House vacation rentals in Chesapeake City

I had an amazing time staying at this Airbnb with my college friends! It was the perfect getaway from the city, offering a peaceful retreat while still having plenty of space to relax and enjoy!! The natural sunlight streaming in through the windows made the place feel so warm and inviting. The kitchen was well equipped and every room had spaces for the whole crew to chill and hangout together! Highly recommend for anyone looking to unwind and recharge!

Beautiful home and very clean!! Fully stocked kitchen, nice linens and beds. Convenient to all attractions and Abigail is very accommodating and kind! Horses came to greet us most times in early morning and evenings which was a nice treat. Also can see the Amish horse and buggies from the house. This awesome home is located on a main highway so if a light sleeper make sure to bring a sound machine or fan. We did fine and would book with Abigail again!

Our family of 7, ranging in age from 62-6, had a blast! The pool was perfect for evening entertainment while cooking on the grill. The bedroom layout was great as we have family member that doesn’t do stairs well. Even if upstairs the number of stairs is minimum. We visited Dutch Wonderland and would stay here again for our next trip up! It had more than expected including pool towels and shampoo and conditioner in the 2 full baths. It also had laundry detergent. Thank you! It was a wonderful place!

We had a fabulous time at Megan's place! The heated pool allowed for us to still enjoy the pool despite some rainy and cooler weather. The rock waterfall into the pool was a unique feature and the surrounding area was private and scenic. The wrap porch with a view of the creek and meadow was also a highlight- especially the fireflies at night! There was plenty of kitchen table space for us and our 3 young kids, where we enjoyed the nature views. We even enjoyed roasting marshmallows in the fire pot and swinging on the rocking swing. We hope to come back again another time!

This home is off the charts in every way. Our family of ten enjoyed every aspect of the property. From the game room, to the wonderful kitchen, to the outside pool and hot tub....everything was top notch. Kris is a wonderful host, and she and her family have gone above and beyond in every way. The beds, oh the comfortable beds!

Caryle’s place was in a very peaceful neighborhood, very private and relaxing. The kitchen had what we needed and the living room was a great place to sit and read. We felt like we were staying at a friend’s house.

We had a great stay at Michelle’s place for our high school friend get together. We wanted a place near Longwood Gardens and a place to relax. We got them both! The surroundings were beautiful and the home was open and lovely! We hope to be back!

Martha’s home was absolutely wonderful—by far the cleanest Airbnb we’ve ever stayed in! Everything was spotless and so thoughtfully maintained. The luxury linens and bedding made for an incredibly comfortable stay, and every bathroom was stocked with plenty of towels and washcloths, which we really appreciated. We felt completely at home from the moment we arrived. Check-in was seamless with no hiccups whatsoever. Zero complaints—just a perfect experience all around!

Nicki was an exceptional host—responsive, thoughtful, and truly dedicated to providing a wonderful experience. The home was absolutely stunning, equipped with everything we needed, and her attention to detail was impressive. She truly thought of everything, making our family trip seamless and memorable. The property was in pristine condition—immaculately clean, set in a peaceful and quiet location with breathtaking views. I honestly can't say enough great things about this home! As a Realtor, I will be recommending it to all my clients, family, and friends. We can't wait to rebook our stay there again soon!

This was my second time staying here with my family and dogs. We absolutely love the property and area! We enjoyed kayaking and are dogs enjoyed swimming and playing along the river. Ina was a great host and was responsive to our needs. It was a great experience and vacation!

My wife and I had the best experience at this guest house. Lisa is an amazing host. Lisa blessed us with fresh eggs in the fridge from the farm. Lisa also had fresh milk, yogurts, apple cider, granola, and homemade cakes for us. The guest house and the whole property will take you back in time. The guest house was squeaky clean from top to bottom and had the perfect amenities for out stay. If you are on the fence between renting this property or another property in the area, rent this property for your vacation. You will not be disappointed!!

We had a great time. There was plenty of space to move around so that everyone was not in each other's space. The place was very clean and well-stocked with some everyday items you would normally have in your house to cook, shower and clean with. Jen was very responsive with any questions we had. Even the small children loved the house, especially the bunk beds. It was easy to get to places we needed to go to. All 11 of us enjoyed our stay and everyone said they wouldn't mind returning for another family staycation.

Our family of 6 was in town visiting for two graduations. Both graduations were about 45min each way. We enjoyed the quiet neighborhood and proximity to restaurants. There homes are situated pretty close, and it seemed like a safe area. At the top level you have some views to see the water, but if you want to take a closer look you can easily walk. The home is three stories, so someone who isn’t able to climb stairs may want to keep that in mind. The stairs are pretty easy to climb though. We ate at The Wellwood Restaurant, and the food was absolutely delicious, the extra large blue crabs were stellar as well as the Oysters Rockefeller!

What a warm and welcoming place to stay in Havre de Grace! We felt right at home and had everything we needed for our stay. We spent quite a bit of time on the lovely deck, enjoying the flowers and birds. So much to do within a short walking distance. We’ll be back!

This house was AMAZING! So much space. The rooms were so large, high ceilings and windows, it was just gorgeous! Trey was very responsive to any questions that we had. Lots of parking, just be sure to leave the far left space open for the host to park, since he lives on site at the back of the home (I missed this piece in the description). We had alot of friends visit that were down for the one day and everyone was blown away by the house, and many want to book in the future. The park next door was great for the kids to spread out..and Saturday was a BONUS, when they had live music playing, a food truck and beer tent..we had our own front row seat all afternoon....can't beat live music, by the campfire, by the water. A few notes for future renters: take your own toiletries (soap/shampoo not provided), the "no access" closet to the right of the stove, is actually where the brooms/trash bags and cleaning supplies are housed and you do have access to it. Thank you Trey!

This was such a peaceful and beautiful getaway. The house was so charming and immaculate. That goes for interior and the exterior. We celebrated Father’s Day weekend here and our husbands had a blast fishing the pier and our littles walking to the beach. The rain head shower head and the heated bathroom floor was to die for, and enjoying a book on all the wonderful porches and beautifully kept backyard! We hope to visit again soon! Thank you so much.

We had a perfect stay! The house is very clean and neat. Had every amenity we could have needed. We stayed in town for a nearby lacrosse tournament for 3 nights. It was a perfect place to unwind at the end of the day with great AC! Having laundry on site was particularly helpful. Highly recommend!

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 loved our stay at Packet Alley. This is probably one of the best rentals I have ever stayed at and I would not hesitate to return. The house and grounds were even better than pictured and we enjoyed peace and quiet on the screened in porch overlooking the river. The downstairs of the house felt larger than the pictures so we had plenty of space and lots of natural light. The kitchen was fantastic and the house had everything we needed. Everything in town was walkable from the pier to the historic area. Definitely use the gift card to The Mercury Cafe we ate there twice and the food and drinks were fantastic. We met the owners there and they were all friendly, welcoming, lovely people.

We visit Delaware City every year, but don’t usually stay right in town. It was great to have a spot so close to the family we visit this year! We traveled with our 3 kids(ages 6, 4, 2) and the space met our needs. The master bedroom is downstairs, attached to the only bathroom. The bed was comfortable, although softer than we prefer. The 2 other bedrooms are upstairs - These beds were much firmer. We loved that the house had a fenced backyard for the kids to run around in. The kitchen had a Keurig machine and a nice selection of k-cups. We used the Roku TV without any difficulty. Each room had an AC unit that worked well. Mu only complaint would be that the lighting was low in some rooms, though the weather was cloudy during our stay so it would have been better with some sunshine through the windows.

Katie was very responsive whenever I needed her! And the property was so beautiful! I went with my family and it was a huge group of adults and kids, and every single one of us has a blast! The house is so spacious and well equipped. Enjoyed every minute of us! I wish the weather was better during our stay, the wind made it so hard to enjoy the kayaks 😢

Great location, lovely home, and very responsive host.

We loved this place! Perfect location for our festivities in Pasadena and very peaceful.

Incredible, serene home with thoughtful design and furnishings. Our family loved the house, which served as a great space to gather over meals, games and stories. The deck on two sides of the house, with great seating, provided a gentle welcome to the nature around with harbor views in the distance. As seasoned Eastern Shore folks, this was an introduction to Rock Hall, which we really enjoyed, especially the refuge. Thanks, Lauren, for your insightful planning and attentive care for the house and your guests.