
Apartment holiday rentals in Annapolis
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Top-rated apartment rentals in Annapolis
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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.

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.

Halcyon house. Lovely views on MD eastern shore.
This charming apartment is located on the Chester river on Maryland's Eastern Shore. The wildlife is abundant and generally very active. The sun rise and sunsets can be spectacular. The property is 20 minutes from Annapolis and 50 minutes from DC. The newly renovated apartment has all new appliances and a well stocked kitchen with many herbs and spices, condiments, coffee, tea, cream and sugar etc. The 8 mile long Cross Island Trail starts a block from the house and leads to several restaurant

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.

Butchershill- Clean, Fireplace, King Bed, Parking!
My name is John S Marsiglia. Always clean, very comfortable new King Mattress, Warm & Cozy Fireplace, Self checkin , Historic 2207 E Baltimore St. Search online. 900 Sq Ft. 12 ft ceilings,Fully equipped kitchen/kitchenette,Coffee,Tea,Cream,Brita filtered water pitcher,50" 4K smart TV, streaming only, Free Netflix, Prime,top speed WiFi, surround sound, comfortable clean furniture, antiques, oriental rugs, workspace w/desk, modern beautiful bathroom, dual shower heads&seats, private full size W&D

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.

Charming 18th C. Apt in DTA
Lower level furnished apartment in one of Historic Annapolis's 10 oldest private residences. Boasts lovely wood, brick & ornamental ironwork Covered keyless entry King Henredon bed Exec desk & chair TV w/ Roku Decorative fireplace Iron & board Robe & slippers Claw foot tub w/ shower Beverage station (coffee maker,mugs wine&bottle opener, glasses, ice bucket, flutes) Microwave Fridge/freezer Cutlery Plates & napkins Bistro table & stools for 2 Limited free street parking 8p-8a

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.

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.

Charming Eastport
You don’t need a boat to enjoy marina living. Safe Harbor Eastport Yacht Center offers a charming, one bedroom apartment in Eastport, just a short walk from Downtown Annapolis and the U.S. Naval Academy. The property is conveniently located next to the Annapolis Maritime Museum and accommodates up to two guests. 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".

Elegant Green Studio In The Heart of Old Town
Discover a unique retreat in the heart of historic Old Town Alexandria! This cozy studio blends charm with comfort, offering a memorable stay. Enjoy modern amenities in a space that exudes character and warmth. Step outside to explore charming streets, boutique shops, and local eateries. Perfect for travelers seeking an unforgettable experience in a vibrant, historic setting.

Private Annapolis Inlaw Apartment
In-law apartment in beautiful Annapolis home. Close to downtown Annapolis but also has easy access to major highways. Quiet neighborhood. Private front entrance to apartment. In addition to king size bed in bedroom there are two queen size blow up beds as well as a large sectional sofa. So it comfortably sleeps 4. Off street parking for 2-3 vehicles.
Popular amenities for Annapolis apartment rentals
Weekly apartment rentals

Pristine Downtown 1-Bedroom in Historic District

Annapolis Main Street Modern Apartment

Gracious Historic Townhouse by JHU

Celebrate Summer In Your Private Pool & Hot Tub

Spacious Beach House Top Floors - Walk Everywhere!

Serene Hideaway

Uptown Condo w 2 Parking Spots

Annapolis 4 Steps to Harbor Backs to Gate 1
Private apartment rentals

Naptown's Nauti Apartment

Book CW26 Walkable Dog-Friendly Apt Yard & Parking

Relaxing Waterfront Apartment!

Oasis in the woods

Luxury Home-DC's Best Walking Neighborhood-Parking

Aspen Woods - Private Garage

Pool Loft Suite | Bay Access & Beach Passes

The Sail Loft
Apartment rentals with a hot tub

Kone Oasis- hot tub, pool, theater/game rm.

National Harbor ~ 3Br/2Ba ~ DC!

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

Private Serene Hideaway Suite with Jacuzzi

Central and Stylish DC Apartment

Beautiful German style cottage Apt w Hot Tub!

Safe, quiet neighborhood close to downtown!

Cozy 1 bedroom suite with jet tub near US capitol.
When is the best time to visit Annapolis?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $291 NZD | $272 NZD | $291 NZD | $322 NZD | $363 NZD | $334 NZD | $354 NZD | $334 NZD | $361 NZD | $397 NZD | $339 NZD | $327 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 5,460 verified reviews to help you choose

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

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

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

Popular amenities for guests
Guests love Kitchen, Wifi 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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- Georgetown University
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