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 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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 $403 total
includes taxes & fees
Oct 5 - Oct 6
Historic Chesapeake City Stay
A kitchen with wooden cabinets, a microwave, a stove, and a coffee maker.

2. HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC

HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC
Chesapeake City
10.0 out of 10, Exceptional, (2 reviews)
"A charming cottage with an amazing backyard overlooking the canal. Communication was exceptional."
United States
Deb D.
The price is CA $205
CA $417 total
includes taxes & fees
Oct 7 - Oct 8
HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC
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 18 - Oct 19
Bohemia Manor Farm
A wooden cabin with a porch, surrounded by dense forest.

4. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (49 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 14 - Oct 15
Country Get Away Studio Apartment
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5. 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.
The price is CA $404
CA $653 total
includes taxes & fees
Oct 8 - Oct 9
Sunset River Shack -amazing waterfront view
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 CA $269
CA $334 total
includes taxes & fees
Oct 5 - Oct 6
Nature's Haven Tiny Home
A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

7. 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 $356
CA $419 total
includes taxes & fees
Oct 7 - Oct 8
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
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 $344 total
includes taxes & fees
Oct 5 - Oct 6
Tiny Home Tranquil Oasis
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

9. 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 $221
CA $522 total
includes taxes & fees
Oct 13 - Oct 14
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
A two-story residential building with a stone facade, a large front lawn, and a driveway.

10. 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 $508 total
includes taxes & fees
Oct 5 - Oct 6
Elegant Family Stay • Quiet Neighborhood • Comfort
A residential house with a brick exterior, a dark roof, and a front porch with a bench.

11. 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 $260 total
includes taxes & fees
Oct 5 - Oct 6
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.

12. 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 $180
CA $271 total
includes taxes & fees
Oct 6 - Oct 7
Cozy 1-bedroom apartment in Lincoln University
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

13. 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, (28 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 5 - Oct 6
Guest Suite for up to 2 in a Victorian on the Chester River
A covered outdoor seating area with a fire pit, wicker furniture, and a Netflix sign.

14. 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 $208
CA $513 total
includes taxes & fees
Oct 26 - Oct 27
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
A room with a large sliding glass door leading to a balcony with a view of the sea and a wooden deck.

15. Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (8 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
The price is CA $523
CA $799 total
includes taxes & fees
Oct 22 - Oct 23
Long Beach Cottage, (romantic couple’s getaway)
A home theater room with a curved seating area, a large flat-screen TV, and a carpeted floor.

16. 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 $255
CA $589 total
includes taxes & fees
Oct 5 - Oct 6
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

17. 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 $366
CA $750 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.

18. 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)
"We love this townhouse, close to everything!"
United States
Judy P.
The price is CA $180
CA $293 total
includes taxes & fees
Oct 5 - Oct 6
New Construction townhome close to everything downtown w/transparent pricing
A beach with a water tower, beach umbrellas, and a hotel in the background.

19. Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
The price is CA $230
CA $284 total
includes taxes & fees
Oct 25 - Oct 26
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Outdoor dining

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 CA $244
CA $278 total
includes taxes & fees
Oct 12 - Oct 13
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

Great Wolf Lodge Perryville

Great Wolf Lodge Perryville

10/10 Excellent
"I loved everything very nice clean and they were very kind"
Beriuska 1-night trip
Posted 9 hours ago
Great Wolf Lodge Perryville

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 $159 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.