Apartment holiday rentals in Annapolis

4.92 out of 5 average rating, 492 reviews

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.

4.98 out of 5 average rating, 287 reviews

Flat in Stevensville

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

4.99 out of 5 average rating, 110 reviews

CIRCA 1885-Historic Annapolis-USNA GATE 1

A stunning home, "Circa 1885" is a restored piece of Annapolis history. Sitting at one of the two major gateways that lead to downtown, our beautifully renovated home sits on the corner of King George and Randall Streets. A distinctive yellow PRIVATE entry door at 4 Randall Street leads to this rental apartment that boasts 2 large bedrooms (K,Q), family room with pull out sofa, 1 bath with antique claw foot tub/shower and a full eat in kitchen. Everything Annapolis is within a 2 block walk.

4.93 out of 5 average rating, 147 reviews

Walk to Water, State House, USNA

Private, 1st FL space in Eastport (architectural) Conservation District. Sleeps 3. Guests' day visitors are welcome; home not appropriate for parties. BR w/king bed, living/dining area w/pullout sofa. FiOS WIFI, 2 Roku TVs. BA w/shower, fully equipped galley - fridge & freezer, DW, disposal, microwave, toaster oven, induction cooktop (portable). WD available. Walk to water; tie up your dinghy gratis at street-end parks. Short walk to downtown, USNA, boating. Stays > 9mos out - pls message!

4.98 out of 5 average rating, 102 reviews

LOCATION!! Steps away from historic Main Street.

I would love to host you in my newly renovated home built in 1857. This home was taken down to the studs, but some original details remain to give you that old time feel. There are 3 separate apartments, one on each floor and all share the main front door to access the units. This unit is the only one with a private back yard, perfect for grilling, relaxing or letting the kids run around. To sweeten the pot, this apartment house is within walking distance to everything Annapolis has to offer.

4.96 out of 5 average rating, 100 reviews

Historic Annapolis Rental Minutes from Downtown

Immerse yourself in all Annapolis has to offer in this newly restored historic home. This charming rental neighbors the Naval Academy and is just a 5 minute walk to the heart of downtown Annapolis. This home has 2 bedroom and 1 full bath. This is the perfect place to stay whether you're looking to explore historic Annapolis, the Naval Academy grounds, or even taking a day trip to Washington D.C. Inside the home you'll find cozy furniture, new finishing's, and wifi throughout the house.

4.98 out of 5 average rating, 132 reviews

Perfect Eastport location

Our nautically inspired 2 bedroom apartment puts you in the middle of the best of annapolis. Walk to Davis Pub, Carrols Creek, The Boatyard, Charthouse or Blackwall Hitch or stroll leisurely to DTA. Visit the Maritime Museum or many other historic landmarks Annapolis has to offer. Relax in your private courtyard . Your space gives you access in over a 1000 sq feet space. We have hosted many yachtsman and navy families from around the country in our private lower level apartment.

4.92 out of 5 average rating, 106 reviews

King George Hideaway

Perfect location for all that downtown Annapolis offers, right across from USNA gate 2. Super convenient, park your car and walk everywhere! Lots of shopping, restaurants, tours, cruises & nightlife. The unit is located on the 3rd floor. My place is perfect for couples, solo and business travelers. There is a large living room space with a full pull out couch, tv and dining table. The bedroom has a queen bed with a tv. There is a small full kitchen and updated bathroom.

Superhost

4.77 out of 5 average rating, 274 reviews

Charming Eastport

Who needs a boat to stay at a marina? Eastport Yacht Center has a quaint one bedroom apartment located in charming Eastport, within walking distance to Downtown Annapolis and the U.S. Naval Academy. Conveniently located next to the Annapolis Maritime Museum. (Two guests maximum) If this apartment isn't available for your time period check out our other studio apartment listed under "NEW lovely studio apartment with onsite parking".

4.97 out of 5 average rating, 274 reviews

Flat in Essex

A unique place on sue creek

Enjoy your private apartment and deck on the water or come sit down by the waterfront and watch the Ospreys, herons, ducks and the occasional eagle. Fishing off the pier and possible small boat docking available. We are close to Rocky Point golf club, Baltimore yacht club, 20 minutes from Camden Yards and M&T stadium. We are 38 minutes from BWI. You will have private parking in a quiet safe neighborhood. Sorry, no pets allowed.

4.91 out of 5 average rating, 156 reviews

Eight Fleet - Annapolis Dock

Welcome to city dock, the heart of historic downtown Annapolis! We are steps from the Maryland State House, US Naval Academy, St. John's College, the Annapolis Arts District, and a wide variety of restaurants, pubs and shopping. This 3-bedroom apartment provides a uniquely fun yet businesslike environment for your stay, in a town where military meets artsy.