Chesapeake City, MD

Travel Guide

Aerial panorama of Chesapeake City Maryland historic fishing town on the Chesapeake Delaware canal with private boats docked in the marina and the Chesapeake City Bridge over the back creek
Autumn Sunset at the Chesapeake City Bridge, Maryland, USA, Chesapeake City, Maryland
Homes on the Chesapeake Bay, in North Beach, Maryland. Sunny day, blue sky.
Hemingway Pier Next to the Bay Bridge outside of Annapolis Maryland at Sunset
chesapeake bay bridge with calm inlet at sunset
Historic Chesapeake City Stay

Historic Chesapeake City Stay

Chesapeake City MD
$265 nightly
The price is $281 total per night from Jun 10 to Jun 11
$281 total
Jun 10 - Jun 11
Total with taxes and fees
Stay at this cabin in Chesapeake City. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Chesapeake City Bridge and The Pell Gardens are ...
9/10 Wonderful! (21 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."

Reviewed on Apr 26, 2026

Historic Chesapeake City Stay
Quality Inn Newark - Wilmington

Quality Inn Newark - Wilmington

2.5 out of 5
65 Geoffrey Dr Newark DE
$71 nightly
The price is $78 total per night from Jun 29 to Jun 30
$78 total
Jun 29 - Jun 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Newark. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Christiana Mall and Hale-Byrnes ...
5.8/10 (1,006 reviews)
"It was surrounded by good restaurants and a very clean area"

Reviewed on Jun 1, 2026

Quality Inn Newark - Wilmington
Great Wolf Lodge Perryville

Great Wolf Lodge Perryville

2 out of 5
1240 Chesapeke Overlook Parkway Perryville MD
$179 nightly
The price is $200 total per night from Jun 2 to Jun 3
$200 total
Jun 2 - Jun 3
Total with taxes and fees
Stay at this hotel in Perryville. Enjoy free WiFi, 4 restaurants, and water park access (surcharge). Popular attractions Hollywood Casino and Garrett Island ...
8.8/10 Excellent! (225 reviews)
"La pace súper bien y los niñas mucho más gracias"

Reviewed on May 31, 2026

Great Wolf Lodge Perryville
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

Chesapeake City MD
Stay at this vacation home in Chesapeake City. Enjoy free WiFi, laundry facilities, and patios. Popular attractions South Chesapeake City Historic District and ...
9.8/10 Exceptional! (6 reviews)
Large Beautiful Home
"We rented Hook, Wine & Sinker for our family to stay in during the weekend of our son's wedding in Chesapeake City, MD. The home is absolutely beautiful, very clean, spacious, and one of the best rentals that I've stayed in with VRBO."

Reviewed on Jun 16, 2025

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Historic Chesapeake City Stay

Historic Chesapeake City Stay

Chesapeake City MD
Stay at this cabin in Chesapeake City. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Chesapeake City Bridge and The Pell Gardens are ...
9/10 Wonderful! (21 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."

Reviewed on Apr 26, 2026

Historic Chesapeake City Stay
Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

Chesapeake City MD
Stay at this vacation home in Chesapeake City. Enjoy private pools, a fitness center, and a garden. Popular attractions Ferryslip Road Park and South Chesapeake ...
10/10 Exceptional! (4 reviews)
"This property was simply amazing & the owners were so kind. The town is so nice to explore and is just down the street. Perfect retreat to unwind and spend time with friends."

Reviewed on May 3, 2026

Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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