
House holiday rentals in Chesapeake City
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Top-rated house rentals in Chesapeake City
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Popular amenities for Chesapeake City house rentals
House rentals with a pool

Family Friendly AFrame w/Pool & Amish Country View
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!

Findley Farm View Cottage (Outdoor Pool!)
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!

Private home - heated saltwater pool & waterfall
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!

Modern Farmhouse: Pool, Hot Tub & Pickleball
Kris's home was absolutely amazing! It was extremely clean and was exactly as described. Kris was responsive, very friendly and helpful. We loved staying here. We enjoyed the beautiful setting, the pool, hot tub, fire pit, game room and pickle ball. The family had an amazing time. All of the bedrooms and bathrooms were so incredible and unique. The farmhouse transformation was done so well. Every detail was thought through! WOW! I can't say enough good things! We have stayed at a lot of AirBnB's. This was a 10 out of 10.

Sweet home w/pool & woods at peaceful Glen Mills
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!

The Hidden Gem•Heated pool•Pickleball Court
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!

Spacious 4-bedroom house with a private pool.
Georges house is a perfect place to stay house is very clean great house👍

The Peaceful Getaway (with private pool & hot tub)
Perfect for a family getaway and retreat. Love how child friendly their home was as well!
Weekly house rentals

Waterfront Paradise on Seneca Creek w/Hot Tub
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!

*Woodland Chalet* Hot Tub - Fire Pit - Grill
Great place for a weekend getaway! Very quiet and private with nice and new amenities. Only thing is that it got a little cold at the house (we stayed there early June) outside of the bedroom but other than that this was great!!

-Scenic Historic Charm- Spruce Edge Guest House
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!!

The Big Barn in Greenville
Host was very accommodating and home was even more impressive in person. One of the best properties I’ve experienced. Wish we could have stayed longer to enjoy the warm fireplace, comfy beds, great water pressure in showers, nice linens, and gourmet kitchen. Will definitely consider this home again next time our travels bring us to this area.

Stay Anchored Chesapeake Bay, 5 bedrooms, 3 bath
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.

Catching Sunsets on the Bay
We're from Massachusetts and in Maryland for a family wedding in Elkton. My husband and I were able to have three other family members comfortably stay with us. We all enjoyed having the living space on the top floor to enjoy the view of the North East River every morning from inside or outside on the deck. The deck outside on the second level, where the bedrooms are, was wonderful for quiet time before turning in for the night to read or just enjoy the peaceful outdoors. While walking through the neighborhood, we met up with some of the neighbors and everyone was friendly. One time we walked to down to the water at closest to the house and people were celebrating a birthday with a cookout and games. We asked one of the people if this access to the water was private property. The answer was, "No. Would you like to join us?" This is a place I'll save on my Airbnb account to return to again.

The Cooper House in Charlestown, MD
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!

Quaint Bungalow
Great location, lovely home, and very responsive host.
Private house rentals

The Sunset House
Sunset Place was a perfect spot and setup for large family or friend gathering. We were in from out of town for a wedding event and the house was so accommodating for what we needed. We have friends and family in the local campground and the house backs to that so it made it easy to enjoy everything down there. The home is welcoming, clean and has everything a family would need for a long trip or vacation. The host was amazing at communication and even helped when we had a snag and left an article in the home after. Each room was comfortable, the hot tub was a huge plus, and the fire pit was a nice addition to the night time when wanting down time. The beach access points are close by and there are a ton of local restaurants and such to enjoy. My mother lived in Northeast and we always visited so it felt like home and we are definitely going to return for family/friend trips yearly when in town. Thank you again for a great spot and amazing renovation to this local home.

Waterfront Paradise w/ Pier - kayak to Chestertown
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!

Two bedroom small ranch with beautiful forest view
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!

Coastal Living in Delaware City
Darlene was a very gracious and responsive host. The space was exactly as advertised, clean and tidy. Everything worked well and the house was very cozy and comfortable. We enjoyed our weekend stay and we would gladly stay here again next time we’re in Delaware City!

Quaint home in charming town
Had a great stay. Booked to stay at after a friends wedding and so happy we did. Hoping to come back in the future just to visit the area for a weekend. Lindsay was very friendly and responsive!

Waterfront Family Vacation Home
Our family of 6 adults and 4 grandchildren was in town for a wedding and we thoroughly enjoyed this property. Other family members visited and the property was a great gathering place with generous parking space. Kitchen was well stocked and very clean. The yard was awesome for the boys playing ball and all the kids LOVED the spider web swing. Watching the trains roll by on the nearby bridge provided additional entertainment for the young ones, and the water view was gorgeous. A nice addition would be dressers in the bedrooms to be able to unpack suitcases, and some lamps as an alternative to the bright overhead lights. Katie was extremely responsive when we asked if an iron and ironing board were available which weren’t, but she had them delivered that evening! My wife and I sleep on a California King at home but the queen bed in the upstairs bedroom was extremely comfortable and all the adults got good night sleeps. Thank you for providing our family great new memories!

Ruby's Sea Glass Cottage near Betterton Beach
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.

Waterfront w/ Hot Tub + Dock | Harbor View Haven
Perfect place to relax and celebrate our daughter’s graduation. Would definitely stay there again! Thank you for sharing your home with us!
Quick stats about house rentals in Chesapeake City
Total rentals
10 properties
Nightly prices starting at
$356 AUD before taxes and fees
Total number of reviews
560 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
10 properties include access to Wi-Fi
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- Pennsylvania Convention Center
- Fortescue Beach
- Lincoln Financial Field
- Betterton Beach
- Citizens Bank Park
- Fairmount Park
- Penn's Landing
- Wells Fargo Center
- Longwood Gardens
- Oriole Park at Camden Yards
- Hampden
- Dutch Wonderland
- The Franklin Institute
- M&T Bank Stadium
- Sandy Point State Park
- Philadelphia Museum of Art
- Philadelphia Zoo
- Patterson Park
- Aronimink Golf Club
- Wissahickon Valley Park
- French Creek State Park
- 30th Street Station
- Marsh Creek State Park
- Independence Hall