14 Best Vacation Rentals With Private Pool In Maryland, USA - Updated 2024

Nicole
Nicole 
Updated
| 5 min read

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.

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55.57 km (34.6 mi) from Sandy Point State Park
186 reviews   Wifi Available
House 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Cleanliness:
very clean and organized
it was impeccably clean inside and out
teri's property is awesome the house is clean and spacious stocked with everything you need
house was clean comfortable and well equipped in a lovely spot with a large yard and water access
Host:
overall teri is a great host who is very responsive
it's obvious the owners care about their property
teri was solicitous responsive and helpful
teri was very responsive and helpful
the house has everything you need and the owners are super helpful
Location:
nice location away from hustle and bustle yet only a short distance to downtown cambridge
this was a perfect place to getaway and relax while teleworking and doing online learning
we're so glad we found this place and we're already looking forward to next year
Read more reviews
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Cambridge, Maryland, United States
55.57 km (34.6 mi) from Sandy Point State Park
PRIVATE VACATION HOME 6 Guests 3 Bedrooms 2 Bathrooms

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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.

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Lusby, Maryland, United States
77.2 km (48.0 mi) from Sandy Point State Park
110 reviews   Superhost Wifi Available
ENTIRE HOME 4 Beds 8 Guests 4 Bedrooms 4 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
oh that pool heated and beautiful all an added bonus
rousby hall is a beautiful well curated home with breathtaking water views and a refreshing pool
the house is comfortable and the setting breathtaking
Cleanliness:
the house was spotless clean and very well equipped
the house was very clean
the home is spotless and very well maintained
Host:
our hosts were so welcoming
host was amazingly responsive
the host was incredibly responsive and helpful
we held a leadership staff retreat and it was perfect
this property is gorgeous and the hosts are lovely
Location:
perfect location perfect host
it's really a special place
truly a perfect location where you could spend the whole day at home or explore southern md
beautiful location clean house nice kitchen and plenty of cozy places to sit and relax
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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.

Stayed at this property?
Chester, Maryland, United States
11.43 km (7.1 mi) from Sandy Point State Park
39 reviews   Superhost Wifi Available
Entire guesthouse 6 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
the pool and the dock provide gorgeous views and sunsets
the property is stunning- the pool the yard the waterfront views and dock
diane’s home was immaculate and comfortable
Cleanliness:
the place is comfortable clean and well located
her guest house is beyond beautiful and incredibly clean
my family had a great time spending five days in this peaceful clean and tastefully decorated waterfront space
Host:
host was very nice and helpful
diane and john were amazing hosts so kind and welcoming throughout
we had a great time staying at diane's place the host was an exceptionally responsive host
beautiful guest home in a stunning location diane was a great host a proactive communicator and very accomodating
diane and her husband were very responsive to all questions and very helpful throughout the stay
Location:
the location is ideal for visiting annapolis and then st
i would recommend this location over and over again
awesome location and amenities
beautiful location comfortable accommodations and a gracious host
the location is gorgeous and everything is beautiful diane is super nice and easy to communicate with
Read more reviews

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.

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Wittman, Maryland, United States
27.83 km (17.3 mi) from Sandy Point State Park
cottage 4 Guests 2 Bedrooms 2 Bathrooms

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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.

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Ocean City, Maryland, United States
129.72 km (80.7 mi) from Sandy Point State Park
PRIVATE VACATION HOME 16 Guests 5 Bedrooms 5 Bathrooms

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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.

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Earleville, Maryland, United States
64.94 km (40.4 mi) from Sandy Point State Park
villa 16 Guests 7 Bedrooms 6 Bathrooms

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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.

Stayed at this property?
White Hall, Maryland, United States
68.28 km (42.5 mi) from Sandy Point State Park
133 reviews   Superhost Wifi Available
Entire chalet 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
was a big fan of the midcentury modern decor
we especially appreciated the hand sanitzer clorox wipes and new unopened kitchen sponge
living room has a great set up for movie watching and catching sunsets
Cleanliness:
excellent hosts super informative and helpful the space was clean and beautiful plus the goats are so cute
Host:
thank you for being such great hosts
mia was also a great host - very attentive and kind
the owners were super nice and helpful
and our hosts were positively wonderful
mia and her husband were so kind
Location:
close to the trails and easy to find
it is at a perfect location which you can walk to ncr trail entrance just under 2 minutes
beautiful place we loved the location the goats and the pinball
mia and geoff are the nicest hosts we loved the location and the goats will be back
not to mention the pinball machines this place is an unbelievable value for what mia and geoff offer
Read more reviews

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.

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49.6 km (30.9 mi) from Sandy Point State Park
74 reviews   Wifi Available
farmhouse 5 Guests 0 Bedrooms 1 Bathroom

Accommodates: 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 house
Cleanliness:
very clean had everything we needed
i had a lovely stay in an elegantly decorated large and very clean room
Host:
the hosts were very kind and helpful
the owners were respectful and available as needed
the property was perfect the owners were so helpful and accommodating
owners were very responsive had very clear instructions
this is a scenically beautiful place to stay the owners are more than accommodating
Location:
great location if you are needing to stay near olney
quiet comfortable homey and conveniently located
we went to both dc and gettysburg great central location
Read more reviews
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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.

Stayed at this property?
Saint Michaels, Maryland, United States
32.67 km (20.3 mi) from Sandy Point State Park
93 reviews   Superhost Wifi Available
Entire cabin 11 Beds 8 Guests 5 Bedrooms 3 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
the pool deck area and backyard were incredible with awesome waterfront views
comfortably fit two families with room to spare
the dining area and kitchen is great and has wonderful views to enjoy your meals
another favorite space of ours was the “game room” as we called it all weekend
the house is very comfortable with an open feel and lots of light
Cleanliness:
it was sparking clean which was appreciated during the covid pandemic
the inside was sparkling clean and tastefully decorated
the house was very clean and stocked with everything you need
plenty of room clean and great location
completely secluded property with tons of room sparkling clean and very comfortable
Host:
our hosts were friendly helpful and very responsive any time we communicated
great kid friendly land with pool and playground
the owner marissa is very attentive understanding and kind
michael's and a responsive and attentive host made for an awesome vacation for the family
great house/great locationwe loved this property first off the homeowners were very hospitable people
Location:
it is an ideal location and has a huge usable yard
great house so close to the town of st michaels
it's great to be so close to the heart of st
a great place to get away
marissa’s place is absolutely beautiful and in a perfect location
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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.

Stayed at this property?
Monrovia, Maryland, United States
79.59 km (49.5 mi) from Sandy Point State Park
110 reviews   Superhost Wifi Available
Entire guesthouse 1 Bed 2 Guests 0 Bedrooms 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
nice pool nice grill great security well lit comfy great smelling wood cabin interior
the pool is amazing surrounded by a beautiful garden and an impressive outdoor kitchen
we loved the pool and outdoor space
the pool and the entire outdoor area is gorgeous
very neat and cozy room and the pool was amazing
Cleanliness:
magical place so clean and quiet
the place was clean and private and quiet
guest house was clean and stylish with everything you would need
the poolside guest house is sparkly clean and cozy with stunning design and details
the place was beautiful spotless and the small thoughtful touches included put it over the top
Host:
andrea was a fantastic host
andrea was a lovely host
andrea was a great host and made us feel very welcome
andrea was an excellent host and very informative
super cozy place and great host
Location:
there are local store near by and amazing food places that andrea suggested
we would definitely recommend this place and would love to come back again
great place don’t hesitate just book if you want a relaxing place to stay
Read more reviews

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.

Stayed at this property?
Swanton, Maryland, United States
253.08 km (157.3 mi) from Sandy Point State Park
99 reviews   Wifi Available
ENTIRE HOME 8 Beds 12 Guests 5 Bedrooms 5 Bathrooms

Accommodates: 12

Top guest reviews
Amenities & Room:
the pool and patio/hottub/firepit and very unique features and my kids loved them
wifi was great which was crucial due to lack of phone signal in the area
the pool and hot tub were amazing although the alarm was annoying it is definitely necessary
the pool alarm can be annoying but once you understand why/how it works it isn't so bad
a great house - spacious well equipped and with excellent facilities
Cleanliness:
very clean house with a great backyard and plenty of space
clean spacious and everything you want from a
very clean well equipped kitchen with all that you would need
beautifully designed supper clean and awesome location
the house was beautiful clean spacious and had great amenities
Host:
the host was terrific as well
matti is the greatest host ever
great host this place was wonderful for my family
the assistant was very helpful and i had an awesome birthday experience
Location:
the location was quiet and beautiful
fantastic place to get away for a long holiday weekend
appreciated the location-close to tennis courts mini golf and golf course
great house great free golf great location will stay again i hope
matti’s house was the perfect place for our family get together
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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.

Stayed at this property?

31.73 km (19.8 mi) from Sandy Point State Park
89 reviews  
estate 10 Guests 5 Bedrooms 5 Bathrooms
Top guest reviews
Amenities & Room:
the views were amazing the beds were comfortable and there were many complimentary items
best equipped kitchen ever and most luxurious furnishings
Cleanliness:
the property was clean and well maintained
the house is immaculate like nothing i have ever seen before
Host:
john was an amazing host and gave very helpful recommendations on local restaurants
owners and managers were great to work with
the 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
Read more reviews
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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.

Stayed at this property?
Queenstown, Maryland, United States
22.28 km (13.9 mi) from Sandy Point State Park
47 reviews  
Entire house 8 Beds 4 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
the pool is amazing and you are surrounded by nature
pool was great (where most of our time was spent)
we had an amazing stay at leslie’s home we loved the pool
Cleanliness:
lovely clean and spacious house
Host:
wonderful host and a great place to stay
leslie was also an amazing host
leslie was a fantastic host and was very responsive
leslie was a great host with excellent communication and caring
one thing to note: this is a kid and pet friendly accommodation
Location:
awesome location central to everything
house in a great convenient location
the house is in an amazing location
a great location and a great outdoor space
calm and quiet property very close to the outlets
Read more reviews

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.

Stayed at this property?

33.04 km (20.6 mi) from Sandy Point State Park
93 reviews   Wifi Available
House 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 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 sunsets
turns out the pool gets full sun until about 4pm and the water is the perfect temperature
Cleanliness:
clean big very nice house
the house was very spacious clean and well stocked
the house was very clean and exceeded our expectations
it is also clean (and uncluttered) and temperature control in the house is also good
Host:
owners are the best and so understanding
the house was very clean and the owner was so wonderful and accommodating
Location:
it's a great place to enjoy the summer days
we rented sandy pines which turned out to be a wonderful well stocked house in a perfect location
our third trip to sandy pines the house is very spacious nice location and lovely grounds
Read more reviews
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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.

Stayed at this property?

Frequently asked questions about the best vacation rentals with private pool in Maryland


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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Nicole is an American expat living in London, England. When she moved from the midwest to London in 2012, it was her first time leaving the US. She has traveled steadily since then, making trips...Read more

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