A historic place steeped in Victorian charm, the scenic Chesapeake City is located on the Chesapeake and Delaware Canal near a spectacular horse country. Taking a trip to this destination makes for an idyllic getaway, especially if you book a beautiful cottage-style vacation home on the waterfront.

Choose the perfect vacation rental
Best Vacation Home Deals in Chesapeake City
Discover a vacation home that meets your preferences among the 24 beautiful options from more than 5 vacation rental websites in Chesapeake City. HomeToGo, a vacation rental search engine, immediately sorts all of these accommodations to help you save up to 22%!
Top-Rated Rentals and Accommodations in Chesapeake City
Recommended Vacation Rentals in Chesapeake City
Find your perfect vacation rental in Chesapeake City: from $126 per night
Budget-friendly Vacation Rentals in Chesapeake City
Vacation rentals with Wi-Fi
Stay connected while traveling and book a Chesapeake City accommodation with high-speed internet.
Vacation rentals and apartments with air conditioning
Keep cool during your trip to Chesapeake City and book a vacation rental with air conditioning.
Apartments With Balconies or Patios
Looking for a home with a balcony? Check out these vacation homes in Chesapeake City with their own private patios and balconies.
Popular Rental Amenities in Chesapeake City
Our search page's filters will help you find the perfect rental in Chesapeake City. You can easily compare and find a rental fitting your criteria in Chesapeake City if you want to tune out with some TV time or you never miss an episode of your favorite show, as most accommodations include "Air conditioning" and "TV." You can also search for a rental in Chesapeake City if you are a grill master as 6 of the listed rentals there provide "Wheelchair accessible."
The Weather in Chesapeake City
You can see our climate diagram above. July is the warmest month in Chesapeake City with average maximum temperatures of 86°. On the contrary, the coolest month is January. The rainiest month is January while the driest month is September.
7-Day Weather Forecast in Chesapeake City
Accommodations for your vacation in Chesapeake City
Information about vacation rentals in Chesapeake City
💳 Possible discounts | up to 22% |
---|---|
🌙 Nightly prices starting at | $126 |
⭐ Popular amenities | Air conditioning, TV and Internet |
🐾 Pet friendly accommodations | 3 properties |
Frequently Asked Questions
What is the average nightly price for a vacation rental in Chesapeake City?
The average accommodation in Chesapeake City is priced at $126 per night. If you’re interested in a house rental, the average price is $703 per night. A bed & breakfast Chesapeake City will cost on average $279 per night.
How many vacation rentals are available to book in Chesapeake City?
There are currently 24 rentals in Chesapeake City to choose from and rent for your next trip.
What amenities are most popular for vacation homes in Chesapeake City?
If you're looking to book a vacation rental in Chesapeake City, others search for accommodation with these amenities: TV, Air conditioning and Internet.
Are pets allowed in vacation homes in Chesapeake City?
In case if you are traveling with a pet in Chesapeake City - 14% of rentals allow pets.
What's the best time to travel to Chesapeake City?
Chesapeake City has its warmest time of year in July and June, with average prices of $126 per night.
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