Places to stay in Chesapeake City

Book unique places to stay, houses, and more on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Chesapeake City places to stay

Other great vacation rentals in Chesapeake City

Guest favorite
A corner of a bathroom features a jetted tub beside a window offering views of the surrounding trees and water. Soft white towels are neatly arranged on the tiled ledge, and a simple vase holds decorative dried grasses.
Home in Galena
4.93 out of 5 average rating, 40 reviews

Connection Pointe•River views•Quiet•Peaceful

JacquelynRating, 5 stars1 week ago
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.
Guest favorite
Cottage in Earleville
4.95 out of 5 average rating, 83 reviews

The Bohemia Charmer

PamRating, 5 stars3 weeks ago
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!
Guest favorite
The modern kitchen features white cabinetry and a spacious countertop with contemporary appliances, including a six-burner gas stove and stainless steel oven. A window offers a view of the water outside, while elegant decorations add a touch of style to the area.
Home in Chesapeake City
5 out of 5 average rating, 9 reviews

Miss Francis Kirk House/Luxury 2Bed/1.5Bath

TraceyRating, 5 stars3 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
Top guest favorite
A spacious backyard garden is surrounded by lush greenery, featuring flower beds with various plants and shrubs. The area is designed with neatly arranged stone borders and soft grass, providing a serene environment for relaxation and outdoor activities.
Home in North East
4.96 out of 5 average rating, 54 reviews

Boho River Cottage

PeggyRating, 5 stars3 days ago
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.
Top guest favorite
A well-equipped kitchen is highlighted by modern appliances and a spacious island featuring two bar stools. Light wood accents complement navy cabinets, while a large window brings natural light to the space. Decorative items, including a paddling oar, add character to the room.
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
A private residence features a wooden deck adorned with blooming flowers and shrubs. A shaded area with climbing plants is visible, alongside a grill. The spacious yard is surrounded by greenery, providing a serene outdoor atmosphere conducive to relaxation.
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
A spacious living area is highlighted by a comfortable sectional sofa and a light-colored chair. A flat-screen television is positioned on a dark wooden stand. Natural light filters through sheer window treatments, illuminating the room's neutral walls and flooring.
Home in Earleville
5 out of 5 average rating, 5 reviews

The Cottage at Crystal

CourtneyRating, 5 stars1 week ago
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.
Top guest favorite
A private hot tub for three is situated indoors, framed by a stone archway that overlooks a lush green landscape. The warm water creates a gentle steam, enhancing the serene ambiance of the space.
Home in Freeland
4.98 out of 5 average rating, 49 reviews

The Oakland House

BrittanyRating, 5 stars3 weeks ago
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.

Destinations to explore

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