House holiday rentals in Kent County

Words can’t describe how incredible this home/property is! You have the option to just sit by the water or in the hammock watching the birds play and fish jump, or you can do one of the MANY activities Molly has provided for you. Kayaks, canoes, paddle boards, pickleball, yards games, pool activities, etc are all provided. The family room is all windows so it not only provides the most incredible breeze- it is great for enjoying all the sights even if you’re not outside in it. Inside there are tons of toys for kids- you do not have to bring a thing if you have kids. They have inside toys, outside toys, kids life jackets, goggles, water balloons, rafts, floaties, pack and play…. Molly and her family have thought of it ALL. We are already talking about coming back. Molly was the best host- responsive, helpful and inviting.

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!!

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!

It was a great stay after a long day roaming around Washington DC and Maryland. The accommodation was clean and nicely decorated with very inspiring words of wisdom providing a cozy and comfortable retreat throughout our stay. Kelly has been very informative and detailed on the instructions to help us on a very smooth check in and check out process. The location was fantastic and quiet neighborhood. Overall, we had a wonderful time and would highly recommend this place to anyone looking for a memorable Airbnb experience!"

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!

This was our 2nd year at Peaceful Waters. It is indeed just that! Peaceful! Perfect and beautiful location. Everything needed is there to assure a wonderful carefree stay. The place is well stocked, clean and is just as it reads and appears! My group of 16 loved the place AGAIN this year. Hopefully, planning to go back next year. Matthew and Rose are great to work with! ❤️

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!

Not only was our stay reasonably priced it was spacious and well equipped. Check out the Bed & Breakfast that is directly behind the house for a good bite to eat! A nice perk was the small community beach was in walking distance.

Lovely immaculately clean home close to rock hall marinas. The beds were really comfortable and hosts super responsive. Loved all the books and board games they had. Kitchen very well stocked. Highly recommend staying here.

A beautiful property, and a beautiful house. Thanks again for the stay!

I’ve been to this location three (3) times now and each time was a pleasure. Communication was great and him allowing a late check out was fantastic (especially with multiple kids, trying to get them ready). I will continue to select this location when we have to come into town for the location, price, communication, and peace of mind knowing exactly what we’ll receive. The only issue with this last stay (and I can only assume it was due to holiday because never happened before) was the trash can being full. I do not suspect this is a regular occurrence as he is very transparent. I’d recommend this place to anyone and again, will be booking multiple times in the future as we will be traveling to MD a lot more.

Immaculate and perfect....look no further if you are searching for a house on Kent Island. We were in town for a wedding and this AirBnb was beyond ideal. Spotless and clean, tasteful decor, and waterfront. All exactly as advertised, but looks even more picturesque in person. We really enjoyed being waterfront on the dock enjoying the mornings and evenings in peace. Highly recommend - it was difficult to leave!

Karin was very responsive to our last minute booking. The house was as described and directions were clear. We cannot thank the hosts for assisting us during a difficult time.

We had a great stay in Rock Hall at Rick’s place for our triathlon race weekend. The house was very clean in a quiet neighborhood. It has a fully equipped kitchen and stocked with extra toiletries; which is always helpful. It’s located in a lovely area by the water with great local restaurants and shops. Communication with Rick was excellent and he’s a very responsive and helpful host.

We had a wonderful stay and the host was very accommodating! Her flexibility was good and location is great for getting around rockhall! I would recommend this place

Grandma's Cottage was adorable, homey and the perfect size for my niece, great-niece and me. We were down in the area for a family birthday party and this was a comfortable and charming place to stay. Kathy thought of everything when she furnished her cottage and we took advantage of being able to cook there and save a little money. The beds were large singles and so comfortable. There is a split system a/c so each bedroom can be set to the the person staying theirs comfort. Kathy has chairs, beach towels and other goodies available for guests. The highlight of the town is its beach area right on the bay. We took chairs down and enjoyed two beautiful sunsets. I know this review is a bit long but the cottage was so cozy and we felt so at home. We got to meet Kathy while we were there and she is such a lovely person. Thanks for having us!

Carey's home is beautiful and comfortable. I wanted to bring the back deck home with me! If you prepare meals, he has a fully-stocked kitchen at your disposal. His home is just two blocks away from the business district of Chestertown, making our stay fully walkable. Because it's a small town, though, it's very quiet. This home offers everything you could ask for.

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.

The house was great. Well done retro decor. Good location to the Main Street with restuarants and bars. House was very clean and Lee is a great host Recommend Zelda’s a speakeasy which is only open on Thursday and Friday. We were in for a wedding at Britland Manor. Would highly recommend staying at the house.

I couldn't have asked for a better place to have a family reunion. The dining room and living room was the day center for the weekend. People were able to relax and enjoy reconnecting. I loved the treeline driveway facing the small church. Yoga on the porchnin the morning was sublime.

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

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’ve stayed in scores of Airbnb’s over the years and this was one of my very favorites. Rob was outstanding and this historic home was just perfect. Thanks Rob! Next time I am in town, I’ll reach out.