Chesapeake City Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Chesapeake City vacation rentals

Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (21 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is ￥17,144
￥44,254 total
includes taxes & fees
May 18 - May 19
Historic Chesapeake City Stay
Exterior

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"Wonderful place and host, very peaceful and quiet with plenty of nature !!!"
United States
Daniel V.
The price is ￥11,112
￥17,668 total
includes taxes & fees
May 25 - May 26
Country Get Away Studio Apartment
1 bedroom, desk, WiFi, bed sheets

White Clay Creek Cottage

White Clay Creek Cottage
Newark
10.0 out of 10, Exceptional, (7 reviews)
"We needed a somewhat local place to stay while my house was sold before moving into the new house a few days later. This was the perfect spot for us. the home was nicely equipped for us and allowed our small dog to visit too. "
United States
tracy g.
The price is ￥15,715
￥31,113 total
includes taxes & fees
May 18 - May 19
White Clay Creek Cottage
Outdoor dining

Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
10.0 out of 10, Exceptional, (2 reviews)
"Property was close enough to stores and restaurants if needed. House is located in the rural area of the county (very peaceful). Property had all of the necessary kitchen utensil, pots, pans, and dishes that was needed for this trip. "
United States
jckglss6 G.
The price is ￥16,985
￥31,005 total
includes taxes & fees
May 18 - May 19
Amish Countryside Escape at Forest Edge Farm
Smart TV

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Elkton
9.8 out of 10, Exceptional, (10 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is ￥19,049
￥25,576 total
includes taxes & fees
May 18 - May 19
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Exterior

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

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
10.0 out of 10, Exceptional, (42 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is ￥27,859
￥33,569 total
includes taxes & fees
May 20 - May 21
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
1 bedroom

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.8 out of 10, Exceptional, (6 reviews)
"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."
United States
Rees L.
The price is ￥15,334
￥28,224 total
includes taxes & fees
Jun 10 - Jun 11
Summer Rustic Camping with AC and King Bed
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
8.0 out of 10, Very Good, (15 reviews)
"Met our needs. Great stay."
United States
Robert C.
The price is ￥10,715
￥14,723 total
includes taxes & fees
May 19 - May 20
Charming 2-bedroom house in Aberdeen with WiFi and AC
Exterior

Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (21 reviews)
"Good place, clean and a good location."
United States
Bernard S.
The price is ￥10,794
￥19,855 total
includes taxes & fees
May 25 - May 26
Guest Suite for up to 2 in a Victorian on the Chester River
Smart TV

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (8 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
The price is ￥23,430
￥32,577 total
includes taxes & fees
May 18 - May 19
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Smart TV

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
10.0 out of 10, Exceptional, (3 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is ￥21,430
￥53,508 total
includes taxes & fees
May 18 - May 19
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Dining

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

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Newark
9.6 out of 10, Exceptional, (21 reviews)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
The price is ￥30,716
￥51,624 total
includes taxes & fees
May 20 - May 21
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Property grounds

New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.8 out of 10, Exceptional, (27 reviews)
"Property was spacious with open kitchen/living room area and 2 bedrooms with their own baths."
United States
Mark F.
The price is ￥17,858
￥34,376 total
includes taxes & fees
May 19 - May 20
New Construction townhome close to everything downtown w/transparent pricing
Terrace/patio

Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Nature’s Haven Tiny Home worked great for us. Karin was a great communicator and we really enjoyed ourselves. "
United States
James S.
The price is ￥30,002
￥37,068 total
includes taxes & fees
May 18 - May 19
Nature's Haven Tiny Home
TV, fireplace

Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (6 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
The price is ￥54,013
￥83,056 total
includes taxes & fees
May 21 - May 22
Long Beach Cottage, (romantic couple’s getaway)
Exterior

Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (19 reviews)
"Everything was good. Had a great time."
United States
Todd H.
The price is ￥34,416
￥79,549 total
includes taxes & fees
May 19 - May 20
Thunder Hill Retreat - Spacious/Deck/Hot tub
Fridge, microwave, oven, stovetop

Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (12 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is ￥31,145
￥46,138 total
includes taxes & fees
May 21 - May 22
Quarry Landing - Center of Town & River View - 3 Bedroom
Terrace/patio

Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
The price is ￥30,002
￥37,861 total
includes taxes & fees
May 18 - May 19
Tiny Home Tranquil Oasis
Beach

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is ￥35,717
￥60,096 total
includes taxes & fees
May 28 - May 29
Waterfront Retreat with Private Dock and Beach
Property grounds

Cozy 1-bedroom bungalow in quaint Darlington with AC

Cozy 1-bedroom bungalow in quaint Darlington with AC
Darlington
10.0 out of 10, Exceptional, (2 reviews)
"very clean and cozy host was very nice . They had everything we needed for our stay. Very convenient to all local activities. Would stay there agin when in area."
United States
Jacquelyn O.
The price is ￥19,049
￥23,557 total
includes taxes & fees
May 26 - May 27
Cozy 1-bedroom bungalow in quaint Darlington with AC
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

Woodspring Suites Wilmington Riverfront

Woodspring Suites Wilmington Riverfront

10/10 Excellent
"Very quiet in our room and on our floor (#3)."
Richard 3-night trip
Posted 3 hours ago
Woodspring Suites Wilmington Riverfront

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

Frequently asked questions

Can I find vacation rentals in Chesapeake City?

Yes, you can find vacation rentals close to popular local attractions in Chesapeake City, or you can select a more secluded option if you want a relaxing place to 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 vacation rentals in Chesapeake City?

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!: This Chesapeake City vacation home rental is located on a river and has a patio, an arcade game 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 you can cook with friends or family. Another good choice for your trip to Chesapeake City is Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows .

How many vacation rentals are there in Chesapeake City?

With 8 Expedia vacation rentals, you're sure 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 vacation rentals like in Chesapeake City?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Chesapeake City. Vacation rentals feature extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for small groups.