10 Best Airbnbs With Pool In Maryland, USA - Updated 2023

| 5 min read

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.

1. Private beach house with awesome view (from USD 162)

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.

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Ocean City, Maryland, United States
137.8 km (85.7 mi) from Annapolis City Dock
198 reviews   Superhost Wifi Available
ENTIRE HOME 7 Beds 10 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
very comfortable huge tv fast internet great beds all the amenities you could need and fantastic location
very peaceful neighborhood and beautiful scenery to read and have breakfast on the deck
from the deck to kayaking to just being cozy and clean
the home was comfortable and the deck was lovely
the well-stocked kitchen is so large and open that 3 cooks can move freely
it was very clean which is always a concern of mine when using airbnb
the madmen house was very clean when we arrived and beautifully decorated
rebecca's house was clean convenient and cozy
very clean relaxing space right on the water
it was very clean an easy walk to the ocean and in a quiet neighborhood
excellent hospitality from the host rebecca
the cramer’s are wonderful hosts
the host is caring responsible and flexible
she is a responsive host available within minutes via text or call
the owner makes sure that you are comfortable and cared for
great location beautiful home
the location was fabulous — everything was so close
this is a great location close to everything
the location was great so close to everything one could need
close to beach and attractions
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2. Quaint cottage amid lush green (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.

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Berlin, Maryland, United States
140.95 km (87.6 mi) from Annapolis City Dock
82 reviews   Superhost Wifi Available
Entire cottage 3 Beds 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
yet you have all the comforts and convenience of the amenities that keep us comfortable and happy
only suggestion would be a small fan for the gazebo in mid-summer for still nights
the pool was lovely and had a great view
a large cedar deck leads to a nice size pool
my daughter loved the pool and it was quiet and the nature was fantastic
the property was gorgeous and the house itself was super clean and had relaxing personality
the house itself was clean and comfortable and kate was very responsive as a host
the kitchen was clean with a fridge dishwasher and coffee supplies
the host was helpful and responsive
kate is quick to respond and a wonderful host
kate was always super responsive to any questions
kate was extremely responsive and helpful with questions before during and after our stay
the host was very gracious and provided many amenities/tasteful gestures that made us feel welcome
the close proximity to there was awesome
such a beautiful location with much to offer
the accommodations and location couldn’t be better
this is a a really classy place very close to assateague island national seashore and state park
the inside of the house is comfy and the central air is fantastic for the summer heat
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3. Peaceful farmhouse with wheelchair access (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.

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Princess Anne, Maryland, United States
113.05 km (70.3 mi) from Annapolis City Dock
76 reviews   Superhost Wifi Available
Farm stay 4 Beds 7 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 7

Top guest reviews
Amenities & Room:
it was a wonderful stay at a cozy spacious home filled with neat treasures and nostalgia
we would not hesitate to stay here again - the pool area looked amazing for the warmer months
the house was very comfortable and we had everything we needed
the house was a treasure and so very comfortable
you can expect a clean cozy and beautiful experience
the upstairs where the beds are felt clean and updated and kept cool on the hot days
the hosts were very pleasant and offered great recommendations
they were so helpful and hospitable
truly lovely hosts so grateful
horses and the people were all friendly and welcoming
beautiful setting and great hosts
great place away from the noise and hustle
fantastic place to spend a relaxing week
tracy’s farmhouse was the perfect place for us to get away for the christmas holiday
it was cool to be able to see the horses up close and feed them carrots
amazing place very quiet nice pool
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4. Fabulous residence with panoramic views (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.

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McHenry, Maryland, United States
255.67 km (158.9 mi) from Annapolis City Dock
30 reviews   Superhost Wifi Available
ENTIRE HOME 7 Beds 14 Guests 5 Bedrooms 6 Bathrooms

Accommodates: 14

Top guest reviews
Amenities & Room:
everyone enjoyed the swimming pool and video games as well as the private putt putt course
great home with a fully stocked kitchen and prefect for larger families with children
communication cleanliness amenities large pool fun arcade games spacious rooms
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5. Swanky penthouse with epic views (from USD 172)

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.

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Ocean City, Maryland, United States
141.37 km (87.9 mi) from Annapolis City Dock
116 reviews   Superhost Wifi Available
Entire condo 6 Beds 10 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
the view was amazing beautiful sunset sparkling clean and comfortable
this was a very comfortable clean and spacious rental
the space is beautiful clean and in a great location
the whole place is very clean has a lot of kitchen stuff
great location overseeing oc
excellent location very comfortable fireplace very nice for off season
this trip was exactly what my family needed and we couldn’t ask for a cleaner better location
beautifully appointed and in a great location we will return comfy beds and quiet penthouse
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6. Modern condo with views of downtown 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.

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Annapolis, Maryland, United States
617 meters (0.4 mi) from Annapolis City Dock
197 reviews   Wifi Available
Entire condo 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
close to downtown lovely view from the very large balcony full kitchen if you want to cook
great apartment overlooking spa creek and downtown annapolis
otherwise there is a memory foam pull-out couch and a very comfortable queen bed provided
the apartment looks like the pictures
condo was clean and perfect for all your needs
clean quiet with a great location
jane’s place was very clean and cozy great location right on the water perfect for a couple
great host we had a wonderful weekend
jane is a very helpful host—offered plenty of suggestions for dining & was very quick to respond
the host was very responsive and provided exceptional communication on everything from parking to the nearby restaurants/cafes
jane was one of the most responsive owners we have worked with
the location is perfect
terrific location and fabulous host
we are a new usna family and this location was perfect to walk into town and to the yard
very conveniently located cute condo could easily walk a few minutes into town
excellent space and hospitality walking distance to the downtown area and waterfront
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7. Gorgeous glamp campervan on Buttonwood Beach (from USD 135)

Looking for a different kind of accommodation from the usual condo or apartment? Then look no further than this homely 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.

Stayed at this property?
Earleville, Maryland, United States
69.47 km (43.2 mi) from Annapolis City Dock
56 reviews   Wifi Available
Camper/RV 1 Bed 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
i'm especially fond of the deck and the screened in room
the trailer opens up into a lovely modern well decorated sun room
we loved the back deck and the park’s pool and beach
very clean and cute
the place was very clean
the property is clean and comfortable
it was exceptionally clean and well stocked with kitchen and bathroom supplies
barbs place is really nice really clean
what an wonderful host and great shaded property
barb was an amazing host
barb was such an amazing host rapidly fast responses and always geared toward making our experience better
she responded quickly and was very helpful
barb was an amazing host and we could not have asked for a better weekend alway
fun location and very family friendly
a unique location lovely place to visit
comfortable clean quiet and located a few minutes walk from the resort store this place had everything
we even took a nice walk along the river on the big sandy beach
perfect place to relax unwind and unplug
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8. Rustic home overlooking the Potomac River

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.

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Fort Washington, Maryland, United States
55.0 km (34.2 mi) from Annapolis City Dock
42 reviews  
Entire house 5 Beds 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
the heated pool was amazing
had an issue with the air conditioning and manager was very responsive
this is a really unique property with unbelievable views and nice pool
a very nice pool and amenities within a 10 min drive if you need something
the house was clean the pool was amazing and the views over the potomac were unbeatable
but other than that this place was charming the beds/bedding was super clean and comfy
the wall is now covered in mold in the picture it is clean and white
in general the house was clean
bedrooms beds and bathrooms were clean
it is an old house( which i liked about it) but clean
hosts were very responsive to address any questions or issues
the host and the house were both great
rob was a great host everything was straight forward nice size house for a group of family and friends
the location was also great
the location is what makes this place amazing it was very close to dc
such a beautiful location the sunset on the water was perfection
amazing location and outside space with a pool
we will definitely choose this place again for future get-away weekends
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9. Cosy one-bedroom studio with indoor heated pool (from USD 274)

This cosy one-bedroom studio comes with an 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.

Stayed at this property?
Highland, Maryland, United States
44.94 km (28.0 mi) from Annapolis City Dock
191 reviews   Wifi Available
Entire guest suite 3 Beds 5 Guests 1 Bedroom 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
great place w/ an amazing heated pool
the private pool private patio with grill and tables were awesome
the delicious heated pool was a dream and so relaxing
beautiful space property and pool
the pool was beautiful and did not disappoint
very clean private and cozy
pool is beautiful clean and warm
the guest house was clean and homey
the living space was very clean organized and cozy
pristinely clean and the pool is amazing highly recommend
thank you to our wonderful hosts for a great stay
the hosts were very responsive and welcoming
hosts are incredibly kind and helpful
theresa and her husband were wonderful hosts
theresa and jim were great hosts and very hospitable
the location was beyond beautiful
we loved everything about the this location
the apartment was the perfect location for our needs
location is very close to bwi yet rural and secluded in a beautiful neighborhood
this is a beautiful house and good location
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10. Lovely oceanfront condo with amazing view

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.

Stayed at this property?
Ocean City, Maryland, United States
141.28 km (87.8 mi) from Annapolis City Dock
161 reviews   Superhost Wifi Available
Entire condo 6 Beds 10 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
great great views from the balcony and the living room
nice balcony by the family room and all three bedrooms
the windows let in plenty of natural light and each room has access to the patio
great views i traveled with my kids and the jack and jill bathroom was excellent
the fires were outstanding and there was enough room to spread out
extremely clean cozy and welcoming
every surface was sparkling clean
the unit was clean spacious and very comfortable
everything was clean and sanitized when we arrived
the place was very clean and we felt very comfortable here
hosts responsive to questions
they are indeed super host
awesome place and amazing host
our hosts were super responsive and clearly communicated with us throughout our stay
the hosts were extremely responsive and friendly
best location on the boardwalk
excellent location and very spacious unit
wonderful place great location right on the boardwalk
location location location great condo with beautiful views
wonderful location right on the boardwalk prefect for a girls weekend
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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.

Stayed at this property?
Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Gary Yang started his career as a suit cum copywriter at an advertising agency more than a decade ago, and subsequently honed his Public Relations skills at Asia Pacific Breweries and Singapore...Read more

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