
House holiday rentals in St. Mary's County
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Top-rated house rentals in St. Mary's County
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Popular amenities for house rentals in St. Mary's County
House rentals with a pool

Waterfront Paradise with a Private Pool
Such an amazing place! Joanne was super responsive and flexible. The views were unmatched! Perfect Mommy and Daddy getaway and we will certainly be back with the kids!

Game-Themed Water Fun! Boats+Pool+Beach+King Bed
Absolutely beautiful stay! The cabin has the cutest theme and the proximity to the water was great and a gorgeous view. Abby and family was so kind, responsive, and great hosts. Would highly recommend this getaway!

Heron Harbor
All I can say is WOW! We were blown away at the beauty of the home AND the view! Relaxing and peaceful. The pool was to die for and Kathleen was one of the best hosts I’ve ever had in all our air bnb travel!!! Will definitely return AND will check out her other properties in the future. Thank you to Kathleen and her staff/team!!

Waterfront Gem: Dock, Hot Tub, Beach, Pool, Kayaks
Andrea was so responsive from day 1 when I had questions about the house! We had 10 people in town for a wedding and her house was only 3 miles from the venue which was ideal! The house was clean and had nice little extra touches; the bottom floor was surprisingly spacious and perfect for hanging out! And the hot tub was a nice add also! Overall, it was a great experience!

Spacious and private waterfront, sleeps 10
The location for this house is beautiful! We loved the private dock and spacious backyard. We stayed in late March so it was a bit cold some days but we still had a great time using the provided Kayaks and sitting on the dock and watching the beautiful surroundings. The location was perfect to have some s'mores nights around the firepit. The hosts were VERY responsive. The few times I had questions they replied within minutes and were very accomodating with our requests. They were very proactive with instructions and generously mentioned a foldable crib for the infant in our group - although we had our own that we used. The kitchen had all of the dinnerware and cookware that we needed for the meals that we made. The living areas were open and inviting. It was perfect for our group. One thing to watch for is the very steep driveway. It took a few times to get used to. We would definitely stay there again when we visit our family in the area.

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit
Our family had such a great time staying at MJ's place last year that we came back again this summer. As before, we all loved the view, pool, firepit, grilling on the deck, and walking down to the neighborhood beach. The house was very clean and the kitchen was well-stocked. All the beds were comfortable, and all bedrooms had well-functioning blinds/shades, which is really helpful when putting younger kids to bed. The lower level bathroom had been renovated since our last stay which was a great bonus. We are looking forward to returning next summer!

Family Friendly: Hot Tub, Grill, Pool & More!
This was one of the most well equipped houses I have ever stayed in. The hosts were very easy to communicate with and responded quickly to each contact. I highly recommend this place!!

The River House
We spent some wonderful days in this house, it's spacious, beautiful and clean. We enjoyed the kayaks, paddle boards, jacuzzi, and the spectacular views of the river. Frank is an excellent host, very responsive. We definitely recommend this house for a relaxing and fun stay.
Weekly house rentals

Enjoy the Sunset at Nomini Bay
This is our 2nd time being here and we were not disappointed! This house has a beautiful view. Pooja is a wonderful host. We were welcome with a basket of snacks. Kitchen and bathroom are fully stocked. Pooja provided more than enough for our stay and we had everything we need. House is clean and beds are comfortable. My family had a great time fishing and kayaking. Thanks Pooja for your hospitality!

200 Year-Old Waterfront Home only 1.5 hours fromDC
This was a great place to stay for a girl's weekend. We each had plenty of space, beds and bathrooms. The pictures don't quite do this place justice. The views of the water are so peaceful. We enjoyed the screened porch for coffee and happy hour. The kitchen is fully stocked and the decor and furnishings are just so cute! Leonardtown is a short drive for boutique shopping and cute cafes. There wasn't really a great place to swim and lounge by the water, but we still really enjoyed our stay. Would highly recommend!!

Beautiful, serene waterfront property
An incredible peace of property! This house has been beautifully renovated and exceeded every expectation. Unbelievable waterfront views from nearly every room in the house, back porch and fire pit. Also a very nice surprise of having a little play area stocked with toys for the little ones! This is a must stay if we’re ever back in the area!

Spacious and peaceful w/ private beach & boat ramp
Loved it so much great view and everything!

Waterfront Dock Kayak Fish Firepit Woods Peaceful
We had a wonderful stay at Presley Creek! The house was clean and comfortable. The porch and with the ceiling fans was delightful! The kitchen had everything you’d need for preparing meals. The location was so peaceful. The property was huge and felt so private & secluded with woods and the water. We enjoyed the wildlife; geese, eagles, herons, otters. We brought our dogs, and they loved running and swimming! We brought all our food with us since we knew stores were not close. Also, if you want a beach, we found a little beach not too far called Vir-Mar, which has a very small public beach. Hughlett Point which is a bit farther is larger but very limited parking. If you are looking for a laid back vibe, I highly recommend this property!

Private Beach Oasis, Arcade & Theater
We had an amazing girls weekend! The home was clean, comfortable, and very quiet. We were blown away by how much private beach space there was. There were a good amount of indoor activities to do as well. Hosts were very responsive to texts, would definitely recommend For future guests, especially those with younger children, be careful while in the water/on the beach! The hosts said river shoes are recommended and I agree. There are definitely sharp rocks at some areas and hard shells hidden in the sand. Luckily there was a well stocked first aid kit inside

Waterfront home, private dock
We had a wonderful vacation here. Although it rained during our stay, we found the treehouse to be a great place just for listening the rain drops and having some inner peace.

Bay Front Beach House
We booked this place for a weekend getaway with our little ones. It was absolutely the perfect place for what we were planning! The private beach was PERfECT for young children! the kids loved being able to ride their scooters under the house. We got some fishing in, daughter was a spot master! The hammock was lost in a storm before we arrived, but our superhost made sure we could enjoy a hammock!! upon hearing that it was the top of the list of kids wish list, she took time out of her day and drove all the way and installed a new hammock for us!! Was even so considerate to offer to pick up any needed items. I believe more than the kids, my dog had the time of his life!! They even had doggy bowls ready!! We will definitely be back!! This place is awesome!! Thank you Dana for you gracious hospitality!!
Private house rentals

Soul Oasis - home on the Chesapeake Bay
Peaceful and private spot just a stones throw from the water. We enjoyed our stay and will be booking again next year! Cozy and comfortable oasis in the woods.

Riverside Dreams -golfcart-screened porch-views
cute little place. definitely will be coming back

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.
Jess' place is fantastic! Truly, our favorite AirBnB to date. We will return when we are visiting the area again. We loved how clean, spacious, and peaceful the home is inside and the beautiful spaces to relax and enjoy outside, too. All five of us had space to spend quality time together and on our own throughout our stay. Very thoughtfully furnished, proactive communication, and simple check-in and out! 10/10.

Waterfront Escape!
We had such a nice visit! Ryan was very responsive to questions and requests. The house is very cute and perfect for a family with kids. Lots of toys and games and outdoor equipment - and a fun tree swing! The little sandy area was just right for our three kids (ages 1, 4 and 7). We ate all our meals outside on the deck overlooking the water. The neighbors were very friendly. Everything was great!

Solomons Yellow House - Waterfront
Came to Solomon’s for a wedding . Had a wonderful stay at John’s Place. All the comforts of home. Very clean, Fantastic location- easy walk to restaurant’s, shops, And Mass on Sunday ! Beautful water front property. Lovely decor- excellent kitchen space. Lovely the unique lighting, screened -in porch, and front porch! Very Comfy beds. Would def stay here again!!

Cozy cottage with water access
Great for a group/family weekend getaway. Erin and Aryn are very hospitable hosts and provided all the essentials. Everything in the kitchen and all the light switches are clearly labeled, making it easy to navigate.

Waterfront Home, Spectacular View & Private Beach!
We had a great stay here. Beautiful views of the water. Hosts were quick to respond. Good WiFi. Large deck with teak table and weber grill. Easy walk to water access. The waterfront is the best I’ve seen on the Bay. Sandy with shady and sunny spots against the cliffs. From the water access, you can walk in one direction to the limestone cliffs for shark tooth hunting. The other direction goes all the way to the marina. We hope to stay here again.

Water House at Scotland Beach
In decades of renting beach houses, hotels, seaside resorts, Air BnBs, etc., I don’t ever think I’ve enjoyed a home or location as much as Water House. The setting brought us such joy - the oaks, the river birches, the fig trees, the magnolia, the loblollies, of course Tanner Creek. And your design aesthetic is so welcoming and elevating. Everything about the interior and exterior of the home is wonderful. Thank you for putting such obvious thoughtfulness and care into your home and its landscape. And what a great location near that wonderful state park. This was our first time in St. Mary’s County and I learned so much about its pre-colonial, colonial, revolutionary, 1812 and of course civil war history. It was a real revelation and Water House was the perfect HQ for those explorations. We also encountered wonderful people in the park and the local restaurants. It was just a perfect stay. Thank you!
Destinations to explore
- Family-friendly rentals St. Mary's County
- Rentals with a patio St. Mary's County
- Rentals with lake access St. Mary's County
- Rentals with a washing machine and dryer St. Mary's County
- Flat rentals St. Mary's County
- Rentals with outdoor seating St. Mary's County
- Rentals with a firepit St. Mary's County
- Rentals with a hot tub St. Mary's County
- Cottage rentals St. Mary's County
- Rentals with pools St. Mary's County
- Pet-friendly rentals St. Mary's County
- Beachfront rentals St. Mary's County
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- Rentals with a kayak St. Mary's County
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- Chesapeake Bay
- Haven Beach
- Gerry Boyle Park
- Ragged Point Beach
- Breezy Point Beach & Campground
- Chesapeake Beach Water Park
- Brownies Beach
- Sandyland Beach
- Rose Haven Memorial Park
- Bayfront Beach
- Oxford Beach
- Piney Point Beach
- Lane Beach
- North Beach Boardwalk/Beach
- Guard Shore
- Langford Sand
- Saint Jerome Beach
- Franklin Manor Community Private Park
- Cordreys Beach
- St George Island Beach
- Cove Point Beach
- Fleeton Beach