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

Chesapeake City Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Chesapeake City holiday 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, (31 reviews)
"This is a great place, to feel comfortable. Exactly as advertised Just around the corner from Schaeffers."
United States
Janice H.
The price is AU$393
includes taxes & fees
25 Oct - 26 Oct
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
9.4 out of 10, Exceptional, (6 reviews)
"Everything was as advertised. Property is not new, but everything was clean and well cared for. Evenings on the water were peaceful and relaxing. We enjoyed our stay and definitely intend to return."
United States
John
The price is AU$423
includes taxes & fees
18 Nov - 19 Nov
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
A brick house with a front porch, a chimney, and a well-maintained lawn.

3. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is AU$467
includes taxes & fees
28 Oct - 29 Oct
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, (51 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is AU$161
includes taxes & fees
29 Oct - 30 Oct
Country Get Away Studio Apartment
A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

5. 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, (7 reviews)
"The host was great and easy to communicate with. It was a first time experience staying on a boat for my family and I and we really enjoyed it. Perfect for a few nights to visit family nearby."
United States
Jessica
The price is AU$419
includes taxes & fees
25 Oct - 26 Oct
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
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 AU$336
includes taxes & fees
25 Oct - 26 Oct
Nature's Haven Tiny Home
Terrace/patio

7. 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 AU$370
includes taxes & fees
25 Oct - 26 Oct
Tiny Home Tranquil Oasis
A modern kitchen with dark cabinets, a stainless steel refrigerator, and a wooden floor.

8. 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 AU$536
includes taxes & fees
27 Oct - 28 Oct
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.

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 AU$492
includes taxes & fees
26 Oct - 27 Oct
Elegant Family Stay • Quiet Neighborhood • Comfort
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, (15 reviews)
"It is in a lovely neighborhood and the hosts were very welcoming of us and my 2 dogs. We were all very comfortable."
United States
Barb
The price is AU$261
includes taxes & fees
25 Oct - 26 Oct
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

11. 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, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is AU$181
includes taxes & fees
2 Nov - 3 Nov
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.

12. 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 AU$489
includes taxes & fees
1 Nov - 2 Nov
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
A spacious room with a large sliding glass door leading to a deck, a dining area with a white table, and a cozy seating area with a view of the water.

13. Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Charlestown
10.0 out of 10, Exceptional, (5 reviews)
"Had a wonderful stay. They really thought of everything. Had everything we could have possibly needed. It's a beautiful place and it was very clean and cared for."
United States
Laura K.
The price is AU$626
includes taxes & fees
26 Oct - 27 Oct
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
A compact kitchen with dark cabinets, a stainless steel refrigerator, a microwave, and a stove.

14. 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 AU$297
includes taxes & fees
3 Nov - 4 Nov
Cozy 1-bedroom apartment in Lincoln University
A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

15. 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, (165 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is AU$700
includes taxes & fees
27 Oct - 28 Oct
5-bedroom vacation home 5 minutes from historic Charlestown
A wooden deck with lounge chairs and a dock extending into calm water.

16. Waterfront house with amazing views. Top of the Chesapeake

Waterfront house with amazing views. Top of the Chesapeake
Perryville
10.0 out of 10, Exceptional, (115 reviews)
"Matt was a wonderful host whi responded to my texts very quickly. The house was perfect for a quick getaway celebrating my dad's retirement. Fishing from the dock was a plus, and everyone caught fish, even some "keepers"."
United States
Joe M.
The price is AU$752
includes taxes & fees
28 Oct - 29 Oct
Waterfront house with amazing views. Top of the Chesapeake
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.

17. 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 AU$138
includes taxes & fees
2 Nov - 3 Nov
Charming 2-bedroom house in Aberdeen with WiFi and AC
A home theater room with a curved seating area, a large flat-screen TV, and a carpeted floor.

18. 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 AU$546
includes taxes & fees
25 Oct - 26 Oct
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
A garden with a fountain, surrounded by lush greenery and flowering plants.

19. 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 AU$273
includes taxes & fees
25 Oct - 26 Oct
New Construction townhome close to everything downtown w/transparent pricing
A patio with a table and chairs, an umbrella, and a view of a grassy yard and trees.

20. 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 AU$324
includes taxes & fees
16 Nov - 17 Nov
Amish Countryside Escape at Forest Edge Farm
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

Red Roof Inn & Suites Newark - University

Red Roof Inn & Suites Newark - University

10/10 Excellent
"Great"
Misty 1-night trip
Posted 15 hours ago
Red Roof Inn & Suites Newark - University

Find out more about Chesapeake City

Everything you need to know about Chesapeake City holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake City holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesapeake City holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake City holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake City holiday rentals we have selected for you start as low as AU$161 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesapeake City rentals

At Expedia, we put the best Chesapeake City holiday 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 holiday.

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 holiday rentals in Chesapeake City?

Yes, there are holiday rentals close to the most popular sights in Chesapeake City, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Chesapeake City has to offer?

Bohemia Manor Farm: This highly rated holiday home rental in Chesapeake City comes with free WiFi so that you can feel at home during your trip. Kitchen amenities include a full-sized fridge, a stovetop and kitchenware. Our travellers also rate Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows as a favourite home for rent in Chesapeake City.

How many holiday rentals are there in Chesapeake City?

With 11 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Chesapeake City?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesapeake City. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip.