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Gybeset Eastport Inn

Enjoy exclusive use of this boutique hotel-styled upstairs apartment in a beautifully restored 1930s craftsman-style building in the heart of Eastport. Private off-street parking. Short walk to downtown Annapolis. Just a few doors away from one of the hottest restaurants in Annapolis, Vin 909. A seasonal farmers' market is located across the street along with restaurants and other amenities. Hotel-like services available for longer stays. Fully licensed by City of Annapolis for AirBnb operation.

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Stay in a Former Fells Point Bar! - Private Studio

Rent a unique studio apt in Fells Point! This is no cookie-cutter Airbnb. We converted a portion of our home, a 19th century construction & mid-20th century Fells Pt bar, into a 500 foot apartment w/private entrance, bathroom, work & living space. The apartment is near Fells bars & restaurants, Canton, Hopkins, the harbor, Patterson Park & downtown. 2 miles from stadiums. There is a 6 in. incline from sidewalk to entrance. Access ramp available. No steps in studio. We only host via Airbnb.

Edgewater/Mayo Getaway!

Charming, spacious single-family home in the heart of Mayo, perfect for families or groups. Comfortably sleeps 6 with space for up to 8 guests. Enjoy a modern, clean design and plenty of room to unwind. Relax in the cozy sunroom or soak in the hot tub overlooking the serene, park-like backyard. Fully equipped with all essentials for a hassle-free stay. Just minutes from Edgewater, 10 mins to historic Downtown Annapolis, 25 mins to Baltimore, and 30 mins to DC. Parking in driveway/garage only.

Independent Access Garage Apartment, Near Downtown

Independent entrance garage apartment located on the back of our house with totally independent entrance. It has a queen size bed, WIFI, 10 minute walk to Downtown. Mini kitchen with a mini-fridge, microwave, and coffee-maker. Plenty of space to store a bike. Great neighborhood with street parking available free on the weekends and two-hour limit during the week. There is free street parking during the week one block away from the apartment. Free EV charging one block away!!

Nautical Charm and relaxing waterview!

Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still in close proximity to Washington DC, Annapolis and Baltimore! Situated in a charming waterfront and sailing community, this separate and private unit has: parking, 1 bath, queen bed, kitchen (limited), TV, high speed WiFi and Bluetooth speaker. Wake up to the cluck cluck of our four resident chickens who are tucked away in their attractive coop. Sit on the porch and take in the view!

Chesapeake Waterfront-Kayaks-Crab-Fish-FirePit-Spa

There's nothing like being directly on the water! Relax and rejuvenate in this Chesapeake waterfront estate home which includes private pier, hot tub and fire pit. Crab or fish off the pier or take the kayak out to see the Chesapeake bay wildlife. Try out paddle boarding! Sit around the fire pit at night or watch the stars at night while soaking in the hot tub. Make wonderful memories. Great place for families and multi family groups.

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Savor our three-bedroom Cottage in this peaceful western shore spot, enjoy two acres of green space, the pier, kayaks, swings, fire pit, shady lawns & sun-drenched loungers, local waterfront dining or eat in, close to Washington, D.C., Annapolis, & Baltimore at this honeymoon-worthy country-like micro-resort. Due to the current COVID-19 situation, we have offered SPECIAL discounts for longer-term rentals

South River Park Apartment

Located minutes from Annapolis, the in-law apartment offers access to Baltimore and DC in under an hour. The apartment offers its own entrance, full kitchen, one bathroom, one bedroom, tile floors, pullout sofa, Wifi, and parking. The apartment is registered with the Anne Arundel County Dept. of Inspections & Permits, #STR-15, for short term rentals.