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

This house is an absolute gem! Beautifully designed, incredibly clean , good quality kitchen ware, great communication, and overall so much character. We loved the spaciousness and the location (very friendly neighbors!) and the back yard was perfect for our puppy. The Blackwater Nature preserve is very close by and is not to be missed. We couldn’t have been happier! I highly recommend this lovely home and will definitely return!

Our extended family of five, including a nonagenarian plus a 2 year old dog spent 3 nights at Mari's place. It was perfect for us and exceeded our expectations. The most outstanding thing was how peaceful and comfortable it is there. It's a great place to just hang out and enjoy a beautiful home with a beautiful view. We would be happy to return any time we get the chance.

Felt like home. Spacious bedrooms and nicely updated bathrooms. Beautiful country setting for our family’s holiday visit to southern Maryland. Loved it!

This house is perfect for large groups. It is very spacious, with plenty of room to spread out and get comfortable. We enjoyed sitting on the dock taking in the serene natural beauty of the Creek and observing the local birdlife, including Kingfishers, Great Blue Herons, and Bald Eagles. The house is situated very near to the entrance of Lookout Point State Park which we greatly enjoyed exploring on bicycles. Seeing a large wedge of Tundra Swans fly overhead was a special moment. If you want to spend some time relaxing in a beautiful setting in a beautiful and very interesting area with a large group, this house will serve you well.

We loved our stay and would not hesitate to stay again. The property was easy to find and in a quiet neghborhood. The fenced in yard was great for our puppy and it even included a ramp for dogs that struggle with steps! Inside was superb, everything we needed was taken care of. The living room was comfortable, the kitchen was well stocked with quality appliances, cutlery, and cookware. The bathrooms were spotless. I hope this property is available the next time we visit North Beach!

We had the pleasure of staying here during the winter while we looked for a place to live. It was perfect! Quiet and peaceful yet super close to all restaurants and stores. We had some snowfall and the views were stunning! Once it warmed up we even got to see some wild life in the woods behind us. Lovely huge porch! Lots of space in garden escape. Can bring the entire family and more!!! Nice big driveway for easy turned around. Patrick was beyond responsive for all my questions.Whether is was just informing be as something as simple as an Internet outage in the area or we had one situation with an unsure smell. Patrick acted immediately on the problem and it was resolved within 2 hours from start to finish. Cannot recommend this place enough!

thanks so much for the lovely stay. I thought it was so sweet they reached out to ask if it was okay to do some light decorations for christmas. I appreciate the consideration and loved them. when I arrived at the home one of the smoke detectors was chirping and I offered to replace it if they could tell me where some batteries were. bill came over right away and took care of the chirping detector. I really appreciate that.

An extraordinary place to rest & recharge. The views, the comfort of the home, and the gorgeous walking trails, through woods & beach are a perfect combination. Everything we needed & then some.

Our family had a great time at Connie’s! The kids had loads to do in the game room and we all enjoyed the scenic views and relaxing environment. Bathrooms were also super clean. The refrigerator is enormous and was helpful because there aren’t too many food places around so we cooked a lot. Connie was responsive and friendly. We would recommend her place!

It was absolutely wonderful staying at Joanne's home. It was very comfortable and loved the outdoor firepit. Very peaceful and lovely home. We would love to come back again for another visit.

House was great with space for everyone whether we gathered for a meal or game wanted to spread out. Super easy walk to the beach and boardwalk. GREAT coffee shop and a few gems of restaurants and shops-we were definitely there in off season and the town was not fully opened - lots of opportunity in the town and lots of places getting opened for the season! Would be a great place for a quick summer getaway

We had the most beautiful Thanksgiving gathering at Casey’s Porch on the bay for an extended family reunion. The house is lovely - spacious, gorgeous and cozy at the same time. The views on the water were amazing. There were plenty of beds and ‘hang out’ spots for our tweens and teens, and 3 private baths for the adult couples were much appreciated. And our hosts could not have been more helpful and friendly. Thank you for giving us this opportunity to make more happy memories together!

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.

This was a great vacation. This place has it all from the pool to the kayaking, fishing, crabbing and the late night fires were we all just sat around the fire and enjoyed the time together. The house was awesome, plenty of room for all. The family had a great time. Definitely would rent this place again.

I can’t say enough wonderful things about Melissa’s place. As soon as you walk in, you feel right at home. She has thought of every possible thing you could need while there. The views were absolutely magnificent and while the beach area is available to the public, it felt super private. My daughters and I plan to come here every year. I had to peel them away from the bay. Melissa, thank you for accommodating us. This was a weekend my girls and I desperate needed and your home was the perfect place to have peace and intentional quality time. Thank you so much!!

Keith was so super sweet! Always texted back if I had a question. He was welcoming since our first contact. The house was amazing. It felt like home and we treated like home. Definitely will be back again. Absolutely stunning!!

Our family enjoyed staying at Roxanne’s loft - from the cozy space, amenities, to the close proximity to the O’Gara Training Center which made our daily schedule seamless. Rox was responsive, proactive and quickly addressed any questions we had. Her attentiveness made us feel taken care of throughout the entire trip - thank you!

Quiet and cozy home in the perfect location. We had a wonderful stay with beautiful views of the water (too cold in Feb to fully enjoy), and it was so convenient to be able to walk to local coffee shops and restaurants. Would definitely stay here again!

This was a great location for being close to things to do in the area; and it also had a large property for our dog to play. Its a basement apartment which can get chilly but there are plenty of extra blankets available. Great place to visit with your pup!

Place nicer than advertised. Although we only stayed 2 nights we definitely had a good time. The private beach was amazing and overall the place was very relaxing. My only complaint would be to make the pet fee as part of the booking process. My own fault that i didn't notice that after booking in the details.

Lara’s place was lovely, beds comfortable, everything just as described. She was kind enough to let us in early, too. Loved that she had dog bowls for our pup.

Second stay at this quaint cottage. Loved the views and assecibility to get to things around town.

We stayed here for 3 nights - family of 3 and a dog. Beautiful house in an amazing setting. Everything we needed was in the house. brand new kayaks, life vests, a grill, a hot griddle, a very nice hot tub, on and on and on. Brian & Clara were super responsive and went above and beyond. There was one minor item that they ran out of (no big deal), but they came over and dropped off late at night, despite me saying its not urgent. Lovely folks! VERY clear instructions on checkout making it easy to follow. You have your own private beach right outside the backyard, a fishing pier to fish or just sit and take in the scenery. Lot of board games to keep you occupied; nice TV; wifi; every single utensil you would need; you will not miss a thing. Thanks Brian & Clara! We will happily return here!

House was comfortable and located in a beautiful location. Easy check in and Mai was super responsive. Would stay again