For those who are unfamiliar, Maryland, USA, is named after the English Queen, Henrietta Maria, who is known in England as Queen Mary. Maryland is known for hosting some of the highest numbers of historic landmarks and is a major centre for life sciences research and development. Tourists to Maryland usually visit Baltimore, the beach resort town of Ocean City, as well as Western Maryland. In Baltimore alone, visitors can check out Harborplace, Baltimore Aquarium, Fort McHenry and Oriole Park at Camden Yards. Among all the sightseeing and things to do, book into one of the best Airbnbs with pool in Maryland, USA, for a relaxing getaway.
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 11, 2024.
1. Beachfront rental with indoor pool, Ocean City (from USD 150)
This Airbnb in Ocean City with a shared indoor pool is one of the best options to stay in Maryland. The seasonal pool is a great place to unwind with a relaxing dip. The two-bedroom rental overlooks the coastal highway and offers shared access to the sandy shores that are just a short walk away. Moreover, parking on the premises is offered for free.
You can cook your favorite dishes in the well-equipped kitchen and do your laundry using the washer and dryer. The rental also features a Smart TV for your entertainment.
2. Cosy one-bedroom studio with indoor heated pool, Highland (from USD 274)
This cosy one-bedroom studio comes with a private indoor heated pool that guests can enjoy all year round, regardless of the outside temperatures. Horses can be seen grazing in the field nearby. The property offers direct access to Schooley Mill (an equestrian park) with scenic wooded trails for horse riding and nature walks. This home also comes with a kitchen that is fitted with necessary utensils and appliances for guests who wish to cook up a storm.
Top guest reviews
Amenities & Room:
great place w/ an amazing heated poolthe private pool private patio with grill and tables were awesomethe delicious heated pool was a dream and so relaxingbeautiful space property and poolthe pool was beautiful and did not disappointCleanliness:
very clean private and cozypool is beautiful clean and warmthe guest house was clean and homeythe living space was very clean organized and cozypristinely clean and the pool is amazing highly recommendHost:
thank you to our wonderful hosts for a great staythe hosts were very responsive and welcominghosts are incredibly kind and helpfultheresa and her husband were wonderful hoststheresa and jim were great hosts and very hospitableRead more reviewsLocation:
the location was beyond beautifulwe loved everything about the this locationthe apartment was the perfect location for our needslocation is very close to bwi yet rural and secluded in a beautiful neighborhoodthis is a beautiful house and good location
3. Fabulous residence with panoramic views, McHenry (from USD 1183)
This grand five-bedroom house is located on top of Wisp mountain and offers spectacular views of Deep Creek Lake and the surrounding areas. It strikes a fine balance between being private but at the same time conveniently located to all necessities. Guests staying in this luxury accommodation can enjoy the indoor heated swimming pool and an outdoor hot tub that overlooks the lake. Furthermore, there is an outdoor sauna situated right next to the hot tub where you can admire a view of the lake. There is also an outdoor gas grill that allows guests to barbecue and hang out with family and friends.
Top guest reviews
Amenities & Room:
everyone enjoyed the swimming pool and video games as well as the private putt putt coursegreat home with a fully stocked kitchen and prefect for larger families with childrenRead more reviewsCleanliness:
communication cleanliness amenities large pool fun arcade games spacious rooms
4. Private beach house with awesome view, Ocean City (from USD 92)
This beach house comes with a private dock, where you can fish or park your own boat or jet-ski. The host also provides kayaks so you can go kayaking or explore the bay and enjoy the spectacular sunsets. That’s not all. The pools and tennis courts are located just a few blocks away too, so you can take a dip or challenge a mate to a game of tennis anytime. There is also a propane grill right below the deck which you can use to put your culinary skills to good use when you feel hungry. The thoughtful host has also installed a new outdoor shower at the side of the house so guests can rinse off the sand before entering the accommodation.
Top guest reviews
Amenities & Room:
very comfortable huge tv fast internet great beds all the amenities you could need and fantastic locationvery peaceful neighborhood and beautiful scenery to read and have breakfast on the deckfrom the deck to kayaking to just being cozy and cleanthe home was comfortable and the deck was lovelythe well-stocked kitchen is so large and open that 3 cooks can move freelyCleanliness:
it was very clean which is always a concern of mine when using airbnbthe madmen house was very clean when we arrived and beautifully decoratedrebecca's house was clean convenient and cozyvery clean relaxing space right on the waterit was very clean an easy walk to the ocean and in a quiet neighborhoodHost:
excellent hospitality from the host rebeccathe cramer’s are wonderful hoststhe host is caring responsible and flexibleshe is a responsive host available within minutes via text or callthe owner makes sure that you are comfortable and cared forRead more reviewsLocation:
great location beautiful homethe location was fabulous — everything was so closethis is a great location close to everythingthe location was great so close to everything one could needclose to beach and attractions
5. Swanky penthouse with epic views, Ocean City (from USD 143)
This swanky penthouse is located in the popular Ocean City and offers spectacular views from its private balcony. Besides the epic views from its balcony and bedrooms, the property also comes with a rooftop outdoor pool, sun deck, putting green, fitness centre and a sauna. Prepare to be pampered as you take a dip in the pool, then head over to the sauna for a steam bath and finish off with a great workout at the fitness centre. This home is also conveniently located on the well-known Boardwalk at Ocean City.
Top guest reviews
Amenities & Room:
the view was amazing beautiful sunset sparkling clean and comfortableCleanliness:
this was a very comfortable clean and spacious rentalthe space is beautiful clean and in a great locationthe whole place is very clean has a lot of kitchen stuffRead more reviewsLocation:
great location overseeing ocexcellent location very comfortable fireplace very nice for off seasonthis trip was exactly what my family needed and we couldn’t ask for a cleaner better locationbeautifully appointed and in a great location we will return comfy beds and quiet penthouse
6. Quaint cottage amid lush green, Berlin (from USD 250)
This quaint and cosy cottage is perfect for nature lovers as it nestles amidst nature and is a short bike ride away from Assateague Island State and Federal park. Berlin and Ocean City are also located nearby. For outdoor lovers, there is also a swimming pool and dock for your unlimited use. This home offers privacy and yet convenience to various attractions and outdoor activities such as kayaking, paddle boarding, swimming, hiking, bird watching and fishing. Guests can also enjoy stunning views in every direction and watch the wildlife in action as the bald eagles and osprey fish for their dinner.
Top guest reviews
Amenities & Room:
yet you have all the comforts and convenience of the amenities that keep us comfortable and happyonly suggestion would be a small fan for the gazebo in mid-summer for still nightsthe pool was lovely and had a great viewa large cedar deck leads to a nice size poolmy daughter loved the pool and it was quiet and the nature was fantasticCleanliness:
the property was gorgeous and the house itself was super clean and had relaxing personalitythe house itself was clean and comfortable and kate was very responsive as a hostthe kitchen was clean with a fridge dishwasher and coffee suppliesHost:
the host was helpful and responsivekate is quick to respond and a wonderful hostkate was always super responsive to any questionskate was extremely responsive and helpful with questions before during and after our staythe host was very gracious and provided many amenities/tasteful gestures that made us feel welcomeRead more reviewsLocation:
the close proximity to there was awesomesuch a beautiful location with much to offerthe accommodations and location couldn’t be betterthis is a a really classy place very close to assateague island national seashore and state parkthe inside of the house is comfy and the central air is fantastic for the summer heat
7. Peaceful farmhouse with wheelchair access, Princess Anne (from USD 232)
This lovely and peaceful farmhouse allows its guests to interact with the resident horses and chickens though there is no horseback riding opportunity. One can also explore the entire farm, which includes a trail through the woods. There is also a swimming pool where you can take a dip or laze by as you while the day away dreamily. The thoughtful host has made the first level of the house wheelchair accessible by adding ramps from the side door near the driveway and to the pool. The bathroom on the first floor is also wheelchair accessible.
Top guest reviews
Amenities & Room:
it was a wonderful stay at a cozy spacious home filled with neat treasures and nostalgiawe would not hesitate to stay here again - the pool area looked amazing for the warmer monthsthe house was very comfortable and we had everything we neededthe house was a treasure and so very comfortableCleanliness:
you can expect a clean cozy and beautiful experiencethe upstairs where the beds are felt clean and updated and kept cool on the hot daysHost:
the hosts were very pleasant and offered great recommendationsthey were so helpful and hospitabletruly lovely hosts so gratefulhorses and the people were all friendly and welcomingbeautiful setting and great hostsRead more reviewsLocation:
great place away from the noise and hustlefantastic place to spend a relaxing weektracy’s farmhouse was the perfect place for us to get away for the christmas holidayit was cool to be able to see the horses up close and feed them carrotsamazing place very quiet nice pool
8. Modern condo with views of downtown Annapolis, Annapolis (from USD 150)
This modern one-bedroom condo offers guests a lovely view of downtown Annapolis and is located a short walk away from the nearby Naval Academy, restaurants, and shops. Guests also have access to the swimming pool and grilling area where they can laze and chill, while grilling up some burgers and sausages. You can also relax at the spacious covered deck overlooking downtown Annapolis on days when you just wish to do nothing but people watch.
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
9. Gorgeous glamp campervan on Buttonwood Beach, Earleville
Looking for a different kind of accommodation from the usual condo or apartment? Then look no further than this homey trailer set in a private waterfront community RV Resort located on Maryland’s Eastern Shore near Chesapeake City. Buttonwood Beach is slowly becoming one of the premier campgrounds of its kind and offers a unique experience for guests who choose to stay here. A very peaceful and quiet venue, you have access to the trailer and Florida room as well as the over-sized front deck and grounds about the trailer. Additionally, the swimming pool and the beach, of course, are also within your reach.
Earleville, Maryland, United States
69.47 km (43.2 mi) from Annapolis City DockAccommodates: 4
Top guest reviews
Amenities & Room:
i'm especially fond of the deck and the screened in roomthe trailer opens up into a lovely modern well decorated sun roomwe loved the back deck and the park’s pool and beachCleanliness:
very clean and cutethe place was very cleanthe property is clean and comfortableit was exceptionally clean and well stocked with kitchen and bathroom suppliesbarbs place is really nice really cleanHost:
what an wonderful host and great shaded propertybarb was an amazing hostbarb was such an amazing host rapidly fast responses and always geared toward making our experience bettershe responded quickly and was very helpfulbarb was an amazing host and we could not have asked for a better weekend alwayRead more reviewsLocation:
fun location and very family friendlya unique location lovely place to visitcomfortable clean quiet and located a few minutes walk from the resort store this place had everythingwe even took a nice walk along the river on the big sandy beachperfect place to relax unwind and unplug
10. Lovely oceanfront condo with amazing view, Ocean City
Located on the northeastern side of Belmont Towers, this three-bedroom oceanfront condo offers its guests an amazing view from its large balcony. You will be spoiled every day with mesmerising views of sunrise across the ocean, as well as the sunset over the bay area. As if that’s not enough, there is even a rooftop pool, sun deck, putting green, fitness centre and a sauna.
Ocean City, Maryland, United States
141.28 km (87.8 mi) from Annapolis City DockSuperhost
Accommodates: 10
Top guest reviews
Amenities & Room:
great great views from the balcony and the living roomnice balcony by the family room and all three bedroomsthe windows let in plenty of natural light and each room has access to the patiogreat views i traveled with my kids and the jack and jill bathroom was excellentthe fires were outstanding and there was enough room to spread outCleanliness:
extremely clean cozy and welcomingevery surface was sparkling cleanthe unit was clean spacious and very comfortableeverything was clean and sanitized when we arrivedthe place was very clean and we felt very comfortable hereHost:
hosts responsive to questionsthey are indeed super hostawesome place and amazing hostour hosts were super responsive and clearly communicated with us throughout our staythe hosts were extremely responsive and friendlyRead more reviewsLocation:
best location on the boardwalkexcellent location and very spacious unitwonderful place great location right on the boardwalklocation location location great condo with beautiful viewswonderful location right on the boardwalk prefect for a girls weekend
11. Rustic home overlooking the Potomac River, Fort Washington
This cosy and rustic home that overlooks the Potomac River is perfect for guests looking to escape the hustle and bustle of city life. This three-bedroom house is just a short drive from Washington and comes with access to a private pool and hot tub. This pet-friendly property also has a large backyard with a swing making it perfect for large families or friends with fur kids. There are also outdoor activities here such as kayaking or a stroll or run along the waterfront.
Fort Washington, Maryland, United States
55.0 km (34.2 mi) from Annapolis City DockTop guest reviews
Amenities & Room:
the heated pool was amazinghad an issue with the air conditioning and manager was very responsivethis is a really unique property with unbelievable views and nice poola very nice pool and amenities within a 10 min drive if you need somethingthe house was clean the pool was amazing and the views over the potomac were unbeatableCleanliness:
but other than that this place was charming the beds/bedding was super clean and comfythe wall is now covered in mold in the picture it is clean and whitein general the house was cleanbedrooms beds and bathrooms were cleanit is an old house( which i liked about it) but cleanHost:
hosts were very responsive to address any questions or issuesthe host and the house were both greatrob was a great host everything was straight forward nice size house for a group of family and friendsRead more reviewsLocation:
the location was also greatthe location is what makes this place amazing it was very close to dcsuch a beautiful location the sunset on the water was perfectionamazing location and outside space with a poolwe will definitely choose this place again for future get-away weekends
Let Maryland wash your stress away
Feeling drained and stressed from the daily hustle and bustle of city life? It’s time to take a break from adulting and recharge your batteries. There is no better place for a vacation than in Maryland, USA, where you can enjoy the great outdoors and the sandy beaches. You can also take a waterfall hike as part of your weekend trip with your loved ones. Go ahead and choose your favourite rental and look forward to a memorable getaway.
Frequently asked questions about the best Airbnbs with pool in Maryland, USA
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