Pet-friendly vacation rentals in Kent County

Great location. Caroline was amazing. Look forward to renting again next year!!

We had a wonderful stay at this beautiful place. Our extended family and dogs thoroughly enjoyed the private and peaceful location. Bobs place was provisioned very well. We appreciated the numerous coffee cups, wine glasses, etc. it felt very much like staying with family. Lovely art throughout too.

5 adults, 2 children under age 6 stayed at Courtney's home, which was just as described and pictured on the airbnb web page. Great location for our stay for wedding weekend; very comfortable furniture (sofas, chairs, beds; many amenities provided for guests; terrific well-stocked kitchen; very large screened-in porch w/ nice view of Chesapeake Bay and surroundings; spacious bedrooms; 4 full bathrooms; very clean when we arrived. I could go on .... Courtney is a very good communicator, and responded quickly to the few questions we really had. She is a great host and the house was terrific for our needs.

We had another lovely stay at Trish’s place and are looking forward to our next stay in September (again!). Our group stays here no-annually for a work trip and it has everything we need. The WiFi is fast, there’s plenty of space to spread out, and we feel at home.

We rented this place for my parents 50th anniversary. The place was amazing and fit 5 families comfortably. The house had everything you could have imagined that you needed and then more. The place was off the beaten path and exactly what we were looking for. It was peaceful and quiet. The amenities including life preservers, kayaks, and paddle boards was awesome. We enjoyed a fire every night. I highly recommend this place!

We had an amazing stay! The house was beautiful, clean, and super comfortable and the views were absolutely breathtaking. Everything was just as described, if not better. Joeanna was a great host and made everything easy. We’d definitely love to come back

The home was absolutely adorable with all of the built-ins. We felt right at home as soon as we got there. Jessica was very thoughtful and left snacks and even a treat for our puppy! She also had delicious muffins from a local bakery and fresh flowers waiting for us when we arrived. Our family would definitely stay here again!

I definitely recommend this house. More than satisfactory for 6 of us for the weekend. Plenty of room and easy to find.

We loved our stay at Molly's air B &B. there were lots of toys to use on the river. The water views from the house were fantastic. The house was clean and comfortable. We loved taking a dip in the pool. Great communication with the host.

The Creek Cottage at RCF is nothing less than amazing. This is the perfect getaway for privacy, peace and nature. We saw deer, foxes, fish, birds and tons of butterflies. The scenery is so beautiful and serene. The house was just enough space for the 5 of us and our dog - who loved sitting on the enclosed porch to watch us at the pool. The pool was perfect, the river was beautiful and it was nice to just sit and watch the scenery. Bryan, the property manager, was also great and suggested we try out the Crab Shack in Easton - these were the best crabs at a price we couldn’t believe (we got a bushel)! The first floor is fully accessible for those with special needs, but note that the bed sits high so a step stool may be needed. Also, beware of the horse flies - they can be pretty aggressive and intimidating, but we found ways to manage. We certainly loved our family staycation at the Creek Cottage and would love to come back in the future!

We had a wonderful stay at this river front home in Chestertown. Evolve and the Jone’s were very responsive and communicative. Will definitely stay here again for future visits to town!

This house was perfect for everything you need. Close to town to walk, cute backyard, bus will take you to the beach. Defiantly worth renting if you are staying in rock hall. Thanks for sharing your home.

Wonderful property with lots of amenities!

My family loved staying here. We had my 3-month old and my sister brought her 8-month old so we were looking for a place that could keep everyone entertained in one location and this place did just that! We enjoyed bird watching, collecting rocks on the beach, swimming in the heated pool, and watching the sunset from the hot tub in the evenings. This was also the first time I could say that the listing looked better in person than the pictures. Thank you Joni for letting us stay here! We made some amazing memories!

My family & I booked for three nights. Thought it was a beautiful and private little area, and just a couple steps away from the beach and a pool. Very quiet and away from noise which was a plus. The house itself was lovely and mostly clean. There were board games available and my kids had a fun time playing with them. We enjoyed barbecuing using the grill provided on the balcony which was nice as well. A plenty of towels and anything you need in the kitchen! Other than a full trash bag left over in the kitchen, finding some clothing items from other guests (I’m assuming) in drawers, and the keurig having what looked like mold inside. Pretty small things when looking at the big picture though. Will most likely come again & we enjoyed our stay!

Piney Grove is perfect! We had our extended family for the weekend and hosted a graduation party for about 40 people. The farm is the perfect location and venue. The beds are amazingly comfortable and all on the second floor. The main level is a livable museum! The kitchen is huge and VERY well appointed. The dining room is an exceptional place to host a dozen or more, and the parlors are perfect conversation areas. But the porches front and back? Those may be the best part of this place. We had our party in the back and it could not have been better! Wait—the actual best part of this place was Jennifer, who made sure we had everything we could ever need and was the most amazing host! I wish we had discovered Piney Grove Farm years ago—it’s our new favorite!! I wish I could give this six stars!

Owner was very responsive and helpful. The house is very spacious and comfortable.

This is a perfect spot for relaxing! The 4 season room was our favorite and the views are great! Off season a lot of the restaurants are closed until Thursday and there’s not much going on Monday through Wednesday.

A wonderful retreat on an unbelievable property. We were so surprised by the amazing views of the Chester River as well as the really well marked hiking trail. A bit out of downtown Chestertown, but totally worth the drive. Benjamin was a great communicator, and very flexible to meet our needs. ps. the cutest goats

We had a really nice stay at the Oysterman House, James was very responsive to all our questions. In the house left on the table was a book with instructions to everything you may need in the house....working the remote, thermostat etc. The house was very charming. I'd also like to point out my favorite part was the screened in porch with ceiling fan I enjoyed sitting out there especially in the morning for my coffee it was so peaceful and rather warm so the fan to circulate the air was the perfect touch.

The Pilot House on the Inn at Haven Harbour property was fantastic! For a family with kids this is the perfect amount of space to be able to spread out with two living spaces and 3 bedrooms. We loved having the outdoor dining space as well. The beds were all comfortable and having the kitchen fully equipped was a huge bonus. The location was probably our favorite aspect- just 2 minutes walking to the pool, the on site restaurant, the playground/beach area, etc. and just a 4 minute drive (15 minute walk) to the Rock Hall Main Street. Overall a great experience and stay!

This apartment was the perfect place to settle into after a fun day at Crow Vineyard! The apartment is spacious and easy to access. We enjoyed our stay in Kennedyville!

Had a wonderful stay! Perfect home for the Rock Hall Triathlon events. Krystyna was extremely responsive and accommodating. Great place!

Great place, well maintained, very clean and plenty of space. We look forward to renting again in the future.