Search Vacation Homes in Chesapeake City

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Chesapeake City vacation homes

Terrace/patio
Amazing Modern house with a full kitchen and parking

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.
$347 nightly
The price is $355
Dec 27 - Dec 28
Total with taxes and fees
Amazing Modern house with a full kitchen and parking
1 bedroom
Summer Rustic Camping with AC and King Bed

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.
$158 nightly
The price is $159
Dec 24 - Dec 25
Total with taxes and fees
Summer Rustic Camping with AC and King Bed
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

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.
$322 nightly
The price is $341
Jan 1 - Jan 2, 2026
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Dining
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Newark
9.6 out of 10, Exceptional, (21)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
$326 nightly
The price is $335
Dec 30 - Dec 31
Total with taxes and fees
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
Interior
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

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

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Elkton
8.2 out of 10, Very Good, (12)
"Nice and quiet place to stay"
United States
Gary M.
$259 nightly
The price is $275
Jan 4 - Jan 5, 2026
Total with taxes and fees
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Property grounds
New Construction townhome close to everything downtown w/transparent pricing

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, (23)
"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.
$198 nightly
The price is $205
Jan 4 - Jan 5, 2026
Total with taxes and fees
New Construction townhome close to everything downtown w/transparent pricing
Interior
Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Bel Air
10.0 out of 10, Exceptional, (5)
"I appreciated how clean and pleasant it smelled! Then it was a beautiful location with lots of places to eat nearby. My only improvement would have been window curtains, especially in the master bath. "
United States
Leah M.
$272 nightly
The price is $288
Jan 5 - Jan 6, 2026
Total with taxes and fees
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Terrace/patio
High Tide Haven Suite

High Tide Haven Suite

High Tide Haven Suite
Kent County
$193 nightly
The price is $200
Dec 29 - Dec 30
Total with taxes and fees
High Tide Haven Suite
Property grounds
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

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

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
$198 nightly
The price is $210
Dec 24 - Dec 25
Total with taxes and fees
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Smart TV
Spacious 4-bedroom house with backyard oasis

Spacious 4-bedroom house with backyard oasis

Spacious 4-bedroom house with backyard oasis
Middletown
10.0 out of 10, Exceptional, (1)
"We had a nice stay at this gorgeous house! Very comfortable and nicely appointed."
United States
Jordan K.
$1,060 nightly
The price is $1,083
Jan 5 - Jan 6, 2026
Total with taxes and fees
Spacious 4-bedroom house with backyard oasis
Private kitchen
A Cool Place to Stay in Wilmington DE

A Cool Place to Stay in Wilmington DE

A Cool Place to Stay in Wilmington DE
Wilmington
$150 nightly
The price is $155
Dec 24 - Dec 25
Total with taxes and fees
A Cool Place to Stay in Wilmington DE
Interior
Heated Pool • Private Backyard • Home Theater

Heated Pool • Private Backyard • Home Theater

Heated Pool • Private Backyard • Home Theater
2.0 star property
Middletown
$512 nightly
The price is $546
Jan 12 - Jan 13, 2026
Total with taxes and fees
Heated Pool • Private Backyard • Home Theater
Outdoor dining
Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
2.0 star property
Nottingham
$202 nightly
The price is $203
Jan 21 - Jan 22, 2026
Total with taxes and fees
Amish Countryside Escape at Forest Edge Farm
Property grounds
3 BD 1.5 Bathrooms, Large fenced yard, Indoor turf gym inside Secluded townhome

3 BD 1.5 Bathrooms, Large fenced yard, Indoor turf gym inside Secluded townhome

3 BD 1.5 Bathrooms, Large fenced yard, Indoor turf gym inside Secluded townhome
Elkton
10.0 out of 10, Exceptional, (1)
"Yes. Very welcoming. Great location. Overall good "
United States
Anonymous traveler
$360 nightly
The price is $382
Dec 24 - Dec 25
Total with taxes and fees
3 BD 1.5 Bathrooms, Large fenced yard, Indoor turf gym inside Secluded townhome
Sun loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown

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, (146)
"Beautiful home right on the North East River. Comfortable and peaceful. We would definitely stay here again."
United States
Cara R.
$567 nightly
The price is $601
Dec 29 - Dec 30
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
Interior
JVA LUXURY HOUSING

JVA LUXURY HOUSING

JVA LUXURY HOUSING
Smyrna
10.0 out of 10, Exceptional, (1)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
$567 nightly
The price is $585
Dec 30 - Dec 31
Total with taxes and fees
JVA LUXURY HOUSING
Interior
Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi

Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi

Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi
Pennsville Township
$286 nightly
The price is $315
Dec 24 - Dec 25
Total with taxes and fees
Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi
Dining
Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!
Abingdon
8.8 out of 10, Excellent, (8)
"Quite lovely house with a gorgeous view over the water. It is definitely a good spot to stay with a large family or friends for a few days with plenty to do (relaxing on the dock, play games inside, not too far from Baltimore and other nice towns, etc). The host was great and very communicative as well.The only downsides were details around cleanliness and the check-out procedures. The house itself was overall fine, but there dishes left in the dishwasher that we had to put away, the bottom...
United States
Benjamin J.
$784 nightly
The price is $831
Dec 28 - Dec 29
Total with taxes and fees
Luxury Waterfront Home Built for Entertaining!
Interior
New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi

New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi

New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
2.0 star property
Hilltop
$253 nightly
The price is $260
Dec 28 - Dec 29
Total with taxes and fees
New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
Smart TV
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
South Wilmington
2.0 out of 10, (2)
"Never heard from host. Expedia had to cancel reservation."
United States
Josh
$120 nightly
The price is $125
Jan 1 - Jan 2, 2026
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington
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

Holiday Inn Express & Suites Wilmington-Newark by IHG

Holiday Inn Express & Suites Wilmington-Newark by IHG

10/10 Excellent
"Everything was just right. Great breakfast Friendly, helpful staff"
James 1-night trip
Posted 4 days ago
Holiday Inn Express & Suites Wilmington-Newark by IHG

Find out more about Chesapeake City

Chesapeake City Vacation Homes information

Number of reviews
206
Accommodation
161 Vacation Homes
Lowest Price
$125
Highest Price
$1,083

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