Search Vacation Homes in Chesapeake City

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23
In one month
Dec 5 - Dec 7
In two months
Jan 2 - Jan 4

Vacation Homes in Chesapeake City

Interior
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
9.8 out of 10, Exceptional, (19)
"This place is beautiful in a quiet neighborhood. The kitchen is well stocked, the bed are so comfortable and the bathrooms are very nice, especially the master bath!!! I'd definitely stay here again."
United States
Lisa Y.
$325 nightly
The price is $333
Nov 9 - Nov 10
Total with taxes and fees
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
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.
$322 nightly
The price is $341
Nov 9 - Nov 10
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
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 dome and surrounding areas looks like it does in the photos, and using the compost toilet, shower, etc were pretty easy even for a camping novice like myself. The farm is beautiful and quiet. Good opportunities for birding too. I never saw or heard the gentlemen who live in the farmhouse, I only saw their cars come and go. I came here for rest and a connection to nature, and that’s what I got. I’d love to come back in the future! I think it would be even nicer later in the spring."
United States
Lady N.
$174 nightly
The price is $176
Dec 8 - Dec 9
Total with taxes and fees
Summer Rustic Camping with AC and King Bed
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)
"Although it was just for a late overnight stay, the house was perfect for our needs. Clean, with hospitable, accommodating host!"
United States
Wendy Z.
$267 nightly
The price is $283
Nov 10 - Nov 11
Total with taxes and fees
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Private kitchen
Room #3 in Elkton, MD – Easy Access to I-95

Room #3 in Elkton, MD – Easy Access to I-95

2.0 star property
Elkton
$125 nightly
The price is $133
Nov 13 - Nov 14
Total with taxes and fees
Room #3 in Elkton, MD – Easy Access to I-95
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, (18)
"Beautiful home. Lisa was so lovely to specially set up a room for my 86 year old mother! We would not hesitate to stay again!!"
United States
becky m.
$216 nightly
The price is $223
Nov 16 - Nov 17
Total with taxes and fees
New Construction townhome close to everything downtown w/transparent pricing
Terrace/patio
High Tide Haven Suite

High Tide Haven Suite

Kent County
$193 nightly
The price is $200
Nov 9 - Nov 10
Total with taxes and fees
High Tide Haven Suite
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
$215 nightly
The price is $228
Nov 9 - Nov 10
Total with taxes and fees
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
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

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.
$288 nightly
The price is $306
Nov 9 - Nov 10
Total with taxes and fees
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Outdoor dining
Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm

2.0 star property
Nottingham
$200 nightly
The price is $201
Dec 8 - Dec 9
Total with taxes and fees
Amish Countryside Escape at Forest Edge Farm
Sun loungers, beach towels
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)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
United States
Ashlee S.
$571 nightly
The price is $605
Nov 10 - Nov 11
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
Interior
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
Nov 8 - Nov 9
Total with taxes and fees
Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi
Fridge, microwave, oven, stovetop
Abingdon Haven Hideaway

Abingdon Haven Hideaway

Abingdon
7.0 out of 10, Good, (2)
"This is a basement apartment and is extremely noisy. You can hear the foot traffic and conversations as if they are standing next to you. Also it appears they were having some sort of event which made it worse."
United States
Sky S.
$363 nightly
The price is $385
Nov 17 - Nov 18
Total with taxes and fees
Abingdon Haven Hideaway
Private kitchen
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.
$571 nightly
The price is $589
Nov 14 - Nov 15
Total with taxes and fees
JVA LUXURY HOUSING
Interior
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
$109 nightly
The price is $116
Nov 9 - Nov 10
Total with taxes and fees
Room #2 in Elkton, MD – Easy Access to I-95
Private kitchen
Room #4 in Elkton, MD – Easy Access to I-95

Room #4 in Elkton, MD – Easy Access to I-95

2.0 star property
Elkton
$127 nightly
The price is $135
Nov 9 - Nov 10
Total with taxes and fees
Room #4 in Elkton, MD – Easy Access to I-95
Fridge, microwave, oven, stovetop
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

Havre de Grace
9.8 out of 10, Exceptional, (6)
"Beautiful house with lots of space for a family gathering. After a couple very hot days at Ripken (only 15 minute drive) the kids enjoyed cooling off in the pool and playing in the large yard. Would definitely stay again! "
United States
melissa d.
$1,268 nightly
The price is $1,344
Nov 8 - Nov 9
Total with taxes and fees
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.
6 bedrooms, iron/ironing board, WiFi, bed sheets
Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!

Abingdon
7.6 out of 10, Good, (4)
"We had such a wonderful stay! The house was spotless, comfortable, and beautifully maintained. The surrounding area was peaceful and welcoming, and perfect for a relaxing weekend. Highly recommend!"
United States
Oluwaseyi E.
$784 nightly
The price is $831
Nov 9 - Nov 10
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

2.0 star property
Wilmington
$244 nightly
The price is $251
Nov 17 - Nov 18
Total with taxes and fees
New Construction 3-bedroom townhome 3 queen beds with central AC and WiFi
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesapeake City Hotel Reviews

Ramada by Wyndham Newark/Wilmington

Ramada by Wyndham Newark/Wilmington

10/10 Excellent
"Breakfast"
Wayne 1-night trip
Posted 2 days ago
Ramada by Wyndham Newark/Wilmington

Find out more about Chesapeake City

Chesapeake City Vacation Homes information

Number of reviews
189
Accommodation
158 Vacation Homes
Lowest Price
$116
Highest Price
$1,344

Explore a world of travel with Expedia