Maryland is a US state located in the Mid-Atlantic region of the country, the area between the northern and southern states along the East Coast. The state has a rich history and was originally inhabited by Native Americans, with Europeans arriving in the area in the 16th century. It was one of the original Thirteen Colonies, and thanks to its location along the Atlantic Ocean, it has many cities that have been seaports for many years. History buffs can visit Fort McHenry National Monument and Historic Shrine, a site that inspired what would become the national anthem. Nature lovers can hike Great Falls, a series of waterfalls. Scroll down for the best vacation rentals with private pool in Maryland, USA.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on February 07, 2024.
1. Peaceful house with a game room and bikes, Cambridge (from USD 330)
This peaceful, three-bedroom house promises a quiet and soothing atmosphere thanks to being located at the quiet end of a cul-de-sac. It has an in-ground pool and a two-person spa for guests to enjoy. The living room has a 50-inch flat-screen TV, Blue-ray player, oversized seating, and large picture windows. There is also a game room that’s furnished with a foosball table, corn hole game, and ping pong table. Four complimentary adult bikes are also included for guests to enjoy.
With that, enjoy a soothing bike ride through the neighborhood as the house is less than 2.1 mi (3.3 km) from Great Marsh Park, Richardson Maritime Museum, Christ Episcopal Church, and Choptank River Lighthouse.
Top guest reviews
Cleanliness:
very clean and organizedit was impeccably clean inside and outteri's property is awesome the house is clean and spacious stocked with everything you needhouse was clean comfortable and well equipped in a lovely spot with a large yard and water accessHost:
overall teri is a great host who is very responsiveit's obvious the owners care about their propertyteri was solicitous responsive and helpfulteri was very responsive and helpfulthe house has everything you need and the owners are super helpfulRead more reviewsLocation:
nice location away from hustle and bustle yet only a short distance to downtown cambridgethis was a perfect place to getaway and relax while teleworking and doing online learningwe're so glad we found this place and we're already looking forward to next year
2. Historic estate home with updated amenities, Lusby (from USD 569)
If you are wondering what it’s like to live in a home with a deep history, this high-end property is worth considering. With a clever mix of preserved artefacts from the past, such as vintage furniture, and state-of-the-art modern features, the rental sets itself apart from other Airbnbs with pools throughout Maryland.
In the riverfront backyard, you’ll spot a seasonal pool that is open from April to October. It stands 4.0 ft (1.2 m) deep and 12.0 ft (3.6 m) wide with a length of 60.0 ft (18.2 m). The pool can even be heated during the colder months of September and October. Surrounding it is a spacious lawned field, where you can find other eye-catching amenities such as a fire pit and garden.
You can even access a private beach here. All of these amenities belong in a private 16.0-ac (6.4-ha) property, offering you extra exclusivity.
Top guest reviews
Amenities & Room:
oh that pool heated and beautiful all an added bonusrousby hall is a beautiful well curated home with breathtaking water views and a refreshing poolthe house is comfortable and the setting breathtakingCleanliness:
the house was spotless clean and very well equippedthe house was very cleanthe home is spotless and very well maintainedHost:
our hosts were so welcominghost was amazingly responsivethe host was incredibly responsive and helpfulwe held a leadership staff retreat and it was perfectthis property is gorgeous and the hosts are lovelyRead more reviewsLocation:
perfect location perfect hostit's really a special placetruly a perfect location where you could spend the whole day at home or explore southern mdbeautiful location clean house nice kitchen and plenty of cozy places to sit and relax
3. Lively guest cottage with marvellous creekside views, Chester (from USD 499)
This Airbnb vacation rental in Maryland sits near the banks of Cox Creek in the quaint and quiet Chester. Its waterfront location results in views worth savouring every minute of your stay, best appreciated while sitting on the dock or chilling by the pool.
Speaking of the pool, guests can take advantage of the property’s renovated built-in swimming pool, especially during hot, sunny days. Furthermore, the private pool has a sun ledge, perfect for those looking to bask in the sun. The guest house also features other wellness facilities, including a fully stacked fitness area. And as the night rolls over, guests can sleep soundly in any of its two bedrooms, plus the sofa bed in the living area.
Top guest reviews
Amenities & Room:
the pool and the dock provide gorgeous views and sunsetsthe property is stunning- the pool the yard the waterfront views and dockdiane’s home was immaculate and comfortableCleanliness:
the place is comfortable clean and well locatedher guest house is beyond beautiful and incredibly cleanmy family had a great time spending five days in this peaceful clean and tastefully decorated waterfront spaceHost:
host was very nice and helpfuldiane and john were amazing hosts so kind and welcoming throughoutwe had a great time staying at diane's place the host was an exceptionally responsive hostbeautiful guest home in a stunning location diane was a great host a proactive communicator and very accomodatingdiane and her husband were very responsive to all questions and very helpful throughout the stayRead more reviewsLocation:
the location is ideal for visiting annapolis and then sti would recommend this location over and over againawesome location and amenitiesbeautiful location comfortable accommodations and a gracious hostthe location is gorgeous and everything is beautiful diane is super nice and easy to communicate with
4. Cottage on a creek, Wittman (from USD 225)
A nature-filled vacation awaits any guest in this two-bedroom cottage on a creek. Located along the Chesapeake Bay, the cottage features a large dock where guests can send off their kayaks, which are provided by the owners, to explore the bay. The cabin’s living area features a recliner, cable TV, VCR player, video collection, dining area, two sofas, and a modern kitchen. There is also a private swimming pool for guests who want to cool off.
As for nearby places to visit, the cabin is only 3.5 mi (5.6 km) from St. Michaels Winery, 3.6 mi (5.7 km) from Chesapeake Bay Maritime Museum, and 5.4 mi (8.6 km) from Phillips Wharf Environmental Center.
5. Luxurious estate with modern amenities, Ocean City (from USD 231)
This large estate boasts 5 bedrooms and 4.5 bathrooms, accommodating up to 16 guests. There’s a spacious kitchen with everything needed to make your favourite meals such as an oven, stove, and dishes and a living room with plenty of space to relax. The master bedroom is a cosy space to get a good night’s rest, with its own fireplace and a jetted bathtub.
The mansion rental in oceanfront Maryland features an in-ground pool, perfect for family parties and special events. Beyond the seasonal facility, you’ll also find beautifully manicured lawns surrounding the rental, a patio, and a fire pit. You can get competitive on the basketball court, if that fancies you.
6. Riverside luxury home with indoor swimming pool, Earleville (from USD 4000)
This home has six bedrooms and six bathrooms, making it an excellent option for a large family gathering. It boasts a spacious well-equipped gourmet kitchen, a cosy living room with a fireplace, and a game room. The indoor pool can allow you to have a relaxing swim. There are large windows, so you can enjoy some gorgeous views. The accommodation also features a hot tub and a poolside bar. On top of that, the home sits on the banks of a river and has a lovely outdoor space with seating areas and a fire pit.
7. One-bedroom hideaway with free parking, White Hall (from USD 145)
This chalet located in a wooded area can be the perfect hideaway for three guests. Surrounded by trees and hiking trails, this home can surely delight outdoor enthusiasts. Inside the chalet, you can find a kitchen stocked with cooking basics. The living room has a TV and a selection of DVDs, so you can sit on the comfortable furniture while you watch a good movie. There is a king-sized bed with a memory foam mattress. The chalet even has its own arcade, so prepare to get competitive at the pinball machines. Plus, there is a pool located on site, so if you feel like taking a dip, you can head into the cool, blue waters.
Top guest reviews
Amenities & Room:
was a big fan of the midcentury modern decorwe especially appreciated the hand sanitzer clorox wipes and new unopened kitchen spongeliving room has a great set up for movie watching and catching sunsetsCleanliness:
excellent hosts super informative and helpful the space was clean and beautiful plus the goats are so cuteHost:
thank you for being such great hostsmia was also a great host - very attentive and kindthe owners were super nice and helpfuland our hosts were positively wonderfulmia and her husband were so kindRead more reviewsLocation:
close to the trails and easy to findit is at a perfect location which you can walk to ncr trail entrance just under 2 minutesbeautiful place we loved the location the goats and the pinballmia and geoff are the nicest hosts we loved the location and the goats will be backnot to mention the pinball machines this place is an unbelievable value for what mia and geoff offer
8. Cosy studio on a working farm, Highland
This studio apartment is nice and cosy and is perfect for five guests. There is a living room area with a TV where you can unwind, a comfortable bed to sleep in, and a fully equipped kitchen. The studio is decorated in neutrals with pops of artistic, colourful flair, providing a calming yet unique environment. During your stay, you can have access to the indoor pool, which is open all year round, so you can have a relaxing swim. The apartment is situated on a working farm, so you might be able to see horses wandering around.
49.6 km (30.9 mi) from Sandy Point State ParkAccommodates: 5
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Amenities & Room:
the pool is beautiful and there were many thoughtful amenities in the houseCleanliness:
very clean had everything we neededi had a lovely stay in an elegantly decorated large and very clean roomHost:
the hosts were very kind and helpfulthe owners were respectful and available as neededthe property was perfect the owners were so helpful and accommodatingowners were very responsive had very clear instructionsthis is a scenically beautiful place to stay the owners are more than accommodatingRead more reviewsLocation:
great location if you are needing to stay near olneyquiet comfortable homey and conveniently locatedwe went to both dc and gettysburg great central location
9. Bright and airy waterfront home for eight, Saint Michaels (from USD 582)
This large home can fit up to eight guests comfortably. It gets lots of natural light and has been wonderfully decorated with a mix of contemporary items and unique vintage finds. There are five spacious bedrooms and three modern bathrooms. The kitchen has an oven and a coffee maker, and the living room features a cosy fireplace and plenty of seats. Here, you can enjoy your own private pool and lovely views of the creek. There is even a swing set for the kids to play.
Top guest reviews
Amenities & Room:
the pool deck area and backyard were incredible with awesome waterfront viewscomfortably fit two families with room to sparethe dining area and kitchen is great and has wonderful views to enjoy your mealsanother favorite space of ours was the “game room” as we called it all weekendthe house is very comfortable with an open feel and lots of lightCleanliness:
it was sparking clean which was appreciated during the covid pandemicthe inside was sparkling clean and tastefully decoratedthe house was very clean and stocked with everything you needplenty of room clean and great locationcompletely secluded property with tons of room sparkling clean and very comfortableHost:
our hosts were friendly helpful and very responsive any time we communicatedgreat kid friendly land with pool and playgroundthe owner marissa is very attentive understanding and kindmichael's and a responsive and attentive host made for an awesome vacation for the familygreat house/great locationwe loved this property first off the homeowners were very hospitable peopleRead more reviewsLocation:
it is an ideal location and has a huge usable yardgreat house so close to the town of st michaelsit's great to be so close to the heart of sta great place to get awaymarissa’s place is absolutely beautiful and in a perfect location
10. Charming house for two, Monrovia (from USD 120)
This charming pool house is perfect for a couple or a solo traveller. The pool house itself is set up like a studio apartment and features wooden walls and unique furnishings that give it a rustic-cabin vibe. It has a full kitchen, a sofa bed, and a private bathroom. Just a few steps from the front door is the pool, which you can have exclusive access to during your stay. The pool area includes a patio and a bar area, so you can enjoy your meals outdoors and enjoy a drink while watching the sunset. The outdoor area is gorgeous, with plenty of greenery and cosy lighting.
Top guest reviews
Amenities & Room:
nice pool nice grill great security well lit comfy great smelling wood cabin interiorthe pool is amazing surrounded by a beautiful garden and an impressive outdoor kitchenwe loved the pool and outdoor spacethe pool and the entire outdoor area is gorgeousvery neat and cozy room and the pool was amazingCleanliness:
magical place so clean and quietthe place was clean and private and quietguest house was clean and stylish with everything you would needthe poolside guest house is sparkly clean and cozy with stunning design and detailsthe place was beautiful spotless and the small thoughtful touches included put it over the topHost:
andrea was a fantastic hostandrea was a lovely hostandrea was a great host and made us feel very welcomeandrea was an excellent host and very informativesuper cozy place and great hostRead more reviewsLocation:
there are local store near by and amazing food places that andrea suggestedwe would definitely recommend this place and would love to come back againgreat place don’t hesitate just book if you want a relaxing place to stay
11. Roomy home with a hot tub, Swanton (from USD 493)
Able to fit up to 14 guests, this spacious guest house rental in Swanton, Maryland, comes with an indoor pool, fully enclosed to provide maximum privacy whilst taking a dip. You can also relax in the hot tub outdoors.
There are a lake and a fishing pond nearby, so you enjoy kayaking or fishing. You can even have free access to a tennis course and golf club. The place has a gourmet kitchen where you can cook your delicious family meals, and the living room has a flat-screen TV if you want to enjoy some of your favourite afternoon shows.
Top guest reviews
Amenities & Room:
the pool and patio/hottub/firepit and very unique features and my kids loved themwifi was great which was crucial due to lack of phone signal in the areathe pool and hot tub were amazing although the alarm was annoying it is definitely necessarythe pool alarm can be annoying but once you understand why/how it works it isn't so bada great house - spacious well equipped and with excellent facilitiesCleanliness:
very clean house with a great backyard and plenty of spaceclean spacious and everything you want from avery clean well equipped kitchen with all that you would needbeautifully designed supper clean and awesome locationthe house was beautiful clean spacious and had great amenitiesHost:
the host was terrific as wellmatti is the greatest host evergreat host this place was wonderful for my familythe assistant was very helpful and i had an awesome birthday experienceRead more reviewsLocation:
the location was quiet and beautifulfantastic place to get away for a long holiday weekendappreciated the location-close to tennis courts mini golf and golf coursegreat house great free golf great location will stay again i hopematti’s house was the perfect place for our family get together
12. Large home on beautiful grounds, Chestertown
This beautiful home is surrounded by plenty of trees, and there’s even a large pond with a fountain. The home features a wrap-around balcony, an outdoor hot tub, and a living room with large windows. It has five cosy bedrooms that can sleep up to ten guests. There are two kitchens and a living room with a fireplace. One of the best aspects of this home is the indoor spa. You can enjoy a workout and soak in the jetted tub afterwards. You can also take a dip in the indoor pool.
31.73 km (19.8 mi) from Sandy Point State ParkTop guest reviews
Amenities & Room:
the views were amazing the beds were comfortable and there were many complimentary itemsbest equipped kitchen ever and most luxurious furnishingsCleanliness:
the property was clean and well maintainedthe house is immaculate like nothing i have ever seen beforeRead more reviewsHost:
john was an amazing host and gave very helpful recommendations on local restaurantsowners and managers were great to work withthe house is one of a kind and exceeds the pictures (a rarity on vrbo)john was accessible and provider a great rundown of helpful information about the house
13. Secluded home with a fire pit, Queenstown
If you’re looking to get away from the city, this secluded home might be an excellent option. There’s plenty of greenery and foliage surrounding the place, providing a calming atmosphere. There’s even a pond with a private dock, where you can enjoy a good book. The home has 4 bedrooms and space to sleep up to 14 guests. There’s a kitchen to cook your own meals and a living room to unwind in. You can go for a swim in the in-ground pool or heat up a barbecue on the grill.
Queenstown, Maryland, United States
22.28 km (13.9 mi) from Sandy Point State ParkTop guest reviews
Amenities & Room:
the pool is amazing and you are surrounded by naturepool was great (where most of our time was spent)we had an amazing stay at leslie’s home we loved the poolCleanliness:
lovely clean and spacious houseHost:
wonderful host and a great place to stayleslie was also an amazing hostleslie was a fantastic host and was very responsiveleslie was a great host with excellent communication and caringone thing to note: this is a kid and pet friendly accommodationRead more reviewsLocation:
awesome location central to everythinghouse in a great convenient locationthe house is in an amazing locationa great location and a great outdoor spacecalm and quiet property very close to the outlets
14. Waterfront home for eight, Bozman
This waterfront home can offer gorgeous views. It has an in-ground pool where you can have a relaxing swim, and the creek in front can allow you to enjoy kayaking and fishing. There are four bedrooms and three bathrooms, providing plenty of space for the guests. The kitchen has everything needed to make your own meals such as a stove and microwave. There is also a screened porch and a bay room where you can unwind and take in the views.
33.04 km (20.6 mi) from Sandy Point State ParkAccommodates: 8
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Amenities & Room:
the screened-in porch was especially nice with comfortable seating for our family to enjoy the spectacular sunsetsturns out the pool gets full sun until about 4pm and the water is the perfect temperatureCleanliness:
clean big very nice housethe house was very spacious clean and well stockedthe house was very clean and exceeded our expectationsit is also clean (and uncluttered) and temperature control in the house is also goodHost:
owners are the best and so understandingthe house was very clean and the owner was so wonderful and accommodatingRead more reviewsLocation:
it's a great place to enjoy the summer dayswe rented sandy pines which turned out to be a wonderful well stocked house in a perfect locationour third trip to sandy pines the house is very spacious nice location and lovely grounds
Have a relaxing stay in Maryland
Maryland offers majestic views and plenty of interesting tourist attractions, ranging from mainland monuments to its countless bayfront marinas and beaches. Each vacation rental with a private pool is worth checking out, so make sure to book from any of them to enjoy a relaxing vacation with your loved ones.
Frequently asked questions about the best vacation rentals with private pool in Maryland
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