Found amidst a bustling port with plenty of recreational activities for a leisurely holiday, Annapolis is very much like a city stuck in time, where sights of historical 18th-century buildings standing tall beside grayscale buildings aren’t all that uncommon here. History buffs will love the Historic Annapolis area, where the entirety of time itself seemed to have stopped moving while the flourishing Annapolis continues to expand globally.
Stay in the heart of the city with 12 of these vacation rentals:
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 08, 2024.
1. Historical flat near downtown Annapolis (from USD 225)
Calm your mind with a touch of zen that this apartment has to offer after a long day of sightseeing. Complete with a yoga corner, indulge in a short meditation session just before the day ends, or observe the intricately carved wall art - a lyrical companion to the calm space presented to you. Accommodating a small family of 4, the double beds will ensure that you fall into a deep sleep upon your head touching the pillow! The grid sofa can also be unfolded into a double sleeper.
Annapolis, Maryland, United StatesAccommodates: 4
Top guest reviews
Amenities & Room:
it's a full apartment underneath her beautiful homeHost:
our host was so gracious wanting us to feel at homeshe is very responsive to messages ready to help if you require assistanceergibe was a very attentive and wonderful hosti am amazed how caring and responsive she was during our stay thereergibe was a warm and gracious hostRead more reviewsLocation:
the location is very quite peaceful and spacious
2. Viridian open-concept home near the Memorial Stadium (from 350 USD)
Spend slow afternoons lounging by the open-air living room - the vivid green themes found on chairs and hanging tapestry dye the room with a beautiful viridian hue, reminiscent of flourishing jungles found in the sub-urban tropics. Featuring a spacious interior, there’s enough space for a crowd of 10! No need to vie for the bed again - the only fight you’ll be getting into is a pillow fight because everyone gets a comfortable double bed to snuggle into!
"Pure Barcelona" (Open-Concept Home)
Address: Near the Memorial Stadium (see map)
Price: from 350 USD
Number of Guests: 10
3. Chic apartment near the Navy Football Stadium (from 228 USD)
Sporting fans, rejoice - the perfect lodging for your next football gig has been found! Situated a short 5-minute walk away from the Navy Football Stadium, this fully air-conditioned home will cool you down after a fiery hot match! With just enough room for a gathering of 7, there’s plenty of recliners in the living room for you to chill out at, all while catching up on your favorite highlights on the huge HDTV. Choose from a wide variety of queen-sized beds, or opt out for the private single sleeper if you like some peace and quiet to yourself.
Admiral Heights Home by N. Academy
Address: Near the Navy Football Stadium (see map)
Price: from 228 USD
Number of Guests: 7
4. Rustic carriage house near the Quaker Meeting House
Wake up to the sounds of birds chirping by your window here at Virginia’s homely abode for 4. Furnished with a minimalist design in mind, the huge glass windows allow plenty of ventilation, keeping you cool during the searing summer heat, while the heaters will keep you toasty warm when the snow starts to fall. Take your pick from the couch-sleeper to the warm double bed, and head out to your private patio for a whiff of crisp morning air.
Annapolis, Maryland, United StatesTop guest reviews
Amenities & Room:
we enjoyed breakfast on the deck every morningthe bed was comfortable ambiance casual and relaxing and scenic view from deckvirginia's carriage house in annapolis is a cozy retreat with water views and a relaxed atmospherevirginia was tremendously welcoming and even though we arrived early she allowed us to have access to the aptthe photos somehow don't do this apartment justiceCleanliness:
the apartment was very clean and invitingthe house is clean with huge windows that let you enjoy the scenic view from every roomher house was beautiful and immaculate with old school charmHost:
she was very friendly and informativeshe was flexible helpful and made us feel at homethe hosts were very friendly and helpfulvirgina was so friendly and welcomingshe provided a lot of helpful informationRead more reviewsLocation:
beautiful convenient location only 2 miles from the naval academy and downtown annapolisgreat location right next to dta and the mallthe location of virginia's listing is wonderfulthe neighborhood is superb and quiet close to the watervery convenient it's in a great location - just a short drive to the historic area
5. Elegant condominium near Dewey Dr (from 375 USD)
Treat yourself to a luxury vacation this holiday - you deserve it! Tucked away in the quiet neighbourhood of Dewey Drive, this condominium is decked out in the luxurious furnishings fit for a king. The ceiling fans will blow you away (no, seriously) on those unbearable summer afternoons, and the fireplace makes for a cosy spot to tell spooky ghost stories during snowy seasons. When you feel your eyelids getting heavy, retreat back to your room for 2 - the day couch makes for a great sleeper too!
Family Friendly Cape Cod - Exceptional Back Yard
Address: Near Dewey Drive (see map)
Price: from 375 USD
Number of Guests: 6
6. 100-year-old home on Severna Park (from USD 110)
Embark on a romantic escapade by booking a stay in this historical home for 2. Built just beside a scenic river, let the gushing waters lull you into a deep sleep when night falls. Enjoy a cup of tea with the lovely hosts, Suzy and Max, as they share with you stories of their own travels - they will even bring you around the neighbourhood if you’d like a tour around! At the end of a long day, retire back to your private room and snuggle under the hand-sewn quilt sheets made lovingly by the hosts.
Severna Park, Maryland, United StatesAccommodates: 2
Top guest reviews
Amenities & Room:
tasty breakfasts on the indoor porch with fantastic river viewthe bedroom while air conditioned by a window unit stayed very comfortable during our stayfound everything as totally comfortable and convenient as 6 months ago when we first discovered itthe homemade breakfast which was included every morning was delicious - particularly the homemade granolathe river was the perfect temperature for swimming very calm and enjoyableCleanliness:
the space was very clean charming and filled with interesting antiques and musical instrumentsa clean and lovely place to stay with welcoming hostsHost:
our hosts were very welcoming and friendlythey were both warm and welcoming hostssuzanne was the warmest host and made us feel right at homeand wonderful hosts who made us feel instantly welcome and at homesuzanne and max were great hostsRead more reviewsLocation:
what a beautiful home and location we live only 15 minutes away but we felt a world awaythe place is pretty close to usna and is perfectly situated on the severn riververy welcoming stay in a fabulous locationgreat location great old house great welcome great conversation & great musica lovely place to stay if you enjoy gardens music and being close to the water
7. Themed rooms near Claude St (from USD 90)
If you’re looking to be a part of all the action in Annapolis, this is this place to be! Featuring 3 themed rooms with unique colours and furnishings, the fluffy queen-sized sleepers will ensure you get enough rest for a full day of adventuring tomorrow. Go bar-hopping with your gal pals at the atmospheric bars a short walk away, or visit the local farmer’s market if you’d like a touch of homeliness in your meals. Just remember to say hi to the pups on the way back - they may be loud, but they all love a good cuddle!
Annapolis, Maryland, United StatesAccommodates: 7
Top guest reviews
Amenities & Room:
the central air conditioning and ceiling fan kept things quite pleasantwe enjoyed a lovely two night stay at dominique's precious air b&b roomthe beds were very comfortablethe house is charming and comfortablewe absolutely loved the room and bathroom which you get to yourself upstairsCleanliness:
bedrooms and bathroom were clean and as advertisedroom and bathroom were as advertised and very clean upon arrivalthe house was clean and well appointedthe house is clean homey and invitingthe house was adorable convenient and cleanHost:
dominique was a great hostdominique was a fantastic hostdominique and joe were amazing hostsour hosts were most welcoming and accommodating as were their wonderful dogsshe was very friendly and informative about the areaRead more reviewsLocation:
easy 20 minute walk to downtowngreat location comfortable roomthe location is good and the neighborhood is nicethe location and neighborhood are greatgreat location for anything in annapolis
8. Luxurious rooms by Severn Grove Road (from 90 USD)
Surrounded by a wooded lot, relax on the porch with a cup of tea in hand as you sway gently on the rocking chairs, with the fluttering trees as a hearty companion on a serene spring morning. Illuminated with an abundance of natural light, the rooms are painted with bright hues of coral shades, adding a touch of warmth to the well-ventilated interior. Choose from the master suite, where you get access to your own private bathroom, or the second bedroom with a soft queen-sized sleeper.
Annapolis PrairieStyle in the Woods
Address: By Severn Grove Road (see map)
Price: from 90 USD
Number of Guests: 4
9. Woody apartment near Eastport Bridge (from USD 360)
If you miss being in the presence of natural sights, have a look around William’s apartment for a family of 6. His love for outdoor activities led him to create a home that embraces the best of nature’s creations - hanging creeper plants decorate the kitchen area, and many of the furniture are carved from various hardwood materials. Feel free to follow William on a hiking expedition on the landscapes of Annapolis, and wash off all the dirt in the fully functional shower space. With a huge day couch that can be extended into a double sleeper, you don’t need to worry about extra guests!
Annapolis, Maryland, United StatesAccommodates: 6
Top guest reviews
Amenities & Room:
all the amenities you’d need for a comfortable stayso the ac was important to us and the ceiling fans were also helpfulnice comfortable yard for entertaining with a large gas grillreasonably well equipped kitchen comfortable beds and seating areas small but nice bathroomCleanliness:
the place was clean and plenty spacioushouse was clean and comfortablewe found it clean and well appointedplace was very cleanbeds were comfortable and place very cleanHost:
hosts were extremely responsivewilliam was a very gracious hostwill is a great host and his place is comfortable and invitingwilliam is an amazing host really cool guy and really cool placewilliam is also a very quick responsible hostRead more reviewsLocation:
great affordable location walking distance from downtownconvenient and easy walk to downtownlocation was absolutely perfect with a short walk to everything downtown annapolisgreat house in a fantastic locationgreat place close to everything
10. Hipster retreat near Lee Dr (from 85 USD)
Found just beside a kayak launch area, you can indulge in a different kind of family vacation this summer here at Sue’s apartment for 4. The full-sized washers and fully-equipped kitchen are a god-send for housewives - no more mud-stained clothes to bring back home! The nearby grocery stores carry a wide variety of cooking ingredients, making it the perfect go-to for dinner if you’d like to taste of home. If you’re tired, head back to your bed for 2, or pull out the gigantic day-sofa for a makeshift sleeper that is equally as comfy!
Private Annapolis Quarters
Address: Near Lee Dr (see map)
Price: from 85 USD
Number of Guests: 4
11. Black River cabin (from 99.00 USD)
For a unique stay that allows you the full cabin experience, together with first-class amenities, check out this Black River cabin property in Annapolis, Missouri. You’re afforded private access to the river itself, as well as access to amenities that include television, free onsite parking, air conditioning, living essentials and a stocked kitchen! Just outside of Lesterville borders, this cabin rental will serve as a deserving introduction to the great outdoors nearby. Whether you’re looking to enjoy fishing, swimming, or simply a nice stroll through the woods at your own pace, this location can deliver it all, and more!
Black River cabin
Price: from 99.00 USD
Number of Guests: 5
12. Bed and breakfast in Annapolis
Treat yourself to the bed and breakfast experience you know you deserve in Annapolis, Missouri, all for a price tag that’s entirely worth your investment. It’s all waiting for you at the Arcadia Academy bed and breakfast, a location especially conducive to couples looking to enjoy a little extra time together. Enjoy a single bedroom, bed, and private bathroom, while at the same time experiencing a unique proximity to local state parks. Amenities on the premises include air conditioning, cable television, laundry provisions, and heating, everything you need for a worthwhile experience in Missouri!
Arcadia, Missouri, United StatesAccommodates: 2
Top guest reviews
Amenities & Room:
was lucky to to book this room for solar eclipse 2017the rooms are beyond nice to the point of superbthe rooms are comfortable and nicely renovatedHost:
outstanding owner fantastic food great locationRead more reviewsLocation:
convenient location and beautiful historic sitethe location is close to several great hiking spots
A relaxing retreat
Take your time when touring the streets of Annapolis. Let the nostalgia of age-old buildings wash you over, all while immersing in the stories that grand museums have to tell. With a wide selection of vacation rentals to choose from, anywhere will feel like home!
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