Vacation rentals in Chesapeake City

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Top-rated vacation rentals in Chesapeake City

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite

Apartment in Chesapeake City

4.95 out of 5 average rating, 63 reviews

cozy garden: hygge= happy + cozy

Chesapeake City is a historic town located on the C & D Canal; it's not unusual to be greeted by locals as you explore the town. The apartment is a bedroom with sitting area, fully equipped kitchen & bath. It's in the heart of the town & walkable to all the boutiques, restaurants & nightlife! It comes equipped with a Nespresso machine, coffee pods,sparkling water, wifi & tv if you just want to chill. It's steps from the canal for lovely sunrise/sunsets! There are bike/walking paths nearby.

May 30 – Jun. 6

$196 CAD per night
Guest favourite

Guest suite in Newark

4.99 out of 5 average rating, 166 reviews

Spacious, light filled studio 2 blocks from UDel

Our quiet, private studio is located in the historic Old Newark neighborhood, next to the Univ of Delaware, only a few minutes' walk to the center of downtown Newark. Newark is a thriving college town with restaurants, history museum, library, small stores erc. The studio is in a quiet, friendly, safe, historic and walkable neighborhood. If you are looking for privacy and serenity in this charming town, this is the place! Guests describe our studio as immaculately clean, private and calming.

Apr. 21 – 28

$157 CAD per night
Guest favourite

Guesthouse in Quarryville

4.99 out of 5 average rating, 222 reviews

The Olde Wash House on Camargo

Come and relax in our newly remodeled, cozy, cottage style home with it's own private entrance, surrounded by working Amish farms, just outside of town. A short 15 minute drive to Historic Strasburg, Sight and Sound Theater, Antique Shopping, Tangor Outlets and more! Hiking Trails close by include Enola Grade Trail, Pinnacle Point, Muddy Run Park, and Sickman's Mill. If golfing is your desire, Tanglewood Golf Club is just 10 minutes away. We hope you enjoy your stay!

Feb. 20 – 27

$148 CAD per night

Popular amenities for Chesapeake City vacation rentals

Stay near Chesapeake City's top sights

Chesapeake Inn Restaurant & Marina41 locals recommend
Schaefer's Canal House33 locals recommend
Cafe on the Bay10 locals recommend
The Bayard House Restaurant16 locals recommend
Prime 22520 locals recommend
Tap Room Inc8 locals recommend

Other great vacation rentals in Chesapeake City

Guest favourite

Guest suite in Chesapeake City

5.0 out of 5 average rating, 75 reviews

Benson House on Bohemia Ave (Back Deck)

Apr. 27 – May 4

$265 CAD per night
Guest favourite

Home in Chesapeake City

5.0 out of 5 average rating, 28 reviews

Charming, updated home in Historic Chesapeake City

Sep. 9 – 16

$617 CAD per night
Guest favourite

Apartment in Elkton

4.98 out of 5 average rating, 53 reviews

Short Term Water Oriented Furnished Apartment

Sep. 1 – 8

$211 CAD per night
Guest favourite

Home in Chesapeake City

5.0 out of 5 average rating, 23 reviews

Wister Loft: Charm & History with Modern Love.

Feb. 16 – 23

$374 CAD per night
Guest favourite

Home in Chesapeake City

5.0 out of 5 average rating, 37 reviews

Chesapeake City Charm at the Boho House!

Oct. 4 – 11

$726 CAD per night
Guest favourite

Home in Chesapeake City

5.0 out of 5 average rating, 16 reviews

McReynolds-Woods House -Private 3 Bedroom Home

Aug. 25 – Sep. 1

$562 CAD per night
Guest favourite

Home in Chesapeake City

4.95 out of 5 average rating, 19 reviews

The Ferry Slip House

Feb. 24 – Mar. 3

$903 CAD per night
Guest favourite

Cottage in Charlestown

4.98 out of 5 average rating, 43 reviews

Long Beach Cottage, (romantic couple’s getaway)

Sep. 21 – 28

$695 CAD per night
Guest favourite

Home in Chesapeake City

5.0 out of 5 average rating, 79 reviews

Spring Season @ Old Lock View Chesapeake City MD

May 31 – Jun. 7

$611 CAD per night
Guest favourite

Home in Chesapeake City

4.96 out of 5 average rating, 25 reviews

HOOK WINE & SINKER sleeps 14 w/ Boat Slip at Inn

Dec. 24 – 31

$1,272 CAD per night
Guest favourite

Guesthouse in Elk Mills

4.97 out of 5 average rating, 37 reviews

Private Country Guesthouse Getaway Minutes from UD

Aug. 4 – 11

$195 CAD per night
Guest favourite

Home in Charlestown

4.91 out of 5 average rating, 66 reviews

Cozy cape cod in water oriented Community near I95

Apr. 3 – 10

$179 CAD per night

Quick stats about vacation rentals in Chesapeake City

Total rentals

20 properties

Wifi availability

20 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

1.2K reviews

Nightly prices starting at

$136 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Cecil County
  5. Chesapeake City