Holiday rentals in Annapolis

Wall to Wall Cool- Filled with Original Art and Sculpture

This apartment is on one end of a larger main house. The shared wall was retro-fit with sound dampening cellulose fill in February of 2018. This enhancement along with many others provide the feel and comfort of being in your own space. This is Listed as 2 bedrooms, however there is no door between the 2 rooms. They are separated by 3 steps and a hallway. Please see pictures for a thorough view of the layout. Proximity to destinations; Vin 909 0.2 miles, Boatyard Bar & Grill 0.3, Eastport bridge, gateway to the downtown area 0.7 miles, City Dock 1.1 miles, Naval Academy 1.2 miles There is a Murphy Queen cabinet Bed, plus a Leather couch that turns into a queen bed allowing 4 to sleep comfortably, 2 to a bed. Very calm and relaxed space, a great place to recharge as you discover the area. Of Note: Hotel cleanliness standards vary greatly; with comforters frequently being a little dubious. Just how many turnovers are factored in before they get washed? High traffic carpeted floors can hide unwanted history. Walking in your bare feet should only make you feel free, never uneasy. Our pledge; every guest will sleep on clean sheets, over a freshly sanitized mattress cover under a bed comforter or bed blanket that was cleaned before their visit. When shams are present, they are laundered every single time. All surfaces are cleaned and if something’s not right, let us know and it will be. Life can be a mystery, but your Airbnb stay should never be. Shared Use of the Front porch to the right of the house. Wifi, (2) 4K TV's one 48" and the other is 60", industrial under counter fridge that will keep everything nice and cold. Dishes, glasses plates are all available. The (2 ) Roku TV remotes have inputs for standard ear buds, so you can stay up way late and watch TV while not waking up your friend/spouse/relative, buddy, just plug in... I'm kind of a non-intrusive, sort of do my own thing sort of person. Very mindful not to step on other peoples good times. Available through text to answer any questions you may have. I've lived in the area most of my adult life and am always happy to help. The house is in the eclectically odd neighborhood of Eastport. It's close to great restaurants, bars, and pubs. Vin 909 Winecafe is less than a five-minute walk from the house, and it's across the street from three more restaurants and a drug store. Walk it man, walk it! it's good for you and what's the rush. Driving downtown can be painful and crowded. Plus why pay the man to park, when you've got free parking at the house? Proximity to destinations; Vin 909 0.2 miles, Boatyard Bar & Grill 0.3, Eastport bridge, gateway to the downtown area 0.7 miles, City Dock 1.1 miles, Naval Academy 1.2 miles The house is on a main road to downtown. So there is a fair amount of traffic in front of the house. There is also a fire station just down the road, so passing sirens often accompany the din of general city traffic. For your comfort there is a white noise machine in the front bedroom area. There is also a small fan in the closet if you prefer to sleep with a fan. Please use caution when pulling out of the drive way. When walking downtown, the side streets are much quieter, so pick the path that best suits you.

Elegant & Authentic Annapolis

Enjoy comfortable elegance in this historic beauty on one of the prettiest streets in Downtown Annapolis--Main Street and the Water only 2 blocks away. This private unit is the full main level with its own eat-in kitchen, living room, front porch and back patio. Bedroom features queen size bed, dresser and walk-in closet. Bathroom has shower/tub and counterspace for your comfort. Street parking is available or public garage parking is a short stroll away. Relish this quiet & convenient location.

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!

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Annapolis Waterfront Condo - Unit #: A-203

BOOK NOW SUMMER 2026 SPRING and FALL BOAT SHOW 1 bed/bath condo, sleeps 4 max, covered comfortable water facing deck, reserved parking! .5 mile walk to dwnt Annapolis and the Naval Academy, 1.9mi to the Navy Football, .25 mi. to boatshows! Great views - 2nd flr. condo (12 stairs, no elevator.) Pool Memorial to Labor Day: MWTh 4pm-8 Tues: Closed FSS and Holidays: 12pm-8 The pool is one of the best places to be on a hot summer day. If hours are unacceptable, pls select another location.

Chesapeake Birdhouse Studio

Private, clean, cozy studio in the heart of Eastport, Annapolis. Quiet, separate, retreat space. Walk 1 block to restaurants and bars in Eastport, hop on the water taxi and you are in the heart of Downtown Annapolis, USNA, and historic areas of Annapolis in minutes. This is an Ideal location for the sailing community or anyone visiting our beautiful city. Free street parking available. You could park your car and never have to move it through out your stay. Walk, bike or water taxi.

Annapolis Garden Suite

Welcome! We’re tucked away on a forested residential street, roughly a 7 minute drive from restaurants, coffee shops and all that Annapolis has to offer. 15m from the coast, 30m from Baltimore and 35m from DC. Tl;dr: this is a private ground-level guest suite with 3 beds, 2 bedrooms, 1 desk (optional standing desk), 1 kitchen with oven, dishwasher + Nespresso/pour over, 2 tvs, laundry room with washer/dryer, fast wifi, a pool, patio and a forest view. We live on the top floor.

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Historic & sunny home steps from USNA/downtown

This beautiful and cozy 3-bedroom, 2.5 bath home built in 1900 is located on Prince George Street, one block from Annapolis City Dock and Gate 1 (main gate) of the US Naval Academy. Filled with sunlit, spacious rooms and equipped with numerous amenities (incl. gas fireplace), this home can sleep up to 8 (on 4 beds in the 3 bedrooms and 1 futon in a private room in the basement) and offers a combination of location and charm that is hard to beat!

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

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.

Weems Creek Cottage, Annapolis Waterfront

Begin your mornings with wraparound views from the queen bed or coffee on the screened porch, with the same water views. "This cottage is a gem! Beautiful location, comfortable lodging, and a helpful host. It was perfect for two people. We can’t wait to return!" (March, 2025)