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

Chesapeake City Vacation Rentals

Find 32 available house rentals from 4 partners
Anytime
1 guest
Anytime
1 guest

Top 15 Recommended vacation rentals in Chesapeake City

Find your perfect vacation rental in Chesapeake City from just $66 per night!

House Chesapeake City
-20%
Mar 3 - Mar 10
House ∙ 8 guests ∙ 5 bedrooms

House with Patio, Garden & Barbecue

Chesapeake City, Cecil County, Maryland, United States
$995$795
per night
Outstanding(59 ratings)
$995$795
per night
View deal
Apartment Chesapeake City
Jul 12 - Jul 19
Apartment ∙ 3 guests ∙ 1 bedroom

Rental Apartment with 1 Room for 3 Persons

Chesapeake City, Cecil County, Maryland, United States
$119
per night
Outstanding(65 ratings)
$119
per night
View deal
Houseboat Chesapeake City
Aug 2 - Aug 9
Houseboat ∙ 8 guests ∙ 4 bedrooms

Pleasant Boat with Grill | Pets Allowed

Chesapeake City, Cecil County, Maryland, United States
$234
per night
Excellent(44 ratings)
$234
per night
View deal
House Chesapeake City
Aug 23 - Aug 30
House ∙ 5 guests ∙ 3 bedrooms

Family-Friendly Vacation Home | Nature View | Pets Are Welcome

Chesapeake City, Cecil County, Maryland, United States
$176
per night
Outstanding(130 ratings)
$176
per night
View deal
House Chesapeake City
May 31 - Jun 7
House ∙ 8 guests ∙ 3 bedrooms

Children-Friendly Pleasant Vacation Home with Patio, Garden & Barbeque | Lake View | Pets Are Welcome

Chesapeake City, Cecil County, Maryland, United States
$352
per night
Excellent(196 ratings)
$352
per night
View deal
House Chesapeake City
Jul 13 - Jul 20
House ∙ 6 guests ∙ 3 bedrooms

Family-Friendly House with Grill & Garden

Chesapeake City, Cecil County, Maryland, United States
$162
per night
Outstanding(90 ratings)
$162
per night
View deal
House Chesapeake City
-17%
Jul 26 - Aug 2
House ∙ 5 guests ∙ 3 bedrooms

House with Barbeque & Patio | City View | Suitable for Remote Work

Chesapeake City, Cecil County, Maryland, United States
$387$320
per night
Outstanding(1 rating)
$387$320
per night
View deal
Cottage Chesapeake City
Jun 14 - Jun 21
Cottage ∙ 8 guests ∙ 4 bedrooms

Children-Friendly Cottage with Barbeque, Garden & Terrace | Dogs Allowed

Chesapeake City, Cecil County, Maryland, United States
$304
per night
Outstanding(94 ratings)
$304
per night
View deal
House Chesapeake City
Jun 28 - Jul 5
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home with Terrace | Suitable for Remote Work

Chesapeake City, Cecil County, Maryland, United States
$236
per night
Outstanding(26 ratings)
$236
per night
View deal
House Chesapeake City
Jul 13 - Jul 20
House ∙ 5 guests ∙ 2 bedrooms

Family-Friendly Pleasant Vacation Home

Chesapeake City, Cecil County, Maryland, United States
$185
per night
Outstanding(3 ratings)
$185
per night
View deal
Cottage Chesapeake City
Jul 13 - Jul 20
Cottage ∙ 4 guests ∙ 1 bedroom

Cottage with Terrace & Garden

Chesapeake City, Cecil County, Maryland, United States
$530
per night
Good(9 ratings)
$530
per night
View deal
Apartment Chesapeake City
Jul 13 - Jul 20
Apartment ∙ 4 guests ∙ 2 bedrooms

Child-Friendly Rental Apartment with Terrace | Nature View

Chesapeake City, Cecil County, Maryland, United States
$200
per night
$200
per night
View deal
Mobile home Chesapeake City
Jul 13 - Jul 20
Mobile home ∙ 6 guests ∙ 1 bedroom

Pleasant Mobile Home with 1 Room for 6 Persons

Chesapeake City, Cecil County, Maryland, United States
$125
per night
$125
per night
View deal
House Chesapeake City
Jul 13 - Jul 20
Free cancellation
House ∙ 4 guests ∙ 1 bedroom

House with Yard

Chesapeake City, Cecil County, Maryland, United States
$530
per night
$530
per night
View deal
House Chesapeake City
May 31 - Jun 7
House ∙ 11 guests ∙ 6 bedrooms

House with Yard, Barbeque & Terrace

Chesapeake City, Cecil County, Maryland, United States
$305
per night
Outstanding(127 ratings)
$305
per night
View deal

Vacation homes and rentals with a yard

Private room  Chesapeake City
Dec 21 - Dec 28
$66
per night
Private room ∙ 2 guests ∙ 1 bedroom

Charming Private Room with Garden

Chesapeake City, Cecil County, Maryland, United States
Yard
View deal
Private room  Chesapeake City
Dec 21 - Dec 28
$66
per night
Private room ∙ 2 guests ∙ 1 bedroom

Charming Dedicated Room with Yard

Chesapeake City, Cecil County, Maryland, United States
Yard
View deal
Bed and breakfast  Chesapeake City
Jan 11 - Jan 18
$187
per night
Bed and breakfast ∙ 5 guests ∙ 1 bedroom

Charming Bed & Breakfast with Sauna, Garden & Patio

4.7
Excellent
Chesapeake City, Cecil County, Maryland, United States
Yard
View deal
See all offers

Best Vacation Home Deals in Chesapeake City

Save up to 66%

Condo Chesapeake City
Jan 18 - Jan 25
-66%
$377
$135
per night
Condo ∙ 2 guests ∙ 1 bedroom

Condo with Pool

Chesapeake City, Cecil County, Maryland, United States
View deal
House Chesapeake City
Jan 11 - Jan 18
-37%
$466
$340
per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home with Yard

5.0
Outstanding(1 rating)
Chesapeake City, Cecil County, Maryland, United States
View deal
Condo Chesapeake City
Jan 18 - Jan 25
-32%
$355
$247
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with Pool

Chesapeake City, Cecil County, Maryland, United States
View deal

Compare the 32 accommodations featured in Chesapeake City and discover the ideal home for a relaxing vacation. HomeToGo, a vacation rental search engine, immediately sorts all of these properties so you can save up to 66%!

Budget-friendly Vacation Rentals in Chesapeake City

Find Fantastic yet Inexpensive Offers

House Chesapeake City
Jun 7 - Jun 14
$871
per night
House ∙ 15 guests ∙ 7 bedrooms

House with Patio & Grill | Nature View

5.0
Outstanding(62 ratings)
Chesapeake City, Cecil County, Maryland, United States
View deal
House Chesapeake City
Jun 7 - Jun 14
$154
per night
House ∙ 2 guests ∙ 1 bedroom

House with Patio, BBQ & Yard | Nature View

5.0
Outstanding(39 ratings)
Chesapeake City, Cecil County, Maryland, United States
View deal
House Chesapeake City
Jun 7 - Jun 14
$1,584
per night
House ∙ 18 guests ∙ 7 bedrooms

Children-Friendly Vacation Home with Terrace, Private Pool & Garden | Nature View | Suitable for Remote Work

4.9
Outstanding(17 ratings)
Chesapeake City, Cecil County, Maryland, United States
View deal

Top-Rated Rentals and Accommodations in Chesapeake City

Book Vacation Rental Offers with the Highest User Rating

House Chesapeake City
Jul 26 - Aug 2
$459
per night
House ∙ 6 guests ∙ 3 bedrooms

Child-Friendly Vacation Home with Grill, Terrace & Garden | Nature View | Pets Are Welcome

5.0
Outstanding(199 ratings)
Chesapeake City, Cecil County, Maryland, United States
View deal
House Chesapeake City
Jun 21 - Jun 28
$367
per night
House ∙ 7 guests ∙ 3 bedrooms

Vacation Home with BBQ, Garden & Terrace

5.0
Outstanding(110 ratings)
Chesapeake City, Cecil County, Maryland, United States
View deal
House Chesapeake City
Jun 14 - Jun 21
$236
per night
House ∙ 6 guests ∙ 2 bedrooms

House with BBQ & Yard | Good for Workation

5.0
Outstanding(35 ratings)
Chesapeake City, Cecil County, Maryland, United States
View deal

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Popular Rental Amenities in Chesapeake City

  • Pool (1)
  • Pet-friendly (4)
  • WiFi (33)
  • Air conditioning (32)
  • Hot tub (6)
  • Kitchen (25)
  • TV (31)
  • Parking (1)
  • Balcony/patio (13)
  • Fireplace (9)
  • Grill (8)
  • Washing machine (14)

Select a filter to search and book a vacation home meeting your requirements among the 32 rentals in Chesapeake City. In Chesapeake City, 1 accommodations include "Pool". Consequently, if you want a rental with a pool, select the Pool filter to compare these accommodations. You can even look for properties if you want a rental providing a crib (4 rentals include "Crib" in Chesapeake City) or if you need a fenced-in backyard (2 rentals in Chesapeake City include "Fenced").

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.

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

🏡 Vacation rentals available 32 rentals
💳 Possible discounts up to 66%
🌙 Nightly prices starting at $66
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 4 homes
879 reviews
Chesapeake City vacation rentals have an average rating of 4.8/5 on 879 reviews left by travelers.

Frequently Asked Questions

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

The average accommodation in Chesapeake City is priced at $66 per night. $1,020 is the average nightly price for house rentals in Chesapeake City. Bed and breakfast rentals in Chesapeake City cost on average $267 per night.

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

Currently there are 32 vacation rentals in Chesapeake City to browse and book for your trip.

What amenities are most popular for vacation homes in Chesapeake City?

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

Are dogs allowed in vacation rentals in Chesapeake City?

If you are traveling with a dog in Chesapeake City - 13% of vacation homes 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 nightly prices around $66.

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