Chesapeake City Holiday Rentals

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan
In four months
30 Jan - 1 Feb

Holiday Rentals in Chesapeake City

Historic Chesapeake City Stay
Marina

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (15)
"Always a nice get away…."
The price is HK$841
HK$2,170 total
includes taxes & fees
13 Oct - 14 Oct
Historic Chesapeake City Stay
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Marina

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

9.8 out of 10, Exceptional, (6)
"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. "
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Exterior

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

10.0 out of 10, Exceptional, (56)
"Amazing weekend on the river with a fantastic house. "
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Smart TV, books

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

10.0 out of 10, Exceptional, (25)
"Very nice cottage, as advertised"
The price is HK$1,366
HK$1,646 total
includes taxes & fees
20 Oct - 21 Oct
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Chesapeake Bay House with Dock & Private Beach
Outdoor dining

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (173)
"Nice property. Large enough for 13. Plenty of space to spread out "
Chesapeake Bay House with Dock & Private Beach
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
Fridge, microwave, oven, stovetop

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

2.0 out of 10, (2)
"Never heard from host. Expedia had to cancel reservation."
The price is HK$778
HK$969 total
includes taxes & fees
14 Oct - 15 Oct
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
Waterfront house with amazing views. Top of the Chesapeake
Terrace/patio

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (100)
"The river house has an absolutely amazing view! My kids were thrilled with the chance to fish off a very long dock and even get their feet in the water on a small beach below the house (when the tide was out). Overall, the house was perfect and just big enough for our large family of seven. Matt was very responsive to a few questions I had and was a wonderful host! "
Waterfront house with amazing views. Top of the Chesapeake
Nancy’s Touch, A Waterfront Paradise!
Terrace/patio

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (171)
"The house was quaint, scenic, well maintained and in a great location with a breathtaking view of the bay. We had a wonderful time there, would definitely recommend it and would love to revisit again. "
Nancy’s Touch, A Waterfront Paradise!
Beachfront Sunsets on the Water at Oakwood Beach
On the beach, sun-loungers, beach towels

Beachfront Sunsets on the Water at Oakwood Beach

10.0 out of 10, Exceptional, (42)
"Stayed here for my daughter’s softball tournament. The house is adorable and had plenty of everything that we needed. "
Beachfront Sunsets on the Water at Oakwood Beach
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Smart TV, books

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (57)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Charming 2-bedroom cabin close to Fair Hill on horse farm
Interior

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

9.6 out of 10, Exceptional, (8)
"Good experience"
Charming 2-bedroom cabin close to Fair Hill on horse farm
Stunning waterfront villa with indoor pool and kids swing set and play area.
Spa

Stunning waterfront villa with indoor pool and kids swing set and play area.

9.8 out of 10, Exceptional, (19)
"Wonderful location, lots to do, close to Chesapeake City, excellent host"
Stunning waterfront villa with indoor pool and kids swing set and play area.
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (50)
"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
Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!
Terrace/patio

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

10.0 out of 10, Exceptional, (3)
"Wonderful property. The owners went above and beyond to make us feel at home and to make a special celebration more memorable. The hose has charm, both inside and out. We enjoyed the four nights and will definitely be staying again. "
Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Interior

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

9.8 out of 10, Exceptional, (19)
"Clean and comfortable stay in quiet neighborhood! Communication with the host was pleasant and prompt."
The price is HK$1,506
HK$2,593 total
includes taxes & fees
13 Oct - 14 Oct
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Waterfront Retreat with Private Dock and Beach
Beach

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (24)
"Quiet and relaxing spot right on the water"
The price is HK$1,362
HK$2,424 total
includes taxes & fees
12 Oct - 13 Oct
Waterfront Retreat with Private Dock and Beach
5-bedroom vacation home 5 minutes from historic Charlestown
Sun-loungers, beach towels

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (145)
"Nice property with amazing views. Celebrated college graduation with family. Young ones had fun looking at ducks. Plenty of room for a large group."
The price is HK$2,515
HK$4,678 total
includes taxes & fees
15 Oct - 16 Oct
5-bedroom vacation home 5 minutes from historic Charlestown
Tiny Home Tranquil Oasis
Fridge, microwave, oven, stovetop

Tiny Home Tranquil Oasis

The price is HK$1,471
HK$1,872 total
includes taxes & fees
12 Oct - 13 Oct
Tiny Home Tranquil Oasis
Summer Rustic Camping with AC and King Bed
1 bedroom

Summer Rustic Camping with AC and King Bed

9.6 out of 10, Exceptional, (5)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
The price is HK$779
HK$1,419 total
includes taxes & fees
3 Nov - 4 Nov
Summer Rustic Camping with AC and King Bed
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Exterior

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

10.0 out of 10, Exceptional, (9)
"My kids and I absolutely loved our stay at the Outlook! So peaceful and relaxing. We spent a lot of time walking around the trails spotting deer and toads. We did a good amount of fishing on the dock, catching catfish. I hope to stay here again in the future."
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
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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Top Chesapeake City Hotel Reviews

Baymont by Wyndham Newark at University of Delaware

Baymont by Wyndham Newark at University of Delaware

10/10 Excellent
"Well woorth the price. THE most important thing in a hotel room: shower....water pressure was awesome!🙂"
Chris 1-night trip
Posted 2 days ago
Baymont by Wyndham Newark at University of Delaware

Find out more about Chesapeake City

Search for holiday rentals in Chesapeake City on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesapeake City using one of the methods below:

  • View our selection of featured holiday rentals in Chesapeake City
  • Use the map to find apartments and other holiday homes in the Chesapeake City neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesapeake City while they last

Look no further and take a look at our great range of rental properties in Chesapeake City!

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?

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows : This highly rated holiday home rental in Chesapeake City is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 7 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 Bay Yacht Harbour 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.