Holiday rentals in Chesapeake City

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Popular amenities for Chesapeake City holiday rentals

Other great holiday rentals in Chesapeake City

Superhost
Cabin in Elkton
4.74 out of 5 average rating, 35 reviews

Fair Hill Cabin-10 min to Newark/UD

JefferyRating, 5 stars2 weeks ago
My family loved the peaceful area around this home. It is quite, peaceful, and we were visited by some dear and rabbits. There is also an orchard down the road where you can visit, but it opened for the season the day after we left. The host was fantastic and wanted to be sure we enjoyed our stay. When we go back to the area to visit family, we will stay here again.
Home in Newark
5 out of 5 average rating, 4 reviews

Spacious 3Bed/2Bath retreat , 2.5 Mi to UD

XiaowenRating, 5 stars1 week ago
This house is very clean, spacious and well organized. It locates in a quiet neighborhood and is close to shopping places and about 8 minutes away from the University of Delaware. Jane is always responsive, polite and accommodating. I highly recommend this house if you are looking for a place to stay in this area.
Guest favourite
Cabin in North East
4.88 out of 5 average rating, 60 reviews

Bayview Cottage

SherylRating, 5 stars9 months ago
With a family wedding in the area, Kerry's cottage was the perfect place for our stay. The area is so beautiful & this home provides an opportunity to enjoy it. Kerry quickly responded & was a huge help when one of our kids left their suit pants behind.
Guest favourite
Home in Chesapeake City
5 out of 5 average rating, 9 reviews

Miss Francis Kirk House/Luxury 2Bed/1.5Bath

TraceyRating, 5 stars4 days ago
Gwedolyn was very responsive and made sure we had everything we needed! Accommodation were great although the shower upstairs was narrow and ceiling was short.. my husband is 6’2” and it was pretty tight for him. But all and all we enjoyed the stay and definitely be back again! Thank you so much for always being there when we needed you.. 5 Star rating
Home in Elkton
4.81 out of 5 average rating, 42 reviews

Waterfront House on the Upper Chesapeake Bay

EphraimRating, 5 stars1 week ago
this was a great place to stay.
Top guest favourite
Home in Chesapeake City
4.96 out of 5 average rating, 54 reviews

The Ferry Slip House

AnnalisaRating, 5 stars2 weeks ago
Great stay, beautiful home. Pristine clean, super easy check in. Walkable distance to everything with an incredible view. 10/10 recommended
Home in Chesapeake City
4.68 out of 5 average rating, 72 reviews

Chesapeake City MD Staycation

AndrewRating, 5 stars5 months ago
We had a great time at Estelle’s Airbnb. The location was very close to everything in Chesapeake City. Estelle was great to communicate with and was very generous to let us check in early. Do not hesitate to stay here is you are looking to stay in town
Home in Chesapeake City
5 out of 5 average rating, 5 reviews

4 Bedroom Vineyard Farm Cottage

DonnaRating, 5 stars6 months ago
We absolutely loved staying in this charming cottage. One of the best things Ashleigh did for us was putting us in contact with Jeff who works at the attached winery. Jeff and his crew were outstanding. We were hosting a Thanksgiving dinner for 15 people. They allowed us to borrow a banquet table as well as some extra chairs. We also ordered our dinner from the connecting restaurant. It was absolutely delicious as well as coming warm and ready to serve. Jeff and his crew also delivered and picked up the table and chairs as well as blowing leaves for us to play some lawn games. Unfortunately, it rained :( Ashleigh was very responsive and timely, but as Jeff was on site, he and his crew took care of all our requests. We look very forward to planning another event at this location and hopefully renting the larger home this time in the summer. Thank you, Donna and John

Quick stats about holiday rentals in Chesapeake City

  • Total rentals

    30 properties

  • Nightly prices starting at

    ₹8,677 before taxes and fees

  • Total number of reviews

    1.7K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

Destinations to explore

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