
Places to stay in Chesapeake City
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Top-rated places to stay in Chesapeake City
Guests agree: these places to stay are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake City places to stay
Other great vacation rentals in Chesapeake City

Connection Pointe•River views•Quiet•Peaceful
We rented this property to attend a family wedding. It was perfect for me, my husband and our 4 adult children. The best word to describe is serene. Martha is an excellent host. So responsive and helpful. The photos are accurate but the feel is so much better. If we ever go back to Galena we would stay here again. Highly recommend.

The Bohemia Charmer
My family and I spent the weekend at Marla’s place while we were in town for a wedding. It was so charming, quiet, very accommodating for what we needed. Very clean and comfortable, and I felt like we were at a cute cottage on the water..so peaceful, a beautiful view, very relaxing vibe. Marla was very responsive and helpful anytime I reached out to her. I highly recommend her Airbnb if you’re looking for a cozy, quiet, place to stay in the Earleville area. I’d absolutely stay at her place again!

Miss Francis Kirk House/Luxury 2Bed/1.5Bath
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

Boho River Cottage
Cece had everything ready for us and our pup. The home was very clean and well stocked. She even had kindling and dry wood ready for the chimania. Instructions were clear and a binder with local attractions and restaurants was ready for us.

The Ferry Slip House
Great stay, beautiful home. Pristine clean, super easy check in. Walkable distance to everything with an incredible view. 10/10 recommended

Chesapeake City MD Staycation
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

The Cottage at Crystal
This was a great place to stay. The view was wonderful the area is quiet. Make sure you bring your supplies if your plan is just to hang since it is a little bit of a drive to stores and restaurants.

The Oakland House
This home provided an incredible setting for restoration, connection, and peace. The home was STUNNING, even more gorgeous and well appointed than the photos. The kitchen had EVERYTHING we needed for us to cook and bake every meal. And the surrounding environment provided a private, unique, and tranquil setting for our girls’ weekend together. We are eager to return soon!
Quick stats about vacation rentals in Chesapeake City
Total rentals
30 properties
Nightly prices starting at
G$20,922 GYD 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
Frequently Asked Questions
How much does it cost to stay in house rentals in Chesapeake City?
Experience the best of Chesapeake City with our house rentals, starting at about $230 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Chesapeake City?
Yes! Work meets play with ease at over 10 vacation rentals in Chesapeake City featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Chesapeake City have wifi?
Absolutely! We offer over 10 house rentals with wifi in Chesapeake City. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Chesapeake City?
Chesapeake City has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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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