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Top Holiday Rentals in Chesapeake City

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

9.6 out of 10, Exceptional, (5)
"Exactly as advertised and Brad was very helpful/responsive!"
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

Historic Chesapeake City Stay

9.2 out of 10, Wonderful, (9)
"Always a nice get away…."
The price is £208
includes taxes & fees
30 Jun - 1 Jul
Historic Chesapeake City Stay

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

10.0 out of 10, Exceptional, (53)
"The house is roomy and was clean and well stocked."
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

Waterfront Cottage on the C&D Canal!

8.0 out of 10, Very good, (5)
"Fantastic location "
Waterfront Cottage on the C&D Canal!

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (263)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (50)
"This was our second time staying at the property with our two kids and the accommodations continue to impress. We will happily stay again."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

10.0 out of 10, Exceptional, (2)
"Great, cozy, quiet little spot! Perfect for 4 adults and a baby. My 1.5 year old loved exploring the deck with an amazing water view, and gained lots of confidence navigating the little steps throughout the house and worked on her balance. Kitchen was well appointed and suited our needs. Would stay here again!"
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Luxury Waterfront Home Built for Entertaining!

2.0 out of 10, (1)
The price is £668
includes taxes & fees
29 Jun - 30 Jun
Luxury Waterfront Home Built for Entertaining!

Charming 2-bedroom cabin close to Fair Hill on horse farm

10.0 out of 10, Exceptional, (1)
"Good experience"
The price is £406
includes taxes & fees
29 Jun - 30 Jun
Charming 2-bedroom cabin close to Fair Hill on horse farm

Chesapeake City Pool Retreat – Waterfront Stay in the Woods

9.0 out of 10, Wonderful, (6)
"Great communication, easy to access, accommodations true to listing. Spacious, renovated living space. Great outdoor pool."
Chesapeake City Pool Retreat – Waterfront Stay in the Woods

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

9.2 out of 10, Wonderful, (174)
"We throughly enjoyed our stay here! The house was absolutely spotless, check in was easy, and kitchen is well appointed. The views are beautiful too. Brian was super responsive and answered all of my questions. Can’t wait to go back! "
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (19)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
Tip Of The Town Fresh and New 3 Bedroom Nest

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

9.8 out of 10, Exceptional, (40)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (25)
"We were a group of all ages and everyone had a good time. It was quiet, peaceful and very relaxing. We were there for a baseball tournament and would definitely stay again."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (20)
"Everything about the place was great! Easy check in and super clean and homey feeling spot. Would recommend to anyone looking for a quiet and comfy place on the eastern shore. We will definitely be booking again if we come back to the area!"
The price is £279
includes taxes & fees
1 Jul - 2 Jul
Waterfront Retreat with Private Dock and Beach

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

10.0 out of 10, Exceptional, (83)
"My friends and I wanted a relaxing getaway with beautiful views and that is exactly what we got. Sue was so wonderful and when there was a massive snowstorm expected to come on our arrival date, she offered to change the dates to accommodate us. Everything was wonderful and we had the best stay."
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown

9.8 out of 10, Exceptional, (88)
"In the area for a wedding. This was a great place for the family to gather in between events. Communication with the owners is top notch. We highly recommend it. "
Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (161)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (138)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is £455
includes taxes & fees
1 Jul - 2 Jul
5-bedroom vacation home 5 minutes from historic Charlestown

Nature's Haven Tiny Home

10.0 out of 10, Exceptional, (2)
"Enjoyed"
The price is £175
includes taxes & fees
29 Jun - 30 Jun
Nature's Haven Tiny Home
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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Frequently asked questions

Can I find holiday rentals in Chesapeake City?

Yes, there are holiday rentals close to the most popular sights in Chesapeake City, or you can select a more secluded option if you're looking for a relaxing stay. Chesapeake City is known for its restaurants and waterfront. Make sure you have time to check out the museums while you're in the area.

What are some of the best holiday rentals that Chesapeake City has to offer?

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!: This highly rated holiday home rental in Chesapeake City is located on a river, and has a patio, an arcade/games room and air conditioning to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chesapeake City?

With 10 Expedia holiday rentals, you're guaranteed to find just the right place for your Chesapeake City stay.

What can I see and do in Chesapeake City?

Cultural attractions include C and D Canal Museum, whereas Canal Wildlife Management Area is a spot to enjoy nature. While here, Chesapeake Inn Marina and Bohemia Vista Marina are other places worth a visit.

What are holiday rentals like in Chesapeake City?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesapeake City. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip.