
Apartment holiday rentals in Annapolis
Find and book unique apartments on Airbnb
Top-rated apartment rentals in Annapolis
Guests agree: These apartments are highly rated for location, cleanliness and more.

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.

Hickory Haven •1B King •Bsmt Apt •Clean •LG
Walk into a generously spacious, open-concept apt. The comfortable furnishings in this home blend authentic styles with modern design. Start your mornings w/ a meticulously clean bathroom. Enjoy movie night in the large living room, or lay on the comfortable king-sized bed. Read through the night by a warm stove fire. Stay in the backyard and enjoy the serenity of Sykesville! Enjoy the high-speed internet and the large space for your work-at-home needs. Stay-a-while and make the place your home.

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.

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.

Just Like Home - Private Entrance Apt in DMV Area
288 SQ FT PRIVATE ENTRANCE Mother-in-law suite/ studio apt, full bed, sofa, roll-away single bed, kitchen, bathroom with small shower stall & 55” Smart TV w/cable, Netflix & WiFi. No guests under 12 years of age. Excellent location: Ft. Meade (14.4 miles), Annapolis (15 m), Andrews AFB (19 m), Washington DC (19 m), Baltimore (29 m) Nearby airports: DCA (23 m), BWI (27 m), IAD (48 m) Public Transportation: Metro Bus Stop (0.2 m), New Carrollton Station Metrorail, Amtrak, & Greyhound (9 m)

Urban 1-Bedrm. Apt. Overlooking Union Square Park
The south-facing, 2nd floor 1-bedroom apartment of an owner-occupied historic townhouse overlooks historic Union Square Park in Baltimore City. Located 2 doors from the author, H.L. Mencken's home place, the neighborhood is primarily residential , but very convenient to the Inner Harbor. The apartment has a full kitchen (with light breakfast items), historic details & eclectic furnishings. Street parking is easy. The space is good for couples and solo adventurers, and business travelers.

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.

Small cabin style- 23 min drive to US Capitol!
This in-law suite is better defined as a small apt. attached to house; own entrance, bathroom, kitchen & free parking! Queen bed, clean sheets, towels, iron, board, kitchen pots, dining table, TV & more. It’s small but with all amenities necessary to live. If looking for a huge space, this will not be it. Good for single/couple cruising by the DMV on a BUDGET! -20 min walk to metro; off DC border, 18 min. drive to center of city.

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".
Spacious & Modern Apt in Historic Neighborhood
Enjoy a retreat in a recntly renovated basement apartment in DC with free street parking and convenient access to all the hustle and bustle of downtown! Amenities include smart lock/alarm allowing for self check-in/out; spacious bedroom with a Duxiana queen bed; living room with comfy couch and smart TV; modern newly renovated bathroom; full kitchen with a coffee maker, kettle, fridge, stove/oven and microwave; and a washer/dryer.

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.

Cozy Waterfront Apartment Chester, MD
Hello travelers!! Looking for a cozy & comfortable place to stay on Kent Island? Come enjoy our clean & beautifully renovated apartment above our family home, overlooking Cox Creek. This apt. Is built above our garage. Private entrance on the side of our house (20 steep steps up). 1 bedroom, queen bed. WiFi included. Private porch to enjoy water view!
Popular amenities for Annapolis apartment rentals
Weekly apartment rentals

Dean Street's Lower Deck House!

Charming Federal Hill! One Bedroom With Vibes

CIRCA 1885-Historic Annapolis-USNA GATE 1

Private, spacious basement suite; great location

Luxurious, modern, great location 1 BR in Shaw

Aspen Woods - Private Garage

Charming, Chic Downtown Annapolis Apartment

*NEW* Luxurious 1 Bed/1 Bath flat in Logan Circle
Private apartment rentals

Naptown’s Nauti Flat

Gardened Apartment Close to JHH

Beautiful Historic Home next to City Dock + USNA

Relaxing Waterfront Apartment!

Elegant Uptown Condo withParking

Historic Annapolis Rental Minutes from Downtown

Annapolis Waterview Condo

Lighthouse Lodge
Apartment rentals with a hot tub

National Harbor 1 Bedroom w/ Balcony

Resort studio apt w/ pool, hot tub, fire pit, gym

Private Serene Suite with Jacuzzi- Non Smoking

National Harbor 1BR Deluxe w/Jetted Tub & Kitchen

2BR/2BA King Deluxe @ National Harbor Boardwalk

National Harbor~2Br Presidential

Central and Stylish DC Apartment

Stylish 1BR Apt | Arlington | Pool, Gym
When is the best time to visit Annapolis?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $291 NZD | $272 NZD | $291 NZD | $322 NZD | $363 NZD | $334 NZD | $354 NZD | $334 NZD | $361 NZD | $413 NZD | $327 NZD | $301 NZD |
| Avg. temp | 1°C | 3°C | 7°C | 13°C | 18°C | 23°C | 26°C | 25°C | 21°C | 14°C | 8°C | 4°C |
Quick stats about apartment rentals in Annapolis

Total holiday rentals
Explore 90 holiday rentals in Annapolis

Nightly prices starting at
Annapolis holiday rentals start at $86 NZD per night before taxes and fees

Verified guest reviews
Over 6,240 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
90 of Annapolis holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Annapolis rentals

4.9 Average rating
Annapolis stays are highly rated by guests—averaging 4.9 out of 5!
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- Nationals Park
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