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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chesapeake City vacation rentals

A living room with a sofa, a coffee table, and a patterned rug. There is a window with curtains, a door, and a small table with chairs.

1. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (30 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."
United States
Martha J.
The price is ￥17,097
￥44,133 total
includes taxes & fees
Oct 15 - Oct 16
Historic Chesapeake City Stay
A bedroom with a single bed, a wooden wardrobe, and a ceiling light.

2. Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
Chesapeake City
9.2 out of 10, Wonderful, (5 reviews)
The price is ￥22,797
￥46,148 total
includes taxes & fees
Oct 21 - Oct 22
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
A bunk bed room with white bedding and blue throw blankets.

3. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is ￥52,970
￥56,148 total
includes taxes & fees
Oct 26 - Oct 27
Bohemia Manor Farm
A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

4. 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
9.8 out of 10, Exceptional, (6 reviews)
"My boyfriend and I had a fantastic night on the yacht. We arrived right on time and found the AC and the lights on and ready for our arrival. I sunbathed on the front of the yacht and danced on the back after dinner at Grain H2O. The restaurant is located at the top of the hill on the marina . There was a band and we could hear the music from the boat. The marina was clean and everyone is friendly. At night it was very peaceful and easy to fall asleep. The morning we enjoyed our last couple of...
United States
Karen
The price is ￥39,578
￥47,058 total
includes taxes & fees
Oct 14 - Oct 15
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
A wooden cabin with a porch, surrounded by dense forest.

5. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (50 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is ￥11,082
￥17,620 total
includes taxes & fees
Oct 22 - Oct 23
Country Get Away Studio Apartment
A covered deck area with a grill and outdoor seating.

6. 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 ￥29,921
￥37,126 total
includes taxes & fees
Oct 13 - Oct 14
Nature's Haven Tiny Home
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

7. 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
9.8 out of 10, Exceptional, (6 reviews)
"Nothing fancy but extremely functional! House was clean, had what we needed in kitchen, beds were comfy. Would highly recommend!"
United States
Shana G.
The price is ￥27,071
￥61,250 total
includes taxes & fees
Oct 20 - Oct 21
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Terrace/patio

8. Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (2 reviews)
"This was a stop over on our way to the beach- it was a convenient comfy space for our family."
United States
Erin C.
The price is ￥29,921
￥42,017 total
includes taxes & fees
Oct 13 - Oct 14
Tiny Home Tranquil Oasis
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

9. 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, (29 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 ￥10,765
￥19,801 total
includes taxes & fees
Oct 19 - Oct 20
Guest Suite for up to 2 in a Victorian on the Chester River
A residential house with a brick exterior, a dark roof, and a front porch with a bench.

10. 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, (14 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is ￥22,005
￥28,863 total
includes taxes & fees
Oct 13 - Oct 14
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
A compact kitchen with dark cabinets, a stainless steel refrigerator, a microwave, and a stove.

11. Cozy 1-bedroom apartment in Lincoln University

Cozy 1-bedroom apartment in Lincoln University
Lincoln University
10.0 out of 10, Exceptional, (2 reviews)
"My girlfriend and I were in town for a wedding and the VRBO was perfect. Great privacy, lovely decor, and comfortable bed. A full use kitchen was great to have. Cheech (the pig!!) was so friendly and the host even dropped off carrots for us to feed him. The host responded to every question in a timely manner and check in and check out were painless."
United States
Zachary Z.
The price is ￥20,090
￥30,217 total
includes taxes & fees
Oct 14 - Oct 15
Cozy 1-bedroom apartment in Lincoln University
A two-story residential building with a stone facade, a large front lawn, and a driveway.

12. Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful well kept property with lots of room to relax."
United States
Daniel J.
The price is ￥39,894
￥56,095 total
includes taxes & fees
Oct 13 - Oct 14
Elegant Family Stay • Quiet Neighborhood • Comfort
A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

13. 5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (163 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is ￥39,324
￥81,621 total
includes taxes & fees
Oct 13 - Oct 14
5-bedroom vacation home 5 minutes from historic Charlestown
A garden with a fountain, surrounded by lush greenery and flowering plants.

14. 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, (30 reviews)
"We love this townhouse, close to everything!"
United States
Judy P.
The price is ￥16,813
￥28,968 total
includes taxes & fees
Oct 19 - Oct 20
New Construction townhome close to everything downtown w/transparent pricing
A covered outdoor seating area with a fire pit, wicker furniture, and a Netflix sign.

15. Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Newark
9.8 out of 10, Exceptional, (7 reviews)
"Enjoyed our stay."
United States
Erik H.
The price is ￥24,449
￥58,486 total
includes taxes & fees
Nov 2 - Nov 3
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
A living room with teal walls, a black sofa, a patterned rug, a flat-screen TV on a wooden stand, and a painting on the wall.

16. Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.6 out of 10, Good, (19 reviews)
"Nice place"
United States
christine
The price is ￥11,256
￥15,288 total
includes taxes & fees
Oct 20 - Oct 21
Charming 2-bedroom house in Aberdeen with WiFi and AC
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

17. 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, (57 reviews)
"Unique charming place to relax."
United States
Nimia N.
The price is ￥27,783
￥33,477 total
includes taxes & fees
Oct 13 - Oct 14
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
A living room with a dark grey sectional sofa, a round wooden coffee table, and a small side table.

18. Cozy, Comfortable, Pet Friendly Home with a fenced in private yard

Cozy, Comfortable, Pet Friendly Home with a fenced in private yard
Wilmington
10.0 out of 10, Exceptional, (1 review)
"Spotless and so cozy. It was like coming home. Our host was communicative and kind. We’d love to come back."
United States
Chris D.
The price is ￥23,509
￥29,632 total
includes taxes & fees
Oct 19 - Oct 20
Cozy, Comfortable, Pet Friendly Home with a fenced in private yard
A patio with a table and chairs, an umbrella, and a view of a grassy yard and trees.

19. Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
9.0 out of 10, Wonderful, (4 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 ￥18,364
￥32,514 total
includes taxes & fees
Nov 9 - Nov 10
Amish Countryside Escape at Forest Edge Farm
Private kitchen

20. 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, (3 reviews)
"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 ￥27,071
￥30,931 total
includes taxes & fees
Oct 13 - Oct 14
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
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 Select Newark Christiana Mall

Sonesta Select Newark Christiana Mall

10/10 Excellent
"Room was very clean & comfortable."
Ralph C 3-night trip
Posted 2 hours ago
Sonesta Select Newark Christiana Mall

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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  • 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 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?

Bohemia Manor Farm: Visitors like this Chesapeake City vacation home rental. It comes with free WiFi so you can feel at home during your trip. Kitchen amenities include a full-sized fridge, a stovetop, and kitchenware. Our travelers also rate Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows as a favorite home for rent in Chesapeake City.

How many vacation rentals are there in Chesapeake City?

With 11 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.