11 Best Vacation Rentals With Private Pool In Maryland, USA - Updated 2023


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.

1. Peaceful house with a game room and bikes (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.

Peaceful Cambridge Home on Jenkins Creek
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
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
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
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

2. Cottage on a creek (from USD 199)

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.

Newly available rental: Relaxing Waterfront Cottage Near St Michaels, Maryland
133 reviews  Wifi Available
cottage 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
the views were spectacular and the cottage was comfortable with everything we needed
the house is bright and spacious with water views from almost every room
the beds were firm (not pillow-top mattresses) and comfortable for us
big windows ensure water views from the front bedroom and living room
the rain shower and the jetted tub in the master bathroom were fabulous
house well equipped and clean thank you
bright colorful comfortable thought of everything and immaculately clean
it felt like a new home inside and was spotless
the home was very clean and well equipped
great location very quiet yet close to st michael’s for restaurants and shopping
amazing location across from river/dock
the location is convenient to tilghman island and saint michael's and a perfect place for riding bikes
great location only few miles outside of terrific restaurants and shops of st
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3. Luxurious estate with modern amenities (from USD 314)

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. It also has beautifully manicured lawns, a patio, and a fire pit. You can get competitive on the basketball court or take a dip in the large pool.

Expansive estate with pool, hot tub, basketball court, & wet bar
Ocean City, MD, US
47 reviews
estate 16 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 16
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
only smart tv was in the kitchen
i liked the spacious rooms and everything except there were alot of fixing in the house needed
replace all tvs with smart tvs
this place was amazing everything was working well pool was nice and clean
cleaned it to near perfection so we and subsequent quests may enjoy
house & location is outstanding pure privacy
very fun for children nice and big house quiet neighborhood
Read more reviews

4. Riverside luxury home with indoor swimming pool (from USD 1573)

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.

Come enjoy our luxurious 10,000 sq
7 reviews  Wifi Available
House 16 Guests 7 Bedrooms 6 Bathrooms

Accommodates: 16
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
it was enormous and the views from every room were just stunning
pool was chilly but adjacent hot tub was magnificent especially the view from the hot tub
the large estate is everything as described with comfortable accommodations in every room
spacious and secluded with a terrific game room indoor pool and kayaks
house was clean and comfortably furnished
liz and amos were wonderful hosts thank you
the hosts were available for questions which was wonderful
so painless we had some questions and the owner was incredibly helpful and available
amos and liz were extremely responsive to communications and are terrific hosts
the views are wonderful and the property manager along with the owner’s are great to work with
great isolated private location with incredible views
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5. One-bedroom hideaway with free parking

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.

Secret Pinball Hideaway by the Gunpowder / NCR
White Hall, Maryland, United States
118 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
excellent hosts super informative and helpful the space was clean and beautiful plus the goats are so cute
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
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

6. Cosy studio on a working farm (from USD 181)

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.

DC, Heated indoor pool in winter. Horse farm 1st floor main level
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
very clean had everything we needed
i had a lovely stay in an elegantly decorated large and very clean room
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
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

7. Bright and airy waterfront home for eight (from USD 679)

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.

Saint Michaels, Maryland, United States
83 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
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
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
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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8. Charming house for two

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.

Poolside Paradise in Monrovia, Maryland.
Monrovia, Maryland, United States
92 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
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
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
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

9. Roomy home with a hot tub (from USD 1455)

This spacious home has room for up to 14 guests. You can take a dip in the indoor pool or relax in the hot tub. 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.

Home in Swanton · ★4.64 · 5 bedrooms · 8 beds · 5 baths
Swanton, Maryland, United States
95 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
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
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
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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10. Secluded home with a fire pit

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.

Private home, sleeps 14, pool, hot tub & fire pit!
Queenstown, Maryland, United States
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
lovely clean and spacious house
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
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
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11. Waterfront home for eight

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.

'Sandy Pines' 4BDRM en Harris Creek con piscina, muelle, tablas de paddle, kayaks, Sunfish
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
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
owners are the best and so understanding
the house was very clean and the owner was so wonderful and accommodating
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

Have a relaxing stay in Maryland

Maryland offers majestic views and plenty of interesting tourist attractions. Book one of the best vacation rentals with private pool in Maryland, USA, and enjoy a relaxing vacation with your loved ones.

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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