
Places to stay near Annapolis City Dock
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Top-rated vacation rentals near Annapolis City Dock
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King George Downtown Annapolis Getaway
This unit has all new furniture, bedding and housewares. Unit is directly across from Gate 2 at the Naval Academy so a block in either direction and you can get onto the Yard. You'll be a short 1 block walk to Ego Alley and all of the restaurants, shops and water taxi. Eastport is a 15 minute walk. This is a beautiful location in historic downtown Annapolis that's convenient to everything that downtown has to offer and is perfect for couples with or without children, solo and business travelers.
4.85 out of 5 average rating, 129 reviews
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.
4.99 out of 5 average rating, 159 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.
4.99 out of 5 average rating, 133 reviews
Villa Annapolitana • Parking 1 min • USNA 4 min
Our 1700s home offers a perfect blend of luxury and comfort. With three beautiful bedrooms, three bathrooms, and a sleek lounge area, it’s a perfect place to relax and unwind. The fully stacked kitchen is ready and waiting for you to cook a perfect meal and enjoy a glass of wine. The location is ideal, with the US Naval Academy just a 5-minute walk away. If you are looking for a peaceful escape or a fun vacation, our property has something for everyone. ✔ King Beds ✔ Smart TVs ✔ Sport E
4.97 out of 5 average rating, 156 reviews
Gorgeous Historic Downtown Annapolis House
USNA grad-owned, this 5 bedroom & 3.5 bathroom elegant house is located in the heart of downtown Annapolis (1 block from USNA Gate 3 & from St. John's College). Cable, WIFI, linens, towels, and a parking pass for one car included (street parking only). Pet requests considered (permission required in advance; there is a $500 pet fee if approved). Beautiful backyard for entertaining. We ask guests to treat the space as if they are guests in our home. We look forward to hosting you!
4.98 out of 5 average rating, 161 reviews
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
4.89 out of 5 average rating, 105 reviews
Annapolis @Gate 1 steps to the Harbor Free parking
Parking included. The heart of Annapolis 1 street from the harbor, fun restaurants & backs to the Naval Academy. This 1st floor 2 bed / 1 ba condo has been fully renovated with new paint, floors, bath & kitchen. 1 Parking space included & additional paid parking on street. Queen Bed & sleeper couch is a full size. Linens included. Kitchen includes refrigerator, stove/oven, microwave, keurig, dishes silverware, pots and pans. High speed internet included & separate work area.
4.91 out of 5 average rating, 153 reviews
USNA downtown house with garage parking EV 3bd/2ba
1992 grad’s downtown home near USNA with GARAGE PARKING & EV charger! Top listing as “Guest’s Favorite” for consistent 5 star ratings. Best location on a private one way street behind Iron Rooster. Enjoy all the modern touches including smART FrameTV with local artist’s work, bluetooth speaker, keyless entry, Nest thermostat, 2 Novaform mattress beds and remodeled kitchen/bathrooms. Garage parking is for small car. Famous photo wall out front. New deck and fence
4.95 out of 5 average rating, 108 reviews
1st Floor Condo in Annapolis
This newly renovated, 1st floor studio is perfectly located just across Spa Creek from historic Annapolis in Eastport. Within easy walking distance of restaurants (3 min), Main Street/City Dock (10 min) & USNA's Gate 1 entrance (14 min), our studio includes a full kitchen, high-speed wifi, free onsite parking lot, a secure building entrance, dock (limited access) and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.
4.96 out of 5 average rating, 179 reviews
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!
5.0 out of 5 average rating, 205 reviews
Charming, Chic Downtown Annapolis Apartment #1
In the heart of Downtown Annapolis. One block from Main Street/West Street/Church Circle. Close proximity to USNA, Ego Alley, Eastport, State House, shops, galleries, restaurants/bars and all other DTA amenities. This private apartment has an open floor plan and is elegantly decorated (with a modern twist). One Full Bathroom with tiled shower. One Bedroom with walk-in closet (with W/D).
4.9 out of 5 average rating, 125 reviews
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. Twin bed can be set up and made up at guest request.
4.96 out of 5 average rating, 268 reviewsPopular amenities for vacation rentals near Annapolis City Dock
Other top sights near Annapolis City Dock
Condo rentals with wifi

Funky Uptown Apt meets Downtown - Hist District
4.96 out of 5 average rating, 127 reviews
Captains Quarters | Waterfront & Pool
4.98 out of 5 average rating, 124 reviews
Anchors Away
4.85 out of 5 average rating, 110 reviews
New Downtown Annapolis Condo With Free Parking
4.98 out of 5 average rating, 166 reviews
Renovated Apt In Historic Dist w/2 Parking Spots
4.94 out of 5 average rating, 454 reviews
Annapolis Condo-1 bedroom King
4.96 out of 5 average rating, 131 reviews
THE ROYAL: Nostalgic Go-Go Theme Suite w/Fireplace
5.0 out of 5 average rating, 99 reviews
Historic Federal hills urban lifestyle
4.86 out of 5 average rating, 291 reviewsFamily-friendly house rentals

Luxury Waterfront Annapolis/ Private Beach & Dock
5.0 out of 5 average rating, 147 reviews
Cozy 2br home w/ parking in downtown Annapolis
4.92 out of 5 average rating, 368 reviews
Sophisticated & Spacious Historic Home w/ Parking!
4.96 out of 5 average rating, 178 reviews
Historic Downtown House with Off Street Parking
4.9 out of 5 average rating, 147 reviews
Charming Renovated Historic Home Downtown wParking
4.91 out of 5 average rating, 243 reviews
Fleet St Retreat in Downtown - Great Location!
4.91 out of 5 average rating, 125 reviews
Iconic Chesapeake. Unparalleled Luxury.
5.0 out of 5 average rating, 217 reviews
Kent Island Waterfront Home with Amazing Sunsets
4.99 out of 5 average rating, 151 reviewsApartment rentals with air conditioning

Charming Eastport
4.77 out of 5 average rating, 305 reviews
Private Annapolis Inlaw Apartment
4.89 out of 5 average rating, 373 reviews
Charming Navy-Themed Townhome | Walk to USNA & DTA
4.93 out of 5 average rating, 118 reviews
Gybeset Eastport Inn
4.88 out of 5 average rating, 307 reviews
Perfect Eastport location
4.98 out of 5 average rating, 148 reviews
Blue Crab Lodge
4.98 out of 5 average rating, 162 reviews
Boutique by the Bay
4.97 out of 5 average rating, 316 reviews
Hideaway in the Middle of Everything AYC 2+BR apt
4.78 out of 5 average rating, 122 reviewsOther great vacation rentals near Annapolis City Dock

Charming Detached Studio w/ easy walk to Downtown.
4.96 out of 5 average rating, 230 reviews
Coastal Waterfront 1 Bedroom Cottage
5.0 out of 5 average rating, 226 reviews
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 472 reviews
Weems Creek Cottage, Annapolis Waterfront
4.98 out of 5 average rating, 167 reviews
Welcome Aboard!
4.97 out of 5 average rating, 116 reviews
Our Annapolis Penthouse
4.97 out of 5 average rating, 464 reviews
Historic Downtown Property
4.81 out of 5 average rating, 315 reviews
Charming Cottage 2 parking spot easy walk downtown
4.94 out of 5 average rating, 214 reviewsDestinations to explore
- M&T Bank Stadium
- National Mall
- The White House
- Walter E Washington Convention Center
- Nationals Park
- FedExField
- Johns Hopkins University
- Federal Hill Park
- Oriole Park at Camden Yards
- Capital One Arena
- Arlington National Cemetery
- Georgetown Waterfront Park
- Howard University
- Betterton Beach
- Washington Monument
- National Museum of African American History and Culture
- National Harbor
- CFG Bank Arena
- Baltimore Convention Center
- Smithsonian National Zoological Park
- Museum of the Bible
- Smithsonian National Air and Space Museum
- Smithsonian American Art Museum
- Patterson Park





