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Chesapeake City Vacation Rentals

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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Bed & Breakfast
Apartment
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

Spend a delightful Chesapeake City sojourn in a charming vacation home

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.

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Save up to 41%

Best Vacation Home Deals in Chesapeake City

Cottage Chesapeake City
Apr 7 - Apr 14
-41%
$533
$312 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Historic Cottage in Chesapeake City with Yard
Chesapeake City, Cecil County, Maryland, United States
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Bed & Breakfast Chesapeake City
Feb 3 - Feb 10
-22%
$221
$173 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Bed & Breakfast in Chesapeake City
4.8
"Excellent" (45 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Bed & Breakfast Chesapeake City
Feb 3 - Feb 10
-22%
$264
$205 per night
Bed & Breakfast ∙ 3 guests ∙ 1 bedroom
Pleasant Bed And Breakfast in Chesapeake City
4.8
"Excellent" (45 ratings)
Chesapeake City, Cecil County, Maryland, United States
Details
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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%!

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Top-Rated Rentals and Accommodations in Chesapeake City

House Chesapeake City
Feb 16 - Feb 23
$424 per night
House ∙ 12 guests ∙ 5 bedrooms
Vacation Home in Elkton with Yard & Grill + Fabulous View
5.0
"Excellent" (159 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Apartment Chesapeake City
Dec 9 - Dec 16
$189 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Rental Apartment in Chesapeake City with Electric Fireplace + City View
5.0
"Excellent" (10 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Apr 8 - Apr 15
-55%
$1,507
$685 per night
House ∙ 14 guests ∙ 5 bedrooms
House in Chesapeake City + Water Views
4.9
"Excellent" (6 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Recommended Vacation Rentals in Chesapeake City

Find your perfect vacation rental in Chesapeake City: from $126 per night

House Chesapeake City
Apr 7 - Apr 14
$341 per night
House ∙ 4 guests ∙ 3 bedrooms
Vacation Home in Chesapeake City with Grill & Yard + Lock View
5.0
"Excellent" (73 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Apartment Chesapeake City
Feb 17 - Feb 24
$192 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Contemporary Apartment in Chesapeake City with Yard & Grill + Gorgeous Views
4.8
"Excellent" (65 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Apr 15 - Apr 22
$125 per night
House ∙ 2 guests ∙ 1 bedroom
Vacation Home in Chesapeake City with Yard & Grill + Water Views
5.0
"Excellent" (17 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Apartment Chesapeake City
Dec 9 - Dec 16
$187 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Rental Apartment in Chesapeake City with Electric Fireplace + City View
5.0
"Excellent" (10 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Apr 8 - Apr 15
-55%
$1,446
$680 per night
House ∙ 14 guests ∙ 5 bedrooms
House in Chesapeake City + Water Views
4.9
"Excellent" (6 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Bed & Breakfast Chesapeake City
Feb 3 - Feb 10
-23%
$322
$248 per night
Bed & Breakfast ∙ 5 guests ∙ 1 bedroom
Beautiful Bed & Breakfast in Chesapeake City
4.8
"Excellent" (45 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Bed & Breakfast Chesapeake City
Feb 3 - Feb 10
-22%
$263
$204 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
B&B in Chesapeake City
4.8
"Excellent" (45 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Dec 23 - Dec 30
$285 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Perryville with Grill
5.0
"Excellent" (258 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Feb 16 - Feb 23
$420 per night
House ∙ 12 guests ∙ 5 bedrooms
Vacation Home in Elkton with Yard & Grill + Fabulous View
5.0
"Excellent" (159 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in Chesapeake City

Apartment Chesapeake City
Feb 17 - Feb 24
$194 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Contemporary Apartment in Chesapeake City with Yard & Grill + Gorgeous Views
4.8
"Excellent" (65 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Apr 7 - Apr 14
$344 per night
House ∙ 4 guests ∙ 3 bedrooms
Vacation Home in Chesapeake City with Grill & Yard + Lock View
5.0
"Excellent" (73 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Apr 15 - Apr 22
$127 per night
House ∙ 2 guests ∙ 1 bedroom
Vacation Home in Chesapeake City with Yard & Grill + Water Views
5.0
"Excellent" (17 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Chesapeake City accommodation with high-speed internet.

House Internet Chesapeake City
Dec 1 - Dec 8
$391 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Chesapeake City with Private Balcony + Water Views
5.0
"Excellent" (90 ratings)
Chesapeake City, Cecil County, Maryland, United States
Internet
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House Internet Chesapeake City
Jun 24 - Jul 1
$300 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Chesapeake City with Large Whirlpool + Water Views
5.0
"Excellent" (45 ratings)
Chesapeake City, Cecil County, Maryland, United States
Internet
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House Internet Chesapeake City
Jan 20 - Jan 27
$732 per night
House ∙ 15 guests ∙ 7 bedrooms
House in Chesapeake City with Grill + Spectacular Views
5.0
"Excellent" (61 ratings)
Chesapeake City, Cecil County, Maryland, United States
Internet
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Chesapeake City and book a vacation rental with air conditioning.

House Air conditioning Chesapeake City
Jan 20 - Jan 27
$341 per night
House ∙ 4 guests ∙ 3 bedrooms
Vacation Home in Chesapeake City with Grill & Yard + Lock View
5.0
"Excellent" (73 ratings)
Chesapeake City, Cecil County, Maryland, United States
Air conditioning
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Apartment Air conditioning Chesapeake City
Mar 9 - Mar 16
$192 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Contemporary Apartment in Chesapeake City with Yard & Grill + Gorgeous Views
4.8
"Excellent" (65 ratings)
Chesapeake City, Cecil County, Maryland, United States
Air conditioning
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House Air conditioning Chesapeake City
Mar 23 - Mar 30
$126 per night
House ∙ 2 guests ∙ 1 bedroom
Vacation Home in Chesapeake City with Yard & Grill + Water Views
5.0
"Excellent" (17 ratings)
Chesapeake City, Cecil County, Maryland, United States
Air conditioning
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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.

Apartment Balcony/Patio Chesapeake City
Apr 8 - Apr 15
$216 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Apartment in Chesapeake City with Private Patio
5.0
"Excellent" (29 ratings)
Chesapeake City, Cecil County, Maryland, United States
Balcony/Patio
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Cottage Balcony/Patio Chesapeake City
Apr 7 - Apr 14
-41%
$531
$312 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Historic Cottage in Chesapeake City with Yard
Chesapeake City, Cecil County, Maryland, United States
Balcony/Patio
Details
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Bed & Breakfast Balcony/Patio Chesapeake City
Jan 6 - Jan 13
-23%
$322
$248 per night
Bed & Breakfast ∙ 5 guests ∙ 1 bedroom
Beautiful Bed & Breakfast in Chesapeake City
4.8
"Excellent" (45 ratings)
Chesapeake City, Cecil County, Maryland, United States
Balcony/Patio
Details
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Popular Rental Amenities in Chesapeake City

  • Air conditioning (21)
  • TV (21)
  • Internet (21)
  • No smoking (20)
  • No pets (17)
  • Kitchen (16)
  • Microwave (16)
  • Fireplace (11)
  • Washer (9)
  • Yard (9)
  • Dishwasher (9)
  • Fishing (7)

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

max.
Min.
39°
27°
12 days 12
max.
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45°
30°
9 days 9
max.
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54°
36°
9 days 9
max.
Min.
64°
46°
10 days 10
max.
Min.
73°
57°
11 days 11
max.
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82°
64°
11 days 11
max.
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86°
70°
9 days 9
max.
Min.
82°
66°
9 days 9
max.
Min.
79°
61°
6 days 6
max.
Min.
68°
52°
7 days 7
max.
Min.
55°
37°
7 days 7
max.
Min.
48°
36°
9 days 9
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

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

Fri, 24 Mar
53°
48°

15%

0 h

6 mi/h

Sat, 25 Mar
66°
44°

15%

0 h

13 mi/h

Sun, 26 Mar
60°
44°

0%

11 h

11 mi/h

Mon, 27 Mar
55°
39°

0%

4 h

7 mi/h

Tue, 28 Mar
50°
41°

15%

0 h

9 mi/h

Wed, 29 Mar
35°
32°

15%

0 h

15 mi/h

Thu, 30 Mar
44°
32°

10%

6 h

4 mi/h

Accommodations for your vacation in Chesapeake City

Vacationers who are interested in house rental in Chesapeake City have plenty of options to choose from, as they are the most typical property type there. Interestingly, the average rental fee for house rental is $703 per night, with an average size of 259 m². Moreover, these properties are perfect if you're going in a group of 9, as that is the average number of guests house rental can accommodate in Chesapeake City. You can also search and find other accommodation types in Chesapeake City. Bed & Breakfast are, for example, another common property type there with 6 listed accommodations. Our data reveals that the standard price of bed & breakfast is $279 per night for an area of 259 m².
Where to find the best food in Chesapeake City?

Seafood under the bridge

The Bayard House Restaurant is a fine-dining eatery, located in an 18th-century house, which not only offers a serving of exquisite seafood but also spectacular views of the waterfront. Another place that serves a delectable assortment of seafood is the nautical-style Schaefer’s Canal House – where you can also lounge on the waterfront patio while enjoying the live band.

Where are the unique attractions in Chesapeake City?

Fun in natural surroundings

Walking on the Chesapeake and Delaware Canal marina is always a pleasurable experience, and the waters are ideal for activities like sailing or fishing. The 1790-acre preserve of Lums Pond State Park, with its picturesque freshwater pond, sports fields, and multi-purpose trails, makes for a recreational destination to spend a fun and relaxed day.

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.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Chesapeake City TripAdvisor Vacation Rentals in Chesapeake City Vrbo Vacation Rentals in Chesapeake City VacationRentals.com Vacation Rentals in Chesapeake City HouseTrip Vacation Rentals in Chesapeake City FlipKey Vacation Rentals in Chesapeake City Homestay.com Vacation Rentals in Chesapeake City Only-apartments Vacation Rentals in Chesapeake City Interhome Vacation Rentals in Chesapeake City Novasol Vacation Rentals in Chesapeake City HomeEscape Vacation Rentals in Chesapeake City

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