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

Popular Filters to find the Perfect Home Rental in Chesapeake City

2 Adults
1 Bedroom
Pool
House
Pets allowed
4 Adults
Cabin

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

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.

House  Chesapeake City
Jun 15 - Jun 22
$126 per night
House ∙ 2 guests ∙ 1 bedroom

Vacation Home in Chesapeake City with Yard, Patio & Grill + Water Views

5.0
Outstanding (27 ratings)
Chesapeake City, Cecil County, Maryland, United States
Balcony/Patio
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House  Chesapeake City
May 30 - Jun 6
$1,054 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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Cottage  Chesapeake City
May 30 - Jun 6
$530 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Historic Cottage in Chesapeake City with Yard & Patio

4.4
Very good (6 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
Oct 5 - Oct 12
$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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Cottage  Chesapeake City
Sep 7 - Sep 14
-25%
$304
$229 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
Yard
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House  Chesapeake City
May 1 - May 8
$322 per night
House ∙ 10 guests ∙ 3 bedrooms

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

5.0
Outstanding (109 ratings)
Chesapeake City, Cecil County, Maryland, United States
Yard
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Vacation Rentals With Fireplaces

Get warm and cozy on cold winter nights in Chesapeake City by booking a vacation home with a fireplace.

Cottage  Chesapeake City
May 4 - May 11
$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
Fireplace
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House  Chesapeake City
Jun 29 - Jul 6
$268 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Charlestown

Chesapeake City, Cecil County, Maryland, United States
Fireplace
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House  Chesapeake City
Jul 13 - Jul 20
$253 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Earleville with Yard

Chesapeake City, Cecil County, Maryland, United States
Fireplace
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Best Vacation Home Deals in Chesapeake City

Save up to 59%

Condo Chesapeake City
Jan 4 - Jan 11
-59%
$513
$209 per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo in Newark with Outdoor Pool

Chesapeake City, Cecil County, Maryland, United States
Free cancellation
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Cottage Chesapeake City
Jul 27 - Aug 3
-20%
$500
$400 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Lovely Cottage in North East with Grill & Yard + Spectacular Views

5.0
Outstanding (4 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 59%!

Recommended Vacation Rentals in Chesapeake City

Find your perfect vacation rental in Chesapeake City: from $72 per night

House Chesapeake City
Jun 15 - Jun 22
$720 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
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Cabin Chesapeake City
May 30 - Jun 6
$120 per night
Cabin ∙ 2 guests ∙ 1 bedroom

Cabin in Chesapeake City

Chesapeake City, Cecil County, Maryland, United States
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Mobile home Chesapeake City
May 30 - Jun 6
$105 per night
Mobile home ∙ 6 guests ∙ 1 bedroom

Wonderful Mobile Home in Chesapeake City

Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Aug 10 - Aug 17
$376 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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House Chesapeake City
Jun 8 - Jun 15
$359 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
Aug 1 - Aug 8
$425 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Chesapeake City with Private Balcony + Water Views

5.0
Outstanding (100 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Aug 17 - Aug 24
$300 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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House Chesapeake City
Jun 29 - Jul 6
$2,715 per night
House ∙ 30 guests ∙ 9 bedrooms

Vacation Home in Chesapeake City with Grill & Pool

5.0
Outstanding (1 rating)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Oct 5 - Oct 12
$1,019 per night
House ∙ 16 guests ∙ 5 bedrooms

Vacation Home in Hack Point with Outdoor Pool + Amazing Views

4.7
Excellent (40 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
Aug 10 - Aug 17
$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
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Boat Chesapeake City
May 1 - May 8
$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
Sep 7 - Sep 14
$294 per night
House ∙ 10 guests ∙ 5 bedrooms

House in Betterton with Yard & Grill + Incomparable View

4.7
Excellent (51 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 27 - Aug 3
$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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Villa Chesapeake City
Oct 5 - Oct 12
$1,258 per night
Villa ∙ 16 guests ∙ 7 bedrooms

Villa in Hack Point with Indoor Pool

5.0
Outstanding (5 ratings)
Chesapeake City, Cecil County, Maryland, United States
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House Chesapeake City
Apr 23 - Apr 30
$419 per night
House ∙ 12 guests ∙ 5 bedrooms

Vacation Home in Elkton with Patio & Grill + Fabulous View

5.0
Outstanding (170 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 (9)
  • 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 bring your pet everywhere, as most accommodations include "Pool" and "Pets allowed." You can also search for a rental in Chesapeake City if you need a wheelchair accessible vacation rental as 8 of the listed rentals there provide "Wheelchair accessible."

The Weather in Chesapeake City

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39°
27°
12 days 12
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30°
9 days 9
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54°
36°
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64°
46°
10 days 10
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73°
57°
11 days 11
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82°
64°
11 days 11
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86°
70°
9 days 9
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82°
66°
9 days 9
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79°
61°
6 days 6
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68°
52°
7 days 7
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55°
37°
7 days 7
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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, 19 Apr
55°
51°

0%

1 h

7 mi/h

Sat, 20 Apr
62°
55°

15%

2 h

13 mi/h

Sun, 21 Apr
57°
55°

15%

2 h

10 mi/h

Mon, 22 Apr
60°
60°

0%

6 h

6 mi/h

Tue, 23 Apr
64°
62°

0%

3 h

9 mi/h

Wed, 24 Apr
64°
64°

15%

2 h

10 mi/h

Thu, 25 Apr
55°
53°

0%

0 h

7 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 $1,061 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 $244 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 59%
🌙 Nightly prices starting at $72
⭐ 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 $72. If you’re interested in a house rental, the average price is $1,061 per night. A bed and breakfast rental Chesapeake City will cost $244 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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