A gem on the Chesapeake Bay, Annapolis, the capital city of Maryland, has plenty of opportunities for sightseeing and outdoor adventures. It takes pride in having beautiful parks, stunning colonial architecture, numerous art galleries, theaters, and festivities. Maryland State House, the oldest U.S. State Capitol, is a must-visit landmark in the city. You can also learn more about the U.S. Navy and Marines in the U.S. Naval Academy Museums. For hiking and biking trails, you can visit Quiet Waters Park. It has an enormous playground where children can run wild and a dog beach. You can also enjoy water activities such as kayaking, canoeing, and more. If traveling with family, visit Sandy Point State Park, a spot for bird-watching, picnics, and boating. For a comfortable stay, check out this list of the best Airbnbs with pool in Annapolis, Maryland.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 12, 2024.
1. Artistic guest house for two (from USD 235)
This guest house has beautiful art pieces and can accommodate two guests. You can kick-start your day with some leisurely laps in the shared pool. You will love to stay longer in the pool because its temperature is just right, not too cold and not too hot.
The living area has comfy couches and a flat-screen television with Netflix. You can comfortably prepare your meals in the fully equipped kitchen. There is a vibrant dining space where you can enjoy your home-cooked dishes. The property is close to some local shops.
Annapolis, Maryland, United States
1.94 km (1.3 mi) from Annapolis City DockSuperhost
Accommodates: 2
Top guest reviews
Amenities & Room:
it was a delight to stay at the "tree top getaway" a charming space that was warm and comfortabletree tops is a lovely comfortable studio apartment with many thoughtful touches in a great locationthe bed was comfortable and the space was cozy and private from the main houseCleanliness:
clean safe and comfortablethe apartment was very nice clean and had a lot of charactermy best friend and i had an absolute blast here it was clean cozy and decorated adorablywe had a great stay the guest house is cute clean and comfortablelinda's place was clean comforting and absolutely filled with characterHost:
linda and jim were the perfect hoststhe hosts were very graciouslinda is absolutely the best host out thereamazing hosts so kind and welcomingthe owners were very friendly and helpfulRead more reviewsLocation:
ideally located close to downtown annapolisthe neighborhood was great and a nice walk to the downtown areathe location was super convenient parking was plentiful and we are already looking forward to our next triploved the stocked fridge pool and great neighborhood walking distance to nice little restaurants and coffee shopsthe 3rd time was the charm also there is a great breakfast place two blocks away cheers linda
2. Lovely waterfront condo with a deck (from USD 150)
Within walking distance of the boat show, this one-bedroom condo features a living area with a flat-screen television, a fireplace, and a sleeper sofa where you can relax while watching your favorite shows. It also has a full kitchen and a dining space. The deck is the perfect place to witness the breathtaking sunrise and sunset views.
You can go for a swim in the outdoor pool while enjoying the stunning views of Spa Creek. There are poolside benches where you can have snacks or sunbathe. The property is a few minutes away from downtown Annapolis.
Annapolis, Maryland, United States
617 meters (0.4 ft) from Annapolis City DockAccommodates: 4
Top guest reviews
Amenities & Room:
close to downtown lovely view from the very large balcony full kitchen if you want to cookgreat apartment overlooking spa creek and downtown annapolisotherwise there is a memory foam pull-out couch and a very comfortable queen bed providedthe apartment looks like the picturesCleanliness:
condo was clean and perfect for all your needsclean quiet with a great locationjane’s place was very clean and cozy great location right on the water perfect for a coupleHost:
great host we had a wonderful weekendjane is a very helpful host—offered plenty of suggestions for dining & was very quick to respondthe host was very responsive and provided exceptional communication on everything from parking to the nearby restaurants/cafesjane was one of the most responsive owners we have worked withRead more reviewsLocation:
the location is perfectterrific location and fabulous hostwe are a new usna family and this location was perfect to walk into town and to the yardvery conveniently located cute condo could easily walk a few minutes into townexcellent space and hospitality walking distance to the downtown area and waterfront
3. Clean and welcoming home with scenic views of Spa Creek (from USD 175)
The pool and the breathtaking views will complete your stay in this beautiful abode close to the U.S. Naval Academy. It sleeps four guests and features a fully equipped kitchen, a dining area, and a living room with a large seating area and flat-screen television.
If you want to freshen up or enjoy the sunny weather, take a lift to the rooftop and plunge into the pool. It overlooks Spa Creek and is a perfect spot to have a breath of fresh air. The accommodation provides easy access to Boat Shows and Navy Football Games.
Annapolis, Maryland, United States
805 meters (0.6 ft) from Annapolis City DockAccommodates: 4
Top guest reviews
Amenities & Room:
good air-conditioning kitchen appliances and necessitiessuch a cool view with tables and chairs set up to eat lunch or enjoy a morning coffeethe heated bathroom light is a nice touchon a hot day relax in the rooftop pool or sit under the awningCleanliness:
apartment was clean and as picturednice and clean and cozyvery convenient and cleanthe apartment was professional-level clean when we arrivedit is stylish and cleanHost:
joe is an excellent host and communicates very wellRead more reviewsLocation:
great condo in a great locationgreat location in walking distance to many shops and restaurantsgreat place that was close to downtownwell stocked and great locationvery central and walkable safe area
4. Pet-friendly house with a backyard (from USD 375)
You don’t need to worry about your furry friends as they are welcome in this lovely house that sleeps seven guests. It is near downtown Annapolis and U.S. Naval Academy. The house also features a fully equipped kitchen, a dining room, a living area, and a workstation.
You can take a refreshing dip in the heated in-ground pool. There are also poolside umbrellas where you can rest and enjoy your meals. The backyard is the perfect place for your furry friends to roam around.
Annapolis, Maryland, United States
2.36 km (1.5 mi) from Annapolis City DockAccommodates: 7
Top guest reviews
Amenities & Room:
the wifi is freethe sleeping accommodations were very comfortable toofinal thoughts: my daughter and i have been lucky enough to visit walt disney's apartment inside disneylandthe heated pool is amazing a true highlight of this annapolis homeyou will love the pool especially at night chatting while the burgers cook on the grillCleanliness:
super fast communicationthe house is kept very cleannot demanding you meticulously clean the place top to bottom before you leave2you'd think the place would be covered in dust given all of the surfaces to cleanthe home was clean and had all accommodations neededHost:
the hospitality and attentiveness from the host was remarkablethe host was extremely communicative and helpful throughout our whole weekendgreat hosts and a great staythe hosts were very accommodating & easy to get in touch withhost is very communicative and the manual was very helpfulRead more reviewsLocation:
great location you can walk downtownbeautiful neighborhood and great locationwhile our event downtown wasn't walking distance there are great places to eat close-bythis was the perfect location for our stayclose to the downtown waterfront for dining and shopping but felt super private while we were there
5. First-floor condo with uninterrupted water views
This first-floor condo gives its guests easy access to restaurants and attractions. It has one bedroom and can fit up to two guests. It features a kitchen, a living room, and a dining area. Throughout your stay, you can use the amenities in the building, including the gym and the pool. You can go for a swim early in the morning to have fun in the sun or at night to unwind after a long day outdoors.
Annapolis, Maryland, United States
618 meters (0.4 ft) from Annapolis City DockAccommodates: 2
Top guest reviews
Amenities & Room:
it has excellent internet/ wifi that is specific to the unitCleanliness:
it was clean and had nice appliances and furnishingsRead more reviewsLocation:
great location on the watersafe neighborhood great locationwalking distance to the best places in annapolisgreat location - very convenient and within walking distance to waterfront area with countless restaurants bars and shopsthe condo is in an excellent location
6. The Petite Resort
This four-bedroom home can comfortably sleep ten guests, making it ideal for family and friends reunions. It features a large kitchen with modern appliances, a bright dining area, and a spacious living room with flat-screen television and elegant seating area.
Kids can splash around in the outdoor pool, while adults can relax and enjoy refreshing drinks by the poolside or on the porch. If you have a child who cannot swim, kindly secure a life jacket. Please note that parties are not allowed. The property also features a hot tub, ideal for a relaxing soak.
Annapolis, Maryland, United States
1.05 km (0.7 mi) from Annapolis City DockAccommodates: 10
Top guest reviews
Amenities & Room:
our time at bernie’s place was fabulous the house is large and full of comfortable furniture and wonderful amenitiescomfortable and abundant seating was especially appreciatedthis house was perfect for a girls weekend we lived on the screen porch and pool sidewe also rented the apartment and that was a perfect solution for my grandkids napsthe comfortable great room and large kitchen were a nice open area where the whole family could congregateCleanliness:
the space was also very clean which was a relief during covid timesthe house is just as pictured and very cleaneverything including pool and hot tub was super clean and functionalgreat house clean convenient to walk to just about everything and bernie is a great hostthis house is awesome - great location comfortable clean (so important) loads of amenitiesHost:
bernie was a great hostshe was easy to communicate with and responsivebernie is an excellent hostbernie was a great host; very communicative and helpfulnot to mention the fact that bernie is a wonderful host that was a phone call awayRead more reviewsLocation:
the location is idealthe location is fantasticgreat location on a quiet street close to historic annapolisgreat location toothe location is ideal in the downtown annapolis neighborhood
7. Contemporary and stylish condo near downtown Annapolis
Comfort and luxury are the things you will experience in this high-end condominium close to downtown Annapolis. It provides its guests with modern amenities and features a cozy living area, a fully equipped kitchen, and a dining room. A dip into the rooftop pool will keep you fresh all day. There are poolside benches where you can rest and enjoy the views. If you fancy dining out, there are several restaurants nearby.
Annapolis, Maryland, United States
803 meters (0.5 ft) from Annapolis City DockAccommodates: 2
Top guest reviews
Amenities & Room:
this cozy well-appointed 1 bedroom condo provides a delightful place to stay in annapolisCleanliness:
it was clean well-appointed and visually pleasinglinda & simon have thought of everything for your stay the place is so clean and comfortablethe location was perfect for exploring annapolis and the condo was very very clean and well appointedgreat location very clean and accommodatingHost:
linda and simon were amazing hostslinda snd simon were excellent hosts easy to communicate with friendly and answered my questions quicklylinda and simon are the best hosts that i have encounter since using airbnbthe roof and goodies from the hosts were nice perksi would highly recommend this unit and hostsRead more reviewsLocation:
great location we walked everywheregreat location easy stroll to restaurants eastport and downtown annapolisperfect location we will be coming backit was easy to park there and walk everywhere we wanted to gothe location is very good (walkable if it wasn't so darn humid outside)
Sail through the beautiful sites of Annapolis
You will witness plenty of yachts and sailboats traveling along the waters of Annapolis. The Sailing Capital of America, the city boasts its rich maritime heritage. A bucket of seafood with live music is a great way to spend your vacation here. For a memorable experience, book any of the above Airbnbs with pool in Annapolis, Maryland.
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