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Chesapeake City vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Chesapeake City

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

Guest favorite
Guest suite in Newark
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.
Mar 25 – Apr 1
$94 per night
4.99 out of 5 average rating, 161 reviews
Guest favorite
Guesthouse in Chesapeake City
High-End Cottage, Water View, Chesapeake City, MD
"Fairwinds Cottage" is a newly renovated coastal themed guest cottage with a water view on the quiet side of the canal in Chesapeake City, Maryland. Enjoy watching the ships pass through the canal, take a walk on the beautiful 17-mile Ben Cardin/Mike Castle Recreational Trail just steps from the house. Walk to Schaefer's Canal House for their amazing crab cakes and libations. Stay with us and learn why Chesapeake City was voted the #1 most charming town in Maryland in 2018.
Oct 15 – 22
$199 per night
5.0 out of 5 average rating, 146 reviews
Guest favorite
Cottage in North East
Persimmon Pastures
A quiet country setting in North East MD..located on a 7 acre horse farm with easy access to I95. Enjoy all the serenity of the country yet close to the shopping, marinas, and within 50 mile access to Baltimore, Wilmington and Philadelphia. The property is also within 30 minutes of Fair Hill Natural Resources Area with 5,500+acres and 80+ miles of trails for hiking, biking, and beautiful scenery. Pets are allowed. A pet (dog/cat) fee of $5/night/pet will be requested.
Sep 10 – 17
$91 per night
4.97 out of 5 average rating, 418 reviews

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 favorite
Townhouse in Port Deposit
Quarry Landing *River View* in Port Deposit
$79 per night
4.96 out of 5 average rating, 138 reviews
Guest favorite
Home in North East
Private home
Feb 24 – Mar 3
$82 per night
4.9 out of 5 average rating, 122 reviews
Guest favorite
Home in Elkton
Appleton Retreat
Dec 24 – 31
$158 per night
4.98 out of 5 average rating, 111 reviews
Guest favorite
Cabin in North East
Waterfront Cabin on the Chesapeake
Jun 9 – 16
$340 per night
4.96 out of 5 average rating, 149 reviews
Guest favorite
Farm stay in Chestertown
Blue Heron Farm Waterfront Chalet
Oct 15 – 22
$266 per night
4.93 out of 5 average rating, 120 reviews
Guest favorite
Home in Earleville
Cozy 4 BR 3 BA Near Chesapeake City
Apr 20 – 27
$226 per night
4.91 out of 5 average rating, 151 reviews
Guest favorite
Apartment in Rising Sun
Cross Keys Tavern
Nov 9 – 16
$125 per night
4.97 out of 5 average rating, 196 reviews
Guest favorite
Cottage in Chesapeake City
Bohemia Bungalow
Dec 5 – 12
$200 per night
5.0 out of 5 average rating, 52 reviews
Guest favorite
Apartment in Chesapeake City
hygge haven: hygge= happy + cozy
Jun 29 – Jul 6
$141 per night
4.95 out of 5 average rating, 61 reviews
Guest favorite
Home in Chesapeake City
Charming, updated home in Historic Chesapeake City
Mar 29 – Apr 5
$312 per night
5.0 out of 5 average rating, 27 reviews
Guest favorite
Home in Chesapeake City
The Ferry Slip House
Aug 28 – Sep 4
$370 per night
4.94 out of 5 average rating, 16 reviews
Guest favorite
Home in Chesapeake City
Chesapeake City Charm at the Boho House!
Sep 8 – 15
$420 per night
5.0 out of 5 average rating, 37 reviews

Other great vacation rentals in Chesapeake City

Guest favorite
Cottage in Charlestown
Long Beach Cottage, (romantic couple’s getaway)
Aug 18 – 25
$531 per night
4.97 out of 5 average rating, 33 reviews
Guest favorite
Home in Chesapeake City
HOOK WINE & SINKER sleeps 14 w/ Boat Slip and Inn
Dec 24 – 31
$733 per night
4.92 out of 5 average rating, 25 reviews
Guest favorite
Cottage in Earleville
The Bohemia Charmer
Mar 12 – 19
$192 per night
4.98 out of 5 average rating, 54 reviews
Guest favorite
Home in Elkton
Waterfront Retreat for Weekends and More!
Apr 14 – 21
$290 per night
4.89 out of 5 average rating, 89 reviews
Guest favorite
Guesthouse in Elkton
Countryside~Stable House~Open Studio~Perfect for 2
Nov 7 – 14
$137 per night
4.93 out of 5 average rating, 70 reviews
Guest favorite
Home in Elkton
Waterfront Sunset River Cottage -perfect getaway
Jul 24 – 31
$294 per night
4.97 out of 5 average rating, 29 reviews
Guest favorite
Place to stay in Airville
~NEW~Waterfront Log Cabin with Hot Tub
Nov 19 – 26
$231 per night
4.96 out of 5 average rating, 54 reviews
Guest favorite
Farm stay in Lincoln University
Pyle Cottage circa 1750
Nov 9 – 16
$152 per night
4.96 out of 5 average rating, 50 reviews
Guest favorite
Home in Elkton
Elk River Cottage
May 13 – 20
$220 per night
5.0 out of 5 average rating, 23 reviews
Guest favorite
Cottage in Earleville
The Cottage at Crystal
Nov 20 – 27
$135 per night
4.94 out of 5 average rating, 35 reviews
Guest favorite
Guesthouse in Elk Mills
Private Country Guesthouse Getaway Minutes from UD
Aug 14 – 21
$114 per night
5.0 out of 5 average rating, 31 reviews
Guest favorite
Home in Newark
2 BR/1 BA/Office University of DE
Jul 6 – 13
$124 per night
4.97 out of 5 average rating, 71 reviews

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

$100 before taxes and fees

Destinations to explore

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