Chesapeake City Vacation Rentals - HomeToGo base64Hash Chesapeake City Vacation Rentals - HomeToGo

Chesapeake City Vacation Rentals

Find 21 available offers from 10 partners
Chesapeake City
Anytime
Guests
Chesapeake City
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Cabin
House
Apartment
Rating
4.5+
4+

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.

Show all 21 properties

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
Mar 30 - Apr 6
$289 per night
Cottage ∙ 8 guests ∙ 2 bedrooms

Cottage in Elkton with Yard, Grill & Pool

5.0
Outstanding (16 ratings)
Chesapeake City, Cecil County, Maryland, United States
Pool
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House  Chesapeake City
Apr 10 - Apr 17
$263 per night
House ∙ 8 guests ∙ 3 bedrooms

House in Warwick with Private Pool

4.8
Outstanding (80 ratings)
Chesapeake City, Cecil County, Maryland, United States
Pool
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Apartment  Chesapeake City
Aug 1 - Aug 8
$171 per night
Apartment ∙ 3 guests ∙ 1 bedroom

Apartment in Newark with Complimentary Parking

4.4
Very good (6 ratings)
Chesapeake City, Cecil County, Maryland, United States
Pool
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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.

Cottage  Chesapeake City
Apr 10 - Apr 17
$530 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Historic Cottage in Chesapeake City with Yard & Patio

4.3
Very good (5 ratings)
Chesapeake City, Cecil County, Maryland, United States
Balcony/Patio
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House  Chesapeake City
Apr 10 - Apr 17
$875 per night
House ∙ 16 guests ∙ 5 bedrooms

House in Chesapeake City with Patio + Water Views

4.8
Outstanding (10 ratings)
Chesapeake City, Cecil County, Maryland, United States
Balcony/Patio
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House  Chesapeake City
Mar 30 - Apr 6
$657 per night
House ∙ 15 guests ∙ 7 bedrooms

House in Chesapeake City with Patio & Grill + Spectacular Views

5.0
Outstanding (66 ratings)
Chesapeake City, Cecil County, Maryland, United States
Balcony/Patio
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Vacation homes and rentals with a yard

Looking for vacation homes with a little extra outdoor space? Check out these accommodations in Chesapeake City with private yards.

House  Chesapeake City
Jun 1 - Jun 8
$286 per night
House ∙ 11 guests ∙ 6 bedrooms

Vacation Home in Betterton with Yard, Patio & Grill

4.9
Outstanding (118 ratings)
Chesapeake City, Cecil County, Maryland, United States
Yard
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House  Chesapeake City
Apr 20 - Apr 27
$313 per night
House ∙ 10 guests ∙ 3 bedrooms

House in Perryville with Grill, Patio & Yard + Amazing Views

5.0
Outstanding (108 ratings)
Chesapeake City, Cecil County, Maryland, United States
Yard
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House  Chesapeake City
May 11 - May 18
$98 per night
House ∙ 3 guests ∙ 2 bedrooms

House in Havre De Grace with Electric Fireplace

4.9
Outstanding (63 ratings)
Chesapeake City, Cecil County, Maryland, United States
Yard
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Best Vacation Home Deals in Chesapeake City

Save up to 29%

House Chesapeake City
Mar 15 - Mar 22
-25%
$395
$295 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Chesapeake City

5.0
Outstanding (2 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Cottage Chesapeake City
Mar 30 - Apr 6
-29%
$304
$215 per night
Cottage ∙ 8 guests ∙ 3 bedrooms

Cottage in Elkton with Grill, Yard & Patio + Water Views

5.0
Outstanding (76 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Apr 20 - Apr 27
-28%
$655
$471 per night
House ∙ 12 guests ∙ 5 bedrooms

Vacation Home in Elkton with Patio & Grill + Fabulous View

5.0
Outstanding (168 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Discover a vacation home that meets your preferences among the 21 beautiful options from more than 10 vacation rental websites in Chesapeake City. HomeToGo, a vacation rental search engine, immediately sorts all of these accommodations to help you save up to 62%!

Recommended Vacation Rentals in Chesapeake City

Find your perfect vacation rental in Chesapeake City: from $73 per night

House Chesapeake City
Mar 29 - Apr 5
$322 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Chesapeake City with Patio, Grill & Yard

5.0
Outstanding (70 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Jul 27 - Aug 3
$306 per night
House ∙ 8 guests ∙ 3 bedrooms

House in Chesapeake City with Large Whirlpool + Water Views

5.0
Outstanding (45 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Boat Chesapeake City
Jun 8 - Jun 15
$260 per night
Boat ∙ 8 guests ∙ 4 bedrooms

Beautiful Boat in Havre De Grace with Grill

4.5
Excellent (16 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Aug 17 - Aug 24
$405 per night
House ∙ 11 guests ∙ 5 bedrooms

Vacation Home in Bear with Grill & Yard

5.0
Outstanding (2 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Cottage Chesapeake City
Mar 8 - Mar 15
$180 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Wonderful Cottage in Cecilton with Patio, Yard & Grill

5.0
Outstanding (152 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Aug 17 - Aug 24
$351 per night
House ∙ 13 guests ∙ 5 bedrooms

House in Perryville with Grill, Patio & Yard + River View

4.9
Outstanding (155 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Jul 28 - Aug 4
$240 per night
House ∙ 8 guests ∙ 3 bedrooms

Lovely House in Havre De Grace with Patio, Grill & Yard

5.0
Outstanding (57 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Sep 21 - Sep 28
$157 per night
House ∙ 9 guests ∙ 3 bedrooms

Vacation Home in Elkton with Yard, Patio & Grill

4.9
Outstanding (41 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Sep 21 - Sep 28
$365 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in North East with Grill, Patio & Yard + Water Views

5.0
Outstanding (193 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Budget-friendly Vacation Rentals in Chesapeake City

Find Fantastic yet Inexpensive Offers

House Chesapeake City
Mar 15 - Mar 22
$258 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Perryville with Grill, Yard & Patio + Expansive Views

4.8
Outstanding (8 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Cottage Chesapeake City
Mar 30 - Apr 6
$155 per night
Cottage ∙ 6 guests ∙ 2 bedrooms

Cottage in Earleville with Yard, Grill & Patio

4.9
Outstanding (65 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Aug 31 - Sep 7
$322 per night
House ∙ 8 guests ∙ 3 bedrooms

Charming House in Charlestown with Yard & Patio + Water View

4.9
Outstanding (42 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Top-Rated Rentals and Accommodations in Chesapeake City

Book Vacation Rental Offers with the Highest User Rating

House Chesapeake City
Jul 12 - Jul 19
$201 per night
House ∙ 4 guests ∙ 2 bedrooms

Beautiful Vacation Home in Newark with Patio & Yard

5.0
Outstanding (12 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Cottage Chesapeake City
Sep 14 - Sep 21
$185 per night
Cottage ∙ 5 guests ∙ 3 bedrooms

Wonderful Cottage in Massey with Yard, Patio & Grill

5.0
Outstanding (130 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Cottage Chesapeake City
Mar 30 - Apr 6
-15%
$224
$190 per night
Cottage ∙ 6 guests ∙ 2 bedrooms

Cottage in Kennedyville with Patio

5.0
Outstanding (39 ratings)
Chesapeake City, Cecil County, Maryland, United States
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Popular Rental Amenities in Chesapeake City

  • Pool (1)
  • Pet-friendly (3)
  • WiFi (21)
  • Air conditioning (20)
  • Hot tub (1)
  • Kitchen (12)
  • TV (17)
  • Balcony/patio (8)
  • Fireplace (8)
  • Grill (6)
  • Washing machine (8)
  • Microwave (12)

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 need wheelchair access as 8 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.
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73°
57°
11 days 11
max.
Min.
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, 29 Mar
51°
50°

0%

6 h

16 mi/h

Sat, 30 Mar
53°
48°

15%

0 h

7 mi/h

Sun, 31 Mar
64°
62°

5%

1 h

10 mi/h

Mon, 1 Apr
48°
46°

15%

0 h

6 mi/h

Tue, 2 Apr
46°
46°

15%

0 h

10 mi/h

Wed, 3 Apr
66°
53°

15%

0 h

15 mi/h

Thu, 4 Apr
48°
48°

15%

1 h

19 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 $1,064 per night, with an average size of 239 m². Moreover, these properties are perfect if you're going in a group of 12, 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 7 listed accommodations. Our data reveals that the standard price of bed and breakfast rental is $264 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 62%
🌙 Nightly prices starting at $73
⭐ 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 $73. If you’re interested in a house rental, the average price is $1,064 per night. A bed and breakfast rental Chesapeake City will cost $264 per night on average.

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

There are currently 21 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, 14% 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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