
Holiday rentals in Chesapeake City
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Chesapeake City
Guests agree: these stays are highly rated for location, cleanliness and more.
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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 reviewsFair 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 reviewsSpacious 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 reviewsBayview 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 reviewsMiss 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 reviewsWaterfront 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 reviewsThe 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 reviewsChesapeake 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 reviews4 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
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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