Chesapeake City Vacation Rentals

Compare 73 available properties from 17 providers
Chesapeake City

Discover a vacation home that meets your preferences among the 73 beautiful options from more than 17 vacation rental websites in Chesapeake City. HomeToGo, a vacation rental search engine, immediately sorts all of these accommodations to help you save up to 10%!

Recommended Vacation Rentals in Chesapeake City

Rent a vacation accommodation in Chesapeake City: from $27 per night

House ∙ 12 guests ∙ 5 bedrooms
Elkton, Cecil County, Maryland, United States
from $587
HomeAway
5.0
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House ∙ 10 guests ∙ 5 bedrooms
North East, Cecil County, Maryland, United States
from $328
VRBO
4.9
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House ∙ 16 guests ∙ 7 bedrooms
Chesapeake City, Cecil County, Maryland, United States
from $571
VRBO
5.0
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House ∙ 14 guests ∙ 4 bedrooms
North East, Cecil County, Maryland, United States
from $507
VRBO
5.0
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Mobile home ∙ 7 guests ∙ 2 bedrooms
North East, Cecil County, Maryland, United States
from $75
VRBO
4.8
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Mobile home ∙ 7 guests ∙ 3 bedrooms
North East, Cecil County, Maryland, United States
from $75
VRBO
5.0
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House ∙ 7 guests ∙ 3 bedrooms
Perryville, Cecil County, Maryland, United States
from $317
VRBO
4.8
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House ∙ 5 guests ∙ 2 bedrooms
Perryville, Cecil County, Maryland, United States
from $268
VRBO
5.0
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Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 6 guests ∙ 3 bedrooms
North East, Cecil County, Maryland, United States
from $314
VRBO
5.0
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Fishing
House ∙ 4 guests ∙ 2 bedrooms
North East, Cecil County, Maryland, United States
from $389
VRBO
5.0
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Fishing
House ∙ 7 guests ∙ 3 bedrooms
North East, Cecil County, Maryland, United States
from $75
VRBO
4.8
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Fishing
House ∙ 8 guests ∙ 3 bedrooms
Warwick, Cecilton, Maryland, United States
from $213
VRBO
4.7
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Vacation Rentals With Fireplaces

Fireplace
House ∙ 8 guests ∙ 5 bedrooms
Chesapeake City, Cecil County, Maryland, United States
from $418
VRBO
5.0
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Fireplace
House ∙ 10 guests ∙ 4 bedrooms
Elkton, Cecil County, Maryland, United States
from $384
VRBO
4.8
View deal
Fireplace
House ∙ 15 guests ∙ 6 bedrooms
Elkton, Cecil County, Maryland, United States
from $806
VRBO
4.8
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Fireplace
House ∙ 12 guests ∙ 5 bedrooms
Elkton, Cecil County, Maryland, United States
from $381
VRBO
4.9
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Dog-Friendly Vacation Rentals

Pet-friendly
House ∙ 16 guests ∙ 5 bedrooms
Earleville, Cecilton, Maryland, United States
from $757
VRBO
4.9
View deal
Pet-friendly
House ∙ 8 guests ∙ 3 bedrooms
Perryville, Cecil County, Maryland, United States
from $238
VRBO
4.9
View deal
Pet-friendly
House ∙ 10 guests ∙ 3 bedrooms
Perryville, Cecil County, Maryland, United States
from $174
VRBO
4.9
View deal
Pet-friendly
House ∙ 6 guests ∙ 2 bedrooms
Perryville, Cecil County, Maryland, United States
from $242
VRBO
5.0
View deal
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Popular Rental Amenities in Chesapeake City

  • Parking (51)
  • Internet (47)
  • AC (43)
  • Microwave (41)
  • Washer (40)
  • No smoking (39)
  • TV (39)
  • Kitchen (33)
  • Grill (29)
  • Pets allowed (28)
  • Yard (25)
  • Dishwasher (23)
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 can't imagine a vacation without internet or you want to tune out with some TV time, as most accommodations include "internet" and "TVs." You can also search for a rental in Chesapeake City if you want a rental with a fireplace as 18 of the listed rentals there provide "fireplaces."

The Weather in Chesapeake City

39°
27°
45°
30°
54°
36°
64°
46°
73°
57°
82°
64°
86°
70°
82°
66°
79°
61°
68°
52°
55°
37°
48°
36°
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 July while the driest month is September.

Vacationers who are interested in hotel rooms 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 hotel rooms is $122 per night, with an average size of 360 ft². Moreover, these properties are perfect if you're going in a group of 4, as that is the average number of guests hotel rooms can accommodate in Chesapeake City. You can also search and find other accommodation types in Chesapeake City. House rentals are, for example, another common property type there with 27 listed accommodations. Our data reveals that the standard price of house rentals is $244 per night for an area of 2,900 ft².

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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Food & Drinks

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.

Local Attractions

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.

We compare more than 300 providers, including:

Booking.com Vacation Rentals in Chesapeake City VRBO Vacation Rentals in Chesapeake City HomeAway Vacation Rentals in Chesapeake City TripAdvisor Vacation Rentals in Chesapeake City VacationRentals.com Vacation Rentals in Chesapeake City HouseTrip Vacation Rentals in Chesapeake City FlipKey Vacation Rentals in Chesapeake City Wimdu Vacation Rentals in Chesapeake City 9flats.com Vacation Rentals in Chesapeake City VaycayHero Vacation Rentals in Chesapeake City PerfectPlaces.com 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 Bedycasa Vacation Rentals in Chesapeake City Novasol Vacation Rentals in Chesapeake City HomeEscape Vacation Rentals in Chesapeake City