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Annapolis Area Waterside Retreat

This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5-star retreat for those who value tranquility over spectacle. Nestled along the Chesapeake, it offers front-row seats to mesmerizing sunsets, where golden light shimmers across the water. Inside, Nordic-inspired design pairs with quiet luxury, featuring award-winning mattresses and sumptuous bedding for deeply restorative sleep. Here, time slows, and luxury isn’t just seen—it’s felt. Discover why so many guests long to return by reading our reviews.

"Hilltop Hideaway"- Private basement suite

Location, location! "Hilltop Hideaway" is a private basement apartment just 16 miles from BWI airport, 10 miles from Fort Meade and Annapolis, and less than 30 miles to Baltimore and Washington, DC! Nestled in a wooded setting on 2 acres, it is perfect for 1-2 adults (25yrs old or older). Not suited for children. Offers living space, bathroom, kitchenette w/microwave, toaster oven, coffee maker, crock pot, apartment size fridge and separate dining nook. Private key code entrance and parking.

Secluded acre near BWI and Baltimore

Secluded suburban acre 8 minutes from BWI Airport, 15 minutes from Baltimore's Inner Harbor and from Fort Meade, and 45 minutes from Washington DC. Private house attached to host house has 1220 square feet of cozy comfort--4 times the size of a hotel room! House includes 2 bedrooms (one queen, one double), 1.5 baths, living room, foyer, dining room, full kitchen, and washer/dryer. The one-acre lot has hundreds of trees and is great for pets. Level 2 charging station is good for all EVs.

Luxury basement apt all private with private entry

Indulge in modern luxury with this 1B 1 SPA like bathroom apartment. This elegant apartment is meticulously designed to offer a harmonious blend of comfort and opulence. This bedroom provides a tranquil oasis, ensuring that your stay is a pleasure. The kitchen is fully stocked. With a dedicated laundry room and coffee/Tea bar. Experience a sophisticated haven with unparalleled location, only over a mile away from Downtown Bethesda, 2 blocks from NIH, All major highways only 5min drive.

Spacious 3 Bedrooms House+Patio+Playground

Spacious 3 bedrooms house with functional patio + private playround located in Edgewater, only 15 mins drive to downtown Annapolis. Fully equipped with designer furnitures, with a sense of home! Huge dining room and fully functional kitchen, perfect to enjoy a great evening with your friends and family! Bedrooms are equipped with your own desks if you want to do some works even in your vacation. Easily fit 2 cars in private driveway. Very quiet neighborhood with proximity to everything!

Charming Downtwn Home- Private Parking Patio&Yard!

Welcome home to this Annapolis gem. An adorable 1930 American foursquare with private driveway, located on a quiet cul-de-sac off in downtowns Art's District. This cozy, three bedroom home can hold you and nine guests with plenty of sleeping arrangements for everyone. Enjoy a spacious backyard patio with string lights and deck chairs giving you and your guests plenty outdoor entertaining options. This house is fully furnished. Short walk to everything downtown offers, it just needs you!

Waterfront Cheerful 5 home

Welcome to this brand-new relaxing home with an 80ft pier by the water for your getaway. It is perfect for vacations, retreats, meetings, family reunion and business travelers’. Create memories and beautiful experiences while enjoying the beautiful 5 Bedrooms, 3 Bathroom .one bed on the first floor and four beds on the second floor. House has a large custom kitchen. It is located 11 miles from BWI airport,11.8 miles from downtown Baltimore,17 miles Naval academy and 40 miles to the DC .

Cozy Annapolis Cottage.

Stay in the heart of Annapolis! 1 Gig Internet speeds. 220v outlet for EV charging (bring your own cable).Walk to downtown, the Naval Academy and Navy Stadium. Meticulously kept home and newly renovated. Professional cleaning team with every turnover of the house. Stay in the comforts of your own home and experience all that Annapolis has to offer. Art throughout home by local artist Amy Holt Cline.

Park View near BWI, Light Rail and I97.

Beautiful all new, cozy 1950's home completely remodeled. All hardwood floors, new paint, brand new kitchen, bath, everything! Clean and quiet home/duplex with a front porch to enjoy morning tea/coffee or evening cocktails. Huge empty park across the street to keep things still. Very quiet neighbors. Owners are onsite and live in the back house for any issues or questions.

12 M to Naval Acadmey | Waterfront

Discover the perfect blend of tranquility and convenience at our charming waterfront property. Nestled away in a serene setting yet close to all the action, this home offers an ideal escape. Imagine unwinding on the expansive screened-in porch, taking in the peaceful views of calm waters, or dropping a crab pot to catch some of Maryland's renowned Blue Crabs.

Historic Downtown in-law suite

This special place is close to everything. One block to the Naval Academy and one block to all the historic and downtown attractions. This in-law suite has a queen bed, full bath, sauna, kitchenette, seating area, and desk/dining table. Welcoming separate, quiet entrance with access to a lovely patio with seating and firepit.