized island with seating for 6. There is also a built-in kitchen table hutch with water-view seating for 8. The adjoining living room has a large Internet Smart TV (decorative fireplace). There is also a full bath on the main floor with a large shower - ideal for those coming in from the outdoors!Head up to the second floor's 4 bedro

Located in Annapolis, Washington, United States. Large Luxury Apartment In Downtown Annapolis 2 Bed/2 Bath Apartment in Historic Downtown Annapolis steps away from the main entrance of the Naval Academy. Upstairs Apartment with master bedroom & bath, kitchen living room, dining room and laundry. Main floor portion of the apartment has an additional bedroom and sitting room separate from the 2nd floor apartment, bath and patio for entertaining. 2 Blocks from City Dock with expansive water views of the Annapolis Harbor and access to numerous bars, restaurants and shopping. Endless activities in Annapolis. Boating, fishing, crabbing, shopping, dining, antiquing, paddle boarding, sailing, historic tours and the ever impressive Naval Academy.

Located in Annapolis, Washington, United States. Beautiful Historic Home With Great Location! The "Philip Clayton House" (Annapolis license STR21-144988) is a fully up-dated, historic home in the Federal style dating from 1834, in easy walking distance to Main Street, City Dock, USNA, St. Johns, St. Mary's, etc. The house has a modern kitchen with a HUGE island and a cozy eat-in area. The large family room has a gas fireplace and a Smart TV. There is a comfy sectional sofa, rocker, and a handmade 'gathering' table that can seat 10. The family room opens out via French doors to a large fenced, brick/stone patio with a firepit, outdoor seating, BBQ grill. The second floor has 3 bedrooms, all with queen beds. The master has an en-suite bath and a second full bath with tub is located off the hallway. The 3rd floor loft bedroom has 2 twin trundle beds that can sleep up to 4. Each trundle bed can be made up as 2 twins (attached) or a king bed (see photos). Due to a change in city regulations, guest parking passes for the resident