Pet-friendly holiday rentals in Kent County

The home was lovely, right on the river, and felt....homey. It was the kind of place I would have if I had a home on the river. There were friendly neighbors who gave us some advice on what to do/not to do in the area and we had a lovely time. This might just be an annual trip for me and my extended family.

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.

This was our second time at Leone's beautiful spot on the Chester River and it did not disappoint! It's such a beautiful place and beautiful location -- we absolutely love it!! Thank you Leone!!!

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!

One of the cuties places we have stayed. This was a perfect place and set up appropriately for our 3 year old granddaughter and our fur baby. Jessica had also left some snacks which we were so thankful for after the drive. Thanks for a wonderful experience.

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 the cottage. Everything was clean and well maintained inside and out. We especially loved the gorgeous surroundings. The property was beautiful and peaceful. We enjoyed daily swims in the pool and time at the dock. Robert was a wonderful host and made everything very clear and easy as well as was easy to communicate with. We couldn't have asked for a better get away. Chestertown is adorable and fun to check out. We hope to return in the future.

We had a great time. The view is one of the best we have stayed at. The hosts have thought of almost everything you could need or want to do. Our kids wanted to come back just to do more of the activities. The interior is obviously dated but it is thoughtful, functional, and clean. We felt cozy and at home! We will be back!

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!

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!

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

Phenomenal NOT-TO-BE-MISSED experience on the Eastern Shore!! What an exceptional historical property - and what a gorgeously tranquil cottage to enjoy on the magnificent waterfront site! The pool was perfect - well-stocked kitchen supported our meal-making - all bedrooms are ensuite - plenty of towels, linens, and space!! We enjoyed fishing on the pier with ospreys, hawks, deers and a rabbit or two looking on. The wrap-around screen porch made every sunrise and sunset a BUG-free treat! The ESVR team was attentive without being intrusive - and we enjoyed their great service *and* our privacy. We can't wait to go back!! Thank you ESVR!!

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.

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.