House vacation rentals in Chesapeake City

Find and book unique houses on Airbnb

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Popular amenities for Chesapeake City house rentals

House rentals with a pool

Superhost
Home in Arnold
4.69 out of 5 average rating, 13 reviews

Mins to Annapolis from Waterfront home Pool, Pier

VickyRating, 5 stars10 months ago
House owners were extremely responsive and informative. House was well stocked , and a great location and view made the stay even better.
Guest favorite
Home in Strasburg
4.94 out of 5 average rating, 141 reviews

Findley Farm View Cottage (Outdoor Pool!)

Don Rating, 5 stars2 weeks ago
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!
Superhost
Home in Parkesburg
4.79 out of 5 average rating, 14 reviews

Cozy 4BR Parkesburg Home with Pool & Sunroom

MaryRating, 5 stars1 month ago
This house is in a quiet neighborhood, and accomodated our family very well while we were visiting the area. The house is older, but everything was clean and tidy!
Guest favorite
Home in Rock Hall
4.95 out of 5 average rating, 37 reviews

Rockfish Keeper

Mary JaneRating, 5 stars1 day ago
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!"
Superhost
Home in Dover
4.67 out of 5 average rating, 12 reviews

Quiet Getaway with pool!

DarlineRating, 5 stars1 day ago
As we opened the door, there was that great, welcoming smell. The place was very clean, beds well made, ready for us. Our host even had snacks for us which were welcoming since we had a 3-hr trip to get there. We definitely recommend this place to a big family!
Top guest favorite
Home in West Chester
4.91 out of 5 average rating, 159 reviews

West Chester, PA entire home

NinaRating, 5 stars3 weeks ago
We had a nice stay at Caryle’s house. It was a nice location to explore Longwood gardens, Wintertur, and Philadelphia. Neighborhood was quiet. The house was nice and clean and we felt right at home. Caryle was very responsive and proactive.
Guest favorite
Home in Severn
4.88 out of 5 average rating, 163 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

Christopher JasperRating, 5 stars1 week ago
Great place, nice atmosphere and big with a lot of rooms. Clean and lovely surroundings. I just wish with how big it is, there’s more bath rooms. Hope to come back when its not cold so pool is not cold. 👍🏼
Guest favorite
Home in Glen Mills
4.92 out of 5 average rating, 131 reviews

Sweet home w/pool & woods at peaceful Glen Mills

AdrienneRating, 5 stars4 weeks ago
Excellent stay. Easy access to our destinations: Winterthur, Brandywine Museum of Art, and great restaurants for lunches and dinners. Lovely and very clean home, very comfortable. Lovely enclosed sunroom in back of house.

Weekly house rentals

Guest favorite
Home in Riviera Beach
4.95 out of 5 average rating, 137 reviews

Waterfront Cheerful 5 home

PolinaRating, 5 stars2 weeks ago
Excellent house for a family reunion, spotlessly clean and very comfortable. It features a huge, well-stocked kitchen, nice mattresses and bedding, and is situated in a quiet neighborhood with beautiful nature. I will definitely return soon.
Guest favorite
Home in West Chester
4.97 out of 5 average rating, 143 reviews

Gorgeous Victorian Style Home

JessicaRating, 5 stars4 weeks ago
Better than expected. Troy's place has everything you need. Although the place itself is not situated in a super private area as its right across the university and its right up against the road and sidewalks. So you'll see lots of folks walking to and from their destinations but all good. Everyone seems to mind their business and its very tranquilo. Definitely nice to sit out on the porch or get some sun in the backyard while you watch kiddos play around. Troy's communication is great and answer's any questions you have. Even though its stated in listing that there is someone there in a separate private living space on property, you would never know lol. We didnt find out til our last day if someone actually was there, they are so quiet. You have all the privacy you need. Beautiful home, lovely area and just overall it was a great deal and find as we visited during a sad time. Thank you Troy.
Guest favorite
Home in Peach Bottom
4.92 out of 5 average rating, 79 reviews

Spacious, Quiet & Peaceful

AlejandroRating, 5 stars1 month ago
Amazing place to stay with family and kids. Enjoyed a lot and will definitely stay here again. Reuben was an amazing host and very flexible! Recommend 100% this Airbnb
Top guest favorite
Home in Wilmington
5 out of 5 average rating, 34 reviews

Charming 4BR in Historic District

ChristineRating, 5 stars2 weeks ago
The house was just lovely and comfortable. We were able to spread out to sleep, then gather in the living room and dining room to catch up and plan. We were in town for a family event so didn't get a chance to explore but the area seemed very nice and the locals were impressed with the location. Common areas were on the ground floor, three bedrooms on second (we had problems regulating the temp at night there) and then a single/twin bed on the top floor. It is an old house but clearly lovingly renovated so that it didn't feel old and creaky, except for the front doorknob coming off. I would stay there again and have recommended it to the Wilmington locals for their guests. All of the hosts were friendly, quick to answer questions, and work with our schedules. Thanks to you all!
Guest favorite
Home in North East
4.96 out of 5 average rating, 108 reviews

Red Point Lighthouse

JohnRating, 5 stars4 weeks ago
Attention to detail both architecture and a fully equipped kitchen with spices etc Visually unmatched sunrise to sunset
Guest favorite
Home in Quarryville
4.89 out of 5 average rating, 160 reviews

Lapp Farmhouse Bed & Breakfast - Amish Country PA

RonRating, 5 stars3 months ago
very much enjoyed our stay... complete with complimentary fresh bread, bacon/eggs, and jar of farm fresh milk! bedrooms clean and comfortable; really only 3 private bdrms, other is open floor space for air mattresses; full kitchen clean, tho could use a few more real coffee mugs! :) nice place to stay, not far from local activities; nice park/playground/picnic/fishing/boating area nearby (Muddy Run Park), and a must stop: Evans Chocolate Candies (Willow Street, PA, just up the road); thanks to Host David for prompt and friendly communications!
Guest favorite
Home in Parkesburg
4.92 out of 5 average rating, 101 reviews

Fenced In Back Yard - Hot tub - King Bed

ChristianRating, 5 stars1 month ago
We had a wonderful stay! The house was beautifully decorated, nice and clean, and there was a cute little toy area 😊.
Guest favorite
Home in Atglen
4.92 out of 5 average rating, 114 reviews

Swan Road Farmhouse, newly remodeled w/ 5 bedrooms

LuellaRating, 5 stars1 week ago
Great place for families or large groups. Huge kitchen. A list of what was supplied in the kitchen would have been nice. Cream for coffee, etc. would have been appreciated. The toilet paper was sub par. Bring your own if you don’t want cheap public bathroom quality stuff. But it was super clean, very spacious. The beds were comfy. Lots of pillows provided. Thank you. We would stay again.

Private house rentals

Guest favorite
Home in Airville
5 out of 5 average rating, 8 reviews

Beautiful Cottage Stay in Southern PA

Barbara JRating, 5 stars3 weeks ago
Our stay at Joshua's place was wonderful. The place was clean and it was very peaceful. The beds were comfortable. Joshua was easy to contact and very responsive. We would definitely stay here again. Thank you Joshua!
Top guest favorite
Home in Glen Burnie
4.96 out of 5 average rating, 448 reviews

Secluded acre near BWI and Baltimore

MRating, 5 stars2 weeks ago
It was very nice staying at Stan's cottage. It's like a tiny oasis in this rapid world of technology, and chaos. Very peaceful, quiet, cozy, and clean. CJ greeted us when we arrived, helped us with our bags, and cut fresh flowers for me when we arrived (super sweet). We got great recommendations for restaurants and take out. And finally, it was a true pleasure spending our last minutes with Stan. We enjoyed hearing about his love of travel and of birding...it would have been nice to stay a little longer...we look forward to hearing "the adventures of Stan" someday soon.
Top guest favorite
Home in New Providence
5 out of 5 average rating, 73 reviews

Charming 3 bedroom home nestled in the woods

SimoneRating, 5 stars1 week ago
We had a wonderful time at Michelle's house! Michelle greeted us when we arrived and showed us everything. The house was immaculate, smelled super nice and had a warm at-home feel. We got lucky with the weather and were able to sit by the fire place on the beautiful deck. The location was great, too. Everything in Amish country is only a short drive away. We would stay there again if we come back to the area.
Superhost
Home in Baltimore
4.83 out of 5 average rating, 6 reviews

Charming Retreat/BBQ/Pet Friendly/ 10 ppl.

StevenRating, 5 stars4 weeks ago
Home was spacious and very clean, nice layout with one bedroom downstairs and 3 bedrooms upstairs, full bathrooms on both floors.
Guest favorite
Home in Wyoming
4.96 out of 5 average rating, 25 reviews

Charming Home in Camden Wyoming

TaraRating, 5 stars3 months ago
Vinay’s Airbnb was cozy, clean, and perfect for our stay. He was incredibly accommodating, especially for a late arrival and during a major snowstorm—walkways were shoveled and salted, which made everything so much easier when we arrived. We also appreciated the thoughtful touches like bottled water and new toothbrush kits, which were a lifesaver when my son left his toothbrush at a hotel in another state. Highly recommend and would definitely stay here again!
Top guest favorite
Home in Glen Burnie
4.98 out of 5 average rating, 44 reviews

Three bedroom house with two full bath near BWI

KenyaRating, 5 stars6 days ago
Excellent time staying here. Courtney was courteous and very responsive to our needs. Definitely a must use if ever in the area! Thank you Courtney!
Guest favorite
Home in Dover
4.92 out of 5 average rating, 59 reviews

Military, Nascar, Lacrosse,FIREFLY, Casino nurses

ScottRating, 5 stars6 months ago
Dana was an awesome host! The home was beautiful and looked just like the pictures on the listing. Nice and quiet neighborhood with plenty of things to do in the area, 5 stars and will definitely stay again.
Guest favorite
Home in North East
4.86 out of 5 average rating, 72 reviews

The Beach House

KarenRating, 5 stars4 months ago
We had a small family group stay at the Beach House in North East for Thanksgiving, and it was perfect in every way for our group. Plenty of room, fantastic location and water views, easy beach access, very well-equipped kitchen, warm and cozy living room area, and great communication from Alexis. We hope to return again soon!

Quick stats about house rentals in Chesapeake City

  • Total rentals

    10 properties

  • Nightly prices starting at

    ﺩ.ﺇ845 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

  • Wifi availability

    10 properties include access to wifi

Destinations to explore

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  2. United States
  3. Maryland
  4. Cecil County
  5. Chesapeake City
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