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Chesapeake City Vacation Rentals

Find 19 available offers from 5 partners
Chesapeake City
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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Bed and breakfast
Rating
4.5+
4+
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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Best Vacation Home Deals in Chesapeake City

Save up to 26%

House Chesapeake City
Nov 10 - Nov 17
-16%
$825
$695 per night
House ∙ 8 guests ∙ 5 bedrooms
House in Chesapeake City with Yard, Grill & Pool + Water Views
4.9
Outstanding (53 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Nov 10 - Nov 17
-17%
$1,054
$875 per night
House ∙ 16 guests ∙ 5 bedrooms
House in Chesapeake City + Water Views
4.8
Outstanding (9 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Apartment Chesapeake City
Mar 16 - Mar 23
-26%
$150
$111 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Rental Apartment in Earleville with Free Parking
4.9
Outstanding (9 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Discover a vacation home that meets your preferences among the 19 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 39%!

Top-Rated Rentals and Accommodations in Chesapeake City

Book Vacation Rental Offers with the Highest User Rating

House Chesapeake City
Mar 23 - Mar 30
$340 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Chesapeake City with Grill & Yard
5.0
Outstanding (74 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Apartment Chesapeake City
Mar 23 - Mar 30
$192 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Contemporary Apartment in Chesapeake City with Yard & Grill + Gorgeous Views
4.9
Outstanding (67 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Sep 28 - Oct 5
$126 per night
House ∙ 2 guests ∙ 1 bedroom
Vacation Home in Chesapeake City with Yard & Grill + Water Views
5.0
Outstanding (24 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 $68 per night

Apartment Chesapeake City
Sep 28 - Oct 5
$104 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Rental Apartment in Chesapeake City with Electric Fireplace + City View
5.0
Outstanding (10 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Cottage Chesapeake City
Oct 14 - Oct 21
$530 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Historic Cottage in Chesapeake City with Yard
3.7
Good (3 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Oct 29 - Nov 5
-39%
$679
$413 per night
House ∙ 8 guests ∙ 4 bedrooms
House in Elkton with Seasonal Pool + Water Views
4.8
Outstanding (80 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Mar 9 - Mar 16
$125 per night
House ∙ 6 guests ∙ 2 bedrooms
House in Havre De Grace
4.8
Outstanding (17 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Cottage Chesapeake City
Dec 9 - Dec 16
-24%
$225
$172 per night
Cottage ∙ 8 guests ∙ 3 bedrooms
Cottage in Elkton with Grill & Yard + Water Views
5.0
Outstanding (53 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Jan 20 - Jan 27
-18%
$577
$471 per night
House ∙ 12 guests ∙ 5 bedrooms
Vacation Home in Elkton with Grill + Fabulous View
5.0
Outstanding (158 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Jul 6 - Jul 13
$147 per night
House ∙ 6 guests ∙ 2 bedrooms
House in North East with Yard & Grill
5.0
Outstanding (12 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Sep 8 - Sep 15
$550 per night
House ∙ 12 guests ∙ 5 bedrooms
Pleasant House in Elkton with Yard & Grill + Magnificent Views
5.0
Outstanding (83 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Mar 23 - Mar 30
$351 per night
House ∙ 13 guests ∙ 5 bedrooms
House in Perryville with Grill & Yard + River View
4.9
Outstanding (123 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Budget-friendly Vacation Rentals in Chesapeake City

Find Fantastic yet Inexpensive Offers

Apartment Chesapeake City
Dec 23 - Dec 30
$68 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Apartment in Elkton with Yard
4.9
Outstanding (25 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Jul 27 - Aug 3
$352 per night
House ∙ 8 guests ∙ 3 bedrooms
Pleasant Vacation Home in Perryville with Yard & Grill
4.7
Excellent (198 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Mar 23 - Mar 30
-33%
$1,889
$1,274 per night
House ∙ 20 guests ∙ 7 bedrooms
House in Elkton with Grill + Waterfront Views
4.9
Outstanding (8 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Vacation Houses With Pools

Make a splash on your next vacation! Over 5% of in Chesapeake City vacation rentals have a swimming pool.

Cottage  Chesapeake City
Dec 9 - Dec 16
$289 per night
Cottage ∙ 8 guests ∙ 2 bedrooms
Cottage in Elkton with Yard, Grill & Pool
5.0
Outstanding (9 ratings)
Chesapeake City, Cecil County, Maryland, United States
Pool
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Cottage  Chesapeake City
Jul 21 - Jul 28
-37%
$750
$475 per night
Cottage ∙ 7 guests ∙ 2 bedrooms
Cottage in Elkton with Private Pool
4.3
Very good (7 ratings)
Chesapeake City, Cecil County, Maryland, United States
Pool
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House  Chesapeake City
Sep 29 - Oct 6
-22%
$181
$140 per night
House ∙ 2 guests ∙ 1 bedroom
Pleasant Vacation Home in Newark with Outdoor Pool
Chesapeake City, Cecil County, Maryland, United States
Pool
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Dog-Friendly Vacation Rentals

Bring Fido on your next trip and book a stay in one of these pet-friendly rentals in Chesapeake City!

House  Chesapeake City
Jul 6 - Jul 13
$157 per night
House ∙ 9 guests ∙ 3 bedrooms
Vacation Home in Elkton with Yard & Grill
4.9
Outstanding (35 ratings)
Chesapeake City, Cecil County, Maryland, United States
Pet-friendly
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House  Chesapeake City
Nov 25 - Dec 2
$350 per night
House ∙ 6 guests ∙ 3 bedrooms
Nice House in Elkton with Yard
Chesapeake City, Cecil County, Maryland, United States
Pet-friendly
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House  Chesapeake City
Jul 27 - Aug 3
$285 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Perryville with Grill
5.0
Outstanding (261 ratings)
Chesapeake City, Cecil County, Maryland, United States
Pet-friendly
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Best vacation rentals with a balcony

Looking for a home with a balcony? Check out these vacation homes in Chesapeake City with their own private patios and balconies.

Bed and breakfast  Chesapeake City
Nov 25 - Dec 2
$186 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
B&B in Odessa with Grill, Patio & Yard
5.0
Outstanding (50 ratings)
Chesapeake City, Cecil County, Maryland, United States
Balcony
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House  Chesapeake City
Sep 23 - Sep 30
$450 per night
House ∙ 12 guests ∙ 4 bedrooms
House in Charlestown with Yard & Grill
Chesapeake City, Cecil County, Maryland, United States
Balcony
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Condo  Chesapeake City
Sep 23 - Sep 30
$213 per night
Condo ∙ 6 guests ∙ 3 bedrooms
Condo in Betterton with Pool & Grill
Chesapeake City, Cecil County, Maryland, United States
Balcony
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Popular Rental Amenities in Chesapeake City

  • Pool (1)
  • Pet-friendly (3)
  • WiFi (18)
  • Air conditioning (18)
  • Hot tub (1)
  • Kitchen (12)
  • TV (18)
  • Fireplace (10)
  • Grill (7)
  • Washing machine (7)
  • Microwave (12)
  • Fishing (6)

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're dreaming of days spent poolside or you are looking for a pet-friendly rental, as most accommodations include "Pool" and "Pets allowed." You can also search for a rental in Chesapeake City if you want a rental with a yard as 8 of the listed rentals there provide "Yard."

The Weather in Chesapeake City

max.
Min.
39°
27°
12 days 12
max.
Min.
45°
30°
9 days 9
max.
Min.
54°
36°
9 days 9
max.
Min.
64°
46°
10 days 10
max.
Min.
73°
57°
11 days 11
max.
Min.
82°
64°
11 days 11
max.
Min.
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, 22 Sep
71°
55°

15%

3 h

9 mi/h

Sat, 23 Sep
60°
55°

15%

0 h

20 mi/h

Sun, 24 Sep
73°
55°

15%

3 h

7 mi/h

Mon, 25 Sep
73°
57°

10%

8 h

3 mi/h

Tue, 26 Sep
73°
59°

10%

2 h

5 mi/h

Wed, 27 Sep
69°
59°

10%

6 h

11 mi/h

Thu, 28 Sep
62°
59°

15%

0 h

15 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 $704 per night, with an average size of 239 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 and breakfast rental are, for example, another common property type there with 6 listed accommodations. Our data reveals that the standard price of bed and breakfast rental is $280 per night for an area of 239 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 39%
🌙 Nightly prices starting at $68
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 3 homes

Frequently Asked Questions

What is the nightly price for a vacation home in Chesapeake City?

The price of a night's stay in Chesapeake City starts at $68. If you’re interested in a house rental, the average price is $704 per night. A bed and breakfast rental Chesapeake City will cost $280 per night on average.

How many vacation homes are available for booking in Chesapeake City?

There are currently 19 vacation homes available for booking for your trip.

What are the most popular amenities for vacation rentals in Chesapeake City?

Three most popular amenities for home rentals in Chesapeake City include accommodations that have: Pool, Pets allowed, and Internet.

Are dogs allowed in vacation homes in Chesapeake City?

If traveling with a pet in Chesapeake City, 16% of vacation rentals allow pets.

When is it better to travel to Chesapeake City?

When choosing a vacation rental in Chesapeake City, consider that rainy season is typically in January or May, with September often being the driest.

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