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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Chesapeake City vacation rentals

A riverside dock with boats, a covered seating area, and a bridge in the background.

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 CA $154
CA $400 total
includes taxes & fees
Oct 15 - Oct 16
Historic Chesapeake City Stay
A kitchen with wooden cabinets, a stainless steel refrigerator, a sink, and a dining area with a chair and table.

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
10.0 out of 10, Exceptional, (3 reviews)
"A charming cottage with an amazing backyard overlooking the canal. Communication was exceptional."
United States
Deb D.
The price is CA $257
CA $482 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $441
CA $467 total
includes taxes & fees
Oct 27 - Oct 28
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 CA $355
CA $418 total
includes taxes & fees
Oct 17 - Oct 18
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 CA $100
CA $159 total
includes taxes & fees
Oct 15 - Oct 16
Country Get Away Studio Apartment
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6. Sunset River Shack -amazing waterfront view

Sunset River Shack -amazing waterfront view
Elkton
9.6 out of 10, Exceptional, (14 reviews)
"This is our 3rd year in a row renting Jessica’s property. We truly enjoyed our stay. Highly recommend staying here. Beautiful backyard looking out to the bay! It has been a highlight staying here visiting for UD graduations. We hope to be back!"
United States
Natasha G.
Sunset River Shack -amazing waterfront view
A covered deck area with a grill and outdoor seating.

7. 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 CA $269
CA $332 total
includes taxes & fees
Oct 11 - Oct 12
Nature's Haven Tiny Home
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 CA $269
CA $342 total
includes taxes & fees
Oct 9 - Oct 10
Tiny Home Tranquil Oasis
A two-story residential building with a stone facade, a large front lawn, and a driveway.

9. 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 CA $359
CA $504 total
includes taxes & fees
Oct 12 - Oct 13
Elegant Family Stay • Quiet Neighborhood • Comfort
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

10. 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 CA $245
CA $556 total
includes taxes & fees
Oct 13 - Oct 14
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
A covered outdoor seating area with a fire pit, wicker furniture, and a Netflix sign.

11. 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 CA $243
CA $550 total
includes taxes & fees
Nov 2 - Nov 3
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

12. 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 CA $360
CA $748 total
includes taxes & fees
Oct 13 - Oct 14
5-bedroom vacation home 5 minutes from historic Charlestown
A residential house with a brick exterior, a dark roof, and a front porch with a bench.

13. 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, (13 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is CA $198
CA $261 total
includes taxes & fees
Oct 23 - Oct 24
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
A beach with a water tower, beach umbrellas, and a hotel in the background.

14. Free Breakfast. Pool. 10 Min Drive to the University of Delaware!

Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
Newark
10.0 out of 10, Exceptional, (1 review)
"Clean rooms close to all things we needed breakfast was good and plentiful wish the afternoon buffet was available would use this place again"
United States
Susan H.
The price is CA $316
CA $394 total
includes taxes & fees
Oct 29 - Oct 30
Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
A home theater room with a curved seating area, a large flat-screen TV, and a carpeted floor.

15. Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
New Castle
8.2 out of 10, Very good, (21 reviews)
"I’ve stayed in much better locations."
United States
Grant H.
The price is CA $269
CA $602 total
includes taxes & fees
Oct 11 - Oct 12
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

16. 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)
"Very unique property, with lots of history. We enjoyed our short stay."
United States
Terry R S.
The price is CA $250
CA $300 total
includes taxes & fees
Oct 11 - Oct 12
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
A compact kitchen with dark cabinets, a stainless steel refrigerator, a microwave, and a stove.

17. 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 CA $200
CA $294 total
includes taxes & fees
Nov 2 - Nov 3
Cozy 1-bedroom apartment in Lincoln University
Interior

18. 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 CA $243
CA $279 total
includes taxes & fees
Oct 20 - Oct 21
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
A two-story house with a deck, a barbecue grill, and a covered patio area.

19. Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (24 reviews)
"Great place to get away! Peaceful, serene with amenities to boast!"
United States
Arthur B.
The price is CA $353
CA $778 total
includes taxes & fees
Oct 19 - Oct 20
Thunder Hill Retreat - Spacious/Deck/Hot tub
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

20. 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 CA $97
CA $178 total
includes taxes & fees
Oct 19 - Oct 20
Guest Suite for up to 2 in a Victorian on the Chester River
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

Hyatt Place Newark - Main Street

Hyatt Place Newark - Main Street

10/10 Excellent
"My son and I had a wonderful stay while we were there for his grad school interviews at the University of Deleware DPT program. We would absolutely stay again when we return."
Kristin 1-night trip
Posted 11 hours ago
Hyatt Place Newark - Main Street

Find out more about Chesapeake City

Everything you need to know about Chesapeake City vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake City vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake City vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesapeake City vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake City. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake City vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake City vacation rentals we have selected for you start as low as CA $218 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesapeake City rentals

At Expedia, we put the best Chesapeake City vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesapeake City rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake City vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake City. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.