A river with a bridge, marina, and residential area.

Chesapeake City Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

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, (25 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is ￥17,425
￥44,979 total
includes taxes & fees
Jul 13 - Jul 14
Historic Chesapeake City Stay
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, (7 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 ￥15,029
￥28,130 total
includes taxes & fees
Jul 8 - Jul 9
Summer Rustic Camping with AC and King Bed
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, (23 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is ￥10,971
￥20,180 total
includes taxes & fees
Jul 8 - Jul 9
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Port Deposit
10.0 out of 10, Exceptional, (1 review)
"Renee & Pat were excellent hosts and we will definitely try to book again when in the area. Everything was as advertised and much more. Being pet friendly was a plus. We enjoyed two restaurants in the area while there, Lee's Landing and Old South Smokehouse, highly recommend!"
United States
Don S.
The price is ￥26,379
￥29,970 total
includes taxes & fees
Jul 8 - Jul 9
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Exterior

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
10.0 out of 10, Exceptional, (12 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is ￥19,361
￥25,995 total
includes taxes & fees
Jul 8 - Jul 9
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Terrace/patio

Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
The price is ￥30,493
￥37,674 total
includes taxes & fees
Jul 8 - Jul 9
Nature's Haven Tiny Home
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
9.8 out of 10, Exceptional, (48 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is ￥28,315
￥33,947 total
includes taxes & fees
Jul 14 - Jul 15
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Exterior

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (43 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is ￥11,294
￥17,957 total
includes taxes & fees
Jul 15 - Jul 16
Country Get Away Studio Apartment
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.8 out of 10, Good, (17 reviews)
"Nice place"
United States
christine
The price is ￥10,938
￥15,030 total
includes taxes & fees
Jul 20 - Jul 21
Charming 2-bedroom house in Aberdeen with WiFi and AC
Exterior

Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (23 reviews)
"Everything was good. Had a great time."
United States
Todd H.
The price is ￥36,578
￥84,013 total
includes taxes & fees
Jul 13 - Jul 14
Thunder Hill Retreat - Spacious/Deck/Hot tub
Property grounds

New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing
Hilltop
9.6 out of 10, Exceptional, (29 reviews)
"There were 3 of us ladies for the week. Lisa was a great host and recommendations were all perfect. We will definitely be back. Everything was clean and neat. We loved staying there. "
United States
Bonnie W.
The price is ￥21,439
￥34,395 total
includes taxes & fees
Jul 14 - Jul 15
New Construction townhome close to everything downtown w/transparent pricing
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, (23 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 ￥31,357
￥53,187 total
includes taxes & fees
Jul 8 - Jul 9
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
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 ￥19,284
￥34,283 total
includes taxes & fees
Jul 13 - Jul 14
Amish Countryside Escape at Forest Edge Farm
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, (12 reviews)
"The house was very cozy and close to my venue Jennifer was very responsive with any questions nice place to stay roomy"
United States
Liza
The price is ￥30,336
￥41,088 total
includes taxes & fees
Jul 8 - Jul 9
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Fridge, microwave, oven, stovetop

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
9.6 out of 10, Exceptional, (4 reviews)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is ￥21,877
￥55,998 total
includes taxes & fees
Jul 13 - Jul 14
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Terrace/patio

Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (1 review)
"This unit is located behind a mansion /b&b. Had what we needed, clean, easy to access and Karin was helpful."
United States
Megan M.
The price is ￥30,493
￥38,481 total
includes taxes & fees
Jul 8 - Jul 9
Tiny Home Tranquil Oasis
Interior

Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (32 reviews)
"Perfect location for that town. "
United States
Hisham M.
The price is ￥26,621
￥46,346 total
includes taxes & fees
Jul 15 - Jul 16
Private 3 room Queen Suite w/Kitchenette
Smart TV, fireplace, DVD player, books

Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group

Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
Wilmington
9.6 out of 10, Exceptional, (5 reviews)
"We very much enjoyed resting in the house between our activities. The kids loved the large room for watching a soccer match. The dining area is exceptionally nice for kids."
United States
Emily M.
The price is ￥36,737
￥70,659 total
includes taxes & fees
Jul 15 - Jul 16
Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
Interior

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Bear
The price is ￥40,335
￥47,797 total
includes taxes & fees
Jul 9 - Jul 10
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
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, (14 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is ￥32,523
￥48,044 total
includes taxes & fees
Jul 13 - Jul 14
Quarry Landing - Center of Town & River View - 3 Bedroom
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

Sonesta ES Suites Wilmington - Newark

Sonesta ES Suites Wilmington - Newark

8/10 Good
"Good breakfast and nice gym area."
Tawny 2-night trip
Posted 10 hours ago
Sonesta ES Suites Wilmington - Newark

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?

Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!: This Chesapeake City vacation home rental offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family. It offers a patio, a garden, and a hot tub so you can immerse yourself in your vacation. Other favorite homes for rent in Chesapeake City are Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows and HYDRANGEA HOUSE Waterview cozy 3-bdrm Getaway in quiet Chesapeake City AC & yard.

How many vacation rentals are there in Chesapeake City?

With 10 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 Bay Yacht Harbour 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.