Chesapeake City Holiday Rentals

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Check prices for these dates

Tonight
26 Nov - 27 Nov
Tomorrow
27 Nov - 28 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Holiday Rentals in Chesapeake City

Marina
Historic Chesapeake City Stay

Historic Chesapeake City Stay

Chesapeake City
9.0 out of 10, Wonderful, (18)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
The price is HK$840
HK$2,168 total
includes taxes & fees
1 Dec - 2 Dec
Historic Chesapeake City Stay
Fridge, microwave, oven, stovetop
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

2.0 star property
Chesapeake City
9.4 out of 10, Exceptional, (3)
"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "
United States
Wayne
The price is HK$1,400
HK$2,605 total
includes taxes & fees
27 Nov - 28 Nov
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
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
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is HK$529
HK$973 total
includes taxes & fees
2 Dec - 3 Dec
Guest Suite for up to 2 in a Victorian on the Chester River
Property grounds
Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment

Elkton
9.8 out of 10, Exceptional, (40)
"Perfect in every way… a great stay"
United States
Robert B.
The price is HK$544
HK$865 total
includes taxes & fees
9 Dec - 10 Dec
Country Get Away 1 Bedroom Apartment
1 bedroom
Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed

Elkton
9.6 out of 10, Exceptional, (5)
"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 HK$582
HK$1,214 total
includes taxes & fees
7 Dec - 8 Dec
Summer Rustic Camping with AC and King Bed
Smart TV
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

2.0 star property
Elkton
9.8 out of 10, Exceptional, (6)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is HK$933
HK$1,253 total
includes taxes & fees
4 Dec - 5 Dec
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Fridge, microwave, oven, stovetop
Cozy loft above ink shop

Cozy loft above ink shop

Bear
9.6 out of 10, Exceptional, (4)
"Second time staying in as many weeks. Place is spot on for what we needed for our quick trips. Close to food and shopping as well as easy access to highways if needed."
United States
Jeffrey R.
The price is HK$644
HK$828 total
includes taxes & fees
1 Dec - 2 Dec
Cozy loft above ink shop
Private kitchen
Room #2 in Elkton, MD – Easy Access to I-95

Room #2 in Elkton, MD – Easy Access to I-95

2.0 star property
Elkton
The price is HK$615
HK$899 total
includes taxes & fees
28 Nov - 29 Nov
Room #2 in Elkton, MD – Easy Access to I-95
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
10.0 out of 10, Exceptional, (1)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is HK$1,050
HK$2,654 total
includes taxes & fees
4 Dec - 5 Dec
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
1 bedroom, iron/ironing board, WiFi, bed sheets
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Aberdeen
The price is HK$628
HK$1,778 total
includes taxes & fees
30 Nov - 1 Dec
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Property grounds
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, (11)
"Great stay in a relaxing community. We loved to be able to walk to places from the house! The hosts were very helpful and easy to communicate with 💙"
United States
Elise E.
The price is HK$1,036
HK$1,658 total
includes taxes & fees
30 Nov - 1 Dec
Quarry Landing - Center of Town & River View - 3 Bedroom
Outdoor spa tub
Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub

Lincoln University
10.0 out of 10, Exceptional, (16)
"Our stay was perfect! We had a wonderful time with family celebrating our daughter's UD graduation."
United States
Heidi Z.
The price is HK$1,502
HK$3,695 total
includes taxes & fees
1 Dec - 2 Dec
Thunder Hill Retreat - Spacious/Deck/Hot tub
Dining
Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking

Smyrna
9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is HK$1,400
HK$2,761 total
includes taxes & fees
28 Nov - 29 Nov
Amazing Modern house with a full kitchen and parking
Terrace/patio
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

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

2.0 star property
Newark
10.0 out of 10, Exceptional, (3)
"Enjoyed our stay."
United States
Erik H.
The price is HK$1,168
HK$2,227 total
includes taxes & fees
16 Dec - 17 Dec
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Exterior
Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette

Port Deposit
10.0 out of 10, Exceptional, (29)
"Perfect location for that town. "
United States
Hisham M.
The price is HK$1,089
HK$2,003 total
includes taxes & fees
27 Nov - 28 Nov
Private 3 room Queen Suite w/Kitchenette
Property grounds
New Construction townhome close to everything downtown w/transparent pricing

New Construction townhome close to everything downtown w/transparent pricing

Wilmington
9.8 out of 10, Exceptional, (22)
"Very nice and clean. We do work on Fire Apparatus in the area and this will be my go to spot when in the area."
United States
Peter F.
The price is HK$1,114
HK$1,592 total
includes taxes & fees
7 Dec - 8 Dec
New Construction townhome close to everything downtown w/transparent pricing
Private kitchen
A Cool Place to Stay in Wilmington DE

A Cool Place to Stay in Wilmington DE

Wilmington
The price is HK$816
HK$1,203 total
includes taxes & fees
24 Dec - 25 Dec
A Cool Place to Stay in Wilmington DE
Smart TV, books
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
10.0 out of 10, Exceptional, (30)
"Wow such a wonderful place, clean, warm, and full of everything you need."
United States
Oswaldo S.
The price is HK$1,365
HK$1,636 total
includes taxes & fees
30 Nov - 1 Dec
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Fridge, microwave, oven, stovetop
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Elkton
8.0 out of 10, Very good, (9)
"Nice and quiet place to stay"
United States
Gary M.
The price is HK$1,050
HK$2,184 total
includes taxes & fees
30 Nov - 1 Dec
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Dining
Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm

2.0 star property
Nottingham
The price is HK$770
HK$1,441 total
includes taxes & fees
2 Dec - 3 Dec
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

Best Western Plus Newark/Christiana Inn

Best Western Plus Newark/Christiana Inn

10/10 Excellent
"Our stay was amazing. The staff went out of their way to make us feel welcome. "
Evelyn 1-night trip
Posted 6 days ago
Best Western Plus Newark/Christiana Inn

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
  • Use the map to find apartments and other holiday homes in the Chesapeake City neighbourhood you prefer
  • 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 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?

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront: This holiday home rental outside of Chesapeake City is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Chesapeake City?

With 10 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 Chesapeake City Docks 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.