Pet-friendly vacation rentals in Chesapeake Ranch Estates-Drum Point

My husband and I had a nice peaceful retreat from city life. Kristin’s cute place was just what we needed. Highly recommend!

Diana’s place was perfect for our family. The house had many of the items we would have had to bring from home. You can tell she wanted people to feel at home and be comfortable. My grandbabies loved the books. The neighbors were friendly. The neighborhood was nice to get a quick walk in before the day started.

Really enjoyed holiday get away . Place was located near water with great views. We enjoyed walking around the neighborhood was quaint. The town was was pretty with water on each side with the Christmas lights at night . We truly enjoyed our relaxing stay . Would definitely book again

This property was centrally located to shopping , restaurants and historic sites. It was a perfect location. I’d rent it again!

My husband and I had a wonderful stay at Trey's home. We have rented many homes in the southern MD area, and this is by far our favorite. The location is beautiful - right on the St. Mary's River, very secluded and quiet, with lots of nature and stunning sunsets. It's right next to Historic St. Mary's City, so there's lots to explore. The house is spacious with a large well-equipped kitchen and dining area, a lovely living room, screened porch and large deck. Trey was very responsive as a host, and flexible with our booking, which we really appreciated! We highly recommend this house to anyone looking for a relaxing getaway, and we look forward to booking it again. Thanks, Trey, for a wonderful stay!

We had a great stay! The yard was perfect for our dog and playing with our grandson. There was plenty of water and the house met all our needs. The neighborhood was fantastic and we loved taking walks and seeing everyone else out walking their kids and dogs! Definitely will come back!!

This Airbnb was amazing!! Honestly even cuter in person compared to the photos! I would recommend this spot to anyone visiting the area!! 10/10 experience!

We had great stay at Tim’s place. The surrounding just very peaceful and the gorgeous sunset view just from the deck, the pier. We stayed 2 nights just enjoying all the peaceful moments without leaving the house. The only thing is that there were many mosquitos when get dark, even we close the door right away but they came in some, they don’t really bite people though but if for those who hate to see them , that’s a thing. Anyway, it’s all about nature. We love nature so it’s not a big deal for us. Thank you Tim for sharing the lovely place to us.

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!

A great stay on the river. The kitchen was well equipped and the rest of the house was comfortable. The screened in porch and access to the dock/beach/river was our favorite part. Our dogs were in HEAVEN. The location is rather remote, so recommend bringing any food you'll want as there are no close stores or restaurants.

Clare and Chris could not be nicer and easier to work with. My family/friends have been getting together since 1994 and have been to many great Airbnb's and VRBO's. My group could not stop telling me how great of a week we had. The primary features that were import to us which the house scored big are as follows: It has a dock (we arrived via boat), The kitchen is big, laid out for many "Cooks", The kitchen was open to the dining room table, The dining room table is open to the sitting areas, The pool was clean and inviting, The fire pit with seasoned firewood was a big hit for our group, All the beds were comfortable, The bedrooms were large and comfortable, The baths were clean, modern & large and The location to "What to do in Cambridge" is only 7-10 miles away. We made prearrangements: Richardson Maritime Museum to have a guided tour with David Williams on Friday and Spocott Windmill with George Radcliff. Both of these tours were fascinating. Our weekend was 5-Stars.

Great place to stay. Hyrum was quick to respond when I messaged him. Neighborhood is quiet but conveniently located to the highway. Would stay here again.

Katharine’s cottage was wonderful. It exceeded our expectations. It was very well equipped. Katharine was extremely responsive and kind; an excellent host. Thank you!

Wonderful place - pictures do not do it justice. Home is spotless and beautifully furnished! We had a great time relaxing on our babymoon. Lots of great restaurants close by and so much to do at the house you never have to leave. Really appreciated the details such as the coloring station and ample beach towels. Hope to stay again in the future!

Truly a 5-star Superhost! The place was spotless, perfectly located, and within easy reach of everything we needed. The host was incredibly attentive—quick to respond and went above and beyond to make sure our stay was comfortable. Can’t recommend this place enough!

⭐️⭐️⭐️⭐️⭐️ 5/5 – Unforgettable Anniversary Getaway! We stayed at Pam and Rick’s beautiful home in Montrose to celebrate our 10th wedding anniversary with family, and it was everything we hoped for. The house was spotless, cozy, and filled with thoughtful touches that made us feel instantly at home. One of the highlights of our trip was going kayaking (my first time)—an unforgettable experience, my family loved it, even my 3-year-old. Pam and Rick had great suggestions for local activities, and their tips helped make the whole outing smooth and enjoyable. The peaceful setting of their home was perfect for relaxing after a day of exploring. We loved sitting out on the patio in the evenings, especially after running after our 2 toddlers. We’re so thankful for this memorable stay and highly recommend their home to anyone visiting Montrose and we would love to return someday!

We had an amazing stay at Nick’s beautiful cabin! It is situated in a very peaceful and pleasant corner of the Eastern Shore. Nick is super responsive, friendly and helpful. Highly recommend!

Great quiet and secluded place. Very clean and roomy. Nice pond that was good finish with the kids. Definitely going back at some point

This house and the amenities are amazing. It was perfect for our family reunion with 5 couples. Enough room for everyone to have space. My favorite part was gathering around the round dinner table with the 10 of us. We also took the kayaks out and up Mattox creek for a wonderful morning of a peaceful paddle. The Lodge was perfect for my husband and I to step away from the group and have some privacy. I highly recommend!!

This was our family's second stay at The River House. We had another relaxing and fun week! Kayaking across to the state park is one of our favorite things to do there. We also enjoy shopping and eating in Leonardtown. We had one rainy day, but reading on the day bed with a beautiful view (in spite of the weather) and working on a puzzle were an enjoyable way to spend the day. We hiked out to Calvert Cliffs State Park one day and enjoyed lunch on Solomons Island on the way back. John's pet friendly Airbnb is such an awesome place to vacation with our dogs. One of them loves to fetch her floating stick off the little beach area and play frisbee in the yard (bring a long leash that you can tie to the badminton net poles). Our other dog loves basking in the sun in the yard and on the deck. There are so many great things about this place, but the sunsets alone are worth the stay!

The house was amazing and beyond our expectations! It was beautifully decorated, impeccably clean, lots of great seating and every amenity you could ever need! Loved the screened porch, firepit and seating area overlooking the creek. The kitchen had everything needed for cooking. Loved this lovely property and being close to nature. Enjoyed a peaceful and restful week. Thank you!

Kelly and Thomas were amazing host. Very responsive and accommodating The home was very clean and the location was great.. 10/10. Definitely would book again!

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.

Jian was an amazing host he replied to us within minutes and had YOUTUBE instructions for all the smarthouse devices . this home is well worth the stay crabbing hanging on the dock the screened in porch. my dogs had a blast exploring the property freely i 1000 precent recommend this property for s peaceful relaxing time with your friends and family